Unlearn: Recent Episodes

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In this episode of the Unlearn Podcast, I sit down with Cass Pratt, Chief Human Resources Officer at Progyny, to explore how HR is evolving into a design discipline that blends human connection with AI-powered productivity. From building bots to boost employee experience to reshaping how we think about roles in an automated world, Cass shares an honest look at how she’s bringing people along on a transformation journey—with curiosity, experimentation, and heart.

We discuss her pivotal decision to say yes to opportunities beyond her comfort zone, the strategic shifts she's leading inside a fast-scaling company, and why the future of HR is about enhancing humanity, not replacing it. If you’re wondering what leadership looks like when AI meets empathy, this one’s for you.

Key Takeaways Unlearning expertise-dependence: Cass shifted from relying on experts to co-creating solutions with AI tools before engaging others. * * AI as a force for elevation: At Progyny, AI is used to give employees time back, not take roles away—enabling deeper focus on human-centric work. * * Low-code leadership: Cass, a self-described non-technical leader, built HR bots and reimagined policies through practical AI applications. * * Scaling culture through consistency: AI chatbots improved response times, standardized answers, and gave insight into employee concerns. * * Embedding experimentation*: Teams are encouraged to ask, "What should I stop doing?"—sparking a culture of reinvention and initiative. *

Additional Insights* Progyny’s “Super Fans” initiative reframes AI gains as an opportunity to deepen customer and employee relationships. * * Training is done in cohorts to build shared understanding and reduce AI anxiety. * * Cross-functional collaboration with junior team members—like the intern who built the HR bot—shows how innovation can come from any level. * * Cass uses AI to simplify and globalize complex frameworks like competency models, improving alignment across teams and geographies. *

Episode Highlights00:00 – Episode Recap

Cassandra Pratt shares how embracing discomfort led her to leap into healthcare, build a transformative HR function, and lead with AI—not to eliminate roles, but to elevate people and amplify their impact.

02:37 – Guest Introduction: Cassandra Pratt

Barry introduces Cass Pratt, Chief People Officer at Progyny, a fertility and family-building benefits company scaling rapidly with a human-first, tech-empowered culture.

04:48 – Saying Yes to Growth

Cass reflects on a missed opportunity that taught her the cost of saying no—and set her on a path to jump into unknowns with conviction.

08:04 – Startup Lessons and Leadership Growth

From 50 to 850 employees, Cass shares what it means to grow with a company and embrace mistakes as part of the journey.

11:00 – Diving into AI Without a Tech Background

Despite lacking technical skills, Cass threw herself into generative AI—learning by doing and discovering intuitive ways to drive value.

13:10 – Unlearning the Expert Reflex

Cass rethinks her default of turning to experts first—instead starting with AI to shape stronger ideas and bring others in as collaborators.

15:13 – Redesigning Processes, Not Just Tools

AI opened up opportunities to rethink workflows from scratch, not just automate existing inefficiencies.

20:35 – Making AI Safe and Human

Cass shares how transparent messaging, training, and cultural reinforcement helps ease AI anxieties and keep the focus on people.

25:00 – Building the HR Bot with an Intern

An intern-built benefits chatbot improved response times, consistency, and surfaced new insights—highlighting the power of junior talent and experimentation.

28:41 – Simplifying Competency Models with AI

Cass uses AI to refine complex frameworks, making them scalable across geographies and easier for leaders to apply.

30:00 – Rethinking Work Through Elimination

By asking what should be stopped—not added—Cass surfaces high-leverage opportunities to transform HR workflows.

34:33 – The Two Extremes of HR and AI Adoption

Cass observes a divide: HR teams either lead AI transformation—or risk being the last to catch up.

40:45 – Cross-Functional Collaboration and Culture

AI transformation is a team sport—embedding HR into company-wide initiatives empowers better collaboration and outcomes.

43:38 – Freeing Up Time to Be Present

Cass highlights how AI helps reclaim time for the most human part of HR: being present, listening, and solving meaningful problems together.

Useful Resources* Progyny: https://www.progyny.com * Connect with Cassandra Pratt: LinkedIn * AI Executive Coaching by Barry: https://barryoreilly.com

Follow the Host* LinkedIn: linkedin.com/in/barryoreilly * Website: barryoreilly.com * Facebook: facebook.com/barryoreillyauthor * Twitter/X: x.com/barryoreilly * Instagram: instagram.com/barryoreilly

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When most leaders think about transformation, they reach for tools and tactics. But real, lasting change doesn’t start with new methods—it starts with culture. In this episode, I sit down with Phil Gilbert, the former General Manager of Design at IBM, who led one of the boldest reinventions in corporate history. After selling his third startup to IBM in 2010, Phil was asked to transform how IBM’s teams worked using design thinking and agile. That effort reshaped the experience of over 400,000 employees and became the subject of a Harvard Business School case study, the documentary The Loop, and coverage in the New York Times and Fortune.

We explore how culture drives outcomes, why the team is the atomic unit of change, and how to design a leadership structure that earns trust and creates momentum. Phil brings sharp insight, rich stories, and practical frameworks drawn from a 45-year career spanning startups, scale-ups, and global enterprises. If you’re leading change—or trying to get others to believe in it—this conversation is your blueprint.

Phil Gilbert is best known for scaling IBM’s global design transformation. He was inducted into the New York Foundation for the Arts Hall of Fame in 2018 and named an Oklahoma Creativity Ambassador in 2019. Since retiring from IBM in 2022, Phil has focused on helping business and military leaders shift culture at scale to improve innovation and team performance.

Key Takeaways Culture is the system: Real transformation means rewiring people, practices, and places—not just teaching new skills. * Teams are the atomic unit of change: Change doesn’t scale through individual mandates. It scales when cross-functional teams deliver new outcomes. * Design scales empathy: Phil shares how design thinking isn’t just about aesthetics—it’s a tool for scaling understanding and improving systems. * Transformation needs protection: Change teams need structural support and a leadership “shell” that shields them while engaging the broader org. * Momentum beats mandates*: Leaders can’t impose change—they must earn it by showing results, listening deeply, and integrating across silos.

Additional Insights "Every day is a prototype": Phil’s mantra that gives teams permission to change, test, and learn continuously. * The virus model of leadership: To spread new ways of working, Phil designed his leadership team like a virus—with spikes into HR, finance, comms, and IT. * Designers aren’t the barrier—systems are: In companies with weak design reputations, the problem isn’t the designers. It’s the culture around them. * Shadow IT kills transformation: Real progress happens when change leaders partner with CIOs—not work around them. * Most AI efforts are missing the point*: Phil argues that AI transformation fails when it focuses on individuals instead of improving team-level outcomes.

Episode Highlights00:00 - Episode Recap

Barry O’Reilly recaps the episode’s theme, discussing leadership challenges, reclaiming strategic focus, and leveraging frameworks, executive habits, and AI to drive impactful business outcomes.

2:26 - Guest Introduction

Barry introduces Phil Gilbert, renowned for leading a major cultural transformation at IBM through human-centered design. He previews Phil’s new book, “Irresistible Change,” and sets expectations for a discussion on leadership, empathy, and executing change at scale.

3:21 - Official Start of Conversation

Phil Gilbert reflects on pivotal career moments, including his experience founding early startups, the challenge of driving adoption for new technologies, and discovering the power of empathy and design. He introduces his guiding philosophy, “every day is a prototype.”

9:15 - The Power of Prototyping and Embracing Change

Phil explains how prototyping and a willingness to challenge the status quo lead to organizational and personal growth. He shares his “every day is a prototype” mantra and stresses the role of openness in innovation.

13:48 - Culture as a Driver of Outcomes

Phil outlines his formula for driving real change, focusing on people, practices, and places. He discusses his use of journaling and intentional observation to systematically build curiosity and support for change in teams.

20:47 - Designing Transformation at Scale

Phil discusses the challenge of leading IBM’s company-wide design movement. He explains his strategy to reach and influence 400,000 employees and the importance of building a diverse leadership team to support transformative efforts.

31:29 - Practical Tactics for Organizational Change

Phil details the need to integrate HR, tooling, and communications into the transformation process, sharing stories about revamping career ladders and piloting new tools. He emphasizes collaboration and transparency with key stakeholders like HR and CIOs.

37:51 - Lessons for Modern AI Transformation

Phil and Barry examine current challenges with AI change efforts, arguing that teams—not just individuals—are the fundamental units for successful transformation. They discuss why team-level outcomes should guide measurement and strategy for adopting new technologies.

41:09 - Hopes and Irresistible Change for the Future

Phil shares his vision for the next wave of business transformation, especially regarding AI. Drawing inspiration from cloud computing’s impact, he hopes leaders will adopt principles that empower teams to drive industry-defining change.

Useful Resources Phil Gilbert – Irresistible Change (book): Buy on Amazon * Connect with Phil on LinkedIn*: Phil Gilbert * Barry’s blog on AI

Follow the Host* LinkedIn * Twitter / X * Instagram * Facebook * Website

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When it comes to product positioning, clarity isn’t just a communication tool—it’s a strategic advantage. In this episode, I sit down with Anthony Pierri, co-founder of FletchPMM, a product marketing consultancy that’s helped over 400 B2B software startups discover and sharpen their positioning. We explore how founders can unlearn generic marketing advice, clarify their message, and activate their strategy through one often-overlooked asset: their homepage.

Anthony brings practical frameworks, real-world stories, and a refreshing candor to a space that’s often muddled with jargon. This is a must-listen for any founder, PMM, or GTM leader tired of being misunderstood—and ready to focus.

FletchPMM is a product marketing consultancy that helps B2B tech startups nail their positioning and bring it to life through a purpose-built homepage. Alongside co-founder Rob Kaminski, he’s helped more than 400 companies craft focused, champion-centered messaging that converts.

Key Takeaways Clarity wins: Positioning isn’t about vision—it’s about specificity, segmentation, and telling your champion’s story. * Unlearn the fluff: Ditch the vague benefits and generic promises. Customers need to know what you do and how it helps them. * Focus = traction: Trying to be everything to everyone dilutes your impact. Specialization creates memorability and repeatability. * Your homepage is your positioning: It’s the one asset every stakeholder sees—customers, investors, your team. Make it count. * Position for the champion, not the budget holder*: Focus your messaging on the person closest to the problem—not the executive who cuts the check.

Additional Insights Positioning is pattern recognition: Anthony shares how lessons from church leadership and freelancing helped him recognize early signs of positioning misalignment—even before he had the language for it. * Inbound scale comes from consistency, not creativity: With over 500 companies served, Fletch’s success has come from delivering one service, the same way, every time—not by chasing new ideas or tactics. * Founders often confuse luck with repeatability: Anthony reveals how many early startup wins come from personal networks—and how this masks the real need for scalable positioning and segment focus. * Mispositioning starts with the homepage: Anthony critiques vague, benefits-only messaging like “Make Yes Work”—demonstrating how the lack of a clear product reference point derails understanding and action. * Repositioning is an organizational act*: Referencing Klaviyo and Meta, Anthony shows how homepage messaging isn’t just about marketing—it forces internal alignment by making strategic bets visible to every team member.

Episode Highlights00:00 – Episode Recap

Anthony Pierri shares how a seemingly minor contradiction in a church’s mission statement became his first exposure to a positioning problem—planting the seed for a career built around clarity.

01:30 – Guest Introduction: Anthony Pierri

Barry introduces Anthony, co-founder of FletchPMM, a consultancy that’s helped 400+ B2B software startups craft focused, conversion-driving homepages.

05:09 – The Real Cost of Doing Everything

Why trying to serve every persona or use case is the quickest way to stall traction—and how narrowing your focus builds momentum.

07:14 – Specialization is a Strategic Advantage

Anthony explains how one service, delivered one way, to one segment unlocked a scalable, inbound engine for Fletch.

11:42 – Sales Strategy or Sales Chaos?

The folly of hiring SDRs before narrowing your GTM focus—and why customer acquisition doesn’t scale without segment clarity.

14:03 – Champion-Centric Positioning

Don’t aim for the budget holder—speak to the person closest to the problem. They’ll become your internal advocate.

22:07 – How AI Will Impact Product Positioning

As software creation and discovery become more agent-driven, Anthony sees the same need for ultra-specific, capability-first messaging.

29:19 – Talking About Yourself Without Talking About Yourself

Positioning isn’t self-promotion—it’s about telling a compelling story that reflects your champion’s reality.

35:15 – The “Tell Me More” Effect

Great positioning doesn’t try to say everything. It just gets the right person to say, “Tell me more.”

38:17 – Your Homepage is Your Most Important Asset

The homepage isn’t just a lead gen tool—it’s the most visible alignment document your org has. Make it reflect your real strategy.

44:53 – Changing the Narrative at Scale

Anthony shares why embedding your positioning on the homepage is more powerful (and more visible) than internal decks ever will be.

46:35 – How to Structure a Homepage That Converts

Barry and Anthony unpack how to use messaging anchors, problem framing, and customer-centric storytelling to guide your homepage narrative.

Useful Resources* FletchPMM Website * Anthony Pierri on LinkedIn * April Dunford – Obviously Awesome * Wynter – Message Testing

Follow the Host* LinkedIn * Outlier Venture Partners * Facebook * Twitter/X * Instagram

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In today’s hyper-connected world, many of us are experiencing a paradox—more digital interactions, but deeper loneliness. In this episode of Unlearn, I sit down with Dr. Ben Rein, neuroscientist and author of Why Brains Need Friends, to unpack why human connection isn’t just emotional—it’s biological. From the neuroscience of loneliness to surprising acts of generosity in mice and minnows, we explore how your brain interprets social disconnection as a threat, and why a full calendar of Zoom calls doesn’t satisfy your social diet.

As someone who experienced this firsthand—working remotely, starting over in a new country—I share my own journey to unlearning the myth of self-sufficiency and redesigning my life to engineer real connection. This conversation is a call to rethink how we connect, show up for each other, and take our social health as seriously as sleep, diet, or exercise.

Key Takeaways Loneliness Is a Biological Threat: Your brain interprets social disconnection like hunger or pain—not just a mood, but a warning signal. * * Small In-Person Moments Matter: Even brief, face-to-face interactions boost mood and cognitive function more than digital ones. * * Isolation Damages the Brain: Chronic loneliness raises cortisol, shrinks memory centers, and can shorten your lifespan. * * Introverts Still Need People: Social time benefits everyone—introverts just hit their saturation point sooner. * * Generosity Is Hardwired: From rats to dolphins, the impulse to connect and give is deeply embedded in our biology. * * Connection Requires Unlearning:* Independence and solitude aren't always virtues—sometimes they’re survival myths in disguise. *

Additional Insights* Social prediction systems in the brain were scrambled by COVID—and many people still haven’t recalibrated. * * Most people think they’re worse-than-average at socializing, which fuels avoidance and false self-judgment. * * Digital tools remove the social cues—tone, expression, touch—that our brains need to feel emotionally nourished. * * Empathy is not automatic—it’s biased and trainable, shaped by exposure to difference and intention. * * Rebuilding community isn’t just good for you—it’s essential for physical, mental, and societal health. *

Episode Highlights00:00 – Episode Recap

Ben Rein discusses the importance of socializing, likening it to sleep, diet, and exercise, and emphasizing its role in overall well-being.

02:07 – Guest Introduction: Ben Rein

Barry introduces Dr. Ben Rein, neuroscientist and author, and outlines the episode’s focus on the biological necessity of human connection.

03:43 – How COVID Broke Our Social Predictions

Ben shares his neuroscience background and explores how societal shifts and the pandemic disrupted the brain’s expectations for everyday interaction.

08:23 – Barry’s Story: “You Sound Lonely”

Barry recounts a personal moment of realization and how a friend’s observation pushed him to rebuild his social life with intention.

11:29 – Why We Miss the Signs of Loneliness

Ben explains why loneliness often goes undetected, how it manifests as stress, and why virtual connection isn’t enough.

16:44 – The Hard Work of Making Friends

Barry reflects on the discomfort of building new friendships as an adult—and why it’s worth the effort for mental and emotional health.

21:10 – The Neuroscience of Social Fear

Ben breaks down why we underestimate the value of interaction, how fear holds us back, and the courage it takes to engage.

25:33 – Designing for Connection

Barry shares how he now intentionally schedules social time as part of his weekly routine—and encourages others to do the same.

29:46 – Writing Lessons: Structure Matters

Ben opens up about his writing process and the hard-earned lesson of keeping a book focused on its core idea.

32:58 – Empathy is in Our Nature

Ben shares surprising studies showing kindness and empathy across the animal kingdom—and what humans can learn from them.

39:22 – Closing Reflections

Barry and Ben wrap with a call to action: prioritize connection, embrace kindness, and use what we know to better ourselves and others.

Useful Resources Why Brains Need Friends* by Dr. Ben Rein * Dr. Ben Rein on LinkedIn * Ben’s popular science content on Instagram and TikTok

Follow the Host* LinkedIn * Personal Site * Facebook * Twitter * Instagram

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What happens when you stop treating HR as a back-office function and start designing it as a competitive advantage?

Theresa Cantwell, Strategic HR Consultant and Director at GSD HR Consulting, believes scaling a company shouldn't mean burning out your team—or yourself. With nearly two decades leading people strategy at companies like Microsoft, ThoughtWorks, and Equal Experts, Theresa has helped organizations across Europe and Asia grow not just fast, but gracefully.

In this episode, we dive into the most overlooked challenges founders face when they scale: losing visibility, clinging to control, and skipping the crucial step of designing people and culture systems that can actually support growth. From shadow planning and succession strategies to why success itself can be terrifying, Theresa shares powerful tools and real talk every startup leader needs to hear.

If you're moving past 20 employees and want to build a company that lasts—without losing what made it special—this conversation is your playbook.

Key Takeaways Start HR Strategy Early: Don’t wait for burnout or lawsuits—build people ops into your scaling strategy from day one. * * Shadow Planning Is Essential: Prepare for the worst by confronting your team’s shadow behaviors and stress reactions before they sabotage growth. * * Succession Planning Isn’t Personal: It's about scalability. Delegate early, document processes, and regularly revisit org design. * * Growth Changes Everything: Founders need to let go to level up. What got you here won’t get you there. * * AI in HR Is a Tool, Not a Fix:* Automate the repetitive, but double down on building trust and strategic visibility. *

Additional Insights* HR should be the connective tissue of an organization—not the "issues and tissues" team. * * Scaling gracefully requires confronting the emotional toll of growth, including fear of success. * * Theresa shares how early experiences at Microsoft and ThoughtWorks shaped her belief in high-trust, high-agency cultures. * * Executive coaching and intentional design can prevent burnout and boost retention. *

Episode Highlights00:00 – Episode Recap

Theresa Cantwell unpacks the emotional complexity of growth—from the fear of success to the need for intentional HR design. With experience scaling organizations across continents, she shares how founders can build people-first cultures that thrive under pressure.

01:54 – Guest Introduction: Theresa Cantwell

Theresa is a strategic HR consultant and founder of GSD HR Consulting, with nearly two decades of experience building and scaling agile-aligned cultures in the tech and digital sectors.

04:43 – Pivotal Moment at Microsoft

Seeing a team she’d hired bonding over lunch sparked her transition from recruitment to building cultures that last.

06:28 – ThoughtWorks and Radical Culture Design

Barry reflects on his own onboarding experience and how Theresa helped him understand the unique culture of ThoughtWorks from day one.

09:33 – From Recruiter to Culture Architect

Theresa shares why she shifted from acquisition to engagement, building full lifecycle HR strategies rooted in trust and clarity.

15:29 – When to Start Thinking About People Strategy

At 20 people, you need to get intentional—mission, values, cofounder conflict prep, and hiring bar must be aligned.

18:51 – Shadow Planning Explained

Why leaders must confront their own stress behaviors and prepare for the worst—before it happens.

22:39 – Handling Employee Departures with Grace

How to de-risk talent exits through succession planning and constant market awareness.

26:39 – Scaling Yourself Out of a Job

Helping leaders delegate, prevent burnout, and imagine new roles for themselves as the company grows.

32:16 – When to Start Succession Planning

The earlier, the better—start once you have traction. Document, delegate, and depersonalize the process.

36:17 – AI’s Role in HR

AI can’t replace the human heart of HR—but it can free you to focus on what matters most.

38:50 – Closing Reflections

Barry praises Theresa’s impact and encourages founders at scaling junctures to seek her wisdom and services.

Useful Resources* Theresa Cantwell on LinkedIn * GSD HR Consulting

Follow the Host* LinkedIn * Website * Facebook * Twitter / X * Instagram

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What happens when you stop chasing returns and start investing in purpose?

Ron Diamond, Founder and Chairman of Diamond Wealth, believes the future of finance isn’t just about building wealth—it’s about what that wealth can do. As a trusted advisor to over 100 family offices ranging from $250 million to $30 billion, Ron has spent more than two decades helping ultra-wealthy families align their capital with causes that matter.

In this episode, Ron shares how the collapse of Drexel Burnham shaped his perspective on loyalty, legacy, and leadership—and why “patient capital” is poised to disrupt the short-termism of private equity. We explore how purpose-driven investing is solving real-world challenges, from cancer to climate, and what it takes to build sustainable family office infrastructure in an era of unprecedented generational wealth transfer.

And the timing couldn’t be more relevant: family offices are no longer niche players. The number of single-family offices has surged 31% since 2019, with projections reaching over 10,700 globally by 2030. As trillions of dollars transition to the next generation, Ron offers a front-row seat to the values, strategies, and systems needed to steward that wealth wisely.

Ron is also the Founder, Host, and CEO of Family Office World Media, and helped establish the Family Office Program for TIGER 21, where he chairs a national peer group. He lectures at Oxford, Stanford, Harvard, and the University of Chicago Booth School of Business, and was recently appointed Editor-in-Chief of The National Law Review’s first Family Office newsletter. A LinkedIn Top Voice, TEDx speaker, and former hedge fund founder, Ron began his career on Wall Street at Bear Stearns and Drexel Burnham.

Key Takeaways People Over Companies: Ron’s experience during Drexel’s collapse taught him that relationships—not institutions—are what endure. * * Patient Capital Is a Game-Changer: Family offices can think in decades, not quarters, offering strategic advantage over traditional funds. * * Purpose Before Profit: Legacy and social impact must anchor investment decisions. * * Professionalization Is Essential: Governance, infrastructure, and talent are what turn capital into capability. * * The Ego Barrier*: Great wealth doesn’t guarantee great management—humility is crucial for longevity. *

Five Core Principles from Ron Diamond1. Guiding North Star: Profit with Purpose

Anchor investments in something bigger than financial return—personal mission, legacy, or societal impact.

→ Tip: Define your North Star early and align capital accordingly.

2. Trust & Relationships First

Back character over credentials. Trust and personal integrity build more resilient partnerships than models or metrics.

→ Tip: Focus on people, not pitch decks.

3. Patient, Long-Term Capital

Think in decades, not exit cycles. Family offices can outperform by holding steady and avoiding short-termism.

→ Tip: Let compounding do the heavy lifting.

4. Professionalizing Family Offices

Family offices must evolve beyond legacy systems—invest in governance, talent, and infrastructure like any top-tier fund.

→ Tip: Treat talent as a profit center, not a cost.

5. Entrepreneurial Philanthropy

Deploy strategic, venture-style capital into social challenges. Purpose and profit can—and should—coexist.

→ Tip: Apply the same rigor to social impact as you do to your investments.

Episode Highlights00:00 – Episode Recap

Ron Diamond shares how witnessing the downfall of Drexel Burnham sparked his lifelong belief in prioritizing people over companies—and why loyalty should lie with individuals, not brands.

01:39 – Guest Introduction: Ron Diamond

Barry introduces Ron Diamond, Chairman of Diamond Wealth and Family Office World Media, and a leading voice in purpose-driven capital and governance reform.

05:13 – Building a Family Office Syndicate

Ron explains his “first call alpha” model—aggregating capital from 100+ family offices to invest together in private markets.

08:40 – The North Star Philosophy

From Milken’s prostate cancer initiative to Eric Lefkofsky’s Tempus Labs, Ron shows how personal purpose drives breakthrough impact.

11:41 – Listening to Find Values Alignment

Ron’s secret to identifying values-driven leaders: listen more, talk less—and show up without an agenda.

16:43 – Growth Mindset Over Scarcity

Competing with others is outdated—Ron champions an abundance mindset rooted in collaboration and long-term thinking.

20:32 – The Operational Trap for New Family Offices

Ron breaks down why most new family offices fail and how professionalization—from mission statements to succession—can change that.

23:41 – The Power and Pitfalls of Patient Capital

He explores how family offices can outperform PE firms by holding long-term and avoiding short-term incentives.

32:42 – Creating a Playbook for Next-Gen Wealth

From Booth to Stanford, Ron is building the first structured family office curricula focused on governance, values, and impact.

39:31 – Investing in Talent Like an Institution

Ron outlines why top talent needs equity, not just salary—and why underinvesting in people is the silent killer of family offices.

44:34 – Finance Meets Philanthropy

Why family offices—not government or corporations—will solve many of society’s biggest challenges in the next 20 years.

45:31 – Closing Reflections

Ron shares how listeners can follow his work and why patient capital is the future of both wealth and impact.

🔗 Useful Resources* Ron Diamond LinkedIn * Ron Diamond Website * Diamond Wealth * Family Office World Media

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What if networking wasn’t about schmoozing but about being seen? David Homan joins me to unlearn the myths of traditional networking and share how vulnerability, deep listening, and small group connection can foster truly meaningful relationships. As a master connector, classical composer, and co-author of Orchestrating Connection, David breaks down the silent skills that build trust, activate communities, and transform the way we gather.

David Homan is the founder and CEO of Orchestrated Connecting, a global community of connectors; Orchestrated Opportunities, an impact-focused advisory firm; and SOAR CONNECT, a start-up focused on the strength of authentic relationships. He hosts the Orchestrated Relationships podcast on developing relationship value, is an active classical composer, and a proud father of two. From middle-class beginnings as the son of a college professor and nonprofit-focused mother, he has built a network that reaches into the most private and powerful circles globally, all while honoring a code of purposeful community building.

Key Takeaways Small Groups Create Big Impact: Starting events with curated small groups breaks social barriers and sets the stage for authentic connection. * Vulnerability Builds Real Relationships: Opening up—even subtly—invites empathy and depth that surface-level networking can't achieve. * Help Without Keeping Score: Giving without expecting reciprocity strengthens your reputation and extends your reach. * Design Moments That Resonate: Successful events don’t depend on cocktails or keynote speeches—they’re built on meaningful first impressions. * Asking Is a Skill, Not a Weakness*: Givers often struggle to ask for support—David’s Impact Ask framework helps mission-driven people share their needs with clarity. *

Additional Insights Most Networking Events Are Designed to Fail: Traditional formats emphasize aesthetics over connection—David redesigns them to foster immediate, meaningful dialogue. * Shared Vulnerability Activates Group Trust: Structured conversations with depth-based prompts unlock faster bonding and community-building. * Music as a Metaphor for Human Connection: David draws from his training as a classical composer to illustrate how relationships, like instruments, must resonate and harmonize. * Clarity Makes Asking Easier: The “Impact Ask” framework simplifies how to articulate passion, purpose, and the kind of help you need. * Your Reputation Travels Faster Than You Do*: David’s work shows that investing in authentic relationships amplifies your presence—even when you're not in the room. * *

Episode Highlights00:00 – Episode Recap

David Homan reveals how he had to unlearn everything he thought he knew about networking—discovering instead that vulnerability, deep listening, and structured intimacy were the keys to building purposeful community.

01:50 – Guest Introduction: David Homan

Barry introduces David Homan, master connector, startup founder, and co-author of Orchestrating Connection, whose work helps leaders create impact-driven relationships through authentic connection.

02:52 – Why Most Events Miss the Mark

David shares why traditional networking events feel awkward—and how his approach to curated small groups flips the script to create meaningful experiences.

04:49 – Start Small, Go Deep

Barry reflects on the power of small group interactions and how vulnerability accelerates meaningful connections.

08:01 – Sharing Real, Not Polished

David explains the importance of self-worth and courage when choosing to open up authentically in conversation.

10:45 – Creating Connection Through Authenticity

Being real invites empathy—and sets the tone for deeper, more rewarding conversations.

13:18 – Your Reputation When You're Not in the Room

David describes how authentic acts ripple through your network, strengthening your reputation and reach over time.

17:39 – Unlearning Transactional Thinking

Helping someone doesn’t obligate them—it expands your access to their trusted circles.

20:36 – Conducting Communities Like a Composer

David draws on his classical music training to explain how relationships can resonate like instruments in a symphony.

25:16 – Event Design That Actually Works

Purpose-driven event planning means matching people’s needs and asks—not just gathering for the sake of it.

28:13 – Why Givers Struggle to Ask

David outlines the “Impact Ask” framework to help mission-driven people communicate their needs confidently.

31:59 – Fundraising as Shared Mission

Barry reflects on how reframing fundraising as an invitation to join a mission transformed his startup experience.

33:59 – The Future of Community

David offers a hopeful vision: intentional communities built on shared values, layered for systemic change.

35:56 – How to Connect with David

David shares how listeners can join his private, connector-driven community—and what qualities matter most.

Useful Resources* Orchestrating Connection – Book * David Homan on LinkedIn

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Paul Hutchinson’s life story reads like a thriller, but his mission is deeply real and urgent. Once a multi-billion dollar fund manager, Paul transformed his life to become an undercover operative, leading more than 70 rescue missions across 15 countries to free thousands of children trapped in sex trafficking. He is the true-life inspiration behind the Sound of Freedom movie and the author of The Sound of Freedom: True Stories That Inspired the Film, offering a raw, unfiltered look at what it takes to confront humanity’s darkest realities and bring hope to the most vulnerable.

This episode goes far beyond heroism. We explore the complexities and personal costs of Paul’s work—from how his background in private equity uniquely positioned him to negotiate with traffickers, to the emotional and psychological toll of seeing trauma up close. Paul also shares vital lessons on protecting your children, what really works in combating trafficking, and why healing—beyond extraction—is the ultimate rescue.

Some stories are tough to face but impossible to turn away from. Paul’s journey is a powerful reminder of resilience, transformation, and what true leadership means when you dare to engage with the hardest truths.

Key Takeaways Trauma Often Hides in Plain Sight: Early exposure to peer counseling revealed the silent prevalence of abuse and shaped Paul’s lifelong compassion. * Leverage Unique Skills for Impact: Paul’s financial expertise uniquely positioned him to negotiate with traffickers and execute high-stakes rescue missions. * Healing Requires Vulnerability: Emerging therapies like psilocybin can accelerate breakthroughs when used intentionally and safely. * Meditation and Gratitude as Daily Practices: Far from clichés, these tools quiet the mind and strengthen authentic connection. * Impact Extends Beyond Rescue: True change is about rehabilitation, restoring humanity, and creating ripple effects of hope. * Material Success Without Meaning is Hollow:* Relationships, purpose, and self-awareness are the real measures of a life well lived.

Additional Insights Redefine Success on Your Own Terms: Society pushes for more—money, power, status—but real fulfillment comes from understanding what truly matters to you. * Embrace Compassion as a Leadership Skill: Genuine empathy transforms how you influence and inspire others. * Healing is a Collective Journey: Trauma and recovery ripple beyond the individual to impact families and communities. * Courage Requires Vulnerability:* Facing your own shadows opens the door to deeper connection and transformation.

Episode Highlights00:18 – Episode Recap

Paul Hutchinson’s journey from multi-billion dollar fund manager to undercover operative rescuing trafficked children reveals a profound transformation—one fueled by confronting trauma, embracing empathy, and discovering the healing power of vulnerability and plant-based therapies.

02:06 – Guest Introduction: Paul Hutchinson

Barry introduces Paul Hutchinson, former private equity executive turned human trafficking rescuer and author of The Sound of Freedom, sharing raw stories behind one of the largest rescue missions and the personal toll it took.

03:53 – Early Compassion & Peer Leadership

Paul reflects on how his early role as a peer counselor exposed him to hidden childhood traumas, planting the seeds of compassion that would later define his mission.

14:34 – First Undercover Mission & The Rescue of 124 Children

Paul recounts negotiating with traffickers in Colombia, orchestrating a risky sting operation that rescued over a hundred children in a single day.

23:59 – Processing Trauma with Psychedelic Healing

The conversation explores the emotional toll of undercover missions and how Paul and his team used plant-based therapies, like psilocybin, to process PTSD and reclaim their lives.

39:10 – Meditation, Gratitude, and Spiritual Connection

Paul shares his daily practice of meditation and gratitude as foundational tools for lasting transformation and alignment beyond material success.

44:53 – Advice for Deep Healing and Self-Transformation

Paul offers guidance for listeners on beginning their own journey of healing trauma through meditation, breathwork, and embracing vulnerability.

47:26 – Closing Reflections

Paul emphasizes the power of storytelling and awareness to inspire change, thanking Barry for amplifying the voices fighting modern slavery.

Useful Resources

• The Sound of Freedom by Paul Hutchinson Amazon Bestseller
• The Sound of Freedom movie (inspired by Paul’s missions)
• Gabriel Maté – Author of The Myth of Normal (https://drgabormate.com)
• Web del x – Plant-based therapy education platform (https://webdelx.com)
• Webdelics - https://www.webdelics.com/

Resources from Guest

• Get the first 3 chapters of Paul’s book for free: www.soundoffreedombook.com
• Liberating Humanity website: liberating-humanity.com
• Child Liberation Website: childliberation.org
• Youtube - youtube.com/@liberatinghumanity
• Instagram - instagram.com/liberating.humanity
• Facebook - facebook.com/liberating.humanity
• TikTok - tiktok.com/@liberating.humanity
• LinkedIn - linkedin.com/in/paulhutch
• X - x.com/paulhutchinson

Follow Barry O’Reilly

• LinkedIn: https://www.linkedin.com/in/barryoreilly
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What if generosity—not hustle—is your greatest competitive advantage?

Brad Feld—co-founder of Foundry Group, Mobius Venture Capital, and startup accelerator Techstars—joins Barry to explore the transformative philosophy of “Give First,” a mindset that’s reshaped how founders, investors, and mentors build lasting companies and vibrant startup ecosystems. Brad has spent over three decades cultivating startup communities by putting people before profit and helping others without expecting anything in return.

In this episode, he shares the mindset shifts that fueled Techstars’ global influence, how mentorship evolves from hierarchy to peer learning, and why sustainable success stems from playing the long game. A conversation full of clarity, candor, and challenge—for anyone rethinking what it means to lead, contribute, and create.

Key Takeaways Generosity Fuels Growth: Giving without expectation of return builds stronger relationships, ecosystems, and companies. * Mentorship is a Two-Way Street: The most impactful mentoring happens when both sides learn, grow, and give. * Play the Long Game: Positive-sum, multi-turn thinking creates more meaningful and lasting impact than transactional wins. * Know Yourself First:* Deep self-awareness—not external success metrics—is the foundation of better leadership.

Additional Insights Redefine Success on Your Own Terms: Society pushes for more—money, power, status—but real fulfillment comes from understanding what truly matters to you. * Build a Network of Givers: Shared values transcend geography. A global community built on generosity leads to collective resilience. * Let Go of the Need for Control: Great mentors—and leaders—create space for co-creation, not dictation. * Disconnect to Reconnect:* Time away from constant input helps surface your clearest thinking and truest desires.

Episode Highlights:00:00 – Episode Recap

Brad Feld reframes mentorship as a shift from a one-way hierarchy to a peer-based relationship.

01:48 – Barry Introduces Brad Feld

Barry introduces Brad's influential work on startup communities and his philosophy of "Give First."

03:12 – Startup Community Origins

Brad shares how the idea of startup communities became a global movement—challenging the belief that tech startups must be in Silicon Valley.

12:54 – The Give First Philosophy

Brad explains why generosity, long-term thinking, and non-transactional relationships are foundational to resilient startup ecosystems.

21:33 – Mentorship as Mutual Growth

A powerful story with mentor Len Fast reveals how Brad came to see mentorship as co-learning rather than knowledge transfer.

27:27 – Knowing Yourself

Brad emphasizes how self-awareness and personal growth are essential to leadership, especially in a world driven by reactive norms.

34:48 – Creating Space for What Matters

A candid discussion on disconnecting from external pressures, valuing inner reflection, and how time off helped Brad refocus on his values.

41:47 – Redesigning Relationships

Brad shares how he and his wife created structure and rules to prioritize their relationship—offering insight into the intersection of discipline and intimacy.

45:41 – Final Reflections

Brad closes with a message on leading through generosity, not transactions—and why playing the long game builds stronger companies and communities.

Episode ResourcesBrad Feld on LinkedIn: Brad Feld

Foundry Group on LinkedIn: Foundry Group

Foundry Group website: foundrygroup.com

Techstars website: techstars.com

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What if becoming a better leader meant letting go of being the expert? In this Unlearn episode, I’m joined by David Tuck, Chief Executive of Waracle, for a thoughtful and human-centered conversation on the mindset shifts required to lead high-performing teams in complex, fast-changing environments.

David’s leadership journey spans over 15 years of agile transformation, commercial growth, and organizational design. He’s held executive roles at Kin + Carta, The App Business, ThoughtWorks, and Scott Logic, and now leads Waracle, a strategic design and technology consultancy that builds trusted digital products for enterprise clients.

Known for his calm conviction and people-first approach, David shares how curiosity, craft, and long-term client intimacy have shaped his leadership philosophy. From stepping back in his career to hone his sales skills, to becoming a CEO who leads experts by asking better questions, David reflects on what it means to grow companies—and yourself—by design.

This episode explores how to lead through inquiry, build trust at scale, and why today’s leaders must become “Chief Unlearn Officers” to stay relevant in an AI-powered world.

Key Takeaways Craft First, Climb Later: David shares why stepping back from leadership to deepen his sales craft at Waracle gave him the clarity and credibility to lead more effectively. * Lead Without Knowing Everything: CEOs don't need all the answers—they need to ask better questions and create space for their teams to excel. * AI Starts with Literacy: Leaders must understand AI fundamentals to steer transformation and avoid becoming disconnected from how value is created. * From Specialist to Generalist: The CEO role is about orchestration—shifting from doing to enabling across functions and disciplines. * Human Connection Still Wins:* At Waracle and beyond, trust, empathy, and meaningful relationships still drive long-term business success in an AI-powered world.

Additional Insights Redefine Leadership as Service: A CEO’s job is to help others succeed, not to control every decision or be the expert in the room. * Ask Better Questions: Using frameworks like the probing pyramid can unlock better thinking and faster alignment across teams. * Don’t Automate the Human: AI can accelerate delivery, but it can’t replace the emotional intelligence and trust that drive real impact. * Create Space for Reflection: Strategic pauses and structured dialogue lead to more thoughtful, inclusive decisions—especially in hybrid teams. * Unlearn to Move Forward:* Leaders need to let go of outdated habits and create the conditions for new thinking to thrive.

Useful Resources

• David Tuck on LinkedIn
• Waracle on LinkedIn
• Waracle Website
• David Bowie’s 1999 interview on the future of the internet
• Waracle’s AI Literacy Program

Follow the Host:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
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What if the biggest risk in your business isn’t building the product but realizing no one wants it? In this Unlearn episode, I’m joined by Alistair Croll, technologist, entrepreneur, and bestselling author of Lean Analytics, for a candid and clever conversation on rethinking product development, marketing, and demand generation.

Alistair’s work focuses on data-driven innovation and human behavior. He co-authored Just Evil Enough: The Subversive Marketing Handbook, a playbook for bending the rules to win in the attention economy. He has chaired global tech conferences like O’Reilly’s Strata and currently leads Startupfest, where he helps founders turn clever ideas into competitive advantage.

Known for blending insight with humor, Alistair unpacks why subversive creativity, not perfection, often wins. From the “fluency equation” to Burger King’s clever customer acquisition tactics, he reveals how unconventional strategies generate meaningful traction. This episode explores the science of subversive marketing, reframes how we think about product launch risk, and dives into the mindset shifts leaders need to stay relevant in the AI era.

Key Takeaways Start with Attention, Not Execution: The first job is proving demand, not building features. * The Fluency Equation: Adoption is driven by desire, but also requires lowering inexperience, complexity, and perceived consequence. * Redefine Product-Market Fit: Medium fit — how people find, try, and pay — is just as important as what you offer. * Reverse Your GTM Strategy:* Work backward from demand instead of forward from the product.

Additional Insights Test Before You Build: Demand validation should come before development or scaling. * Have a Disagreement with the World: Bold startups are born from challenging norms, not just meeting expectations. * Use Familiar Behaviors to Drive Adoption: Anchoring new tools to existing habits lowers friction and boosts engagement. * Practice Ethical Persuasion:* Subversive tactics work best when they respect users and build long-term trust.

Episode Highlights:00:00 – Episode Recap

Alistair reframes startup risk with a clever hand-raising test: building isn’t the danger, indifference is.

03:16 – The Beach-Read Business Book

Why Just Evil Enough was built to entertain and educate, and how surprise fuels learning.

07:30 – The Real Startup Risk

Most teams focus on building because it feels safe. But the real risk is customer indifference.

08:41 – Subversive Marketing in Action

The Whopper Detour: How Burger King used playful tactics to achieve strategic goals.

13:20 – The Fluency Equation Explained

A new way to understand user hesitation and remove behavioral friction.

19:14 – AI, Fluency, and Leadership Gaps

Why executives aren’t using AI, even when they know they should.

26:00 – Decision-Making Matrix for Innovation

A two-by-two framework to help teams run smarter experiments with lower risk.

31:01 – The Fourth Miscapitalization

Why companies are still over-investing in engineering in an AI-native era.

35:55 – How to Start with Demand First

Real-world examples of flipping the build-first model by validating before committing.

39:14 – The Subversive Mindset

Disagreeability, creative risk, and how to spot the systems you're trapped inside.

41:36 – Ethical Persuasion

How to avoid crossing the line from clever to manipulative.

Useful Resources:

• Alistair Croll on LinkedIn
• Just Evil Enough by Alistair Croll & Emily Ross
• Lean Analytics by Alistair Croll & Ben Yoskovitz
• Unlearn Episode with Emily Ross
• Startupfest
• Never Split the Difference by Chris Voss
• How Minds Change by David McRaney

Follow the Host:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
• Personal site: https://barryoreilly.com
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Today on the Unlearn podcast, we welcome Jamie Dobson, technologist, entrepreneur, and a leader known for building systems that connect innovation with purpose. He joins us to share a deeply reflective journey: spanning childhood curiosity, extreme programming, leadership challenges, and the hard truths of building a company with intention.

Jamie Dobson is the co-founder and former CEO of Container Solutions, a consultancy helping organizations adopt cloud-native technologies. A self-proclaimed management nerd and lifelong learner, Jamie’s early career as a software engineer evolved into a calling to improve the world through better people management. He’s the author of Visionaries, Rebels, and Machines, a sweeping narrative on the evolution of computing and leadership. Jamie now advises executives and writes about how systems, both technological and organizational, can be redesigned for the better.

Known for his systems thinking, sharp wit, and grounded view on management, Jamie has spent decades bridging the gap between technological innovation and human-centered leadership. Whether he’s decoding the transistor’s origins or dissecting what makes a high-performing executive team, Jamie is always seeking out better ways to work, grow, and lead with clarity and courage.

This episode explores the mindset shifts required to lead through ambiguity, the costs of integrity in leadership, and how discipline, self-awareness, and naivety can sometimes be your greatest assets.

Key Takeaways Act on Inspiration Fast: Jamie shares why taking immediate action on a good idea is a rare but powerful leadership move. * Leadership as a Moral Responsibility: Decision-making isn’t just strategic—it’s ethical, emotional, and deeply human. * Naïveté as a Strength: Why approaching challenges with curiosity and a beginner’s mindset can spark unexpected breakthroughs. * Letters to Self as Feedback Loops: How Jamie uses journaling to reflect, recalibrate, and lead with discipline. * Psychological Safety Isn’t Optional: The timeless (and still underused) foundation of every high-performing tech team. * Bullsht Detection 101: From recognizing deceptive behavior to building a culture of honesty, trust, and clarity. * Managing Technologists is Solved: The real challenge isn’t how to manage engineers—it’s having the discipline to do what works.

Episode Highlights00:00 – Episode Recap

Jamie reflects on how childhood curiosity and Maslow’s philosophy laid the groundwork for a career blending tech and leadership.

04:27 – Acting on Inspiration Immediately

Why most people hesitate—and how taking fast, decisive action can be a leadership advantage.

07:42 – Leadership as a Moral Weight

Jamie discusses the emotional cost of doing the right thing and why real leadership isn’t always rewarded.

11:14 – The Loneliness of Idealism

From bold bets to navigating skepticism, Jamie shares what it’s like to hold the line on your values.

15:31 – Shifting Systems, Building Trust

What it really takes to lead teams through technological and cultural transformation—and why trust is the hardest part.

18:41 – Spotting Bullshit in Business

Jamie breaks down how to recognize deception in the workplace—and how to protect your team from it.

23:20 – From Sympathy to Self-Responsibility

Letting go of victimhood narratives and embracing accountability as a leadership discipline.

28:09 – Journaling, Feedback, and Decision Hygiene

Jamie shares the personal practices that help him lead with clarity and consistency.

32:03 – Psychological Safety Still Wins

Despite all the change in tech, one thing remains constant: teams thrive when they feel safe to speak up.

Resources Mentioned Visionaries, Rebels, and Machines – Jamie Dobson * Maslow on Management – Abraham Maslow * The Hard Thing About Hard Things – Ben Horowitz * Spy the Lie – Philip Houston et al. * Continuous Discovery Habits – Teresa Torres * The Soul of a New Machine* – Tracy Kidder * Peter Drucker’s writings on action and management

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Today on the podcast, we welcome Jeremy Shankle, full-stack engineer, AI strategist, and early adopter of automation tools across work and life at Nobody Studios.

With decades of experience in web development, startup leadership, and product strategy, Jeremy shares how going all-in on artificial intelligence has transformed how he works, lives, and thinks.

From debugging code to managing projects and planning weekends with his son, Jeremy has embraced AI as a true co-pilot. His story isn’t about replacing people—it’s about unlearning old work patterns, reducing context switching, and building smarter systems for productivity and purpose.

In this episode, we talk about Jeremy’s journey from web design and blockchain to AI-first development, and how adopting a multithreaded mindset helped him balance leadership, creativity, and everyday life in a more focused, high-leverage way.

Jeremy Shankle has worked across large tech organizations, startups, and now contributes to a fast-moving venture studio, helping teams use AI to build better products with fewer people. His thinking blends engineering discipline with human-centered innovation—exploring how tools like GPT-4 and Codex are reshaping the future of work.

Key Takeaways: Going All-In on AI: Jeremy shares what happened when he decided to run everything through GPT tools—from coding to shopping. * * Unlearning Multitasking: Why AI helps him focus more by batching work, parallelizing tasks, and context switching less. * Human First, Tech Forward: How AI frees up space for better thinking, parenting, and problem-solving. * Changing How We Work: Smaller teams, higher output, fewer blockers. * Life OS Upgrade*: From weekend planning to debugging code, AI is now part of Jeremy’s daily operating system.

Episode Highlights:01:50 – Guest Introduction: Jeremy Shankle

Barry introduces Jeremy as a product thinker and engineer at the intersection of AI, software, and strategy.

03:20 – Why Jeremy Went All-In on AI

In December, Jeremy dove deep into agents that search the web and modify code—and he hasn’t looked back.

04:02 – From Tandy 1000 to Tech Trailblazer

At age 5, Jeremy started coding on a Tandy 1000. That early start shaped his approach to learning and tech.

07:49 – Strategic Thinking Without the Switch Costs

AI helps Jeremy stay focused—no more jumping between roles or work personas all day.

10:32 – Fixing Bugs and Finding Basketball Clubs

Jeremy shows how he uses AI to squash code bugs and research activities for his son—at the same time.

15:23 – Smarter Task Management with AI

Jeremy explains how AI-infused project management tools let him create and assign tasks with ease.

22:11 – AI as an Anxiety Reducer

Whether prepping for embassy visits or crafting emails in another language, AI gives Jeremy a calm confidence.

32:31 – Confidence Without the Code Dependency

Barry shares how AI helped him stop second-guessing and start building—without always calling in an expert.

37:48 – AI Made Me Smarter, Not Dumber

By automating the grunt work, Jeremy has more time to understand the why behind every technical decision.

42:35 – What’s Next? Agent-to-Agent Collaboration

Jeremy’s most exciting frontier: AI tools that talk to each other—and get things done without constant prompts.

Resources* Jeremy Shankle * Nobody Studios * OpenAI Codex * GPT-4 with Memory and Deep Research Tools * Tools Mentioned: ChatGPT Pro, Operator, Browser MCP, Codex

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Welcome to UNLEARN, the podcast where we talk about bold ideas, fresh thinking, and the mindset shifts needed for real change. Today, I’m excited to welcome John Avrett, former U.S. diplomat, aerospace and electrical engineer, and now Founder and CEO of Hive Modular. With past roles in the U.S. Air Force, U.S. Navy, and Department of State, John is leading a new wave of modular home building in the Philippines, tackling the global housing crisis with factory-made homes and smart design.

John isn’t just a builder; he also loves solving big problems and making homes better for everyone. His journey from engineering and diplomacy to modular homes shows how thinking differently can help fix housing issues in new ways, especially by building smarter and faster in places that need it most.

John has worked across engineering and global trade before starting his company to build homes in a new way. At his factory in the Philippines, his team makes modular houses using a process like a car factory, helping build faster and cheaper. He focuses on smart design and shipping, bringing homes to places that need them, while using skills from aerospace and diplomacy to guide his work.

Key Takeaways:* Fixing Housing Problems: John shares how factory-made homes can help more people. * Starting a Business: What he learned from taking a big risk to follow his dream. * Thinking Differently: Why new ways of thinking are key to solving old problems. * Global Experience: How living and working abroad shaped his big ideas. * Smart Building: How using a car-like factory process makes building homes faster.

Additional Insights:* Mixing Tech and Building: John shows how factory skills can improve home building. * Working in New Markets: What it takes to build homes in places with big needs. * Learning from the Past: How John’s old jobs help him find smart new ways to build. * Solving Real Problems: How he uses design to make homes faster and cheaper. * Adapting to Change: Why being open to new ideas helped grow his company.

Join John Avrett as he shares how bold ideas, smart building, and global thinking can help solve housing needs and spark new ways to grow in today’s world.

Episode Highlights:[00:10] - Episode Recap

"John Avrett joins to talk about solving housing issues with modular homes and lessons from past careers."

[01:38] - Guest Introduction: John Avrett

"John is an ex-aerospace engineer and U.S. diplomat now building smart, factory-made homes in the Philippines."

[04:48] - Museum Visit Sparks a Big Idea

"A prefab home exhibit opened John’s eyes to a better way of building and inspired his mission."

[07:25] - From Engineer to Diplomat to Builder

"John shares how his global work helped him spot the housing crisis as a real problem to fix."

[10:09] - Why Housing Innovation Fell Behind

"Homes take longer and cost more today than in the 1960s, John explains why change is overdue."

[13:07] - Rethinking Risk to Start a Company

"Leaving a stable job was tough, but learning to see risk in a new way helped John take the leap."

[14:53] - Turning Homes Into a Factory Process

"John explains how car-style production lines and steel frames help build better, faster homes."

[19:42] - Blending Standard Design with Custom Feel

"Standard frames and flexible layouts allow homes to feel unique while staying easy to build."

[22:24] - Labor and Logistics in Home Building

"Even in a factory, homes take skilled work, and every site brings its own tricky challenges."

[27:02] - Strategy, Scaling, and a Life-Changing Book

"John explains how scaling isn’t about more small homes but bigger impact and how a book by Annie Duke helped shape his thinking."

[33:18] - Global Momentum and What’s Next

"John shares why support from countries like Canada and Australia shows prefab housing is gaining ground and how rising costs may push the U.S. to follow soon."

FOLLOW THE GUEST:

LinkedIn Accounts:

• John Avrett: https://www.linkedin.com/in/john-avrett-26891944/
• Hive Modular: https://www.linkedin.com/company/hivemodular/
• US Department of State: https://www.linkedin.com/company/doscareers/
• US Navy: https://www.linkedin.com/company/us-navy/
• United States Air Force: https://www.linkedin.com/company/united-states-air-force/

Websites:

• Hive Modular: https://www.hive-modular.com/
• US Department of State: https://www.state.gov/
• US Navy: https://www.navy.mil/
• United States Air Force: https://www.airforce.com/

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Today on the podcast, we welcome Faisal Hoque, author, entrepreneur, and thinker behind Transcend. With over 10 books and years of business leadership, Faisal shares how life, purpose, and challenges have shaped his journey of learning, growth, and helping others.

Known for books like Everything Connects and Transcend, Faisal blends Eastern wisdom with modern leadership. He’s worked with global firms, led startups, and speaks widely on purpose, resilience, and human-centered innovation.

In this episode, we talk about Faisal’s journey of self-growth and leadership, exploring how unlearning, flow states, and personal purpose can reshape how we lead, work, and grow in today’s fast-moving world.

Faisal Hoque is Founder and Managing Partner at Shadoka and NextChapter, Strategic Partner at CACI International Inc., and a Judge and Mentor at MIT. He’s also an investor, board member, and former CEO across various tech and business ventures. A contributor to Fast Company and IMD, he was shortlisted for the 2023 Thinkers50 Distinguished Achievement Award. Faisal is also a public speaker and former Chair of Research and Education at Altea Federation, as well as ex-Product Manager and CTO at GE Capital and Dun & Bradstreet.

Key Takeaways:* Unlearning past beliefs helps us grow and adapt in a changing world. * True purpose comes from small daily actions, not big goals. * Flow, gratitude, and reflection can boost personal and work life.

Additional Insights:* Let go of chasing success and focus on work that feels meaningful. * Use reflection, meditation, and learning to stay sharp and inspired every day.

Join Faisal Hoque as he shares how purpose, reflection, and human connection can guide us to grow and lead in today’s fast-changing world.

Episode Highlights: [01:00] - Episode Recap

"Faisal Hoque joins the show to talk about purpose, self-actualization, and how life’s challenges shape our leadership."

[01:34] - Guest Introduction: Faisal Hoque

"Faisal is a tech entrepreneur and author of Transcend, blending neuroscience, leadership, and personal growth."

[03:13] - Early Startups and Key Life Lessons

"My second startup failed despite big clients, then I bootstrapped my next one and wrote my first book."

[04:30] - Eastern Roots and the Search for Meaning

"Trips to Japan reconnected me with Eastern philosophy and sparked the idea for Everything Connects."

[06:01] - Redefining Self-Actualization with Purpose

"After life’s ups and downs, I began to ask: What does real success and impact look like for me now?"

[08:13] - Finding Fulfillment in Small Daily Actions

"It’s not about changing the world, it’s about helping one person and finding joy in the process."

[11:02] - The Paradox of Purpose and People in Work

"Mission statements often miss the mark, leaders must connect goals to individual purpose to inspire teams."

[14:08] - Building Regenerative and Connected Cultures

"Good leadership means creating space where people can grow, connect, and even leave to find their calling."

[18:18] - Writing, Reinvention, and Radical Openness

"Writing helps me unlearn and grow. Being open to ideas I disagree with pushes me out of my comfort zone."

[23:30] - Meditation, AI Tools, and Personal Growth

"Daily meditation and tech experiments help me reflect, stay grounded, and find new ways to improve."

[30:01] - Finding Ideas from Life and Observation

"Inspiration comes from watching the world, and writing weekly helps me reflect on change and uncertainty."

[32:51] - Focus on Effectiveness, Not Just Efficiency

"Instead of chasing speed, we must use tech to stay human, be thoughtful, and lift each other up."

FOLLOW THE GUEST:

LinkedIn Accounts:

• Faisal Hoque: https://www.linkedin.com/in/faisalhoque/
• NextChapter: https://www.linkedin.com/company/nextchapterorg/
• Shadoka: https://www.linkedin.com/company/shadoka/
• CACI International Inc: https://www.linkedin.com/company/caci-international-inc/
• MIT: https://www.linkedin.com/school/mit/
• Fast Company: https://www.linkedin.com/company/fast-company/
• IMD: https://www.linkedin.com/school/imd-business-school/
• Altea Federation: https://www.linkedin.com/company/alteafederation/
• GE Capital: https://www.linkedin.com/company/gecapital/
• Dun & Broadsheet: https://www.linkedin.com/company/dun-&-bradstreet/

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Today on the podcast, we welcome Ja-Naé Duane, systems thinker, innovator, and author of Super Shifts. With over 20 years as a behavioral scientist and 4-time entrepreneur, Ja-Naé has guided organizations, governments, and communities through future-focused transformation.

Recognized by outlets like NPR and Businessweek, she’s passionate about reshaping how we live and work in the age of superintelligence, leveraging AR/VR, AI, and blockchain. Ja-Naé has worked with top firms like Deloitte and PWC, and is a sought-after speaker at Singularity University.

In this episode, we explore her transformative frameworks for both personal and organizational growth, highlighting the power of unlearning, integrating systems thinking, and embracing change in a tech-driven world.

Dr. Ja-Naé Duane is a Research Fellow at MIT, Faculty Director of Brown’s Innovation Management program, and a mentor in its Tech Leadership program. She’s also a Council Member at The Stimson Center, an Investor at CollX, and a Co-Founder of The Revolution Factory. At Singularity University, she teaches futures thinking and lectures in Information Systems at Bentley University, where she’s on the Blockchain Advisory Council. She’s the bestselling author of McGraw-Hill and an advisor at Teleportec.

Key Takeaways:* Stress isn’t the enemy; using it intentionally can fuel growth and resilience. * To thrive in the future, we must unlearn outdated systems and develop an antifragile mindset. * Superintelligence and AI are crucial tools for creativity, reflection, and decision-making.

Additional Insights:* Let go of outdated thinking to make room for fresh, innovative approaches. * Use AI and other tools to boost productivity and enhance creativity in your work.

Join Ja-Naé Duane as she discusses transformation, unlearning habits, and creating resilient systems that thrive with technology and nature.

Episode Highlights:[01:00] - Episode Recap

"Today’s guest is Ja-Naé Duane, author of Super Shifts, discussing personal and organizational transformation in the age of superintelligence."

[01:56] - Guest Introduction: Ja-Naé Duane

"Ja-Naé Duane is a leading behavioral scientist and author, helping individuals and organizations navigate the world of AI and technology."

[03:55] - Inspiration Behind Super Shifts and the Pandemic Pivot

"During COVID-19, I was called to help restart Europe, which sparked the Super Shifts concept."

[06:10] - Exploring Decentralized Systems and Resilience

"We studied nature’s decentralized systems and explored how businesses can adopt similar models to thrive under stress."

[08:33] - Unlearning Comfort and Embracing Stressors

"I realized I was too comfortable. We must introduce stressors to evolve and adapt."

[12:11] - Physical Stressors for Growth and Self-Awareness

"Physical challenges like mountain climbing help build resilience and self-awareness for my work."

[15:29] - Using AI for Productivity and Holistic Living

"We should use AI for efficiency, but also focus on creativity, wellness, and meaningful connections."

[18:56] - Transformative Models and Organizational Impact

"By unlearning old mindsets, the Transform Model helps organizations shift to sustainable, adaptable systems."

[25:07] - Embracing AI for Leadership and Change

"AI can revolutionize leadership and decision-making while keeping us human in how we integrate it."

[30:10] - AI, Time Management, and the Future of Work

"AI tools free up time by automating tasks, but we must rethink how we spend our time and adapt to new ways of working."

[35:40] - Creating Space for Innovation and Long-Term Vision

"Leaders must create space for innovation, even if uncomfortable, to shape the future."

[42:28] - AI Tools, Growth, and Embracing Change

"Our AI-native studio uses automation to streamline tasks, reduce manpower, and embrace discomfort to adapt for future success."

Follow Our Guest

LinkedIn Accounts:

• Ja-Naé Duane: https://www.linkedin.com/in/janaeduane/
• MIT: https://www.linkedin.com/school/mit/
• Brown University School of Professional Studies: https://www.linkedin.com/school/brownsps/
• The Revolution Factory: https://www.linkedin.com/company/the-revolution-factory/
• Pre-order the First Edition Hardback of Super Shifts today at https://www.target.com/p/supershifts-by-ja-nae-duane-steve-fisher-hardcover/-/A-1001693948

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
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• Email: hello@barryoreilly.com

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Tap into a network of bold thinkers and industry leaders by sponsoring the Unlearn Podcast.

Contact here: https://bit.ly/contact-barryoreilly

____________________________________________________________

Today on the Unlearn Podcast, I’m thrilled to be joined by Francesca Cortesi, CPO and Founder of Prodotto Collective, a product visionary, transformational leader, and someone who truly understands what it takes to build beloved products and high-performing teams.

Francesca was the Chief Product Officer at Hemnet, Sweden’s leading property platform, where she played a pivotal role in scaling the product organization and driving the company through a successful IPO in 2021. Under her leadership, Hemnet achieved consistent double-digit growth, became one of Sweden’s most appreciated apps, and stood out as a top performer on the Swedish stock exchange.

But her story goes far beyond business metrics. Francesca led cultural shifts too, transitioning the company language to English and increasing female representation in tech, proving that growth and inclusion can go hand in hand.

In this episode, we explore how Francesca thinks about unlearning as a tool for personal and organizational growth, building product excellence at scale, and creating environments where diverse teams thrive.

Key Takeaways: Changing careers: Francesca switched from fashion in Milan to tech in Sweden after many rejections, showing strong resilience. * Product Management: Asking many questions helped her shift from project management to product management. * Asking for Help: Great leaders don't need to know everything; asking for help builds stronger teams. * Idea company size: Francesca thrives best in scale-up companies (40–400 people), not large corporations. * Unlearning and Growth:* Every new role required Francesca to "unlearn" old ways to adapt to new challenges.

Additional Insights: Changing Roles: Your job changes when your company grows, so be ready for change. * Know your strength: Understand clearly what you’re good at and where you fit best. * Start Fresh:* Always approach new tasks like you're learning for the first time.

Get ready for a powerful conversation with Francesca Cortesi on embracing change, scaling with intention, and building inclusive, high-performing product teams that thrive through continuous unlearning and growth.

Episode Highlights: [01:00] - Episode Recap

"Welcome to the Unlearn Podcast, Exploring career shifts, new leadership styles, and how to build strong product teams."

[02:03] - Guest Introduction: Francesca Cortesi

"Francesca, former Chief Product Officer at Hemnet, helped scale the product and led the company to a successful 2021 IPO."

[03:22] - From Milan Fashion to Stockholm: The First Career Pivot

"I worked in fashion, got a translator job in Sweden, and decided to move."

[07:10] - Facing Rejection and Redefining Identity

"I tried returning to fashion, but it wasn’t working, time to move on."

[10:13] - Discovering Product Management Through Curiosity and Questioning

"I kept asking questions, turns out, that curiosity led me into product management."

[15:20] - What Francesca Had to Unlearn

"As a product manager, I had to leave behind what worked before, it’s always contextual."

[19:56] - Transition from Individual Contributor to Product Leader

"My first leadership role taught me to stop copying others and find my own style."

[24:54] - Why Role Expectations Must Be Rewritten During Scaling

"Too many questions about roles and success? That’s your sign to pause and redefine expectations."

[27:52] - Realizing Where She Thrives: The Scaleup Stage

"My sweet spot? Companies ready to scale after finding product-market fit."

[37:24] - From Operator to Advisor: Unlearning and Redefining Impact

"New roles come with new expectations, especially the ones you set for yourself."

Follow Our Guest:

LinkedIn Accounts:

• Francesca Cortesi: https://www.linkedin.com/in/francesca-cortesi/
• Prodotto Collective: https://www.linkedin.com/company/prodotto-collective/
• Hemnet: https://www.linkedin.com/company/hemnet/

Websites:

• Prodotto Collective (Francesca’s Personal Site): https://www.francescacortesi.com/

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
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• Instagram: https://www.instagram.com/barryoreilly/
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Welcome back to the Unlearn podcast! Today, we're exploring neuroscience with Dr. Marcia Goddard, a top neuroscientist and high-performance expert. As the founder of Brain Matters, a LinkedIn Top Voice, TEDx speaker, and a Neuroscientist. She's known for making science practical for business success. Her work with Formula 1, where she studied behavior and culture within teams to develop comprehensive strategies that enhance performance, along with her contributions to Leiden University, and The Contentment Foundation has helped leaders and teams boost performance and teamwork. She is also the Board Advisory Member of Equalture. Tune in for an insightful talk on unlocking human abilities and building creative workplace cultures!

She is a respected neuroscientist who is dedicated to guiding young professionals and bringing fresh ideas into different industries. Dr. Marcia’s work is a valuable resource for anyone aiming to make a big impact in technology and business.

Dr. Marcia Goddard, a neuroscience expert with over 10+ years of experience, applies brain science to boost workplace performance and culture. She has consulted with high-performance teams, including Formula 1 and Fortune 500 companies, optimizing team dynamics. Her thought leadership focuses on psychological safety and inclusion, guiding organizations toward innovation and growth.

Key Takeaways:* Expanding Globally: Dr. Marcia Goddard’s strategies for international growth. * Overcoming Challenges: Solutions for fast-changing industries. * Adapting to Change: Stay flexible, ditch outdated methods. * Personal Experience: Dr. Goddard’s lessons in action.

Additional Insights:* Effective Strategies: Dr. Marcia Goddard on reshaping industries. * Thriving in Growth: Tips for fast-expanding businesses. * Experience to Innovation: Dr. Goddard’s journey to better solutions.

Get ready for an enlightening conversation with Dr. Marcia Goddard on infusing new ideas into business strategies and fostering a culture of innovation and growth.

Episode Highlights: [00:36] - Episode Precap

"Welcome back to the Unlearn podcast, where we challenge conventional thinking to unlock high performance and breakthrough innovation."

[01:17] - Guest Introduction: Dr. Marcia Goddard

“I'm joined by Dr. Marcia Goddard, a neuroscientist, author, and keynote speaker specializing in applying brain science to workplace performance and culture.”

[02:30] - Navigating Introversion, Networking Opportunities, and Career Growth

"My career was once a series of what I called coincidences, but I no longer believe they were."

[06:46] - Unlearning Misconceptions in Neuroscience

"There are two answers to that. My favorite quote is, 'If the brain were simple enough for us to understand, we would be too simple to understand it.”

[10:26] - Practical Tips for High-Performance

"It's a good question, especially in individual coaching. I think that's what it's related to."

[12:40] - The Importance of Reflection in Decision-Making

"We often tell ourselves we must decide now, but that’s rarely the case."

[15:58] - Enhancing Team Communication

"The most common thing I see at a team level, especially in growing organizations."

[18:44] - Remote Work and Maintaining Connections

"For remote organizations, let’s be clear: I don’t support full-time office work."

[26:04] - Future of High-Performance Teams

"Looking ahead, what excites you most in the industry, and what do you think needs to be unlearned?"

[29:31] - Rethinking Diversity and Inclusion Programs

"We need to unlearn the notion that ticking boxes creates impact and that DEI is just the right thing to do."

[35:52] - Future Trends in Neuroscience and Performance Teams

"Looking ahead, what excites you most about the future of performance teams and neuroscience?"

Follow Our Guest

LinkedIn Accounts:

• Dr. Marcia Goddard: https://www.linkedin.com/in/mngoddard/
• Brain Matters: https://www.linkedin.com/company/brainmattersconsulting/
• Formula 1: https://www.linkedin.com/company/formula-one-management-ltd/
• Equalture: https://www.linkedin.com/company/equalture/
• The Contentment Foundation: https://www.linkedin.com/company/the-contentment-foundation/
• Leiden University - Faculty of Archaeology: https://www.linkedin.com/company/faculty-of-archaeology-university-of-leiden/

Websites:

• Brain Matters: https://brainmattersconsulting.com/
• Formula 1: https://www.formula1.com/
• Equalture: https://www.equalture.com/
• The Contentment Foundation: https://www.contentment.org/
• Leiden University - Faculty of Archaeology: https://www.universiteitleiden.nl/en/archaeology

____________________________________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
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Welcome to UNLEARN, the podcast where we will discuss the transformative journeys, innovative tactics, and the pivotal mindset shifts necessary for authentic progress and development. Today, I'm thrilled to welcome Kristie Edling-Day, the current Executive Vice President and Chief Information Officer of Advisor Technology at LPL Financial, and former Principal and Chief Information Officer at Vanguard, a pioneer in strategic development and information management.

Kristie is not just a leader; she also loves helping young professionals grow and bringing new ideas to different industries. The book ‘Innovate to Elevate: Transforming Markets and Minds in Southeast Asia’ explores groundbreaking insights, offering valuable strategies for those aiming to drive change in technology and business.

Kristie has worked in the Financial Services industry for over 18 years, helping improve technology and develop new products. At LPL Financial, she manages Client Works, a platform that helps over 20,000 advisors with important tools for handling accounts, investments, trading, advisory programs, and compliance. She also leads LPL’s strategy for AI, making sure the company and its advisors have access to the latest in what technology can do both for efficiency and growth.

Key Takeaways:* Growing Businesses Worldwide: Kristie shares how to expand companies across different countries. * Facing Challenges: Tips on handling problems in fast-growing industries. * Learning and Adapting: Why being open to change and unlearning old ways helps with innovation. * Using Personal Experience: How Kristie solves problems based on her own challenges.

Additional Insights:* Smart Strategies and Strong Operations: Kristie explains how these key skills can change industries. * Succeeding in Fast-Growing Markets: How to handle challenges in quickly expanding businesses. * Turning Experience into Innovation: How Kristie uses her own experiences to create better business solutions.

Get ready for an insightful talk with Kristie Edling-Day on bringing fresh ideas into business strategies and building a culture of innovation and growth.

Episode Highlights:[00:37] - Episode Introduction

"Systems like LPL’s ClientWorks platform are so important and they help over 20,000 advisors manage their work more effectively and stay compliant. "

[01:35] - Guest Introduction: Kristie Edling-Day.

“I did not join Vanguard thinking I wanted to be an executive in technology."

[05:20] - Turning Point in Career Growth Choices and Embracing Uncertainty.

“On my first day at the new job, I realized that I didn't really know the boss or even the names of all the divisions in the company."

[10:05] - Nurturing Passion and Building Effective Leadership Teams

"What are the things you were doing when you chose to stay late, didn't mind, and in fact, were excited or couldn't wait to get up the next day?"

[16:28] - Adjusting to New Roles and Unlearning

"I think it is one of the most profound realizations that two organizations can think about roles and define them very differently."

[24:05] - Discovering Aha Moments in Personal Growth

"Some of the things that helped you, like those aha moments? Now that you have new clarity, what are you doing differently?"

[28:54] - The Need for Unlearning in Industry Evolution

"Things most exciting about in the industry, and what do you think needs to be unlearned? I’ve noticed both individuals and organizations often resist asking for help, preferring to go it alone."

[36:04] - Conclusion and Future Aspirations

"It's been absolutely phenomenal to have you on the show. Thank you for sharing your story so openly and humbly. This is what people love listening to."

Follow Our Guest

LinkedIn Accounts:

• Kristie Edling-Day: https://www.linkedin.com/in/kristie-edling-day-10690623/
• Vanguard : https://www.linkedin.com/company/vanguard/
• LPL Financial : https://www.linkedin.com/company/lpl-financial/

Websites:

• Vanguard : https://investor.vanguard.com/corporate-portal

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
• Personal site: https://barryoreilly.com
• Facebook: https://www.facebook.com/barryoreillyauthor/
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• Email: hello@barryoreilly.com

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Welcome to UNLEARN, the podcast where we explore the transformative experiences, strategies, and mindset shifts essential for true innovation and growth. Today, I’m honored to host Crystal Lee Gonzalez, a trailblazer in strategic growth and innovation across Southeast Asia.

Born and raised in the Philippines, Crystal has spent the last fifteen years shaping and scaling some of the region’s most prominent brands. She is the Co-Founder & CEO of NoneAway and was previously the Co-Founder of PICK.A.ROO. Her leadership has left a significant mark on multiple industries, serving as the Former CEO of Canva Philippines & Southeast Asia, Former President & Managing Director at HonestBee, and Former Regional Head of Southeast Asia at Viber. With a career spanning top-tier organizations, she also held key roles as the Group Account Director at Tribal Worldwide, Head of Branding at Lazada Group, and Marketing Head at YAHOO.

Beyond launching and leading businesses, Crystal finds deep fulfillment in mentoring emerging talent and reshaping industries through innovation. Her expertise is now encapsulated in her upcoming book, Innovate to Elevate: Transforming Markets and Minds in Southeast Asia, a must-read for those looking to make a lasting impact in technology and strategic development.

Key Takeaways:* Scaling Global Startups: Crystal details her strategies for business expansion in Southeast Asia. * Embracing Challenges: Insights into overcoming obstacles in high-growth environments. * Unlearning for Growth: How adapting and unlearning fuels innovation. * Leveraging Personal Experiences: Crystal's approach to creating solutions from personal pain points.

Additional Insights:* The NoneAway Model: Crystal demonstrates how strategic thinking and operational excellence revolutionize real estate. * Adapting in High Growth Markets: Mastering the challenges of rapid expansion and market dynamics. * Innovative Solutions from Personal Insights: How Crystal’s personal experiences inspire practical business innovations.

Prepare for an insightful conversation with Crystal Gonzalez on Bringing fresh ideas to startup strategies and cultivating a culture of innovation and strategic growth.

Episode Highlights: [00:35] - Episode Introduction

"In the Philippines, there are 120,000 reported scammers in real estate. This is why, even with a legitimate broker, I felt unease and anxiety until I received the keys to my house."

[01:18] - Guest Introduction: Crystal Lee Gonzalez

"Welcome to the Unlearn Podcast. Today, I'm honored to host Crystal Gonzalez, a leader in strategy and growth who has developed and scaled renowned brands across Southeast Asia."

[03:03] - Viber's Launch Story

"It started when I met Talmon, the founder. My first question was simple: Why are you in the Philippines?"

[07:50] - Nurturing Empathy and Innovation

"Okay. So interesting fact. I promise you this is connected to my answer. So my dad and actually my sister, now my younger sister, they're both psychiatrists."

[16:15] - The Role of Relatability in Product Adoption

"When we added more words to our copy and analyzed our data, we changed our messages to offer free chat and calls for your family and friends abroad"

[26:08] - Discussion on Market Needs and Solution Development

"I kid you not, my earliest memories involve playing role-playing games with my childhood friends where I was signing checks."

[31:27] - Vision for a Seamless Real Estate Experience

"I've always promoted and highlighted issues, even if I wasn’t the founder or creator."

[42:11] - Building Trust in Philippine Real Estate: A Digital Solution

"I didn’t feel safe. Despite dealing with legitimate brokers, the anxiety of 120,000 reported real estate scammers in the Philippines lingered until I held the keys. I kept wondering.why hasn’t this been solved yet?"

[53:51] - Conclusion and Future Aspirations

"Just the way you discuss this issue, your previous achievements, and the team you are building indicate you're set to do something truly amazing."

Follow Our Guest

LinkedIn Accounts:

• Crystal Lee Gonzalez: https://www.linkedin.com/in/crystalleegonzalez/
• NoneAway : https://www.linkedin.com/company/noneaway/
• PICK.A.ROO: https://www.linkedin.com/company/pickaroo/
• Canva : https://www.linkedin.com/company/canva/
• Honestbee: https://www.linkedin.com/company/honestbee/
• Viber: https://www.linkedin.com/company/rakuten-viber/
• Tribal World : https://www.linkedin.com/company/tribal-worldwide/
• Lazada: https://www.linkedin.com/company/lazada/
• Yahoo: https://www.linkedin.com/company/yahoo/

Websites:

• NoneAway: https://noneaway.com/
• PICK.A.ROO: https://pickaroo.com/
• Canva: https://www.canva.com/
• Honestbee: https://www.honestbee.com/
• Viber:https://www.forbusiness.viber.com/
• Lazada : https://group.lazada.com/
• Yahoo: https://www.yahooinc.com/

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
• Personal site: https://barryoreilly.com
• Facebook: https://www.facebook.com/barryoreillyauthor/
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• Instagram: https://www.instagram.com/barryoreilly/

Email: hello@barryoreilly.com

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Welcome to UNLEARN, the podcast where we explore the stories, strategies, and mindset shifts that drive real innovation and growth. Today, I’m glad to be joined by Diana Stepner, a true trailblazer in the world of product management and people-centered leadership.

A Silicon Valley native, Diana has spent over two decades building and leading global product teams for companies like Monster, Cheapflights (later acquired by Kayak), Salesforce, and Razorfish. As Co-Founder, at Product Gold and Former VP of Product Management at Pearson, she has honed her expertise in creating impactful solutions. Along the way, she discovered that while launching great products is exciting, helping people launch their careers is even more rewarding..

Diana’s passion for fostering talent and preparing organizations for the future shines in her new book, Next-Gen Product Management: Future Proof Your Career. It’s a must-read for anyone navigating the rapidly evolving landscape of technology, teams, and innovation.

We dive into her journey, the lessons she’s learned, and the practical advice she has for product leaders looking to thrive in an ever-changing world.

Check out her website at www.dianastepner.com to learn more.

Key Takeaways:* Product vs. Project Management: Diana explains the key differences. * Supercharging Product Managers: How top contributors maximize impact. * Winning with Teams: The power of cross-functional collaboration. * Breaking Into Product Management: Trends shaping new career moves.

Additional Insights:* The Product Gold Framework, Diana shows how adaptability and empathy unlock market opportunities. * Engagement in the Digital Age by mastering attention in a world full of distractions. * Thinking Differently in Business: How challenging norms drives big advancements.

Prepare for an enlightening discussion with Diana Stepner on transforming traditional product strategies and fostering a culture of creativity and innovation.

Episode Highlights: [00:33] -Episode Introduction

"One of the trends that we're seeing in product management is this rise of a super IC. People are able to do a whole lot more because of AI than they could have done before."

[01:33] - Guest Introduction

"Today, we’re joined by Diana Stepner, an expert in product management and people-centered leadership. Diana has built leading global product teams at companies like Product Gold, Monster, Salesforce, and Razorfish."

[03:08] - Shift from Project to Product Management

"People kept saying, 'Oh, you're a project manager.' And I'm like, 'No, I'm not a project manager. I am a product manager.' Over time, people began to realize that it actually was a skill or an expertise."

[10:44] - The Role of Collaboration in Product Management (corrected from 10:49)

"You need all of those instruments to come together to really make the music sing, and companies still don't realize that."

[16:08] - The Rise of Super ICs

"You're having these people be able to go much farther down the development path than what they did previously. And I think that's fascinating because it makes total sense."

[19:18] - The Evolution of the Mini-CEO & One-Person Unicorns

"For me, it feels like it's the incarnation of the mini-CEO. Now there's this billion-dollar unicorn narrative where one person is expected to do everything with AI."

[27:00] - The Role of Asynchronous Communication & AI in Workflow Efficiency

"It's funny, sometimes people get freaked out when I summarize a meeting in three minutes and email them key points before they've even left the call!"

[30:48] - The Future of Product Management

"I believe we need to evolve, but that also means we need to welcome in the next generation who bring their own unique perspectives."

[35:33] - Conclusion and Next-Gen Product Management Book Promotion

"My book, Next Gen Product Management, is for those who want to future-proof their careers and thrive in this evolving industry."

Follow Our Guest

LinkedIn Accounts:

• Diana Stepner: https://www.linkedin.com/in/dianas/
• Product Gold : https://www.linkedin.com/company/productgold/
• Monster: https://www.linkedin.com/company/monster/
• KAYAK: https://www.linkedin.com/company/kayak/
• Salesforce: https://www.linkedin.com/company/salesforce/
• RazorFish: https://www.linkedin.com/company/razorfish/
• Pearson: https://www.linkedin.com/company/pearson/

Websites:

• Personal Website: https://www.dianastepner.com
• Product Gold: https://www.productgold.com/
• Monster: https://www.monster.com/
• KAYAK: https://www.kayak.com/
• Saleforce: https://www.salesforce.com/ap/
• RazorFish: https://www.razorfish.com/
• Pearson: https://www.pearson.com/
• Get your copy of Next-Gen Product Management today! Order now at https://www.nextgenproductmanagement.com/

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
• Personal site: https://barryoreilly.com
• Facebook: https://www.facebook.com/barryoreillyauthor/
• Twitter: https://x.com/barryoreilly
• Instagram: https://www.instagram.com/barryoreilly/
• Email: hello@barryoreilly.com

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Welcome to the UNLEARN Podcast! Today, we’re joined by Emily Ross, co-author of Just Evil Enough and a leader in brand strategy and creativity. With a career spanning tech innovation, marketing, and even circus performance, Emily approaches challenges from unconventional angles.

As Director of Brand Strategy at X (formerly Twitter) for EMEA, Emily also serves as an Advisory Board Member at SXSW and GoGreen Routes, an EU funded, pan-European research project on nature-based connectedness, as Co-founder of Resonance Festival (Resonance-Lough Derg), and a mentor to startups across Europe.

In this episode, she shares her approach to subversive marketing, reframing obstacles as opportunities and using bold tactics to achieve extraordinary results. Drawing inspiration from disruptors like Tesla, Emily reveals how creativity and curiosity can transform business outcomes. Whether you’re looking to reimagine your marketing strategies or disrupt the status quo, Emily’s expertise is an invaluable guide.

Key Takeaways:

• Unconventional marketing tactics involve reframing challenges and using bold strategies like zero-day exploits to help brands stand out.
• The power of creativity lies in applying attention-grabbing skills across industries, as seen through lessons from a diverse career.
• Turning flaws into strengths, as seen with Tesla and Space Invaders, shows how weaknesses can become powerful advantages.
• Consistency over brilliance emphasizes that success stems from daily effort and experimentation, not rare moments of genius.

Additional Insights:

• The Recon Canvas Framework uncovers market opportunities and shows the need for constant adaptability as strategies evolve.
• Capturing attention in the digital age requires standout marketing in a noisy, distracted world.
• Subversive thinking from Just Evil Enough shows how breaking rules can drive business success.

Get ready for a fascinating conversation with Emily Ross on rethinking traditional approaches, embracing creativity, and crafting strategies that disrupt the status quo!

Episode Highlights:

00:37 - Introducing Emily Ross

"Emily is a powerhouse in brand strategy, creative leadership, and co-author of Just Evil Enough. She’s reshaping how global brands stand out in noisy markets."

03:15 - Lessons from the Circus The Power of Attention

"I spent years as a fire performer, and it taught me that attention is a superpower. Learning to capture and hold attention is a skill every marketer needs."

05:14 - Subversive Marketing Tactics Explained

"Subversive marketing is about being bold, counterintuitive, and creative. It’s not growth hacking, it’s about playing the long game to stay ahead."

09:47 - Turning Bugs Into Features

"The famous Space Invaders bug is a perfect example of how flaws can create differentiation. As the game progressed, it got faster, making it more exciting."

15:10 - The Product-Market Fit Myth

"Product-market fit isn’t real, it’s actually product-medium-market fit. Success lies in how you connect your product to the audience through the right medium."

20:33 - Zero-Day Exploits and Subversive Marketing

“We call those zero day exploits. So in cybersecurity, a zero day hack is one that is a kind of a finite hack."

22:42 - Underdog Success Using Unconventional Tactics

"When smaller forces use unconventional tactics, they can flip the odds. It’s how underdogs win in both marketing and warfare."

29:36 - The Recon Framework and Attention Economy

"One of the most practical pieces of the book is the recon canvas. We are drowning in noise, and Herbert Simon coined the term ‘attention economy’, where the thing in shortest supply becomes the currency of the day."

31:28 - Just Evil Enough: Unexpected Validation

"When I pitched the idea of Just Evil Enough sitting beside Alchemy on the shelf, I never imagined Rory Sutherland would not only read the book but offer such high praise. It was an amazing moment of recognition."

Follow Our Guest

LinkedIn Accounts:

• Emily Ross: www.linkedin.com/in/emilyrossonline/
• Twitter: www.linkedin.com/company/x-corp/
• Resonance Festival (Resonance-Lough Derg): www.linkedin.com/company/resonance-loughderg/
• SXSW: www.linkedin.com/company/sxsw/

Websites:

• Twitter: https://x.com/
• Resonance Festival (Resonance-Lough Derg): www.resonance-loughderg.com/
• SXSW: www.sxsw.com/
• Pre-order the First Edition Hardback of Just Evil Enough today at www.justevilenough.com/

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
• Personal site: https://barryoreilly.com
• Facebook: https://www.facebook.com/barryoreillyauthor/
• Twitter: https://x.com/barryoreilly
• Instagram: https://www.instagram.com/barryoreilly/
• Email: hello@barryoreilly.com

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Welcome to the UNLEARN Podcast! Today, we’re joined by a thought leader and prolific voice in product management and organizational design, John Cutler. With a unique ability to navigate the “beautiful mess” of product development, John has spent his career exploring the complex overlaps of product, UX, and strategy.

Currently serving as Head of Product at Dotwork, John has previously held impactful roles such as Senior Director of Product Enablement at Toast and Product Evangelist at Amplitude, where he collaborated with thousands of product teams worldwide. His extensive experience spans B2B SaaS giants like Zendesk, Pendo, and AppFolio, as well as B2C, ad-tech, banking, and media industries.

Known for his insightful writing, John has authored nearly a thousand posts across various platforms, captivating readers with his deep understanding of product dynamics. Whether you’re seeking to level up your product thinking or gain practical tips on team enablement, John’s expertise offers unparalleled insights.

Key Takeaways: The Beautiful Mess of Product Development: John’s approach to embracing complexity and context in product management to uncover innovative solutions. * Unlearning and Growth: How letting go of rigid practices and adapting to change can unlock greater potential for teams and leaders. * Writing as a Catalyst for learning:* The power of consistent writing in shaping ideas, refining strategies, and building meaningful connections in the product community.

Additional Insights: Product Ecosystems in Flux: John talks about the dynamic nature of product management, highlighting how roles and best practices evolve with organizational and market shifts. * Gamifying the Creative Process: Insights into how John uses tools and techniques to make writing, ideation, and problem-solving more engaging and productive. * Rethinking Organizational Models:* Exploring how companies can overcome challenges by reimagining structures, roles, and team dynamics for the modern era.

Get ready for a thought-provoking conversation with John Cutler on embracing complexity, fostering innovation, and mastering the art of unlearning!

Episode Highlights: 00:36 - Episode Introduction

"I don't think we need a product manager for every 4 to 7 people. A software as a service company is much more of a service ecology."

01:15 - Introducing John Cutler

"John is one of the most insightful voices in product management, with a career spanning roles at Toast, Amplitude, and beyond."

03:46 - Discovering the "Beautiful Mess" of Product

"I’ve always been fascinated by the overlaps—where product, UX, and strategy collide in unpredictable ways."

11:27 - The Importance of Writing and Sharing Ideas

"I realized that writing wasn’t just for others—it was for me to process and refine my thinking."

15:59 - Finding Your Path Through Experimentation

"Everybody finds their way if you're willing to experiment and try. It's like software—the rate of iteration and the velocity of creation allow you to refine and improve over time."

33:06 - Lessons in Unlearning

"It’s not just about adopting new practices; it’s about letting go of the ones that no longer serve the team or the context."

40:59 - What Excites John About the Future of the Industry

"The future of product management lies in embracing complexity and experimenting with new ways to scale and deliver value."

Follow Our Guest

LinkedIn Accounts:

• John Cutler: www.linkedin.com/in/johnpcutler/
• Dotwork: www.linkedin.com/company/dotworklabs/
• Toast: www.linkedin.com/company/toast-inc/
• Amplitude: www.linkedin.com/company/amplitude-analytics/
• Zendesk: www.linkedin.com/company/zendesk/
• Pendo: www.linkedin.com/company/pendo-io/

Websites:

• Dotwork: www.dotwork.com/
• Toast: www.pos.toasttab.com/
• Amplitude: www.amplitude.com/
• Zendesk: www.zendesk.com/
• Pendo: www.pendo.io/

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
• Personal site: https://barryoreilly.com
• Facebook: https://www.facebook.com/barryoreillyauthor/
• Twitter: https://x.com/barryoreilly
• Instagram: https://www.instagram.com/barryoreilly/
• Email: hello@barryoreilly.com

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Welcome to the UNLEARN Podcast! Today, we’re joined by Lee Vorthman, Vice President of Strategic Security Initiatives at Oracle. Lee leads a global team to protect and strengthen Oracle's operations. He is also a Global CISO Advisory Board Member at HMG Strategy and an Advisory Board Member for Phoenix Security.

His career began in the US Navy, and he has since held key roles across defense, technology, cloud, education, and oil & gas industries. Lee’s past roles include Chief Security Officer for Oracle's Advertising group, leading Global Security Engineering at Pearson Education, and serving as Chief Technology Officer for Federal Civilian Agencies at NetApp.

In this episode, Lee shares insights on leveraging technology for growth, navigating cultural transformations, and building resilient organizations.

Key Takeaways: Mastering Security Fundamentals: Lee highlights the importance of staying grounded in foundational security practices while adopting innovative technologies like AI to address evolving challenges. * Building Trust and Influence: Discover Lee’s techniques for fostering collaboration, psychological safety, and cultural change to drive impactful security initiatives. * The Power of Diverse Skills:* Learn why developing a broad skill set across disciplines like engineering, finance, and HR is essential for empathetic leadership and effective problem-solving.

Additional Insights: Cultural Change in Security: Get ready for a thought-provoking conversation with Lee Vorthman on leadership, innovation, and building resilient organizations! * Balancing Speed and Resilience: Insights on how businesses can prioritize innovation while maintaining strong operational fundamentals. * The Future of Cybersecurity:* Exploring emerging trends like AI and their implications for addressing new and complex threats.

Get ready for a thought-provoking conversation with Lee Vorthman on leadership, innovation, and building resilient organizations!

Episode Highlights: * 00:36 - Episode Introduction * "We're always going to have new technologies. But that doesn't negate the fact that you still have to master the fundamentals." * 01: 03 - Barry introduces Lee Vorthman as a seasoned cybersecurity expert and VP of Strategic Security Initiatives at Oracle. * 02:27 - Personal Background and Military Influence * "I grew up in a military household and started in technology before joining the military." * 05:33 - Evolution of Security Leadership * "Security leadership now touches every aspect of a business, requiring a broad understanding beyond just technology." * 11:15 - Navigating Accountability vs. Ownership * "In the civilian world, I’m accountable for risks I don’t always own, which requires building alliances." * 15:05 - Techniques for Overcoming Resistance * "Two techniques I use to convince people: the switcheroo and Jedi mind trick for breaking resistance." * 22:35 - Challenges in the Security Industry * "The industry tends to chase shiny new technologies while neglecting critical fundamentals." * 28:06 - Excitement About Emerging Technologies * “I love when new technology comes out because it allows security people to put their hats on to make it safe.” * 30:25 - Closing Remarks * "It’s been an amazing journey, and I appreciate sharing these stories on the podcast."

Follow Our Guest

LinkedIn Accounts:

• Lee Vorthman: https://www.linkedin.com/in/leevorthman/
• Oracle:https://www.linkedin.com/company/oracle/
• US Navy: https://www.linkedin.com/company/us-navy/
• HMG Strategy: https://www.linkedin.com/company/hmg-strategy-llc/
• Phoenix Security: https://www.linkedin.com/company/phoenixsecuritycloud/
• Evanta, a Gartner Company: https://www.linkedin.com/company/evanta/

Websites:

• Lee Vorthman (Blog): https://blog.370security.com/author/lee1fbb48c29971/
• Oracle: https://www.oracle.com/
• US Navy: https://www.navy.mil/
• HMG Strategy: https://hmgstrategy.com/
• Phoenix Security: https://phoenix.security/
• Evanta, a Gartner Company: https://www.evanta.com/

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
• Personal site: https://barryoreilly.com
• Facebook: https://www.facebook.com/barryoreillyauthor/
• Twitter: https://x.com/barryoreilly
• Instagram: https://www.instagram.com/barryoreilly/
• Email: hello@barryoreilly.com

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Welcome to the UNLEARNPodcast! Today, we’re joined by an inspiring leader in global banking and transformation, Ani Filipova. With over two decades of experience, Ani has made her mark as a former international banking executive, setting up and managing three banks, including Citibank Bulgaria. She also led the transformation of a $2 billion business across 16 countries as Regional COO for Citibank Treasury and Trade Solutions in Asia.

Ani’s path to success was anything but conventional. Fueled by a passion for travel, she overcame rejections and seized every opportunity to explore the world and build a remarkable career. Now, Ani is reshaping her journey through a “portfolio career,” as the Founder & CEO of Change Advisory, drawing from her wealth of experience to inspire others with insights on leadership, transformation, and reinvention.

Key Takeaways: Exploring Beyond Boundaries: Ani’s journey of growing up behind the Iron Curtain, finding creative ways to explore the world despite restrictions. * Speaking Up and Taking Risks: Strategies Ani used to conquer anxiety, master the art of speaking up, and embrace bold decisions in high-stakes situations. * Global Team Collaboration*: Insights on fostering alignment and driving collaboration across diverse teams to achieve success in complex, multinational organizations.

Additional Insights: Embracing Change: Ani highlights the challenges and rewards of adapting to digital transformation. * Cross-Cultural Collaboration: Understanding local customs as a foundation for trust and teamwork. * Unlearning to Grow*: Letting go of old habits to thrive in evolving business landscapes.

Get ready for an inspiring and transformative conversation with Ani Filipova on embracing change, leadership, and the power of reinvention!

Episode Highlights: * 00:36 - Episode Introduction

"If you don't speak up, if you don't show your work. If you don't share your opinions, that's not good at all.

• 01:27 - Introduction to the Episode: Barry introduces Ani Filipova

‘’Ani Filipova, an inspiring leader whose journey spans across continents, industries, and perspectives’’

• 03:10 - Growing Up Behind the Iron Curtain

"I saw the world through books... Pippi Longstocking inspired me to dream about traveling to far-off places."

• 12:59 - Leadership Across Cultures

"You can’t pretend to care about people’s aspirations—you have to truly understand what drives them to build trust and alignment."

• 25:01 - Overcoming Personal Challenges in Leadership

"I realized I needed to stop taking everything personally—it was a turning point that helped me approach challenges more confidently."

• 27:56 - Speaking Up in Leadership Meetings

"I remember waiting for the right moment to contribute, and when I did, the adrenaline rush was overwhelming, but it was worth it."

• 37:44 - Adapting Banking to the Digital Era

"Transitioning from three-day payments to three-second transactions required rethinking systems, processes, and customer expectations."

• 42:11 - The Challenge of Unlearning

"To succeed in today’s fast-changing world, leaders must unlearn old habits and embrace continuous listening and collaboration."

• 45:33 - Closing Reflections

"It’s about reinvention—helping others see their own potential and embrace transformation in their careers."

Follow Our Guest

LinkedIn Accounts:

• Ani Filipova: www.linkedin.com/in/anifilipova
• Citibank: www.linkedin.com/company/citi
• Change Advisory: www.linkedin.com/company/the-change-advisory
• AdVentura Works SA.: www.linkedin.com/company/adventura-works

Websites:

• Ani Filipova - Change Advisory: www.anifilipova.me
• Citibank: www.citigroup.com/global
• AdVentura Works SA.: www.adventura.works

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
• Personal site: https://barryoreilly.com
• Facebook: https://www.facebook.com/barryoreillyauthor/
• Twitter: https://x.com/barryoreilly
• Instagram: https://www.instagram.com/barryoreilly/
• Email: hello@barryoreilly.com

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Welcome to the UNLEARN Podcast! Today, we’re joined by a true pioneer in digital transformation and customer strategy, David C. Edelman. With over three decades at the forefront of marketing and digital transformation, David most recently served as Chief Marketing Officer at Aetna/CVS, where he led transformative shifts in customer engagement. Before that, he co-led McKinsey’s Global Digital Marketing and Sales Practice and held key leadership roles at Digitas and Boston Consulting Group (BCG), advising top executives worldwide.

Now, David is bringing his expertise to Harvard Business School, where he shapes the next generation of leaders and advises CXOs on driving digital agility and building resilient teams. In this episode, he shares insights from his latest book, Personalized: Customer Strategy in the Age of AI.

We’ll explore the different types of AI, where and how to use them, and the evolving role of AI across the C-suite. Get ready for an enlightening conversation with David Edelman on the future of customer strategy in the age of AI.

Key Takeaways: Personalized Connections with AI: David’s “five promises” framework—Empower, Know, Reach, Show, Delight—guides personalized customer experiences. * AI Beyond Marketing: Personalization extends beyond marketing into a holistic, C-suite-level strategy. * Data to Value: Examples from Aetna using data to simplify interactions and deliver targeted recommendations. * Balancing Innovation and Trust*: David stresses trust in AI, focusing on data privacy and ethical personalization.

Additional Insights: Promise and Pitfalls of AI: Emerging AI tools make data integration accessible, helping smaller companies compete with industry giants. * Managing Expectations: The importance of transparency and data use comfort in creating personalized, non-intrusive customer experiences. * Unlearning Old Mindsets*: David encourages that leaders must shift from traditional tactics to a customer-centric, AI-driven approach.

Episode Highlights: 00:00 - Episode Introduction*

"If you’re trying to connect with customers using personalization, there are essentially five promises that you’re making to them."

• 01:35 - Introduction to the Episode: Barry introduces David Edelman, a veteran in digital transformation and customer strategy.

“David has spent over three decades at the cutting edge of marketing and digital transformation.”

• 03:06 - Early Influences: Creativity and Leadership in Marketing

“I became the music director of my high school show from just simply being a saxophone player.”

• 08:33 - From Marketing to AI-driven Strategy

“The thing I had to unlearn is that it’s not just about marketing... it’s about strategy and customer experience.”

• 10:03 - Using AI for Personalization: Shopify and Brinks Case Studies

“So Shopify, who has a free trial and then offers to convert people to paid subscriptions... it’s over 500 combinations.”

• 19:26 - Educational Personalization: The Aetna Video Initiative

“People don’t understand it, they make mistakes... so we found a provider that could create personalized videos.”

• 25:25 - The Five Promises of Customer Strategy

“Empower me, know me, reach me, show me, delight me.”

• 37:59 - Closing Thoughts and The Future of AI in Personalization

“We’ve got to show good things, good experiences that are happening in ways that are trustful and appropriate.”

Follow Our Guest

LinkedIn Accounts:

• David C. Edelman: https://www.linkedin.com/in/daveedelman/
• Aetna: https://www.linkedin.com/company/aetna/
• McKinsey: https://www.linkedin.com/company/mckinsey/
• BCG: https://www.linkedin.com/company/boston-consulting-group/
• Digitas: https://www.linkedin.com/company/digitas-north-america/
• Harvard Business School: https://www.linkedin.com/school/harvard-business-school/

Websites:

• Aetna: https://www.aetnacvshealth.com/
• McKinsey: https://www.mckinsey.com/
• BCG: https://www.bcg.com/
• Digitas: https://digitz-digitas.com/
• Harvard Business School: https://www.hbs.edu/

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
• Personal site: https://barryoreilly.com
• Facebook: https://www.facebook.com/barryoreillyauthor/
• Twitter: https://x.com/barryoreilly
• Instagram: https://www.instagram.com/barryoreilly/
• Email: hello@barryoreilly.com

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Mastering venture capital and ethical growth is essential for startup success. Today’s guest, Andy Budd, shares insights from his journey as Founder and CEO of Clearleft, Venture Partner at SeedCamp, and Founding Member of Adobe’s Design Circle. Andy has evolved from a designer to an investor and advisor, bringing a focus on ethical growth practices and high-impact startup development.

As the author of The Growth Equation, Andy draws on over 20 years of experience to help companies achieve product-market fit and sustainable growth. His work with SeedCamp and other startups focuses on behavioral science and ethical growth strategies to build resilient, user-centered businesses.

In this episode, host Barry O'Reilly explores Andy’s approach to venture capital, leadership, and how his design roots influence his support for founders.

Key Takeaways: The Transition from Design to Venture Capital:* Andy shares his journey from designer to venture capital partner, highlighting the unique insights that his design background brings to his work with startups.

• The Importance of Humility in Leadership: Andy emphasizes the value of hiring individuals who excel in areas beyond one’s own expertise, fostering a team culture of shared growth and continuous improvement.

• Supporting Startups Through Challenges: Known for working closely with startups facing obstacles, Andy describes how his collaborative approach helps companies pivot, adapt, and ultimately thrive.

• Ethical Growth Over “Growth Hacking”: Andy discusses the significance of ethical growth practices, contrasting them with conventional “growth hacking,” and focusing on strategies that promote sustainable and user-centered growth.

Additional Insights: The Influence of Behavioral Science in Product Development:* Andy explains how understanding human behavior enhances product design and growth, encouraging founders to integrate behavioral science for more meaningful user engagement.

• The Role of Patience and Empathy in VC: Andy reflects on his approach to venture capital, prioritizing empathy and patience with founders to cultivate trust and strong, lasting partnerships.

• The Changing Landscape of Startup Investment: Andy shares his views on how venture capital is evolving, especially as design-thinking and user experience become increasingly vital for high-growth startups.

Episode Highlights: 0:39 - Introduction to the Episode: Barry introduces Andy Budd, Startup Advisor, Investor, and Coach.*

“Andy has extensive experience in design and startup advisory.”

• 03:31 - Transition from Design to Venture Capital

"I've always been inspired by others...there was an agency that really inspired Clearleft back in the day called Adaptive Path."​

• 06:58 - Unlearning Practitioner to Leader

“The main thing I had to unlearn was moving from a practitioner to a leader, where you need to let go and trust others.”

• 15:56 - Emphasis on Character and Integrity in VC

“If you're rude to the driver or the person at reception, it shows a lot about your character.”

• 24:34 - The Growth Equation: Helping Founders Find Product-Market Fit

"One of my reviewers said it’s like having a pocket coach. Why spend thousands on an online course when you can get the framework in a book?"​

• 33:32 - Role of Behavioral Science in Growth

"I'd demonstrate it with an example. So an example is economics... economists thought we were rational actors, that we’d make logical decisions about the future, like saving for retirement. But people tend to choose instant gratification, which is where behavioral economics comes in."​

• 37:26 - The Ethical Approach to Product-Led Growth

“Product-led growth has been one of the biggest trends in the last few years, around how we can use our products and the way we design them to attract more users and drive engagement.”

• 45:13 - Andy’s Thoughts on Growth Hacking vs. Ethical Growth

"A big part of my book is actually about how you look at growth, but in a more moral, reasonable, and acceptable way. I hate the idea of growth hacking."

• 46:42 - Wrap-up & Final Thoughts: Barry and Andy discuss the ongoing importance of community and knowledge-sharing.

"Everyone, get yourself a copy of The Growth Equation!”

Follow Our Guest

LinkedIn Accounts: Andy Budd, Clearleft, Adobe, Seedcamp

Websites: Andy Budd - Personal Site, Clearleft, Adobe, Seedcamp

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now: https://bit.ly/InnovationPortfolioWorkbook

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
• Personal site: https://barryoreilly.com
• Facebook: https://www.facebook.com/barryoreillyauthor/
• Twitter: https://x.com/barryoreilly
• Instagram: https://www.instagram.com/barryoreilly/
• Email: hello@barryoreilly.com

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Mastering executive search and building lasting business relationships are essential for successful transformations. Today’s guest, Michael A. Morell, shares insights from his journey at Riviera Partners, a top executive search firm, and as a former member of the Technology Advisory Board at Bridgewater Associates.

Michael A. Morell is the Founder and Managing Partner of Riviera Partners, with over two decades of experience in executive search. After starting his career in technology, a poor interview experience sparked his idea to create a better approach to recruiting. Today, Michael and his team help tech companies make high-stakes hires, transforming how top talent is identified and placed in Silicon Valley and beyond. Riviera Partners continues to deliver executive search solutions for some of the most innovative companies around the world.

In this episode, host Barry O’Reilly explores Michael’s approach to executive recruitment, the importance of patience in relationship-building, and how Riviera Partners leverages technology to deliver consistent, high-quality results.

Key Takeaways: The Power of Patience in Relationship Building:* Michael shares why patience is critical in executive search and enterprise sales, where building strong, lasting relationships can lead to long-term success.

• Consistent Delivery of High-Quality Experiences: Michael emphasizes how consistent, positive experiences set Riviera Partners apart, explaining how a focus on quality service helped them build a reputable brand in executive recruitment.

• The Role of a Clear Vision: Michael discusses the importance of a simple and clear company mission that empowers employees to make decisions aligned with the company’s values.

• Adapting to Technological Advances: As technology has evolved, so has Riviera Partners. Michael shares how the firm leverages data and technology to enhance the recruitment process and provide better insights for clients.

Additional Insights: Learning Through Experience:* Michael’s shift from technology to recruitment highlights the value of diverse experiences and risk-taking in meaningful work, as he reflects on the challenges of building Riviera Partners.

• The Changing Recruitment Landscape: Michael discusses how tools like LinkedIn have democratized recruitment and shares his excitement about AI and machine learning’s potential to transform executive search.

• The Future of Workplace Flexibility: Michael reflects on the pandemic’s impact on remote work, emphasizing the balance between flexible environments and the importance of in-person interactions for leadership roles.

Episode Highlights: 00:40 -*Introduction to the Episode: Barry introduces Michael A. Morell, Founder of Riviera Partners

“Michael has over two decades of experience in executive search.”

• 03:19 - The career transition into recruitment

“About 3 or 4 years into that, I got a random call from a recruiter who said, 'Hey, we’d love to grab coffee.' Long story short, I had coffee, she showed me a couple of opportunities—this was around the 2000 timeframe—and it was just the most awful experience I’ve ever had."

• 06:34 - Michael applies his long-term sales experience to relationship-building in executive search

“I had the patience to develop these relationships, but I thought, it couldn't be that complicated.”

• 15:27 - Delivering Consistent, High-Quality Experiences

“For us, it was really about one thing: how do we consistently deliver a great experience?”

• 24:17 - Navigating the shifts in recruitment technology

“The Rolodex became LinkedIn, and suddenly all the information was democratized. You can start to anticipate changes, but fundamentally, every client and every candidate is unique.”

• 34:02 - Embracing workplace flexibility and hybrid models

“We went from everyone needing to be on-site to realizing remote could work. Now, we’ve evolved to a hybrid model, balancing in-person and remote roles.”

• 36:59 - The future of recruitment with AI and machine learning

“I’m excited to see how AI can enhance our processes, from finding insights in data to improving client and candidate experiences.”

Follow Our Guest LinkedIn: Michael A. Morell, Riviera Partners,Bridgewater Associates. * Websites:* Riviera Partners, Bridgewater Associates

_________________________________

Download my free innovation map I use to help companies like Google and Nike figure out the gap between their current state and desired state.

Download Now:

https://bit.ly/46uZ7q0

FOLLOW THE HOST:

• LinkedIn: https://www.linkedin.com/in/barryoreilly
• Personal site: https://barryoreilly.com
• Facebook: https://www.facebook.com/barryoreillyauthor/
• Twitter: https://x.com/barryoreilly
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• Email: hello@barryoreilly.com

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Driving innovation in technology and business transformation demands visionary leadership, seamless integration of business and tech strategies, and a willingness to take risks. Today's guest, David Gledhill, exemplifies these qualities as he shares his experience leading DBS Bank through a remarkable digital transformation and beyond.

David Gledhill is a seasoned technologist and business leader. As the former Group Chief Information Officer at DBS Bank for over 11 years, he spearheaded the bank’s technology and transformation efforts, building a high-performance culture and integrating technology into the core of the business strategy. Under his leadership, DBS achieved global recognition for its digital transformation, and David’s journey has been featured in Harvard Business Review as one of the top global transformations. After his time at DBS, David held a senior role at Lloyds Banking Group, further enhancing his expertise in large-scale transformation. He is now a non-executive director at companies like Singapore Airlines and serves as a senior advisor to McKinsey & Company.

In this episode, host Barry O'Reilly invites David to discuss his leadership journey, from reshaping the technology at DBS to embracing a digital-first strategy. David offers insights on making tough decisions, aligning business with technology, and leading organizations through massive change.

Key Takeaways: Technology as a Strategic Driver:* David emphasizes the shift from viewing technology as a support function to recognizing it as a core driver of business strategy. He explains how leading with a digital-first mindset can unlock new growth opportunities.

]

• Bold Decision-Making in Leadership: David shares the importance of making tough decisions early in leadership roles. He describes how scrapping failing projects and resetting strategies allowed DBS to pivot successfully.

• Building a High-Performance Culture: David highlights the significance of creating a culture where business and technology teams share accountability. His “two in a box” leadership model at DBS encouraged joint ownership of goals and outcomes.

• Learning from Tech Giants: Drawing inspiration from companies like Google and Amazon, David discusses how studying these tech giants helped DBS adopt cutting-edge practices in cloud computing, data analytics, and agile development, setting them apart in the banking industry.

Additional Insights: Fostering a Culture of Storytelling:* David highlights the importance of storytelling in driving organizational change. At DBS, he brought in a journalist to craft compelling narratives around early successes, which helped engage teams and build momentum for transformation.

• From Technologist to Strategic Leader: David’s transition from a technical expert to a strategic business leader is a testament to the evolution required in leadership roles. He reflects on how moving from deep technical work to overseeing large-scale business transformation broadened his leadership perspective.

• The Role of Technology in the Future of Banking: David reflects on the future of the financial industry, noting that technology will continue to play a critical role in driving innovation and improving customer experiences. He emphasizes the need for continuous adaptation to stay competitive in the fast-changing digital landscape.

Episode Highlights 00:00 - Introduction to the episode*

Barry introduces David Gledhill, highlighting his role as former Group CIO of DBS Bank and his contributions to the company’s digital transformation.

• 04:12 - David on his early career and technical roots

"I started off even when I was 11 or 12, building stuff with electronics and did computing electronics at university."

• 05:13 - The turning point of joining DBS

"When my career progressed, I became more of an exec... And then back in 2008, an opportunity came to join DBS Bank and become a CIO again, and get really back into tech."

• 12:21 - Scrapping the core banking system

"They’d spent like $300 million of a $200 million budget. And the estimate was this is going to take another five years and another billion dollars to complete."

• 12:36 - Rebuilding the technology strategy at DBS

"I had to basically scrap that whole program and restart... it was a total reset of strategy, roadmap, people, everything from scratch."

• 17:31 - Creating success with the ‘buy, sell, hold’ strategy

"We came up with this what we call the buy, sell, hold diagram... I love the system, and do more with it. Sell it to get rid of it. Hold is kind of meh but it'll keep going for now."

• 24:21 - The platform model and joint leadership

"We created a ‘two in a box’ leadership model, where a business leader and a tech leader had joint KPIs... business KPIs, customer service levels, tech modernization – everything."

• 31:47 - The ‘Gandalf’ moment and digital-first strategy

"We looked at Google, Amazon, Netflix, Apple, LinkedIn, Facebook, and I came up with this idea of what if we were the D in Gandalf?"

• 37:33 - Lessons for the future and technology’s role in business growth

"It’s hugely satisfying when you see that happen... they’re doing some super risky things, which may or may not play out, but that’s great fun to be part of."

Follow Our Guest

• LinkedIn: David Gledhill
• Website: DBS Bank, Lloyds Banking Group, Singapore Airlines, McKinsey & Company

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Leadership in technology and operations requires a strategic focus on scaling businesses, empowering teams, and driving innovation. Today's guest, Richard Lennox, exemplifies these qualities as he shares his journey from leading Skyscanner through rapid growth to scaling healthcare innovation at Current Health.

Richard Lennox is an experienced technologist and business leader. As Senior Director at Skyscanner, he led the company’s engineering and operations teams through a pivotal period of scaling, focusing on high-performance teams and continuous delivery. After Skyscanner’s successful exit, Richard transitioned to COO at Current Health, where he helped scale the business, focusing on home healthcare delivery through technology. His leadership experience spans multiple industries, making him a valuable mentor and guide for those navigating startup growth and innovation.

In this episode, host Barry O'Reilly invites Richard to discuss his journey, from his early days at Skyscanner to his role at Current Health. Richard provides insights into scaling startups, the importance of data-driven decision-making, and the operational challenges of growing high-performance teams.

Key Takeaways:

• Customer Value at the Core: Richard emphasizes the importance of focusing on delivering customer value in all areas of business, whether in technology or healthcare. Customer needs should drive product development and operational strategies.

• Scaling High-Performance Teams: Richard discusses how growing from small teams to larger, cross-functional squads allowed for better alignment with business goals at Skyscanner. He shares the challenges and successes of implementing a squad model to foster accountability and autonomy within teams.

• Rapid Decision-Making: Making fast decisions and knowing when to reverse them is critical to maintaining agility in a growing company. Richard stresses the importance of empowering teams to make decisions based on data and customer outcomes.

• Holistic Leadership: Transitioning from a function-specific mindset to a broader business operations perspective allowed Richard to lead with a focus on scaling the entire organization, not just the technology function.

Additional Insights:

• Empowering Teams through Data: Richard highlights the value of real-time data in empowering teams to make informed decisions. At Skyscanner, instrumentation of key metrics allowed teams to focus on customer outcomes and make data-driven decisions at scale.

• Transitioning from Tech Leadership to Business Leadership: Richard’s journey from Senior Director at Skyscanner to COO at Current Health showcases the evolution from technical leadership to overseeing broader business operations. He reflects on the mindset shift required to focus on business outcomes over functional expertise.

• The Future of Healthcare at Home: Richard shares insights into the growing importance of delivering healthcare in the home environment, using technology to monitor patients remotely and operationalizing care at home programs. This innovation is essential for reducing the burden on hospitals and improving patient outcomes.

Episode Highlights:

• 00:00 - Download free innovation map
• 00:41 - Introduction to Richard Lennox
• 03:36 - Early career and decision to join startups

"I got really lucky early on in my career, joining an early startup, which shaped my thinking about delivering value to customers."

• 07:48 - Learning from setbacks and focus on customer value

"There has to be a better way to deliver value consistently without causing setbacks for the business."

• 14:48 - Rapid decision-making and empowering teams

" I think the tricks for scaling are rapid decision making and how you invert the decision when you make it wrong. The more you hang on to a wrong decision, the worse the impact is."

• 24:21 - Richard’s Transition to COO at Current Health and Leading Healthcare Innovation

"Current Health provides a platform to enable care to be delivered at home."

• 32:12 - Future of Healthcare at Home and Operational Excellence

"Our job was to operationalize care at home programs, and that required a whole new set of tools and thinking."

• 38:06 - Wrap Up

Follow Our Guest

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• Website: https://www.currenthealth.com/
• https://www.linkedin.com/company/skyscanner/

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Leadership in government and technology requires not only innovative thinking but also a deep commitment to public service. Today's guest, Paola Santana, exemplifies these qualities as she shares her journey from law and politics to becoming a trailblazer in government technology.

Paola Santana is a lawyer, public procurement expert, and serial tech entrepreneur who is revolutionizing government systems. As the founder and CEO of Glass, she is pioneering G-commerce, a new way for governments to procure goods and services. Her prior experience includes co-founding Matternet, a company leading the way in drone logistics networks. Under her leadership, Matternet worked with the White House, U.S. Congress, and NASA to establish the first U.S. drone regulations, leading to the first drone delivery platform authorized for permanent operations over a populated city.

In this episode, host Barry O'Reilly invites Paola to discuss her remarkable journey, from her early career in law and government to her groundbreaking work in technology. Paola offers insights into the challenges and opportunities of transforming public systems through entrepreneurship, emphasizing the importance of agility, data-driven decision-making, and the crucial role of small businesses in economic development.

Key Takeaways:

• Holistic Approach to Innovation: Sustainable change in government systems requires integrating public and private sector strategies, emphasizing agility, and leveraging technology.
• The Importance of Small Businesses: Small businesses are the backbone of economic development. Empowering them through government procurement can lead to more dynamic and effective public services.
• Procurement as a Catalyst: Effective procurement is essential for materializing government initiatives. It's not just about contracts; it's about ensuring that public funds are spent in ways that truly reflect the needs and priorities of the community.
• Embracing Technology: The future of procurement lies in the intersection of e-commerce and government processes. Leveraging data and AI can make government procurement more efficient and aligned with public policy goals.

Additional Insights:

• From Law to Tech: Paola's transition from law and public service to tech entrepreneurship highlights the power of interdisciplinary approaches to solving complex public sector challenges.
• The Role of AI in Procurement: AI and data analytics are crucial in making government procurement more transparent and efficient, ensuring that public funds are used effectively to meet community needs.
• The Value of Persistence: Paola’s journey shows that persistence and a willingness to challenge conventional wisdom can lead to breakthroughs, even in highly regulated sectors like government procurement.

Episode Highlights:

• 00:00 - Download free innovation map

• 00:41 - Introduction to Paola Santana

• 02:05 - Paola’s Career Clarity and Influence

The first thing is that for the level of clarity that someone like me has, where I've always known or carved moments to get very clear on where I wanted to go..."

• 07:26 - Transition from Law to Tech

"I love this saying attributed to Steve Jobs: You can only connect the dots looking backwards."

• 21:24 - Founding Glass and the Importance of Transparency

"Glass is literally the name that came very intuitively to me, and I've been unpacking what the name of Glass means."

• 22:39 - Contrasts Between Public and Private Sectors

"Entrepreneurship is grueling. Like, you know, you either have results or you don't."

• 47:29 - Small Businesses and Economic Development

"The future of procurement is not procurement. The future of procurement is e-commerce."

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• LinkedIn: https://www.linkedin.com/in/paolasantanam/
• Website: https://www.linkedin.com/company/glassgovtech/

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Leadership in digital ecosystems requires a commitment to safety, trust, and ethical practices. Our guest today, Dave Byrne, founder of Trust Raise and a member of the Irish Digital Board, shares his journey from major tech giants to establishing a company dedicated to improving the integrity of digital platforms.

Dave Byrne has had an illustrious career, holding significant positions at Google, TikTok, and Spotify, where he spearheaded initiatives in brand safety and platform integrity. Now, as the founder of Trust Raise, he focuses on helping smaller companies navigate the complex landscape of digital safety. His work is driven by a deep commitment to creating ethical digital ecosystems that prioritize user needs and improve industry standards.

Host Barry O'Reilly invites Dave to discuss his career journey, the challenges of maintaining digital safety in a rapidly evolving industry, and the inspiration behind founding Trust raise. Dave shares valuable insights into the importance of adaptability, the evolving role of AI in digital safety, and how smaller companies can leverage his expertise to build safer digital platforms.

Key Takeaways:

• Resilience Through Failure: Early career setbacks can teach invaluable lessons about humility, perseverance, and the importance of continuous effort.
• Navigating Global Teams: Success in a fast-paced, global environment requires strong relationships, effective collaboration, and the ability to work across different time zones and cultures.
• Overcoming 'Golden Handcuffs': Comfort and security in large tech companies can sometimes hinder innovation. Pushing oneself out of the comfort zone is crucial for personal and professional growth.
• AI’s Potential in the Workplace: AI has the potential to enhance productivity and creativity. Those who leverage AI effectively will be at the forefront of industry innovation.

Additional Insights:

• Personal Reflections on Failure: Dave shared how an early career setback taught him invaluable lessons about resilience, humility, and the importance of continuous effort. This experience has profoundly influenced his work ethic and approach to leadership.
• AI's Potential to Revolutionize Work: Dave is optimistic about AI’s potential to enhance productivity and creativity. He believes that those who learn to leverage AI effectively will be at the forefront of the industry, taking on more dynamic roles and contributing to a more innovative tech landscape.
• The Importance of Ethical Tech Development: Throughout his career, Dave has been a strong advocate for ethical practices in tech. He stressed the need for companies, big and small, to prioritize user safety and trust, especially as technology continues to evolve rapidly.

Episode Highlights

• 00:00 - Download my free innovation map
• 00:39 - Introduction to Dave Byrne
• 03:00 - Dave’s unexpected start in his career and the impact of failure.

“This career in Google, TikTok, Spotify was not at all planned whatsoever... I actually ended up in Google because I lost a student union election in Trinity College."

• 07:35 - The rise of brand safety concerns and the 'Apocalypse.'

"The Adpocalypse... Brand safety became something that YouTube started caring about, Meta started caring about."

• 11:18 - Eroding Brand Perception

“ we're eroding brand perception of our customers. Again, scary things for any business to be facing, never mind the scale of the brands you're going to be working with within Google at the time.."

• 25:12 - The complexities of the tech ecosystem.

" I think when people think of the digital ecosystem, they think of the Googles, they think of the metas, they think of the TikToks of the world. And yes, they take up a huge amount of people's time and engagement but there are thousands of companies that make up this ecosystem, like just the ad ecosystem itself."

• 44:38 - The impact of AI on job roles and democratizing work opportunities.

" AI and the tools that we're seeing are democratizing like these skills and like the ability for these folks to actually participate in, in areas where they couldn't have before."

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• LinkedIn Profile: https://www.linkedin.com/in/davebyrned/
• Website: https://www.trust-raise.com/

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Cybersecurity is an ever-evolving field that requires continuous learning, adaptability, and a deep understanding of both the technological landscape and human behavior. Today’s guest, Dave Mahon, a seasoned cybersecurity expert with extensive experience in both the private and public sectors, shares his journey from the FBI to leading global cybersecurity efforts in the corporate world.

Dave Mahon served as a Senior Advisor for Deloitte, where he was instrumental in developing and executing strategies to safeguard information, technologies, and data. Prior to Deloitte, he was the Global Chief Security Officer for CenturyLink, now Lumen Technologies, and also served as a Special Agent for the FBI, focusing on federal crimes involving cyber threats, terrorism, and more. In this episode, Dave discusses the critical thinking skills he developed over his 20-year career in the FBI and how he applied them in the private sector to tackle emerging cybersecurity challenges.

Host Barry O'Reilly invites Dave to explore his career journey, the lessons he learned, and the importance of mentorship, team building, and strategic thinking in cybersecurity. The conversation delves into the nuances of transitioning from public service to corporate leadership, the evolving nature of cyber threats, and how businesses can better prepare for future challenges.

Key Takeaways:

• The Importance of Adaptability in Cybersecurity: As technology and business models evolve, so do the tactics of adversaries. Cybersecurity professionals must continuously adapt to stay ahead.

• Holistic Approach to Cybersecurity: Successful cybersecurity strategies involve not just technical defenses but also understanding the motivations and methods of adversaries.

• Mentorship and Leadership: Effective leadership in cybersecurity requires understanding the diverse skills and motivations of team members, providing the right guidance, and fostering a culture of continuous learning.

• Corporate Culture and Cybersecurity: Transitioning from the public to the private sector requires understanding corporate dynamics, including ROI and business objectives, to effectively integrate security measures.

Additional Insights:

• FBI Experience: Dave’s early career in the FBI instilled in him a deep understanding of critical thinking, investigation, and a life of purpose, which he has carried throughout his professional journey.

• Adapting to Corporate Culture: Moving from a black-and-white, rules-based environment in the FBI to the nuanced world of corporate security presented unique challenges, particularly in understanding business motivations and the need for clear ROI in security investments.

• The Future of Cybersecurity: As organizations move to cloud-based infrastructures and remote work environments, the strategies of cyber adversaries will continue to evolve, requiring constant vigilance and innovation from cybersecurity professionals.

Episode Highlights

• 00:00 - Introduction to the episode.
• 00:02:47 - Dave's early life and influences

"There's a couple of key parts of everybody's life... because it starts to set the foundation for how you think about your life going forward and how you're going to make the decisions."

• 00:03:58 - Joining the FBI and early career challenges

"And all the standard corporations were there that you could imagine... and ultimately get hired by the FBI."

• 00:07:38 - Undercover work and relocation challenges

"So I literally went undercover for four years... and next thing I know, I was doing computer forensic work."

• 00:12:35 - Challenges of early cyber investigations

"A couple of things you start to realize around cyber that was so very different... there was a lot of learning."

• 00:22:15 - Developing leadership skills and understanding team dynamics

"You have to understand people... and what motivated them at what stage they were in their career."

• 00:39:00 - Evolving cybersecurity threats and the importance of staying ahead

"Bad guys don't go away, they innovate... we need to be moving in cyber to stay ahead."

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• LinkedIn Profile: https://www.linkedin.com/in/david-mahon-0751074/
• Website: https://www.linkedin.com/company/deloitte/

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Innovation and Inclusivity in Motorsports are about breaking barriers, fostering innovation, and making the sport accessible to all. Today's guest, Rob Smedley, founder and CEO of the Smedley Group, shares his journey from Formula One engineer to entrepreneur, revolutionizing the motorsport industry.

Rob Smedley is known for his work with top Formula One teams like Ferrari and Williams. Using data technology to drive innovation, Rob has now embarked on a new venture to create a global karting league, making motorsports accessible to a wider audience. His career is marked by his commitment to innovation and his belief in the potential of young talent.

Host Barry O'Reilly invites Rob to discuss his path from a disengaged student to a top engineer and now an entrepreneur. Rob shares valuable lessons on embracing discomfort, committing to goals, and continuously innovating. The conversation highlights the importance of inclusivity in motorsports and the exciting future of the Global Karting League.

Key Takeaways:

• Embracing Discomfort: Success often involves stepping out of your comfort zone and committing to figuring things out as you go along.
• Innovation Culture: True innovation requires a willingness to make mistakes and learn from them. Companies must create environments that foster this mindset.
• Making Motorsports Accessible: The Global Karting League aims to democratize motorsports by significantly reducing costs and complexity, making it accessible to a wider demographic.
• Building High-Functioning Teams: Success in both engineering and entrepreneurship involves surrounding yourself with high-functioning individuals and creating a synergistic team environment.
• Continuous Learning: Whether in the pit or in the boardroom, continuous learning and adaptation are crucial for sustained growth and success.

Additional Insights:

• Personal Journey: Rob's unconventional path from a disengaged student to a top engineer and entrepreneur highlights the importance of perseverance and adaptability.
• Innovative Approach: Rob’s approach to the Global Karting League demonstrates how rethinking traditional models can lead to significant industry changes.
• Team Dynamics: Managing a team of innovators involves balancing different personalities and ensuring that each team member can contribute effectively.

Episode Highlights

• 00:00 - Introduction to the episode
• 02:09 - Rob on committing to something and figuring it out

"Commit to something, don't be scared and figure it out as, as you go along."

• 04:00 - Rob’s academic journey and lack of engagement in school

"I wasn't a great student at school. I absolutely was a terrible student."

• 09:33 - The importance of innovation and feeling uncomfortable

"If you're not uncomfortable, you're probably not trying hard enough."

• 18:26 - How Formula One teams innovate

"Innovation is just embedded in the business of Formula One."

• 25:35 - Democratizing motorsports with the Global Karting League

"We've taken about 95 plus percent of the costs out of it."

• 36:19 - Transitioning to an entrepreneurial role and learning new skills

"I've had to unlearn coming into what I would call the outside world."

• 42:25 - What excites Rob about the future of the Global Karting League

"What I'm most excited about is team work, right? I love being part of a really strong, high performing team."

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• LinkedIn Profile: https://www.linkedin.com/in/rob-smedley/
• Website: https://www.smedleygroup.com/about#1

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Leadership is about embracing sustainable practices, fostering continuous improvement, and aligning personal values with professional goals. Today's guest, Annastiina Hintsa, CEO of Hintsa Performance, shares her insights on achieving peak performance in both business and sports.

Annastiina Hintsa is the CEO of Hintsa Performance, a world-leading evidence-based coaching company that helps top athletes and business professionals achieve sustainable success. Driven by science and guided by people, their methods have been tested in some of the most challenging business and sporting environments. Annastiina's journey began with her father, Dr. Hintsa, whose pioneering work with athletes like Haile Gebrselassie laid the foundation for their holistic performance model. Annastiina has expanded this legacy, working with over 50% of Formula One drivers and Fortune 500 CEOs, ensuring they reach and maintain high performance.

Host Barry O'Reilly invites Annastiina to discuss her journey and the impact of Hintsa Performance. From her early involvement in the company to her leadership role today, Annastiina shares valuable lessons on balancing professional and personal well-being. The conversation covers the holistic nature of high performance, integrating physical activity, nutrition, mental energy, and more. Annastiina emphasizes the importance of defining personal success and maintaining perspective through life's challenges.

Key Takeaways:

• Holistic Performance: Sustainable high performance involves a balance of physical activity, nutrition, sleep, mental energy, general health, and biomechanics.

• Defining Success: Personal success should be clearly defined, considering who you are and what you want beyond professional achievements.

• Maintaining Balance: Regularly scheduling recovery and downtime, both on a macro (yearly vacations) and micro (daily detachment rituals) level, is crucial for long-term success.

• Perspective and Resilience: Building resilience through multiple identity pillars helps maintain performance and happiness despite setbacks.

• Continuous Learning and Adaptation: Embracing a mindset of continuous improvement and being open to unlearning outdated practices is key to sustained growth.

Additional Insights:

• Personal Influences on Leadership: Annastiina’s father, Dr. Hintsa, played a pivotal role in shaping her understanding of high performance and well-being.

• Handling Setbacks: Viewing setbacks as opportunities for growth and maintaining a broad perspective helps in overcoming challenges.

• Technology and High Performance: The rapid advancement of technology necessitates leaders to stay mentally, physically, and emotionally prepared for continuous adaptation.

Episode Highlights

• 00:00 - Introduction to the episode

• 02:56 - Annastiina on her early career and her father's influence

"I worked with my dad early days. I was employee number three in the very, very early days..."

• 03:25 - The turning point of joining the family business

"when my father got sick. So he was, uh, he was diagnosed with pancreatic cancer in 2015, passed away 16 months after. And it was a turning point for for me personally"

• 07:26 - Defining and achieving sustainable high performance

"Our mission is to help people live better lives and as a consequence, perform better..."

• 27:29 - Importance of balance and avoiding the middle gear

"We get stuck in the middle gear. We get stuck in this kind of like execution mode where we're constantly just, you know, yeah, we're not we're not at our peak. We're also not recovering and resting. We're at this middle gear checking our emails, you know, responding, uh, executing. But when the time comes, when we would actually need to get to that high gear, get to the peak performance"

• 31:40 - Technology's impact on high performance and the need for human readiness

"how do we make sure that we as humans are ready for that shift?"

• 36:03 - Practical tips for achieving better performance

"start with the critical questions and you start with that. Do you know who you haven't really think of? Who are you as a person, not just you at work or your job title. How do you actually define success? What is it that you really want? What are the different points of success for you? And then the final question is around sort of control, which is as much as it is about, you know, what are the things that we can control and we can influence."

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• Website: https://www.hintsa.com

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Leadership is about embracing the process of unlearning outdated practices, fostering a culture of continuous improvement, and aligning your team with visionary goals. Today's guest, with his esteemed 29-year tenure at one of the largest asset managers in the world, Vanguard, shares how he successfully navigated this journey.

John T. Marcante is a renowned technology and business executive with expertise in digital transformation, business strategy, financial planning, and cybersecurity. He is the US CIO in Residence at Deloitte, providing strategic guidance to clients and leadership.

Previously, John was the Global CIO at Vanguard, where he led digital transformation and drove growth to $9 trillion. He modernized Vanguard's technology and promoted an inclusive workplace. He also developed Vanguard’s global advice platform, making financial planning accessible to millions.

John has contributed to the WSJ CIO Journal and Harvard Business Review. His awards include Business Insider Top 50 CIOs and ORBIE CIO of the Year. He holds degrees from The Pennsylvania State University and Saint Joseph’s University.

Host Barry O'Reilly invites John to share his journey at Vanguard and beyond in leadership, culture transformation, and gratitude. Inspired by his father's legacy in technology, John discusses how he aligned tech with business goals at Vanguard. Barry highlights John’s approach to direct client engagement and open feedback. They also explore John’s commitment to servant leadership, maintaining company values, and his future goals of mentoring new leaders and giving back to the community. This episode offers personal insights into what drives effective leadership with gratitude.

Key Takeaways: Leadership and Transformation:* Transformations should align technology initiatives with business goals, led by C-suite executives.

• Servant Leadership: Building a culture of servant leadership is crucial for successful transformations.

• Client Engagement: Direct client feedback, really listening and a take-action approach are essential for quick and effective improvements.

• Maintaining Values: Sticking to core values and supporting clients and employees ensures long-term success and engagement.

• Future Aspirations: Coaching future leaders, staying engaged in technology, and giving back to the community are key aspects of making a positive impact.

Additional Insights:

• Personal Influences on Leadership: John’s father played a crucial role in sparking his interest in technology and instilling values of gratitude and support.

• Handling Client and Employee Relations: Prioritizing core values and employee well-being, even when making tough decisions like firing abusive high-net-worth clients, ensures long-term success.

• Learning from Mistakes and Building Trust: Creating an environment of trust and open communication allows employees to voice opinions and make mistakes, fostering innovation and continuous improvement.

Episode Highlights:

00.00 - Introduction to the episode

02:58- John's reflections on recent thoughts and his father's influence on his career

"I think the last thing that popped in my head since we just went through Father's Day, as I was kind of reflecting on my own father…"

05:29- Cultural transformation and leadership at Vanguard

"So I think I go back to a point you just made, which is, if this transformation is a technology transformation, if it's a technology initiative, then it's already lost, right? Because nothing's a technology initiative. Everything is, a business, a client transformation and that alignment..."

05:53- Leadership and servant leadership in transformation

"I always felt like that the transformation was a C-suite and CEO-led transformation. You know, technology, lean, agile. They'll roll out across the company, not just in technology, but across the company really took that level of focus and alignment."

15:00-Engaging and aligning with clients

"if you want to drive engagement and give a group of people an outcome that's meaningful to clients and give them access to clients, and you said, yes, it's a wonderful when they when they could do something, they see the impact."

15:21- Feedback on improving processes and client satisfaction

"And if you have a nimble, very, very nimble foundation that allows you to very quickly take that feedback and turn it."

18:38- Dealing with high-stakes decisions and maintaining company values

"Not every business is good business. Stick to your mission and purpose, and always have your clients' and employees' backs."

20:47 Discussing the importance of mission alignment in leadership

"It's also you feel connected to the mission of the organization. Like what I do every day has to be connected. But the mission, I have to sleep well at night knowing that the company has my back, but more importantly, that I'm actually doing good for society."

21:45- Personal anecdotes on handling client interactions and maintaining values

"this is one of the things I think that, uh, again, it shines about the company. Like sticking to the values, leaning into your principles, I know, and making tough decisions around that.."

23:52- Building Trust Through Commitment to Solutions

"And even if you don't know the answer that you know you're committed to getting the answer, I think you then build trust in the organization."

25.45- Servant leadership and employee engagement

"If your intention isn't good and you make a mistake, well, then we'll deal with that later, right? But if you're doing work for a client and your intention is good that you have nothing to worry about, even if it goes south..."

32:34- Embracing Grace as a Core Mission in Leadership

"I think as a father, that's our mission as a leader. That's our mission. Like, be gracious, you know, be gracious even when someone doesn't hit the record button"

35:09- Transitioning into a new chapter and future plans

"I want to be part of, uh, coaching and developing the next generation of leaders that I want to be part of that team, whatever team that is. Count me in, because that was the best part of my job. Second technology. I mean, like, come on, like, I mean technology, AI, generative AI."

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◦ Profile- https://www.linkedin.com/in/john-t-marcante/

◦ Deloitte- https://www2.deloitte.com/us/en.html

◦ Website- https://marcantejohn.wixsite.com/technologyleadership

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Description:

AI is transforming the world, and William is working on how IP is impacted in an AI world…



William Carbone is an AI expert, former IBMer, and now a seasoned entrepreneur with over a decade of experience in aerospace, quantum computing, and AI.

At IBM, William’s main focus was to identify opportunities, driving business & technology strategies and roadmap for the industries worldwide. He led the Business Development for IBM's Global Automotive, Aerospace & Defense industries.

Currently, William is the CEO and co-founder of Evalify, a flagship venture under Nobody Studios, and the CEO and co-founder of The Adjacent Possible. He also serves as the Program Director for the Master in AI at the Rome Business School (RBS) and advises the European Commission as a senior consultant. From creating an innovation studio to developing cutting-edge tools for intellectual property assessment, His work spans Quantum, Spacetech, AI, and various domains.

In this episode hosted by Barry O’Reilly, William discusses his journey, including his transition from corporate life and the transformative experiences that shaped his entrepreneurial path. He delves into the practical aspects of innovation and intellectual property, offering advice on navigating these complex areas. This episode is packed with insights for anyone looking to improve their approach to entrepreneurship and understand the value of mental health in the process.

Key Takeaways from the episode include:

• Entrepreneurial Journey: The transition from corporate life to entrepreneurship involves significant rewiring of the brain and requires navigating uncharted territories with curiosity and resilience.

• Parallels with Music: William's self-taught journey as a pianist highlights the importance of playfulness and self-expression, which he parallels with the creative process in entrepreneurship.

• Innovation and IP Assessment: William discusses the development of a tool that evaluates the patentability and intellectual property risks of startup ideas, providing investors with quick and affordable insights.

• Unlearning Traditional Methods: The necessity of unlearning conventional approaches to intellectual property and embracing new technologies and methodologies to stay competitive.

• Mental Health for Founders: The critical importance of mental health for entrepreneurs, with William sharing his experience of attending a silent meditation retreat to find clarity and balance.

• Future of Intellectual Property: The potential of AI and advanced tools to democratize access to intellectual property insights, helping entrepreneurs and investors make better-informed decisions.

Additional Insights:

• Leadership and Innovation: This episode emphasizes the role of leadership in fostering a culture of innovation and collaboration within startups.

• Role of AI in IP: The discussion involves the advancements in AI that have made tools like E-Verify possible, highlighting the transformative potential of these technologies in the intellectual property space.

• Practical Applications: This episode provides insights about real-world examples of how the IP assessment tool has helped investors make quicker and more informed decisions, reducing the risk and enhancing the potential for successful investments.

Episode Highlights:

(00:00) Introduction to the episode

(01:25) Importance of rewiring the brain and transformative journey of entrepreneurship

[01:43] “There is no one making things for you… You have to take the tools on the way and find the way.”

(02:23) William shares parallels between learning music and his entrepreneurial journey

[3:53] “Music has always been there for me in the journey, even in difficult times or more challenging situations.”

(05:14) Barry discusses the importance of following curiosity in entrepreneurship

[7:39] “There was a lot of untapped potential in that space, like in billions of dollars that have been spent on patents that have been just never commercialized…”

(08:35) Introduction of E-Verify and its capabilities in de-risking investments

(11:43) The evolution of AI and its impact on intellectual property assessment

[13:22] “But the biggest unlearning there was how to make the industry, to unlearn how they approach LLP. That was the biggest challenge, right.”

(13:23) The challenges and benefits of helping the VC industry unlearn traditional approaches to IP

[14:27] “I would say the biggest challenge for us and for the investors is to understand that the IP can be a valued friend and partner…”

(15:17) Barry shares his experiences with continuous delivery and automation in software development

[17:34] It's not that we're taking the humans out of the process, it's we're allowing them to focus on high-value tasks…”

(19:10) The concept of patent viability assessment and its impact on investment decisions

[21:13] “So these are all great indicators that are simply not available, or maybe no one has the intuition to look for them and find competitors for a startup.”

[22:03] “Some investors will tell you.. revenue speaks louder than IP. Others say, okay, IP is so fundamental.”

(24:13) William's vision for the future of IP and entrepreneurship

[25:29] “There is already a populated market in the direction that you haven't seen before with your business analyst.”

(26:27) The democratization of patent information and its impact on founders and investors

(30:39) William's entrepreneurial journey and the importance of mental health retreats

[30:48] “Actually what is not so much covered is mental health or founders - I would say that's the number one priority.”

(33:29) The importance of balance and intention in life and work

[34:48] “We live in the attention economy, like everything, trying to grab our attention.”

(35:35) Conclusion and final thoughts from Barry and William

FOLLOW THE HOST:

LinkedIn: https://www.linkedin.com/in/barryoreilly

Personal site: https://barryoreilly.com

Facebook: https://www.facebook.com/barryoreillyauthor/

Twitter: https://x.com/barryoreilly

Instagram: https://www.instagram.com/barryoreilly/

Email: hello@barryoreilly.com

FOLLOW OUR GUEST:

William Carbone: https://www.linkedin.com/in/williamcarbone

Personal Site: www.williamcarbone.com

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The definition of success can change everything. Properly defined, you have an agile organization where each team member can contribute fully. Poorly defined, you have stagnant teams and users that don’t like the products. In this episode of the Unlearn Podcast, host Barry O'Reilly sits down with Josh Seiden, a sought-after designer, strategy consultant, and coach. Together, they explore the importance of understanding user behavior, how that behavior can be translated into goals, and how company alignment on Outcomes and Key Results can drive business outcomes.

Josh Seiden has collaborated with top-tier brands such as PayPal, Johnson & Johnson, and 3M. His expertise lies in launching and building innovative products and services, as well as fostering agile and entrepreneurial mindsets within organizations. He is the author of “Outcomes Over Output” and co-author of “Who Does What By How Much,” "Sense and Respond," and "Lean UX," all cementing his reputation as a thought leader in the field of user-centered design and business strategy.

When User Experience Became Design

We know now that understanding how users will experience a product is a critical part of designing a new product, but back in the 90’s when Josh began his career in the industry, it was a radical idea. "A friend told me, 'We’re hiring designers here,' and I laughed, 'Why are you telling me this? I’m not a designer.' But that thing you’re doing here, we call that design," Seiden recalls. This unconventional designation became an entire industry, and his unconventional path to it meant he brought a unique perspective to the field of user experience design. Barry notes that this is a story that gets told again and again on the Unlearn podcast; that the conventional wisdom on how to find or become an expert is often wrong.

Don't Forget Why You’re Building What You’re Building

Barry points out that companies often measure things like the speed of production, but forget to measure the consumer behavior change that would really demonstrate the value of the project. Josh explains that measurability is important over the life of a project, but keeping the focus on outcomes for actual people is the most important thing to track. This is the key premise of Outcomes over Output that answers the question: what is an outcome? Josh’s definition, “An Outcome is a measurable change in user behavior that creates value.” If you need to identify the outcome you should be measuring for your company, answer three questions: Who?, Does What?, and By How Much?

The Evolution of OKRs in Large Organizations

Design thinking works at the team level very easily, and as the industry developed the question became how to do it at scale? Objectives and Key Results (OKRs) have emerged as a tool for helping large organizations work in agile ways. Josh explains how OKRs can be used to manage outcomes at scale: “The O is an objective. What's the big audacious goal? And then the KR is the result. How do you measure it? The key result. For most people who look at the system, they understand that [...] you want those Key Results to be outcomes." This way of thinking helps large enterprises maintain focus and drive impactful results by clearly defining and measuring success as it matters to the people using the product.

Read full show notes at BarryO'Reilly.com

Resources

Josh Seiden on the Web, LinkedIn, X, Medium

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Accelerator, Incubator, Venture Capital, Venture Studio? There are a lot of ways to get a new startup off the ground. Ben Yoskovitz, founding partner at Highline Beta, joins Barry O'Reilly on this episode of the Unlearn Podcast to talk about exactly that, and Ben shares insights into the world of venture studios, discussing his journey from founding Year One Labs, a venture studio before there were venture studios, to establishing Highline Beta. Ben's expertise in creating and scaling startups provides a unique perspective on the dynamics of venture studios and the strategies for success in the startup ecosystem.

Trend Towards More StartupsYou always learn the most from failure, and in sharing the difficulties he had with Standout Jobs in the late 2000’s, Ben highlights the importance of building things that people actually want. By applying Lean Startup principles and working with some incredible entrepreneurs, what he was really doing was learning how to build products and companies more effectively. Failure after failure isn’t fun, but being willing to share what you learn can help you create something incredible. “Founders do need to hear from other founders. you know, sometimes you need a shoulder to lean on,” Ben says, “and that might not be a blog post, or a podcast, that might be actually talking to another human.”

Understanding the Inflection PointsHow do you make an entrepreneur panic? Tell them they’re locked into a single idea for 25 years. Barry notes that “this idea of pursuing multiple ideas in different domains, but doing it in parallel…” lets the multi-passionate and the multi-skilled create value. Ben talks about the difficulty in working with corporate partners and investors when building startups, because they’re not speaking the same language, and the same challenges keep happening again and again - this was the impetus to find a better way to create new companies. The same challenges kept happening at the same inflection points, which means it can be systematized.

Scaling a Venture StudioBen talks about the challenges and strategies involved in scaling a venture studio, emphasizing the need for effective people management and business model refinement. He reflects on his own experiences and acknowledges the importance of recognizing strengths and weaknesses in leadership roles. Ben discusses the evolution of Highline Beta and the considerations involved in scaling the business, including generating revenue, hiring the right talent, and defining the future direction of the studio. "I think studios are meant to create shortcuts for founders. Not in a bad way, but give me the shortcut tools to validate faster, get to market faster, raise capital faster, recruit a team faster." This can make all the difference for a new startup.

Specialization in Venture StudiosBen and Barry discuss the trend of specialization in venture studios, with Ben highlighting the emergence of more specialized studios focusing on specific industries or markets. He emphasizes the potential benefits of vertical venture studios, where the playbooks are standardized and refined for targeted sectors. Ben envisions a future where studios become experts in niche areas, leveraging their experience to create value and drive better outcomes for startups. The conversation explores the concept of hyper-focused studios and the impact of specialization on the startup ecosystem. Ben makes a prediction: "I think we will see more specialized studios so that the systems that the studio is building and the playbooks are refined and refined and refined."

Resources:

Ben Yoskovitz on LinkedIn

Highline Beta

Lean Analytics

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The innovative spirit of startups is one of their strengths, something that seems to disappear as a company matures. Does it have to be that way? In this episode of Unlearn, host Barry O’Reilly is joined by Elliott Parker, CEO of High Alpha Innovation, who is an expert in corporate innovation and entrepreneurship. Together, they explore how corporations can regain the innovative spirit of startups to drive growth and transformation, and it begins with changing how they think about traditional metrics and strategies.

Elliott Parker is a seasoned entrepreneur with a deep-rooted passion for innovation and problem-solving. With a background in working for large corporations and witnessing firsthand the power of entrepreneurship in his family, he brings a unique perspective on the intersection of startups and established companies.

Unlearning to Achieve Big Objectives

In a rapidly evolving business landscape, the ability to unlearn traditional practices and embrace new ways of thinking is crucial for fostering innovation and staying ahead of the curve. Elliott's experience with disruptive events like the collapse of a well-established company highlighted the importance of taking control of fate and exploring alternative paths, even if they involve risks. Elliott seeks to challenge conventional wisdom and to be open to new approaches, so that organizations can adapt to change, drive growth, and seize opportunities that may not have been apparent before.

Nature's Innovation Process vs. Corporate Innovation

What can organizations learn from the Amazon jungle? Resilience and innovation. Elliott shares how companies can draw inspiration from nature to drive creativity and problem-solving. By emulating the decentralized, bottom-up approach to innovation seen in natural ecosystems, businesses can encourage experimentation, embrace uncertainty, and uncover novel solutions to complex challenges. Just as diverse organisms in the jungle adapt and thrive in response to constraints and opportunities, companies can benefit from fostering a culture of exploration and learning at all levels.

Scaling Innovation with Corporations

When startups collaborate with corporations, they have access to resources, expertise, and networks that help them tackle complex issues and bring innovative solutions to the market at a much larger scale. Not only does innovation itself become scalable, it’s also a unique opportunity to address significant societal problems and drive meaningful change. Not only can this approach accelerate the pace of innovation, but it also creates a ripple effect that begins in the company and reaches society as a whole.

Impact of Broadening Insights Portfolio

Thinking of insights as valuable assets, like a diverse investment portfolio, is key to expanding knowledge within a company. By exploring different ideas, trying new things, and questioning the usual way of doing things, businesses can discover fresh opportunities for growth and change. Encouraging a culture of ongoing learning and curiosity while steering clear of strict rules and top-down communication helps companies stay flexible, evolve, and succeed in a constantly shifting business world.

Resources

Elliott Parker on LinkedIn | High Alpha Innovation

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What problem are you trying to solve? Is it even the right one? In this episode of Unlearn, host Barry O’Reilly is joined by Renee Hawkins, a skilled technology and transformation practitioner. Together, they discuss problem solving, aligning business strategies with purpose, and how to pivot your organization successfully. With practical tips on networking, market research, and seeking advice, Renee offers a roadmap for anyone looking to make a meaningful impact in the business world.

Renee Hawkins, a technology and transformational practitioner with over 25 years of experience, brings a wealth of knowledge from her time at Thoughtworks and her current role as a fractional COO. Renee's approach of asking for help, networking, and continuous learning serves as an inspiration for aspiring fractional leaders.

The Influence of Thoughtworks and Roy Singham

During his time at Thoughtworks, Roy Singham was a visionary leader who influenced Renee’s entire approach to business. Roy led with purpose and kept social justice and inclusivity top of mind, which made Thoughtworks an incredible organization, internally and externally. When you take time to study the impact of influential leaders like Roy, you can gain insights into creating a culture that drives innovation and fosters a sense of purpose among your team.

Transforming Business Models

To deal with the challenges and leverage the opportunities of changing a business model, you need to ensure that your team, operations, and value stream are consistent with the new goals of your business. When you divide the transformation process into achievable steps and concentrate on urgent needs, you can manage complicated changes and prepare your company for success.

Building Effective Communication Strategies

Communication is essential for keeping teams on the same page and achieving business outcomes. Renee values storytelling, honesty, and frequent updates as ways to keep everyone updated and involved. By using effective communication methods, such as weekly reports or town hall meetings, you can make sure that your team remains in sync, inspired, and oriented towards common objectives.

Embracing Fractional Work and Portfolio Careers

Working fractionally and having a portfolio career can be very advantageous in the changing world of business today. Renee tells us how she went from conventional roles to providing fractional assistance to various companies. By being flexible, learning constantly, and exploring different opportunities, you can use your skills in different projects and sectors while keeping a good balance between work and life.

Resources

Renee Hawkins on LinkedIn

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They say those who don’t learn from the past are doomed to repeat it. As true a statement as it is, it’s missing one crucial element. If you never confront the reality of the present and get to the heart of why you are where you are, you won’t be able to unlearn the habits that got you there in the first place. In this episode of Unlearn, Barry O’Reilly talks with Dom Price, Work Futurist at Atlassian, who shares insights on facing the reality of the present, unlearning outdated practices, and embracing new ways of working to drive meaningful change and growth in organizations.

Dom's early work experience started in London at Deloitte, where he spent three years as an accountant. His job left him unfulfilled and passionless, but that all changed over sushi. Don’s boss at Deloitte offered him the opportunity to work in either New York or Sydney. Despite the allure of New York's size and boldness, Dom chose Sydney for its smaller team environment, where he could have a more hands-on, full-stack experience. This decision marked the beginning of a diverse and interesting career journey that eventually led him to Atlassian.

Embracing Reality and Unlearning Past Practices

Dom highlights the importance of facing the honest reality of the current situation in organizations. When leaders truly acknowledge where they are today, they can pay homage to the past while also identifying areas that need to be unlearned or improved. Not only will this allow those leaders to eliminate what is holding an organization back, it will also shine the light on what is exceptional and should be elevated. Taking this approach will help break away from average practices and strive for continuous improvement.

Collaboration Over Silos

Barry and Dom discuss the significance of breaking down silos within organizations to foster better collaboration and communication. This begins with recognizing that the entire company runs day to day on the hundreds of small tasks that require input from every team member and department. When collaboration and breaking down silos becomes a priority, a company can enhance its efficiency, productivity, and overall effectiveness. Equally as important, this type of culture honors the diverse perspectives they bring.

Seeking Growth and Avoiding Plateaus

Over time, companies trend toward mediocrity and status quo, but Dom stands firmly against the plateaus that seem inevitable. There is always a place for growth and improvement, and it requires each person involved to challenge themselves, step out of comfort zones, and actively seek new opportunities. Instead of complacency, a mindset of continuous learning, adaptation, and growth will ensure excellence and innovation.

Practical Change Initiatives Over Theoretical Transformations

Dom discusses the pitfalls of theoretical transformations, such as Agile transformations, that lack a clear understanding of the underlying goals and realities of the organization. Instead, he advocates for practical, action-oriented change initiatives that address specific needs and challenges within the organization. By focusing on tangible outcomes and being honest about real issues, companies can drive sustainable change and meaningful progress.

Balancing Heritage and Innovation

Not all of a company’s past should be unlearned, nor should its achievements be forgotten. There is a balance to strike between an organization’s rich heritage and the need for innovation and adaptation. Dom shares how companies can find a balance between honoring the past and embracing innovation, and companies can leverage their heritage while staying relevant and competitive in a rapidly changing environment.

Resources

Dominic Price on LinkedIn | Atlassian

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How well would you fare in the high-stakes world of blockchain and cryptocurrency? Could you navigate the complexities of decentralized technology and its potential to revolutionize society? In this episode of Unlearn, Barry O'Reilly sits down with Anne Connelly, a blockchain expert passionate about leveraging technology to transform lives in emerging economies.

As a faculty member at Singularity University and Boston University, who has also lectured at Oxford University, Anne teaches about how blockchain can enable us to redesign the foundations of society . She is also the author of "Bitcoin and the Future Fundraising," a guide that guides charities on how to accept crypto donations. Anne shares her journey from the nonprofit sector to the world of crypto, highlighting the importance of risk-taking and unlearning traditional structures to embrace innovation.

Embracing Risk and Making Tough Decisions

Anne's journey into the blockchain space began with a pivotal decision to forgo a promotion in the nonprofit sector for a career in an emerging industry. She reflects on the momentous choice she made, stating, "I would rather try and fail than never have tried at all." Even in the face of extreme uncertainty, there are times to take a risk and be open to new opportunities. Anne's story serves as a reminder that sometimes the path less traveled can lead to unexpected and fulfilling outcomes. As she navigated the decision-making process, Anne's willingness to embrace uncertainty and step outside her comfort zone ultimately propelled her toward a path of innovation and growth.

Transformational Experiences at Singularity University

Anne's experience at Singularity University's Global Solutions Program marked a turning point in her understanding of the potential of technology to address global challenges. She discusses the fusion of her passion for social impact with the innovative solutions offered by technology. Anne believes in rethinking the traditional approaches to problem-solving, stating, "We could make this a little bit better, but why? If we completely transformed it, we could make such a difference." Anne is a champion for using the power of technology to drive meaningful change on a global scale through a holistic and impactful approach to addressing societal issues.

Decentralized Autonomous Organizations (DAOs)

Decentralized Autonomous Organizations have an incredible disruptive potential in reshaping how we govern ourselves as a society. Anne explains how DAOs enable groups to collaborate without traditional hierarchies, leveraging blockchain technology for transparent decision-making processes. She highlights a real-world example of Constitution DAO, where a collective effort raised funds to purchase a copy of the US Constitution. These decentralized systems offer unique possibilities by democratizing decision-making, which allows for meaningful innovation in traditional governance models.

Onboarding and Adoption of Crypto Technology

Anne shares the challenges of onboarding newcomers into the crypto and blockchain space, especially when it comes to accessible entry points. She shares a story about introducing a group of skeptics to Bitcoin. Their resistance held firm until they had a true, hands-on experience, which shifted their perceptions entirely. There’s a disparity in crypto adoption rates across different groups and regions, and Anne highlights how crypto often resonates with populations facing financial instability or limited access to traditional banking. If we want to encourage broader participation in the crypto ecosystem, we must focus on creating more inclusive strategies.

Read full show notes at BarryO'Reilly.com

Resources

Anne Connelly on the Web | LinkedIn | X(Twitter)

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Would you be willing to take on mission critical, make or break projects as your career? How would you handle the challenges that arise from situations like bankruptcies and mergers while managing the extreme pressure that comes from such high stakes?

Daniel Henry doesn’t just take on high stakes projects as they arise. He actively seeks them out. Daniel’s fascinating career has spanned EDS, American Airlines, and most recently, CIO at McDonald’s. He has gained invaluable insight in building teams, developing leadership, and taking on hard things to help you grow. And one of the best insights he offers is how to make big problems small.

Embracing Simplicity in Problem-Solving at Large Companies

In the realm of large corporations, the ability to simplify complex problems is a crucial skill. Daniel emphasizes the significance of breaking down overwhelming challenges into smaller, more manageable tasks, so that teams can navigate the complexities of technology and business transformation. His advice to "make the problems really small" serves as a valuable strategy for initiating progress and innovation within large organizations.

The Importance of Working on Mission-Critical Projects

Engaging with mission-critical projects can be a defining factor in one's career growth and development. Daniel reflects tackling projects that have the potential to make or break a company, which helped him resilience and leadership skills. His advice to focus on the most critical tasks resonates with the idea of continuous learning and self-improvement.

Building and Leading High-Performance Teams

High-performance teams are a cornerstone of success in any organization. Daniel highlights the importance of aligning team members with a clear purpose to drive collaboration and goal achievement, and the type of leadership that will get them there. When you embrace the critical role of purpose-driven leadership and foster a shared understanding of objectives and strategies, you’re able to develop strong, innovative teams within any organization.

The Role of Storytelling in Attracting Top Talent

Storytelling plays a pivotal role in attracting top talent to organizations, especially in the technology sector. A powerful narrative that includes the journey of technological transformation and the challenges that were overcome, companies can more easily attract top talent who are seeking meaningful and impactful work. Daniel also underscores the importance of transparency in the narrative and the workplace culture it builds.

Scaling Technology Innovations Globally

Daniel discusses the importance of starting small and learning fast when expanding technology solutions across global, diverse markets. Sweeping changes, especially with technology, require a strategic and iterative approach. Daniel’s approach begins with running ‘experiments’ in smaller regions, analyzing the data, and basing the wider implementation on those data-driven insights to ensure smoother transitions for companies and their customers.

Resources:

Daniel Henry on LinkedIn | X(Twitter)

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What was your biggest personal transformation? More importantly, who helped you achieve it? Read this blog and episode of the Unlearn Podcast for top leadership transformation mindset advice from a world-class leadership coach.

Sabrina Braham is an executive coach, mastermind group leader, author, and leadership and career development expert with almost three decades of experience, but she nearly walked away from that journey before it ever began. What kept her going? A teacher who was more like a coach. He encouraged and believed in her, which helped her completely transform what she thought about herself and her future. And now, Sabrina does that for others.

There’s a reason that 97% of all CEOs in the United States have coaches for leadership transformation mindset advice. Asking for feedback is a powerful tool for personal growth and development. Embracing the discomfort of asking questions can lead to valuable insights, accelerated learning, and improved decision-making.

Embracing Growth Mindset and Overcoming Self-Doubt

We all have moments that transform us. For Sabrina, it was when her psychology teacher refused to let her quit and had her enroll in the most difficult classes. "He totally believed in me," she reflects. This experience sparked a shift from self-doubt to a growth mindset, and the encouragement helped her see and embrace her full potential. Often, a big part of transformation is identifying the self-imposed limitations we have created, and Sabrina’s journey from uncertainty to academic excellence is an inspiring example of how a single act of faith from another can catalyze our growth and help us transcend our perceived barriers.

The Power of Asking for Feedback

Many of us live in a precarious balancing act every day: personal turmoil, parenthood, entrepreneurship, partnership. Sometimes we need the voice of clarity to help us make sense of it all. But first, we need to ask that voice to speak. Asking for feedback is not a sign of weakness, but a brave step towards self-betterment, and it’s not about uncovering flaws alone. It’s all about acknowledging and harnessing our inherent strengths. When we embrace vulnerability, we can actively seek out the insights that will propel us forward.

Building Relationships and Political Savvy

Workplace dynamics are an intricate dance, and it’s critical to nurture relationships and develop political acumen. Sabrina challenges the notion that career advancements are merely the result of nepotism, suggesting that the key lies in "deepening your relationships with people." The subtleties of professional success include both genuine connection and strategic navigation of organizational landscapes, which lead to recognition and advancement. In other words, how we interact with others will significantly influence our career trajectory.

The Role of Mastermind Groups in Accelerating Growth

Sabrina is passionate about leading executive mastermind groups, describing them as a collective committed to mutual growth, where "everybody in the group helping the person that's talking." These groups act as a powerful catalyst for personal and professional development, offering a space where shared experiences and diverse viewpoints can lead to unexpected insights and breakthroughs. A well-run mastermind group is the ideal community for leadership transformation mindset advice. They become your own personal “board of directors”. Mastermind groups harness collaborative intelligence, allowing each member to contribute to and benefit from the collective wisdom. It's a testament to the idea that by coming together, we can amplify our learning and accelerate our journey towards our goals.

Resources

For full show notes, go to BarryO'Reilly.com

Sabrina Braham MA MFT PCC on the web | LinkedIn | Leadership Podcast

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What if success isn't about being the best but about continuous improvement?

Global executive James Williams shares his journey from leading Olympic campaigns to empowering startups and teaching MBA students. Discover how his focus on performance, purpose, partnerships, and people has shaped his career and why he believes that embracing discomfort is the key to personal and professional growth.

Now, as an advisor at Nobody Studios and a mentor to the next generation of marketers, James shares his insights on personal growth and the art of embracing new challenges with purpose and performance in mind.

Success isn't a straight climb to the top; it's about the courage to be imperfect and the grit to improve, even if it means stepping off the peak to explore new paths.

Embracing Improvement Over Winning

James emphasizes the importance of focusing on personal and professional improvement. "Fundamentally, it's not about winning. It's about improving. And that's what I mean by performance." The conversation delves into the concept of continuous learning and the mindset of always striving to get better.

James shares his personal experience of realizing that success isn't always about being the best but rather about making incremental improvements. By embracing improvement as the ultimate goal, individuals can foster a growth mindset and continuously push themselves to reach new heights.

The Power of Teamwork and Overcoming Personal Challenges

Dyslexia was a major challenge for James, especially since he grew up in a hypercritical environment. He highlights the value of teamwork and collaboration: "If I work with a bunch of people, there are certain things I'm not very good at. And there are some things I'm very good at. And if I can build those balances, then it doesn't mean I'm constantly trying to hide that I can't spell or say things like that."

Embracing strengths and weaknesses is transformational, and by recognizing and honoring the strengths of each team member, individuals can create a collaborative environment that fosters growth and success.

Setting Personal and Professional Goals

Personal and professional goals drive growth and progress, and James sets his goals at the beginning of each year. He shares his approach to goal-setting and the importance of feedback and continuous learning. "Each time, I would then sit down and look at those and say, 'How am I doing?'"

Whether the goals you set are short- or long-term, they will enable you to have a clear direction and purpose in your personal and professional life. As you regularly reflect and evaluate, you can stay focused and motivated and will continuously improve yourself.

The Importance of Partnerships in Business

Partnerships are more than just transactional. "Partnership is where you find the added value in that relationship." James stresses the importance of long-term partnerships that drive society's impact. When you align your partnerships with your goals and values, you can maximize both your own personal growth and the impact you can have.

James believes that businesses need to integrate partnerships into their strategies. Much like team members relying on one another’s strengths, businesses can build partnerships with other organizations that will drive innovation, growth, and positive change.

The Intersection of ESG and Marketing

When companies integrate environmental, social, and governance (ESG) factors, that integration needs to reach their marketing teams. "You can still drive commercial impact, consumer engagement, but also have a positive impact rather than a negative one."

When companies fully embrace ESG principles as part of their core marketing strategies, they can build trust, engage consumers, and contribute to a more sustainable and inclusive future.

Resources

James Williams on LinkedIn

Nobody Studios

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How can the lessons learned from a childhood of tinkering and a career influenced by tech visionaries like Bill Joy and Andy Bechtolsheim guide us toward a more sustainable future for technology?

We’re joined today by Adrian Cockcroft, a trailblazer in cloud architecture at Netflix and a proponent of open source at Amazon Web Services, who is now channeling his expertise into the vital cause of sustainability in cloud computing.

Adrian shares his journey from the early days of building computers to his influential roles in shaping the tech industry and how these experiences have informed his current focus on sustainability.

Together, we can build a future that is not only technologically advanced but also environmentally responsible.

Early Career Experiences and Influence

Adrian shares the experiences that shaped his professional life, especially his time at Sun Microsystems, and the influence of visionaries like Bill Joy and Andy Bechtolsheim. He discusses the power of thinking into the future and anticipating trends.

"It was clear [Bill] lived five years in the future... that was one of those inspiring moments." This experience alone highlighted the significance of forward-thinking and the impact it can have on shaping one's career trajectory. It serves as a reminder to embrace curiosity and explore emerging technologies and trends, as they can lead to groundbreaking opportunities and shape the future of industries.

The Power of Putting Ideas Out There

Sharing ideas can be transformational. Adrian and Barry, both authors, discuss the importance of writing and publishing, which goes beyond the unique experience of writing a book or the influence it has on the readers. It also shapes and influences their own organizations. Being open and vulnerable might be difficult, but the rewards are priceless.

“Everyone should write a book. It's 10 times harder than you think." Putting your ideas out there helps you overcome self-doubt and fear of judgment and embrace the opportunity to contribute your unique perspectives and insights to the broader discourse.

Transitioning to a Focus on Sustainability

Adrian doesn’t just preach sustainability; he lives it. In addition to his current work, Adrian was also an early adopter of solar panels and electric cars. Professionally, Adrian shares his experience championing these values within AWS and helping his peers understand the importance of transparency and accountability in addressing environmental impact.

Companies need to do more than give lip service to a better future. They must also align their actions to those values and actively seek ways to reduce their environmental footprint. Sustainability is not just a buzzword but a fundamental responsibility that requires commitment and action.

Challenges in Achieving Sustainability in the Cloud

Barry and Adrian delve into the challenges faced by companies in achieving sustainability in their technology infrastructure. It’s not enough to have accurate measurements and proper reporting of carbon emissions. Organizations must also ensure their supply chain adheres to the same standards and values.

Allocation and attribution of carbon emissions on a global scale can be incredibly complex, so if we hope to address emerging climate risks and create a sustainable future, complying with regulations and being transparent is key.

The Need for Measurement, Reporting, and Action

Organizations need to go beyond measurement and reporting. Instead, the actions a company takes to ensure sustainability should be used as a measure of a company’s quality and care.

Consumers can take an active role in encouraging companies to be sustainable and holding them accountable when they aren’t. The mix of regulations, reporting, market demands, and social pressure will cause companies to think about the future of the environment and take action, not just internally but also in their supply chains.

Resources

Adrian Cockcroft on LinkedIn | X(Twitter)

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Connie Kwan is a seasoned product and marketing expert with over two decades of experience in a variety of fields. During her time at Microsoft and Atlassian, she honed her skills in simplifying complex concepts and navigating ambiguous situations with powerful questions. She’s currently putting those skills to work as the Chief Product Officer at Nobody Studios. Connie joins Barry O’Reilly to delve into the concept of unlearning perfectionism in the professional world, how to balance perfection and practicality, and how letting go of the former can lead to more authentic and effective communication on all fronts.

Embracing Imperfection and Building Connections

In a world obsessed with perfection, Connie illuminates the paradoxical beauty of imperfection. She shares, "being ‘not perfect’ builds connections," highlighting a profound unlearning process. The pursuit of flawlessness often leads to isolation, whereas embracing our raw, unpolished selves can foster genuine connections. Connie's journey from a perfectionist mindset to one that values authenticity serves as a powerful testament to the humanizing effect of imperfection in both personal growth and professional collaboration.



The Importance of Learning What to Ignore

Connie recounts a pivotal piece of advice from her mentor at Atlassian: "You'll learn what to ignore." This new perspective on setting priorities helped Connie transition from absorbing every detail to mastering the art of strategic ignorance. This shift is not about negligence but about honing the ability to sift through the deluge of data and focus on what matters. Connie and Barry underscore the significance of discernment in leadership and the power of letting go to achieve greater impact.

Transitioning to Open Collaboration

Connie shares her vastly different experiences at Microsoft, a traditional ‘buttoned up’ company, and at Atlassian, who valued transparency at every stage. She had to adjust to sharing her works in progress publicly. She describes the Atlassian philosophy: "you write one sentence and that sentence is now public to everybody at the company on a page." This approach not only sped up processes but also serendipitously connected people across the company, fostering a culture of trust and collective intelligence. Transparency can be a catalyst for efficiency and innovation.

The Impact of AI and Communication Tools

Connie's enthusiasm for the intersection of AI and communication tools is palpable as she discusses the potential for these technologies to revolutionize the way we share ideas. She envisions AI-generated narratives tailored to different audiences, enhancing our ability to connect and be understood. Connie and Barry explore how advancements in language models could democratize communication, making it more inclusive and effective. Connie's insights into the transformative power of AI in storytelling and communication underscore the potential for a more interconnected and empathetic world.

Balancing Innovation with Responsibility

The conversation takes a critical turn as it addresses the potential pitfalls of innovation without foresight. Connie points to Slack's interface change debacle as a cautionary tale, where a product update led to widespread user frustration. She argues for a balance between the drive to innovate and the responsibility to consider the user's experience. "It just wasn't a well-considered launch," Connie remarks, emphasizing the need for products to be both groundbreaking and grounded in user needs. She points to the real-world impacts of their creations and the importance of measured, thoughtful innovation.

Resources

Connie Kwan on LinkedIn | X (Twitter) | Nobody Studios

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Sahra-Josephine Hjorth, co-founder and CEO of CanopyLab, joins Barry O'Reilly on this episode of the Unlearn Podcast to explore the interconnectedness of different skills, fields and interests. Sahra’s career has spanned diplomacy, startups, creating social learning experiences and inventing the first AI course authoring tool, and she has been recognized for her innovative contributions to education, including being selected for Barack Obama's Leaders in Europe program in 2022. Sarah and Barry talk about redefining success, the intersection of technology and education, the importance of adaptability in both personal growth and business development, and what kind of environments we create for students - and for entrepreneurs.

The Evolution of Learning Experiences

Sahra-Josephine’s work revolves around the concept of 'empowerment through diversity' - the belief that embracing varied talents and perspectives leads to greater collective success. This insight first dawned on her in 2009, when she returned to Denmark and began volunteering for the United World College. Tasked with selecting scholarship students, Sahra's role extended beyond academic assessment to fostering resilience and multifaceted growth. Her approach challenged conventional wisdom, and that while "we really want to put humans in a box,"- we can’t and should be designing systems that don’t try to.

Entrepreneurial Unlearning and Financial Independence

“Money is not important for the sake of money, but the freedom it gives you.” Sahra-Josephine states, emphasizing the empowerment that comes from financial independence and self-direction. This can be a challenge when you discover that you don’t like or can’t use elements of the path you started on. Sahra-Josephine experienced this when she decided that a life of diplomacy was not for her and that while learning a language is always valuable, mediocre Russian is not exactly useful. These shifts, however much they felt like failure, opened doors to a unique intersection of artificial intelligence, education, and human rights policy. Experiences that seem very disparate can actually be highly interconnected, and skills honed in one area can become invaluable in another, unexpectedly shaping a niche where few others have ventured.

The Birth and Growth of CanopyLab

Barry points out that CanopyLab is “a fascinating juncture of technology and education and learning, and also meeting people where they're at, rather than trying to categorize them for the sake of simplicity” and asks Sahra-Josephine what she has had to learn and unlearn while growing the company. She shares that she isn’t sentimental about her business and that as she started to become a creator and work directly with the type of students she wanted to serve, she realized "we have to become a software company." All of the current research about learning indicates it’s done best socially, so building a learning system that worked like a social media one meant that the users could integrate it on all of their platforms. As AI technology becomes more sophisticated, adding a high level of personalization has become possible. It all comes down to analyzing user data, feedback and trends.

For full show notes, go to BarryO'Reilly.com

Resources:

Sahra-Joseph Hjorth on the Web | Instagram | LinkedIn | X (Twitter) | Canopy Lab | Obama Foundation

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Dr. John Lowry, CEO of Thrivence, a management consulting firm based in Nashville, TN, joins Barry O'Reilly on this episode of the Unlearn Podcast to talk about John's journey from being a lawyer to teaching negotiation skills worldwide. John uses his diverse background in law, consulting, entrepreneurship, coaching, and university administration to bring a unique perspective to negotiation. He currently serves as the President of the Lowry Group and teaches at Pepperdine University's Straus Institute for Dispute Resolution. In this week’s show, John shares insights from his bestselling book, Negotiation Made Simple. He emphasizes the importance of understanding human motivations in negotiation and highlights that decisions are often influenced more by emotion and ego than reason. By focusing on interest-based negotiation and avoiding positional debates, negotiators can create win-win deals in both business and personal situations.

From Lawyer to Negotiation Specialist

98% of John’s work as a lawyer centered around negotiating settlements. “What I learned was, … most of the problems started as human problems, then they became legal problems,” John tells Barry. “And then the really sophisticated negotiators, they got them resolved as human problems again. And the litigation process didn't allow for the human element to come back in. It was only the negotiation process that allowed for that.” He became passionate about developing expertise in interest-based negotiation focused on the human problems underlying legal conflicts. He eventually started training others in these skills to facilitate deals and restore relationships earlier in disputes. He tells Barry that he focuses on negotiation more than litigation because "that was the process that brought healing to the injured party. That was the process that brought peace."

Understanding Emotional Triggers in Decision-Making

A study by Harvard Business School showed that only 30% of business investment decisions are based on reason or analysis; 70% are driven by emotion. The emotional trigger, in particular, was found to be related to ego—how individuals felt about themselves when contemplating doing business with the other party. This insight highlights the significance of emotions in decision-making during negotiations. Barry reflects on this, emphasizing the importance of understanding how much the other party likes you, as it plays a crucial role in the negotiation process.

Counterintuitive Negotiation

Barry asks John what we should unlearn to become sophisticated negotiators. “Negotiation is a very counterintuitive process,” John responds. He debunks the misconception that negotiations always end with a win-win or a friendly resolution. He defends teaching competitive negotiation, arguing that it prepares individuals for the reality of negotiating with counterparts who are ready to compete. Competition can be cooperative in certain circumstances, he comments, emphasizing the role of ritual and uncertainty in negotiation dynamics.

Looking Ahead

John believes that in the future, neuroscience will help us understand how emotions and psychology impact decision-making and negotiation results. While AI can make data analysis more efficient, it probably won't fully replicate the complexity of human interactions and the diverse interests involved. As Barry points out, humans still play a crucial role in setting machine parameters. However, the collaboration between humans and technology will keep advancing the field of neuroscience and negotiation.

Read full show notes at BarryO'Reilly.com

Resources

Dr. John Lowry on Website | LinkedIn | Negotiation Made Simple

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What if we have barely scratched the surface of human potential? According to Nichol Bradford, a pioneer in technology and human transformation, we need to challenge the assumption that machines will surpass humanity. Nichol has led operations for gaming giants like Activision Blizzard and Epic Games in China. She built communities that connected people globally through the power of shared narratives. Now she lectures at Stanford and Singularity University, while investing in startups focused on wellbeing and personal growth. In this episode of Unlearn Podcast, Nichol and host Barry O’Reilly discuss how we can use technology to unlock our emotional intelligence, creativity, and cognition. Rather than a dystopian future of humans versus machines, she proposes a human-centered path to amplify our abilities.

A Passion for Human Transformation

While writing a book and reflecting on her life's path, Nichol realized she's always cared about the "act of transformation" - how someone becomes their best self. She first recognized this passion at age 13, when she vowed to overcome her shyness and find her place in the world. By senior year, through purposeful effort, she went from wallflower to popular student. This early experience showed Nichol the power of deciding who you want to be and taking action to become that person. Barry highlights that stepping outside your comfort zone can unlock tremendous self-learning. Some of his most formative moments were from personal choices to pursue the unknown. Though uncomfortable, these experiences expanded his worldview and self-knowledge.

Unlearning Limiting Beliefs that Restrict Human Potential

“What I'm interested in is human potential realized,” Nichol tells Barry. “And then how do we use technology to amplify that?” Our long-held assumptions place artificial limits on how we envision human potential. In reality, we have barely begun to tap the capabilities of the human body and mind, she remarks. Neuroscience research reveals the brain's uncanny abilities that operate below our conscious awareness. In one study analyzing AI-generated images, people's conscious minds were fooled by fake faces, but their subconscious brain activity showed they could distinguish real from fake 100% of the time.

State of Flow

When people are in rapport, their nervous systems synchronize in measurable ways; for example, their pupils dilate in rhythm, their voices harmonize, and their movements align subconsciously. This state is called synchrony. It is visible during group flow states, like when a sports team is "in the zone" together. However, synchrony alone doesn't guarantee group flow, Nichol says. The key distinction is that group flow always involves synchrony, but people can exhibit synchrony without experiencing group flow. Barry adds that high performing teams often have natural synchrony, but explicitly naming it as a goal and measuring it could be powerful. Computers and AI can now detect synchrony objectively by analyzing video, audio, and physiological signals.There is enormous potential in applying technology like synchrony tracking to amplify human collaboration and group intelligence, Nichol and Barry agree. For example, if teams had a "synchrony score" during meetings, it could help them intentionally build more synchrony.

For full show notes go to BarryO'reilly.com

Resources

Nichol Bradford on Website | LinkedIn | X (Twitter)

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Drewe Broughton - “The Fear Coach” - is a former professional footballer who now helps athletes and executives overcome obstacles and unlock their potential. His approach involves guiding his clients to explore their true selves and confront difficult emotions like fear and shame. He believes that people can find genuine, lasting success through self-awareness and personal fulfillment. In this episode of Unlearn, Drewe joins Barry O’Reilly to share thoughtful perspectives on fear, vulnerability, and being your authentic self - even in high-pressure environments.

Seeking Truth

Drewe reflects on a pivotal moment in his life when he was in rehab, facing the truth about his struggles. He describes the moment of surrender and a sense of peace that washed over him as he acknowledged how unmanageable his life had become. “It was the first time I probably sat with that level of truth. And I remember an overwhelming sense of peace washed through me,” he shares. Barry adds, “A huge part of the entrepreneurial journey is seeking the truth. A lot of people don't want to seek the truth. They want people to tell them their product's beautiful... but it sucks. And just like people, …we create a facade of who we are and how perfect our life is, and yet we all know the truth: there's a lot of tough moments lurking there.” Drewe emphasizes the importance of seeking one's truth and the challenges of ego collapse. His own self-discovery during the 30-day rehab period, unraveled that he was lost in his career and personal life. “It was never the external pressure, it was never the fans... It was me, ” he tells Barry.

The Art of Unlearning

“I talk a lot about unlearning [because] there [are] some behaviors that actually can lead to massive success, but they also can limit us, too,” Barry says. Drewe shares his perspective on unlearning, drawing parallels with religious stories, such as the Buddha's enlightenment under a tree. You need to collapse your ego and strip away external influences to discover your true self, he remarks. He highlights the often-overlooked aspect of courage in the pursuit of success, contrasting it with the prevalent emphasis on hard work. “It's all …more grind, more hustle. But beyond that, the courage piece, the courage to stay who you are and keep doing it,” he says.

External Noise

Leaders often operate in high-pressure environments. They have to contend with pervasive external noise and pressure, which can significantly impact their decision-making and overall performance. Drewe and Barry discuss the intricate relationship between fear and uncertainty, emphasizing how these emotions manifest in the entrepreneurial world. Detrimental consequences can result when leaders fail to take decisive action in the face of such challenges.

Read full show notes at BarryO'Reilly.com

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Drewe Broughton on the Web | LinkedIn

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Sophie Wade is a thought leader in workforce innovation, flexible working, and the future of work. With an enviable background in strategic development, financing, and entrepreneurship, Sophie has become a sought-after speaker, author, and consultant, helping organizations navigate the ever-changing landscape of work. She is particularly known for her insights into how businesses can adapt to the changing nature of work, embracing flexibility, and leveraging technology, including AI. Sophie is the author of Embracing Progress: Next Steps for the Future of Work, and Empathy Works: The Key to Competitive Advantage in the New Era of Work, in which she explores the intersection of technology, culture, and the modern workplace. In this episode of the Unlearn Podcast, Sophie joins Barry O’Reilly to share insights on the modern workplace, discussing generational gaps, cultural awareness, the impact of AI, and the anticipated cultural shift in the coming years.

Culture Chameleon

Cultural awareness plays a pivotal role in shaping your professional life, influencing your interactions, decision-making, and overall success in the work environment. Having lived in various countries, Sophie emphasizes the importance of adapting to the climate around you, flexibility, and cross-cultural communication. She shares how in Hong Kong, work consumed a significant part of daily life, in contrast to Germany, where a clear separation existed between work and personal life.

The Gen Z Problem

Sophie's awareness of generational differences did not stop with millennials. She also tried to understand Gen Z, recognizing the distinct perspectives and relationships they have with technology. Millennials, and subsequently Gen Z, grew up with technology as an integral part of their lives, she recognized. This helped her appreciate how technology influences their communication styles, preferences, and worldview. It’s important to stay current to adapt to the dynamics of the workforce, she points out. “Constantly being aware and gathering information to try and understand is one of my key ways to just keep current, to keep questioning myself. Am I actually understanding what's going on?”

The AI Crisis

According to Sophie, technological advances and the introduction of AI have decreased the half-life of skills from ten years to five years, increasing the need for upskilling and reskilling. The skills needed are changing rapidly, especially in areas like cloud computing, where upskilling is needed every 4.5 months. The introduction of AI means that jobs are not just augmented but can be disrupted and changed. While the changes brought by AI are exciting, they can also be risky and nerve-wracking for individuals, especially in terms of how jobs will evolve. Individuals need to keep moving and adapting to the changes in technology.

Looking Ahead

Sophie anticipates a significant cultural shift in the next few years, driven by several factors related to the evolving nature of work, the integration of AI, and the changing expectations of employees. She refers to the shift as a move toward “modern work,” characterized by flexibility, adaptability, and responsiveness, reflecting a departure from the rigid structures of the past.

Visit BarryO'Reilly.com for full show notes.

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Sophie Wade on the Web | LinkedIn | Twitter

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Hope Gurion is a seasoned professional with a background in product management, business development, and coaching within the tech industry. As the founder of Fearless Product, she plays a pivotal role in advising and supporting product leaders and teams. Hope's career traces back to the early stages of the internet, where she contributed to shaping digital experiences. She held positions at AOL, Jobster, CareerBuilder, and Beachbody, and she brings a wealth of experience in dealing with various challenges in product development, business growth, and leadership. In this episode of the Unlearn Podcast, Hope joins Barry O’Reilly to discuss her career journey, emphasizing the importance of persistence, adaptability, and shared vision within product teams.

The Reach of Shared Vision

Hope reflects on her experience at AOL, particularly in AOL Shopping. Despite creating a detailed Product Requirements Document (PRD), the disconnect between her vision and the final designs revealed the necessity for shared understanding among team members. This disconnect eventually led to a breakdown in trust. Hope emphasizes that everyone should comprehend the business context and constraints. “It was just a learning moment for me in terms of, do you really have [a] shared vision?” she tells Barry. “Does everybody on the team really understand the business context of what we're trying to do?” This situation was common in the early 2000s tech landscape, Barry says. “There's still plenty of companies living in that world of siloed teams, lack of cross-functional groups.”

Jack of Many Trades

Hope shares a key moment from her professional evolution, recounting a significant turning point when Matt Ferguson, the CEO of CareerBuilder, offered her a position. Hope initially turned down the role due to personal reasons, but Matt persisted, expressing a genuine belief in her potential and leaving the door open for future collaboration. This persistence became a catalyst for Hope's subsequent transition to CareerBuilder. It demonstrates how a leader’s perseverance can reshape an individual's career trajectory. Hope's career evolution also highlights her adaptability. She navigated various roles, from AOL to CareerBuilder. Her eagerness to find ways to grow the business and diversify revenue streams led to her role as Chief Product Officer.

From Chief to Coach

Hope’s transition from being a leader in various companies to becoming a coach and advisor wasn't a predetermined career move, she shares. Barry prompts Hope to reflect on this shift, asking about the triggers and the unlearning process required. Hope’s career shift was triggered by certain constraints she experienced in her role as CPO. At CareerBuilder, she faced the challenge of training and developing individuals from diverse backgrounds into product-related roles due to certain constraints. This experience became foundational for her belief in the coachability and trainability of product leader roles. Her coaching venture was a result of requests for interim consulting, leading to her collaboration with Teresa Torres. Reflecting on her coaching transition, Hope shares, “Knowing what types of skills I think are coachable and trainable, and knowing that was something that I got a lot of satisfaction doing and had seen a lot of different scenarios [of], is what gave me confidence that I could do this to a certain segment of people."

Looking Ahead

Hope advises listeners to focus on fundamental questions such as understanding the customer, evaluating alternatives, and articulating the unique value proposition, emphasizing the importance of alignment and shared understanding within product teams to drive forward progression.

Resources

Hope Gurion on LinkedIn | X(Twitter)

Fearless Product

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Peter Walker is a data-driven content marketer known for his expertise in using data and analytics to create insightful and engaging content. In his role as Head of Insights at Carta, Peter's work often revolves around visualizing data in a way that makes it accessible to a broad audience, helping people understand complex topics and trends. He has contributed significantly to the field of data-driven content marketing and is known for his ability to provide valuable insights through his work. In this episode of the Unlearn Podcast, Peter joins Barry O’Reilly to discuss the use of data and analytics in content marketing. He shares insights into his experiences in transitioning from a data analyst to a data-driven content marketer and offers valuable advice for those looking to embark on a similar journey in data-driven marketing.

The Data’s in the Details

When building a business, you may come across instances where you feel like you’ve hit a wall - especially in the budding stages, when you’re doing the job of three people. “There's always the chance that you're going to hit it big, but in practice I think the responsibility and adaptability that you need to survive in a startup is [often] more important than the equity you receive,” Peter says. Being adaptable and open to exploring new skills takes you far. For example, Peter's career shift from data analyst to product marketer helped him discover his passion for data visualization and design. This shift allowed him to bridge the gap between data and communication effectively.

Carta’s Magna Carta

There are two main approaches to data analysis at Carta, Peter explains. The first approach is to create reports that answer clear questions by presenting data in a clear and concise manner. The goal of this approach is to provide readers with a straightforward understanding of key metrics, such as valuations and funding rounds. This approach is not about creating flashy graphics, but rather about delivering clarity and answers to specific questions. The second, more interesting approach is the discovery and exploration phase. Peter mentions the value of tools like Tableau, which allow him to dive into data without a predetermined goal. He often starts with scatter plots to understand data distributions, and then applies filters to investigate various dimensions such as time, stage, or industry. The key is to find the most compelling and distinct visual representation of the data.

Looking Ahead

Peter's primary piece of advice is to start by collecting questions from the audience. By listening to what their target audience is wondering about and collecting those inquiries, aspiring data marketers can identify valuable topics to explore. He emphasizes the importance of addressing questions that genuinely matter to the audience.

Read full show notes at BarryO'Reilly.com

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Peter Walker on LinkedIn

Join Carta’s data newsletter

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With a strong emphasis on rapid development and accelerating ideas into tangible products, Adam Bragg believes in the ethos of "launching". He introduced the concept of "activity networks," a fresh take on community-building, where people congregate based on shared activities rather than just online interactions. He has been involved in several projects that unite diverse groups of enthusiasts, giving Adam rare insight into the evolving landscape of tech and human connection. In this episode of Unlearn, Adam joins Barry O’Reilly to discuss the transformative power of launching ideas and products into the world and the lessons that come from confronting the fears and vulnerabilities tied to this process.

From Vaulting to Ventures

Adam’s Ukrainian coach, Nikolai Doroshenko, emphasized the importance of visualizing routines multiple times before executing them. This technique, which he has since integrated into various aspects of his life, is not only applicable in pole vaulting but transcends into business. “I've been applying that same kind of [visualization] of the future moment and [trying] to work [my] way backwards into constructing it,” he explains. Picturing a business's potential impact before its inception is essential, he points out. Barry reinforces this perspective by drawing parallels between the mental preparedness demanded by high-stakes sporting events and the uncertainties of launching a business. “It's a muscle that you can build and improve as you become more familiar,” he tells Adam. Certain principles are universal - whether in the athletic realm, the healthcare sector, or in business launches across diverse sectors, the process remains consistent: visualize, appreciate, execute, and then learn from the outcome.

Betterment is in the Eye of the Beholder

Visualization is also important for senior executives. Barry asks, "What will success look like in one to two years? How will stakeholders be different?" It is all about creating a detailed mental picture of success in order to better navigate the steps to achieve it. Adam highlights the importance of visualization in his career, from his early days in engineering and history to his ventures in creating tech solutions for education and community building. He discusses his exploration of AI and large learning models, notably the GPT models. His development of "Cat GPT," a personality-driven AI bot that responds like a sassy cat, is a testament to how AI can be made approachable and fun. It is a unique juxtaposition of technology and human-like personality traits. Adam underscores the potential of AI, not just as a functional tool but as an entity that can facilitate relationship-building. The future of AI interaction will likely be more character-driven, he predicts.

Looking Ahead

Adam is deeply excited about the evolution and potential of technology, especially in the context of human creativity and the swift pace of development. He touches on the ongoing projects at his studio, particularly emphasizing their work on the "ThoughtForma," an intelligent no-code platform that is empowering individuals, regardless of their tech background, to create and deploy technology products. This platform can help anyone, from a local library to vast audiences on social networks, bring their ideas to life. Furthermore, Adam expresses enthusiasm about the "activity network" concept, introduced to him by their CTO. Unlike typical social networks, activity networks center around groups of individuals engaging in similar activities or sharing interests. He sees these networks as a way to consolidate tightly-knit communities that can seamlessly merge physical and digital interactions.

Read full show notes at BarryO'Reilly.com

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Adam Bragg on the Web | LinkedIn

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Marcos Fernandez is a visionary in the fintech sector, characterized by his profound understanding of its evolving dynamics and the importance of strategic collaborations across industries. His vast network, ranging from prominent banks to venture capital, underlines his dedication to fostering strategic partnerships and ensuring financial inclusivity. He champions the creation of innovative ways to finance the future startups of tomorrow. In this episode of Unlearn, Marcos joins Barry O’Reilly to discuss the evolving dynamics of venture capital, funding startups and how to differentiate from traditional venture investing.

Fiat Ventures

Marcos joined Fiat Ventures with the goal of helping founders and brands make a big difference in the financial services industry. After recognizing his talents lay more in finding visionaries rather than bringing their visions to life, he realized that he didn't have to wait to transition into the venture capital world. He contrasts his previous roles as an “operator” with his current position as an investor, highlighting the differences between the two roles: “In startup mode, you break things, see what works and what doesn't, and then move on. But as an investor, you can't go around breaking things.” This shift required Marcos to develop more robust processes and ensure due diligence in his investment practices, noting the importance of building sustainable investment models.

A New Approach

Unlike traditional venture capitals, Barry states, Fiat Ventures doesn’t jump straight into investment; their approach prioritizes working alongside startups, understanding their market, considering the idea of investment, and only then taking the plunge. Being an amalgamation of venture capital, incubator, and accelerator, they employ a structured five-stage process in developing startups. This process starts with ideation, where the primary focus is on understanding the team dynamics rather than the idea itself. Marcos mentions the value of prolonged collaboration, saying, “It's a long time to be on these journeys together and you need to derisk that somehow.” Barry agrees, noting the importance of having the right team and advisers, stating, “It's the founders who try to keep everything close to their chest and not bring on advisors... they would rather have a smaller slice of a much bigger pie.”

Being Involved Participants

Marcos emphasizes the hands-on, engaged approach that his firm takes when sponsoring deals or taking board positions. He mentions their efforts to systematize the process, making insights and networks more accessible through a repository. Barry acknowledges the value of such a method, noting that businesses now look beyond just capital—they are keen on the full package offered by partners. He cites growth marketing expertise as a pivotal point for assessment and collaboration. Fiat Ventures is committed to supporting startups by providing them with funding and using their connections to help them build relationships in the fintech community and with corporate partners. Marcos elaborates on their extensive networks in the fintech space, which are instrumental in forging partnerships with a wide range of organizations, from large banks to regional credit unions. These relationships, he explains, have become a valuable flywheel for their operations, further boosting their brand's stature. Marcos has a unique perspective on the evolution of fintech. He emphasizes that while the initial wave of fintech involved disrupting financial services, the next phase will be more low-key, operating behind the scenes to offer seamless financial solutions across various industries.

Looking Ahead

Marcos invites founders who are looking to be the next fintech or consumer-focused B2B business to consider partnering with Fiat Ventures.

Read full show notes at BarryO'Reilly.com

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Marcos Fernandez on LinkedIn

Fiat Growth | Ventures

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Casey Ebro is a veteran editor who has significantly contributed to the publishing world. She formerly served as an Executive Editor with the Business Group at McGraw Hill Professional. In this role, she was responsible for acquiring, editing, and publishing business books in various subjects such as leadership, workplace culture, entrepreneurship, and innovation. She has been responsible for bestsellers and notable titles, including “Madoff Talks” by Jim Campbell, which inspired a Netflix documentary series, and the Wall Street Journal bestsellers “Connect First” by Melanie Katzman and “Zero to IPO” by Frederic Kerrest. Casey played a pivotal role at McGraw Hill in establishing the healthcare category into a robust multi-million dollar program, which featured prominent titles like the New York Times Science bestseller “The Digital Doctor” and “The Cleveland Clinic Way”.

Starting Up and Striking Out

Casey’s journey into the world of editing began in her formative years as a passionate bookworm. In high school, she took a significant step toward her publishing dreams by becoming the English editor for her school’s literary publication called “Facets”. She reveled in the collaborative process with other editors and took pleasure in discovering the literary talents of her peers. Her passion further intensified in university, where she joined the literary publication named “Heights”, participating in deeper, more advanced discussions about submitted works. These university experiences exposed her to diverse opinions and debates, making the editing environment incredibly stimulating and enriching for her.

A Book is a Business

“Writing a book is like starting a business,” according to Casey. Authors are entrepreneurs introducing a unique product to the market. In essence, the book is a reflection of the author’s ideas and beliefs, and its promotion doesn’t end post-publication. Some successful books keep selling years or even decades after their release, and this continued success comes from the author’s dedication to the ideas and ensuring they reach as many readers as possible. Publishing a book is a long-term commitment that requires careful execution, planning, and motivation. “A lot of people think about it in terms of the first three months or the first six months or first year or first three years after a book is published. I think that’s really short sighted because if the ideas are good, they’re good from now till kingdom come,” Casey shares. A book, like a product, needs to find its audience, establish product-market fit, and receive investment for growth, Barry agrees. “It never ends.”

Investing in Ideas

Barry and Casey discuss the challenges of book publishing. Barry remarks that the journey isn’t just about having a great idea; it’s about putting in the necessary work to present the idea, penning an entire chapter about it, and then devising a plan on how to maximize its potential. Likening this to the startup experience, Barry notes, “It’s almost like I had to have a pitch deck. What’s the problem I’m solving? Who’s the target customer? What’s my go-to-market plan? How am I going to generate sales and then also write a chapter to exemplify the idea?” Casey comments that selecting a manuscript is similar to venture capitalists choosing a startup to invest in.

Looking Ahead

Casey wants authors to confidently claim their space, believing they are uniquely positioned to address a topic due to their specific experiences, inventions, or groundbreaking insights. This individuality becomes crucial when competing against established names in the industry, given that readers will be investing both money and time in their book.

Read full show notes at BarryOReilly.com

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Casey Ebro on LinkedIn

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Kyle Hermans is the CEO and co-founder of Be Courageous, a globally recognized business consultancy that helps ambitious leaders and brands grow and transform. They do this through improving company culture, strategy, innovation, technology, research, and ESG/SDG. Kyle has led transformation initiatives for hundreds of Fortune 1000 companies and startups throughout his distinguished career. He is a faculty member at Singularity University and a guest lecturer at several prestigious institutions such as Berkeley, USC, and UCLA. Kyle joins Barry O’Reilly to explore the concept of courage, the necessity of unlearning and relearning, and how these ideas have shaped his personal and professional life.

A Long Way From Home

Kyle's father bought him a one-way ticket from his native South Africa to the Netherlands, where he experienced a big culture shock. This was his first encounter with the idea of courage and unlearning. In the Netherlands, everything was different and he had to forget his old ideas about the world. He said, "Everything I ever thought about my reality [was] just gone.” After adjusting to his new life, Kyle got different jobs in business, including consulting and being an executive at design agencies. But he found out that his energetic personality and quick ambition didn't match the usual corporate way of working. This led to his decision to make his own way to fully reach his potential, which he calls his “Schiphol Moment”. This decision led him to his current job at Be Courageous. There, he explores courage, creativity, and transformative leadership in professional situations.

Courage is Creativity

Kyle’s connection to the notion of courage began while working at an innovation agency called Synectics, which heavily influenced the origins of design thinking. He used the quote, “Another word for creativity is courage” in hundreds of workshops around the world. This quote resonated with Kyle, encouraging him to seek out his 'Schiphol moments'—intentionally placing himself in unfamiliar environments to shock the system and trigger growth. “The pursuit of courage is staying humble,” he shares, “I'm not going to get too trapped by the things I've done or be too defined by where I've been.” Kyle believes that everyone harbors an unexpressed idea or dream within them, the pursuit of which demands a great deal of courage, particularly in hostile, difficult, and vulnerable conditions. Showing up to transformative experiences and attempting to effect change within successful organizations is an act of courage in itself, according to Barry, given the immense pressure to conform to pre-existing systems. “Creation is actual courageousness,” he remarks.

Courage Is Not the Absence of Fear

Kyle believes that courage is a quality that everyone can choose to have, not just a mental trait. He says, "Where there is fear, there is courage, and where there is courage, there is fear." He emphasizes that fear and courage are linked, and people often forget that courage can be found when facing fear and self-doubt. He asks, "What's the courage needed in this moment?" Recognizing the courage needed to beat fear is often the start of becoming brave. Kyle talks about being intentional, having a purpose, being curious and open, taking risks, and being selfless. He emphasizes that these qualities come out when people decide to confront their fears and tackle challenges directly. These traits enable people to take responsibility, direct their actions, and embrace the unknown. Most notably, he mentions, "The fastest way to bring courage into your world is to accept what is."

Looking Ahead

Kyle reminds listeners of the bridge between courage and unlearning. “We must unlearn that fear is the only way to design our lives,” and choose to see life through a lens of courage instead, he shares.

Resources

Kyle Hermans on the Web | LinkedIn | Twitter

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Kyle Byrd is a seasoned product strategy and uncertainty leader with a background in industrial design. He was the former Head of Product at Atlassian, where he led the product strategy for Jira Align, a leading enterprise agile planning software. He is also the founder of the Uncertainty Project, a community initiative aimed at exploring decision-making models to manage uncertainty. In this episode of the Unlearn Podcast, Kyle joins Barry O’Reilly to share his unique perspective on embracing uncertainty and problem-solving, drawing from his experiences in transitioning from hardware to software products. He discusses the importance of deep domain expertise and the value of diverse perspectives in decision-making processes.

An Unconventional Foundation

Kyle shares his journey from industrial design to software product management "I'm forever thankful that I got an art degree in college, which was industrial design. It really forces you to unlearn that there is a right answer in a very uncomfortable way," he says. Kyle's unique perspective on problem-solving has shaped his career, leading him to view the world from a "problem to problem perspective" rather than an "answer to answer perspective." This mindset has been instrumental in his work, particularly in his transition from hardware to software, where he found the flexibility to match solutions to problems. His passion for customer engagement and problem-solving was evident during his time at Agile Craft, a startup that was later acquired by Atlassian and transformed into Jira Align, Atlassian's fastest-selling product. "Product management is one of those worlds where it is all about finding problems, finding fixes, unlocking the next problem,” Barry adds, “and it’s an endless iteration of that.”

The Art of Business, Choices, and War

Being deeply invested in a problem is crucial to find its solution, Kyle shares. During his transition from a hardware-focused role to a software-focused one, Kyle found himself becoming "hyper obsessed" with understanding why organizations work the way they do. This obsession led him to spend his weekends reading and learning about organizational structures and decision-making processes. Growing up in a military town and being fascinated by the structure of large organizations like the military, he found that many models and techniques used in business have their roots in military strategies. Concepts like wargaming, scenario planning, and Commander’s Intent have found their way into business strategy and decision-making, particularly in large, complex organizations.

Looking Ahead

Kyle shares his excitement about the future of The Uncertainty Project, particularly in translating the theoretical aspects of decision-making under uncertainty into practical applications that can impact the way people work and make decisions. He encourages listeners to engage with the content on The Uncertainty Project's website and to think about how the concepts discussed can be applied within their own organizations.

Read full show notes at BarryO'Reilly.com

Resources

Kyle Byrd on the Web | LinkedIn

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Wendy Steele is a changemaker and has the honor of being recognized on Forbes’ 50 over 50. She is the founder and CEO of Impact100, a global network of chapters that each raise $100,000 to fund grants for local nonprofits. In the past 20 years, Impact100 has awarded more than $123 million in grants, making it one of the largest women-led philanthropic organizations in the world. In this episode of the Unlearn Podcast, Wendy joins Barry O’Reilly to share her story of how she founded Impact100 and the impact the organization has had on communities around the world. She also discusses the importance of women's leadership and the power of collective action.

The Power of Empathy

The power of empathy and problem-solving is often the driving force behind meaningful innovation. “When you're bothered by a problem and you can't really get it out of your head, I believe that's because you've got some part in solving it,” she tells Barry. Wendy started Impact100 from a place of empathy and a strong urge to address a problem she noticed in her community. As a banker she noticed that many women felt they didn't have enough resources to make a difference in their communities. After documenting these barriers, she started brainstorming solutions, leading to the birth of Impact100, a global nonprofit organization that empowers women to create transformative impacts in their communities. Barry resonates with Wendy's approach, drawing parallels with his own entrepreneurial journey and emphasizing the importance of customer discovery and understanding obstacles to unlock unmet needs.

The Impact100 Model

The innovative, democratic model of Impact100 brings together 100 women from various backgrounds to make significant contributions to their communities. This democratizes the philanthropic experience, Wendy explains. By setting a standard donation amount, each woman, regardless of her economic standing, contributes equally, empowering her with a sense of agency in the decision-making process. Chapters of Impact100 exist across different regions, and although the model is primarily women-centric, some chapters are gender-neutral, further underlining its inclusive nature. Barry remarks on how negative assumptions about individuals and situations can prevent us from exploring new possibilities; Wendy's model offers a refreshing departure from this mindset. The “power of the crowd” is the same approach they are taking to build Nobody Studios, he tells Wendy.

Looking Ahead

Wendy wants to grow and sustain the Impact100 movement. She aims to provide better support to existing Impact100 chapters so they can reach their highest potential, and to facilitate the launch of new chapters in underrepresented communities. She tells Barry, “Impact has always been built on diversity. Diversity of skill set, experience in every demographic definition... But if we rely on people to raise their hands, we're automatically leaving communities out. And so the best thing we can do for Impact100 to really reach its full potential is to have the ability to evangelize, to go into communities, tell the story, and then help women bring this important movement into their own backyards and watch it grow.”

For full show notes, please visit BarryO'Reilly.com

Resources

Wendy Steele on Website | LinkedIn | Twitter | Facebook

Impact100 Global

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Daniel Stillman, an executive coach, and facilitator, is an authority in the field of conversational leadership. With a wealth of experience as a conversation designer and an author, Daniel has dedicated his career to enhancing the way we communicate. His book, Good Talk: How to Design Conversations That Matter, is recognized for its impactful insights into communication dynamics and strategies. In this episode of the Unlearn Podcast, Daniel joins Barry O’Reilly to explore the importance of collaboration and how to create an environment conducive to productive dialogue, particularly in the context of leadership.

Conversational Leadership

Conversational leadership, as defined by Daniel, refers to an approach to leadership that emphasizes the importance of effective communication and dialogue. It relies on the power of conversation to inspire, motivate, and engage individuals or teams in a meaningful and productive manner.

“You cannot have a divergent, emergent and convergent conversation truly all in one go,” Daniel quotes from Chris Ertel’s book, Moments of Impact. “Everybody wants to be in the conversation, and it's not effective if everyone's in the conversation, because everyone can't talk all the time and there's only so much time we can have together.” He explores the mechanics of designing productive meetings, especially in a remote work landscape. He explains that strategic collaboration, hinged on appropriate tools and methods, is integral to making meaningful progress. Barry comments, “This idea of opening, exploring, and closing - it gives people a framework [to have conversations with].”

The Nine P Model

Daniel introduces his holistic Nine P Model of Conversation Design. This includes:

• Purpose (the reason or aim of the conversation),
• Principles (the agreed norms and values to be adhered to),
• Process (the methods or steps to be followed),
• Place (the physical or virtual space where the conversation occurs),
• Pitfalls (potential risks or problems),
• Progress markers (indicators of progress),
• Product or outcome desired (the tangible or intangible results expected from the conversation), and
• People involved (the participants in the conversation), and Potential outcomes (the possible consequences of the conversation).

Link to learn more about the Model is here.

Looking Ahead

Daniel is looking forward to the way collaboration, conversation and AI will intersect to foster more effective communication and goal achievement. He emphasizes the significance of adapting our thought processes, referencing the "Ask/Tell" two by two matrix (more on that here) and 'triple loop learning' (more on that here) as valuable tools for changing how we approach problem-solving and action. Daniel views AI as an assistive component that can enhance our conversations and relationships.

Resources

Daniel Stillman on the Web | LinkedIn | Twitter

Read full show notes at BarryO'Reilly.com

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Diana Kander is a keynote speaker, bestselling author, and a vanguard when it comes to memorable pitches. She is the author of Go Big or Go Home, a book that teaches readers the art and science of making impactful pitches for film, sports, business, and philanthropy. Her pioneering research reveals the direct correlation between emotion and memory, offering insights into enhancing audience engagement and recall. In this episode of the Unlearn Podcast, Diana joins Barry O’Reilly in a thought-provoking conversation about making presentations more engaging and memorable. They unpack the concept of co-creation in presentations and provide real-world examples of successful pitches that involve audience participation.

Go Big or Go Home

Diana shares the genesis of her book Go Big or Go Home, shedding light on her journey into the world of memorable pitches. "I was approached by the CEO of a company who was struggling to keep his audience engaged during presentations. This triggered my exploration," she recalls. The CEO's predicament posed a compelling challenge for Diana, propelling her investigative journey into what makes pitches memorable. This challenge was a catalyst for her bestselling book. She researched the real-life struggles of professionals to create an impact with their pitches. The result was a book that unveiled the secrets behind delivering pitches that are not just heard, but remembered.

Creating Emotional Resonance

"Connecting emotionally helps the audience remember your message long after the presentation is over," Diana tells Barry. Her research unveiled five tools needed to create emotional resonance in presentations:

• The element of surprise keeps the audience engaged and alert.
• Analysis helps the audience to understand and connect with the data or information being presented.
• The pitch order, or how the information is arranged, can evoke different emotional responses.
• Using 3D objects during presentations provides a tangible element that can make the pitch more memorable.
• Co-creation involves the audience in the presentation or problem-solving process, creating a sense of ownership and engagement among them.

By using these tools, Diana believes presenters can create a deep emotional resonance with their audience that outlasts the presentation itself.

Co-creation: Including the Audience

Co-creation is a strategic tool in presentations where the presenter involves the audience in the process of problem-solving or idea generation. Rather than being passive recipients of information, the audience actively participates in the creation process. Diana views co-creation as a pivotal tool in the success of a presentation. She states, "Co-creation is not just about soliciting input from the audience; it's about immersing them in the process. This participatory approach creates a sense of ownership among the audience, enhancing their connection with the material and, ultimately, the presenter." Co-creation transforms the conventional presentation dynamic into a shared journey. "Involving the audience in problem-solving can create a mutual sense of accomplishment. This shared ownership is an essential part of engagement and retention," Barry remarks.

Looking Ahead

Diana also announces a free digital copy of her book to anyone who reaches out via email.

Read full show notes at BarryO'Reilly.com

Resources

Diana Kander on the Web | LinkedIn | Twitter

Go Big or Go Home

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Diana Kander is a keynote speaker, bestselling author, and a vanguard when it comes to memorable pitches. She is the author of Go Big or Go Home, a book that teaches readers the art and science of making impactful pitches for film, sports, business, and philanthropy. Her pioneering research reveals the direct correlation between emotion and memory, offering insights into enhancing audience engagement and recall. In this episode of the Unlearn Podcast, Diana joins Barry O’Reilly in a thought-provoking conversation about making presentations more engaging and memorable. They unpack the concept of co-creation in presentations and provide real-world examples of successful pitches that involve audience participation. 

Go Big or Go Home Diana shares the genesis of her book Go Big or Go Home, shedding light on her journey into the world of memorable pitches. "I was approached by the CEO of a company who was struggling to keep his audience engaged during presentations. This triggered my exploration," she recalls. The CEO's predicament posed a compelling challenge for Diana, propelling her investigative journey into what makes pitches memorable. This challenge was a catalyst for her bestselling book. She researched the real-life struggles of professionals to create an impact with their pitches. The result was a book that unveiled the secrets behind delivering pitches that are not just heard, but remembered.

Creating Emotional Resonance "Connecting emotionally helps the audience remember your message long after the presentation is over," Diana tells Barry. Her research unveiled five tools needed to create emotional resonance in presentations: 

The element of surprise keeps the audience engaged and alert. 

Analysis helps the audience to understand and connect with the data or information being presented. 

The pitch order, or how the information is arranged, can evoke different emotional responses. 

Using 3D objects during presentations provides a tangible element that can make the pitch more memorable. 

Co-creation involves the audience in the presentation or problem-solving process, creating a sense of ownership and engagement among them. 

By using these tools, Diana believes presenters can create a deep emotional resonance with their audience that outlasts the presentation itself.

Co-creation: Including the Audience Co-creation is a strategic tool in presentations where the presenter involves the audience in the process of problem-solving or idea generation. Rather than being passive recipients of information, the audience actively participates in the creation process. Diana views co-creation as a pivotal tool in the success of a presentation. She states, "Co-creation is not just about soliciting input from the audience; it's about immersing them in the process. This participatory approach creates a sense of ownership among the audience, enhancing their connection with the material and, ultimately, the presenter." Co-creation transforms the conventional presentation dynamic into a shared journey. "Involving the audience in problem-solving can create a mutual sense of accomplishment. This shared ownership is an essential part of engagement and retention," Barry remarks.

Looking Ahead Diana also announces a free digital copy of her book to anyone who reaches out via email.

Read full show notes at BarryO'Reilly.com

Resources Diana Kander on the Web | LinkedIn | Twitter Go Big or Go Home

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Victor Chima and Boina Babu are the founders of LearnCrunch, business partners, and former co-workers at Spotify. LearnCrunch is a live cohort-based interactive learning platform that helps tech professionals learn business-critical skills they can apply on the job to increase their impact. Both Boina and Victor are continuous learners, working in data and other industries to build the best learning experience for tech professionals. In this episode of Unlearn, Boina and Victor discuss upskilling with Barry O’Reilly, sharing the importance of learning and why companies need to actively facilitate it on the job.

LearnCrunch: Origins Victor shares how LearnCrunch came to be. After realizing he felt the most fulfilled helping other people grow on the job, he ventured into management to continue doing it at a larger scale. Empowering people was something he was good at and loved doing, so he considered how to maximize this skill and passion. Over drinks, Victor and Boina commiserated over the difficulty of transferring knowledge from one person to another, and thus MentorColor was born. This platform allowed them to connect professionals with mentors from top companies. But that only solved part of the problem, Victor says. The resources for learning were accessible, but that didn’t make the learning experience magically easy. The next challenge was knowing what resources to use, where to find them, and which ones to trust. “We decided to help people get through the noise and focus on the things that actually matter,” Victor explains.

Building MentorColor  Barry asks Victor and Boina to share some things they unlearned while transitioning from Spotify to MentorColor, and then to LearnCrunch. “For a lot of the things we did at MentorColor, we had already done them at Spotify,” Victor replies. One such thing involved hiring. When it comes to getting access to opportunities and knowledge, people are often penalized by being in the “wrong” geography. This is something Victor is intimately familiar with, being from Nigeria, so he made it a point to attract as much talent as he could from around the world.

Making the Leap Everything remains a side project until you start giving it 100% of your focus, Victor says. MentorColor was a side project, but LearnCrunch is their obsession. What they do in a month at LearnCrunch was a year’s worth of work at MentoColor. “We thought to ourselves, ‘We either get serious with this or not; we can’t know if it's working the way we want it to work unless we're giving it everything that we can,’” he shares.

No Man is an Island “We wouldn’t have a platform if we didn’t have the relationships we do,” Victor remarks. He sees LearnCrunch as a two-way street; everyone is there to support each other, to align interests and solve a problem together. Victor talks about the importance of learning. “How do you create an environment where we can ensure that people get the learning outcomes they want?” Companies tend to solve this problem by hiring new people; they don’t facilitate learning, so the current talent pool just keeps working based on the knowledge they had previously. Then, the companies complain about a lack of talent. “What about upscaling those that are there? Sometimes, they need [the company’s] support to do it because they're very focused on execution.”

Looking Ahead What’s exciting to look forward to is that it’s a new market, Boina says.”We’re working on something that is big enough to be passionate about, to be focused on.” He is very motivated by the fact that they will be connecting people to awesome instructors like Barry and impacting their lives in monumental ways.

Read full show notes at BarryO'Reilly.com

Resources LearnCrunch MentorColor Victor Chima on LinkedIn  Boina Babu on LinkedIn

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Sharena Rice is a neuroscientist, cybernetician, and storyteller. As an advisor and consultant to startups, she works at the intersection of artificial intelligence and natural intelligence, and health and wellness. Her life’s goal is to take as much suffering in as she can in this lifetime and invert it. Focused on her health and wellness domain, Sharena helps Nobody Studios through her background knowledge of biomedicine and startup skills. In this episode of Unlearn, Sharena shares her experience as a systems neuroscientist and how it has helped her in life. She and Barry O’Reilly discuss the importance and benefits of trying hard things, and debunk some misconceptions about cybernetics.

Getting Good at Failing Doing hard things forces you to get out of your comfort zone. As a self-described former high school band geek, Sharena shares that music, especially jazz, teaches you a lot about experimentation and improvisation. In trying things that are initially hard, you put yourself in the position to be uncomfortable. By consistently doing this, you slowly get acclimated to practice and failing, which progressively grows your capabilities. It also has the added benefit of reducing your levels of self-consciousness. “Success and failure are just feedback mechanisms,” Sharena claims. They tell you if you’re going in the right direction or if you need course-correcting. “You have to keep attempting as you go through that process, rather than getting caught up in how successful you are, or how you failed.”

The Career Crossroads Barry asks Sharena about her diverse career and how she got started. Sharena majored in biochemistry and double minored in philosophy and psychology in undergrad, but she didn’t feel as if she belonged in just one of those three boxes. There were elements of all fields that spoke to her, and she found herself conflicted on what path she should take. After linking them all together, she realized the common thread they all shared had something to do with the mind. Neuroscience was the perfect mix. She discovered, with the help of her advisor in grad school, that she was a systems neuroscientist. And from there, she found another passion in cybernetics.

Tech for Situational Understanding Sharena debunks some misconceptions about what makes for good technology. Most people think of artificial intelligence and machine learning when they hear of cybernetic technologies - humanizing technology, to be specific. Rather than making technology human, it may be best to make technology that has great situational understanding so it can be great at solving the problems it encounters.

Finding the Next Right Thing Barry asks Sharena to disclose some tips for figuring out the next step. “[My] biggest thing is [my] orientation towards figuring out how to make the biggest positive impact in this lifetime,” she responds. “How do I take as much suffering as possible and invert it? That’s a different equation than if someone were to ask how they can help people in a certain domain.” Rather, it’s a big and overarching goal.

Looking Ahead Sharena is currently working as a research scientist for a public benefit corporation in medical technology.

Read full show notes at BarryO'Reilly.com

Resources Sharena Rice on the Web | LinkedIn | Twitter

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Min Bhogaita is Managing Director of the IdeaLab at Nobody Studios. Since leaving Deloitte, where he worked for 25 years, Min has helped over 14 startups and scaleups grow, pivot, and connect. He also serves as an advisory board member and director for multiple organizations. In this episode of Unlearn, Min shares his experience in the corporate world, and he and Barry O’Reilly emphasize the importance of staying true to yourself. They also discuss how technology is changing the way we work and how startups can benefit from this change.

Balancing Introversion with Leadership Min admits to struggling with speaking up. During his school days, his teachers would talk about how quiet he was in class and his aversion to speaking unless spoken to. This was something he had to unlearn when breaking into the corporate world. “I was fortunate in the leaders I worked for - they knew my style, so they would coach me,” he shares. They would intentionally create opportunities for Min to share his ideas and opinions, which gradually taught him to come out of his shell and learn that behavior. “If you can recognize that there are behaviors you need to change, [you should change them].” In a serendipitous turn of fate, it was when he was learning to speak up that Min got to start his own team.

Building Confidence Barry asks Min about his leadership experience in various fields. One of the traits Min developed was confidence in himself every time he changed a role. Min admits that he was actually a novice when he transitioned from ethical hacking to forensics. A recruiter’s recommendation that he’d be good in the field inspired him to go into it. “Just because he believed in me, I [went for it],” he tells Barry. “Thirteen years later, I was still in that role and doing the world’s biggest fraud investigations.”

Protecting Your Team If you don’t have the right environment, people are going to burn out. This was made evident during the pandemic, but it was true even before then. Min talks about protecting his team to prevent that burnout. “Sometimes [we’d get] a deadline, and I’d push back.” If a deadline was Friday, but the document review was Tuesday, he’d request that submission be moved to late Monday to prevent his team having to work through the weekend. If you’re always pounding your team, he adds, they’re not going to do their best work.

Reinventing Min Min talks about his decision to move on from consulting. After having worked in the field for 25 years, he thought it was now or never; he was either going to do it until he retired, or he would reinvent himself again. He was doing more work with founders and startups in the analytics lab, and grew more and more attracted to the practicality of their work. When he left consulting, his network started buzzing. People were reaching out to him, asking him to help them open the door - which, coincidentally, was his open door to new work. “I’ve made more of a living out of who I know as opposed to what I know,” he jokes.

Looking Ahead Min’s dream is to have IdeaLabs for Nobody Studios around the world, where people can come in, share their ideas, and get started.

Read full show notes at BarryO'Reilly.com

Resources Min Bhogaita on LinkedIn | Twitter

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Bobby Soper is former president & CEO of Mohegan Sun, and current president & CEO of Sun Gaming & Hospitality. Initially beginning his career in law, Bobby moved into the role of CEO where he had the opportunity to lead an incredible operation. Through mentorship guidance, he learned how to lead great teams. Today, Bobby is the Investor and Chairman of the Hospitality Board at Nobody Studios, helping to build companies that will innovate and disrupt the future. In this episode of Unlearn, Bobby and Barry O’Reilly explore mentorship guidance, servant leadership, and the gaming industry. 

The Role of a Mentee Bobby attributes much of his growth and success to having a great mentor. Bill Gallardo was an exemplary role model who taught him, through demonstration, the importance of respect, humility, relationships, and hard work. Bobby shares how he cultivated that relationship and talks about the role of a mentee. “Sometimes people feel like they can reach out to anyone and hopefully ask them to be a mentor, but what you're talking about is putting yourself out there, doing hard work and demonstrating excellence,” Barry comments. Through that effort, more opportunities will come. 

How Mentorship Actually Works  Mentorship is more organic than approaching someone you admire and asking them to mentor you, Bobby shares. A better approach would be to ask if you can shadow them for a day. You’ll learn more from working with them and observing how they do things than sitting with them for coffee hoping to download all their esteemed knowledge. “The measurement of my success is based on how well [the people I work with or who report to me] succeed,” he adds. “I’m very fortunate because a lot of the folks I hired… have grown and become very successful as their own CEOs. To me, that is the best measurement of my success, not how much money I make or my job title.”

Being a Good Leader As general counsel for Mohegan Sun, Bobby’s responsibilities involved managing people. What that role taught him was that everything comes down to relationships. The most valuable education comes from being in the trenches with the ground floor workers. It teaches you how to understand people, respect them, and show them that you aren’t above them.

Technology as a Leveraging Agent Bobby discusses what led to his advocacy for using technology to leverage customer experience. The gaming industry is young, starting in the 70s and becoming more prolific in the last 3 decades. The demand for casino gaming has existed for hundreds of years, but there wasn’t always a supply. The old adage of “if you build it, they will come” applied to the gaming industry significantly, due to the supply-demand imbalance. The problem with that, Bobby tells Barry, is that it wasn’t a competitive environment. Without competition, there’s no need for innovation. Now, the industry has matured and innovation is starting to pick up. However, some gaps remain.

Looking Ahead Bobby believes digital is the future. When you look beyond Generation X, the customers are mostly online, and the gaming industry has to adapt. In addition, the digital systems in the hospitality industry need innovation and improvement.

Read full show notes at BarryO'Reilly.com

Resources Bobby Soper on LinkedIn

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Jason and Gareth Edge are co-founders of ThoughtForma, the intelligent no-code platform with a mission to help people unlock and realize their purposeful ideas. As CTO and CEO respectively, they aim to break the barriers to entry that technology itself often represents, and obliterate the obstacles to creativity and enterprise in the digital space. Both brothers are VPs of Technology at Nobody Studios. In this episode of Unlearn, Jason and Gareth share their story with Barry O’Reilly, discussing how they built their company and obstacles they faced in the technology space.

How It Started Gareth shares the inspiration behind ThoughtForma. Building software is a hard thing to do and people - both individuals and organizations - often struggle during the process. Even with a team of skilled technologists with great track records, it’s still difficult to deliver robust solutions. Coupled with a shortage of technical skills, this leads to many projects never seeing the light of day. “That’s [what] puts a fire in my belly,” Gareth says, “this notion of ideas staying locked in people’s heads is completely unacceptable to me.”

A Pleasant Coincidence Gareth pitched the idea to his brother Jason, who happened to be working on something related. “I was able to dovetail into his vision and we came up with the ideal, no-code platform, which is our answer to the Al Gore problem,” Jason explains. He approached building the platform via an unconventional route, as he had been working for a consultancy specializing in the implementation of Master Data Management Systems. He was hitting some walls in implementing these systems. Jason started thinking about how he could capture the data he wanted without having to rebuild and redesign, and how he could put such a tool in the hands of consultants so they wouldn’t have to rely on people to build things for them. “It turns out that the ideas I came up with were so flexible that you can actually apply them to describe and manage anything, even all the ingredients of a web or mobile application. That realization became the underpinnings of where we are today,” he shares.

Startup Land It doesn’t matter how good you think your product is - you won’t escape Startup Land, Gareth advises. “I feel fortunate that I was so naive from the start,” he tells Barry. “I fell into the trap of the field of dreams. ‘If we build it, the users are going to come. Why wouldn’t they?’ That was the first unlearning for me.” They faced many hurdles in building the platform and the company. Scarcity of capital was one issue, as was the realization that they were lacking many skills. “How important marketing is, how important financial planning, how to build companies, how to build startups - it [was] all a massive learning curve.”

No-code, Serverless Technology Jason describes how they got around technical debt. In the software space, technical debt refers to an issue in development where you gradually create a problem you’ll later have to solve. Jason got around that by using templates to write the system, rather than manually rewriting everything. This way, if he wanted to make significant changes in architectural approach, he could just change the templates and regenerate the system.

Looking Ahead Jason and Gareth are launching a new pattern matching and recognition feature in the near future. “[This] is a key point in our growth story because that now… allows [our users] to self-service so that if they hit upon a feature that ThoughtForma doesn't currently support codelessly, they can build it themselves, and then share that back into the community.”

Read full show notes at BarryO'Reilly.com

Resources Gareth Edge on LinkedIn Jason Edge on LinkedIn | Twitter  ThoughtForma

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Ray Leonard Jr is co-founder of Nobody Studios and CEO of Ovationz, the premier talent marketplace allowing SMEs, artists, speakers and athletes to monetize their time and skills effortlessly. The son of legendary boxer ‘Sugar’ Ray Leonard, and a two-sport divisional collegiate athlete, Ray founded and sold his own sports agency, going on to become one of the great coaches, mentors and trainers for others looking to try and build businesses. His high energy and penchant for leadership drew him to the world of motivational speaking, where he is now one of the most in-demand speakers throughout the globe. In this episode of Unlearn, Ray and Barry O’Reilly explore the lessons he learned throughout his personal and professional journey. 

Growing Up and Out Appreciating the diversity of the world was something Ray was privileged to experience growing up. Traveling around and meeting people from different cultures, backgrounds, and socioeconomic levels transformed his life in many ways, teaching him how to be a good-hearted person, friend, and business person. One of the little moments that helped shape him as a person happened early on in his life. He remembers his grandfather’s advice to this day: always remain humble, because success can be temporary; when better, you do better; and don’t live life with your foot on the accelerator - sometimes you have to slow down and pay attention to the small things that matter.

Making His Way Naivete paved the way to clearing his own path about what he wanted to achieve, Ray confesses. “I never believed I should be in anyone's shadow.” Even with all his successes, during high school and after in his professional life, it never felt like it was enough. He knew he had so much more to give after selling and exiting his sports agency, so he went back to the drawing board. His curiosity about money led him to the financial sector. Throughout this journey he experienced soaring highs and humbling lows, and though the lessons took a little time to stick, he came out of it wiser and more experienced, ready for life’s next challenge.

Ray’s Next Big Move Ray’s first foray into motivational speaking came at the request of his business partner at the time. A military veteran, she had asked him to speak to the Navy base, as he had been doing some coaching for his kids and her kids. At first, he was reluctant - he wasn’t a public speaker, so why would he? Sure, he had some resonance with the kids when he spoke, but those were kids. Despite his concerns, he went down to the base and spoke. Then he was invited to speak again. After his second time, they offered to pay him. “I said ‘oh, that’s a thing,’” Ray tells Barry. This snowballed into ten years of traveling across the world speaking to militaries and corporations about his experiences.

Sometimes, You Have to Hit the Brakes “A lot of times I would run so fast because I thought I had to be somewhere at a certain time, on my time,” Ray tells Barry. Life has a way of telling you that sometimes it moves on its own time. No matter how fast you think you have to move, you’re going to miss some things if you don’t slow down to appreciate them. “The greatest thing about being present in the moment to tell your story is knowing there’s more to write. You don’t take a book and skip the pages - you have to read every page to get the full context.” That’s where Ray is right now, he shares.

Looking Ahead “We’re on the precipice of building something that not only connects people but builds a more prosperous world. It makes you want to get up every single morning to create and not worry about everything that distracts you,” Ray shares.

Read full show notes at BarryO'Reilly.com

Resources Ray Leonard Jr on the Web | LinkedIn | Twitter  Nobody Studios

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Bryce Hoffman is a bestselling author, speaker, and unconsultant who believes that individuals have the power to transform companies and cultures through great leadership and applied critical thinking. He is one of the world’s foremost experts in decision-support red teaming, a revolutionary methodology inspired by the US military and intelligence agencies to help leaders make better decisions in today's complex and rapidly changing world. In this episode of Unlearn, Bryce and Barry O’Reilly explore red team thinking, contrarian techniques and what you can learn from failure.

Getting Started Bryce describes his experience writing his first book, American Icon. One day, after sending the meatier chapters to his editor, they called him and encouraged him to think about what consultant practice he would launch along with the book release. “I said, ‘What? I’m trying to get this book finished, what are you talking about? I’m not a consultant,’” Bryce shares. His editor believed people would be flocking to Bryce for help in implementing the ideas from his book, but he was of the opposite opinion. He just wanted to tell a story. True to his editor’s predictions, however, calls came in from left to right when the book launched.

Red Team Thinking Bryce defines red team thinking. “[It’s] a cognitive capability that helps individuals and organizations engage in critical thinking, enable distributed decision making, and most importantly, encourage diversity of thought.” These things all come together to help people make decisions faster in the complex world we live in today. He continues, “I discovered this concept called red team decision-support that had been developed by the military and intelligence community after 9/11… that became the top of my second book.” He took the tools and techniques for the high-stakes world of military and intelligence, and imported those ideas to help business leaders apply the same approach.

Contrarian Techniques Red Team Thinking has a group of tools called contrarian techniques, designed to challenge the plan you’ve developed and force you to come up with different options. It’s been scientifically proven that humans tend to work on a problem until they find the first viable solution and then execute that. The problem with that, Bryce explains, is that the best solution might not actually be the first one that comes to you, and because you’ve stopped there, you’ve missed the opportunity that the other one presents. “Some people say ‘I don’t have time for that.’ It’s not a matter of time, it’s a matter of perspective,” he advises.

Learning from Failure In the corporate world, people only do things they’re confident in, Barry claims. They don’t take risks, and are afraid to be wrong because they are wary of the treatment they will receive. He finds that in innovative companies, though they may not know all the answers, they have systems in place to figure them out. They try things - some things work, and some don’t, and they use both pieces of information to take another chance and try something differently. “If you don’t have the ability to fail, you’re never going to take the risks that are required to have real innovation,” Bryce adds. Good companies are good at letting their R&D teams do this, but very few companies let their leaders do this.

Looking Ahead Red Team Thinking is working with federal fire agencies in the United States National Park Service US Forest Service, teaching them how to use their tools and techniques to make life and death decisions on the fire line about where to deploy resources and how to work together effectively with different agencies.

Read full show notes at BarryO'Reilly.com

Resources Bryce Hoffman on the Web | LinkedIn | Twitter Red Team Thinking

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Becky Flint is founder and CEO of Dragonboat, the responsive portfolio platform for product teams to build products customers love and deliver business results. In her career Becky has built and scaled portfolio management at Shutterfly, Feedzai and BigCommerce. She is an expert in managing ProductOps portfolios with an outcome-focused approach. In this episode of Unlearn, she and Barry O’Reilly discuss how Dragonboat is changing the game in portfolio management, and why you should make the shift to become outcome-focused.

Finding Her Way Becky’s entrepreneurial journey wasn’t linear. She moved to the US with a medical background to study business, then went on to do tech, until she finally found her calling in product. She founded Dragonboat by piecing together the best bits of her experiences in these industries. One of the things that emboldened her to step out her comfort zone and go into completely different domains was her confidence in her ability to learn new things. Becky believed she could build on top of the skills she already had and learn what she didn’t know. It was better than starting from zero, with no skills, knowledge or experience to speak of, she shares.

Building Dragonboat The development of the portfolio management at PayPal was originally a connect-the-dots for certain systems, according to Becky. Data revealed business outcomes, product strategy and execution, and resourcing weren’t properly communicating, so Becky created a middle engine to put all the messy stuff together. Barry remarks, “Even a few hours ago, I was in a session with some teams… and you could see that people were struggling because sometimes their corporate strategy just feels so far removed from their day-to-day work.” Becky’s “phenomenal” portfolio management makes a typically difficult process significantly easier.

Outcomes Over Outputs One of the biggest debates in the product management industry currently is the notion of becoming more outcome-focused, Barry comments. However, not only is it difficult, but it’s also a huge change in the way people manage their work. Most people are primarily focused on output-based measures of success, such as being on time and being on budget. Becky describes some of the growing pains she experienced in helping people shift their mindsets. “Output focus really came from the industry era… the executive would make all the calls, and the team would just do what they were told, but then we realized the executive doesn’t know everything, they don’t have the latest information, so they have to rely on the team to stay competitive,” she explains.

Making the Decision to Make a Decision Every time you make a decision, you must consider the upside, the limiting factor of time, and the resources you have available. “Not making a decision means you already failed,” Becky advises. “You definitely don't have resources for all of them. If you want to do all of them and you don’t have the resources, everything will take forever and you won’t get any outcomes.”

Looking Ahead “What I'm most excited to see really is the trend moving from the output-focused command and control to the outcome-focused empowerment,” Becky notes. “I really believe you need alignment to be able to empower your team. Alignment and autonomy need to come together, so not too much control or the chaos of no control.”

Read full show notes at BarryO'Reilly.com

Resources Becky Flint on the Web | LinkedIn | Twitter

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Katelyn Bourgoin is a marketer by trade and founder by choice. She is CEO and Lead Trainer of Customer Camp, where she helps teams make smarter marketing decisions with buyer psychology. A marketing powerhouse, Katelyn has been nicknamed “The Customer Whisperer,” and called an “influential entrepreneur” by Forbes; she is also one of the Top 20 Wonder Women of SaaS Marketing and Growth. In this episode of Unlearn, she and Barry O’Reilly discuss her customer discovery journey and where she found breakthroughs where others have struggled.

Effective Customer Discovery After a brief, failed venture into making a tech company, Katelyn discovered something about customer discovery she previously misunderstood. She knew the importance of understanding and targeting your audience, but was left stumped when she did things as she was supposed to and achieved poor results. She underestimated the true value of market research, and tried selling a solution at the start, instead of starting with the customers’ needs and working backwards to the solution.

Job to be Done (JTBD) Your ideal customer profile shouldn’t be based solely on demographics, but on the job your customers need your product or service to help them perform. Katelyn learned the Jobs-to-be-Done (JTBD) philosophy at a webinar by Forget the Funnel and it has influenced her approach to marketing ever since. Essentially, JTBD posits that people hire products and services to help them get a job done. They will continue to use that product for as long as it fulfills their needs and circumstances, and helps them move closer to where and who they want to be. “People don’t buy products and services willy-nilly,” Katelyn explains. “...We actually have a job we’re trying to get done.” Once that solution stops working, they will find a new one.

The Buyer Journey Interview Integrating JTBD into buyer journey interviews -also called switch interviews - is the next step in elevating your market research. Katelyn’s mentor Bob Moesta was the one to make this discovery, and it happened by accident. Due to his dyslexia, Bob would draw a timeline of his clients’ stories instead of jotting down notes since this visual method was more effective for him. While drawing these images, it hit him like a brick: customer researchers were doing interviews all wrong. They had a siloed approach to solving customer problems, focusing on a specific issue under specific circumstances rather than getting the full picture of what led a customer to them in the first place.

Who Are Your True Competitors? Katelyn talks about April Dunford’s exercise to understand who your real competitors are, and what the real job to be done is. If your product didn’t exist, what alternative solutions would people use? What are they using right now, if not your direct competitor’s products? Getting into the layers of who your real competition is and deeply understanding the job being done helps you see your solution in an innovative way, Katelyn shares. ConvertKit is one company that is successful at this: they don’t see themselves as email marketing software, but as a platform that helps creators make a living creating. Their concierge service and their recent sponsor network program demonstrate their mission, and sets them apart from other email service providers.

Looking Ahead In following her dream scenario of building a scalable business that doesn’t require too much of her time, Katelyn is building out her newsletter, Why We Buy, into a media company. She has halted her consulting work to focus on this new venture, which she is doing with an amazing team of contractors as opposed to individual employees.

Read full show notes at BarryO'Reilly.com

Resources Katelyn Bourgoin on the Web | LinkedIn | Twitter Customer Camp

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Shawn Flynn started his career in Beijing, China, by founding, scaling, and successfully exiting a company. He is now the Principal of a premier middle market investment bank specializing in mergers and acquisitions, capital markets, financial restructuring, and valuation. In this episode of Unlearn, he and Barry O’Reilly talk about acquisitions and exiting. 

Intro to investment banking Unlike most people in the profession, Shawn did not have an undergrad economics degree, MBA, or a jam-packed resume. He was overseas for roughly 8 years after graduating from college with a mechanical engineering degree, seizing the opportunity to travel to Costa Rica, China, Europe, and back to China, where he started a few companies. One of them did well, and the others were learning experiences. After returning to the States in 2013, he got a job as an account executive for a company that unfortunately folded, but through that experience, he was able to meet and network with many angel investors and one group who eventually took him under their wing. He became the investment director for the second oldest angel group in Silicon Valley.

Debunking misconceptions The real work in investment banking is client-facing - keeping conversations and engagement going, making people feel comfortable, and asking the necessary questions so there’s no skeletons in the closet about the company. “The people skill is so huge in this line of work and I had no idea going into it,” Shawn confesses. “I thought if you were good at Excel, you’re a good investment banker, but in reality anyone can do that. The real skill is finding the deals, being able to build that rapport and keep everyone engaged through the entire process.”

Open door policies When planning an exit, you actually want employees to not have heard from you or contact you with urgent news in months. That’s a sign that things can and are operating smoothly without you - exactly what you need when exiting. Everyone knows their KPIs, the systems they’re running and how to get there, and what they’re doing every quarter. You want the people at the top to be able to go for vacation any time they want and not have the company destroy itself.

Time is of the essence Time kills all deals, Barry says. At Nobody Studios, they value getting things done in a timely fashion. The number one deal killer is time. Stall too long, and you are very likely to lose the deal altogether. Anything can happen, Shawn comments, so when you’re in the marketing phase, the prime time for closing a deal is while all parties, (the buyer and the seller) are still excited.

An emotional process Having an outside advisor during the selling process is invaluable because they prepare you for everything - and preparation is something you will need, as exiting tends to be quite emotional. Building a company can consume much of your life, and letting go can get complicated, even when selling has been the plan all along. When potential acquirers come asking questions and trying to understand some of the decisions you’ve made, it’s easy to feel like they’re attacking you. Then, when it’s time to go out to market and you get no response after a few days, it’s disheartening.

Looking forward Shawn is looking forward to resuming in-person events, like the half-day summit he held recently. He’s also excited about collaborating with foreign companies interested in setting up operations in the US. “People have had all these dreams built up for the last 2 years, and now they’re sharing them with the world and saying ‘I gotta catch up on 2 years of stuff, let’s move fast,’” he adds.

Please visit BarryO'Reilly.com for full show notes.

Resources  Shawn Flynn at Twitter | LinkedIn The Silicon Valley Podcast

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Kaspar von Grünberg has extensive experience running software companies. His current role is founder and CEO of Humanitec, a product that enables companies to build internal developer platforms using their Platform Orchestrator. It enables platform engineers to build golden paths that developers love and standardizes app and infra configs by design. In this episode of Unlearn, he and Barry O’Reilly discuss becoming world class.

Becoming World Class  “I'm telling everybody who works with me: you don't have to be world class today, but you have to know, ‘What is my relative position to elite status?’" Kaspar believes that everyone can fulfill their highest potential, and that a leader’s job is to facilitate this. His father’s early advice about choosing the right advisors directly influenced his approach to leadership. He tells Barry, "There is a lot you have to learn and you have to learn that really fast." As such, having the right mentors is crucial.

Finding Problem-Mentor Fit Mentorship is a powerful way to bolster your company’s growth, Kaspar and Barry agree. Kaspar’s experience over the years has shown that there’s a correlation between professional maturity and effective problem-solving skills. He also observed that senior and junior personnel approach problem solving differently: senior staff members usually start inquiry with basic questions before delving deeper to find answers to urgent problems. This is the model he wants all his employees to adopt, and mentorship is an effective way to make this happen. That’s why he looks for humility and coachability when hiring new talent.

Why Internal Developer Platforms Are the Future Kaspar goes on explaining why he is so passionate about platform engineering and enabling engineering organizations to build Internal Developer Platforms. Kaspar’s experience in building software teams from the ground up several times ultimately made him understand that many of the industry challenges had psychological underpinnings. Some of these included monopolizing key projects and domains, which left businesses without knowledge when personnel left, along with concerns with abstraction. His observations were guided by the following questions: 

How can you reduce cognitive load so that developers can actually focus on the business logic? 

How can you design systems that drive standardization by design?

Convincing Teams of the Value of Standardization Kaspar points out that the fear of standardization and abstraction is too often the underlying fear of being “optimized away.” He points out that this is ultimately a job of culture and communication to take this fear away. “If you don't believe that doing something faster will yield 10% more, then you don't believe in personal growth and in growth of your company,” Kaspar argues. Similarly, he believes leaders should unlearn ideas about abstraction. “Intelligent opaque abstraction that doesn't go at the expense of context, is actually a good thing for your career,” he points out. This applies to software as it applies to anything else we do. Yet if you standardize and abstract you can never do so at the expense of context.

Looking forward Kaspar thinks platform engineering is here to stay. Every team with more than 50 developers will have a platform team by 2025. Humanitec’s Platform Orchestrator will be at the core of the Internal Developer Platforms built by these teams. His ongoing passion is the platform engineering community. “Every single day I have people reaching out and contributing and sharing ideas,” he says. “I hope that is something that continues in the end.”

Read full show notes at BarryO'Reilly.com

Resources  Kaspar von Grünberg at Twitter | LinkedIn Humanitec

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On this episode of the Unlearn Podcast, Barry O'Reilly chats with Brian Elliott, Senior Vice President at Slack and Executive Leader of the Future Forum, who also served as an Executive Product Leader at Google. Having observed Brian’s work, Barry says, “I was constantly inspired by the work Brian and his team were doing in the Future Forum, researching challenges about the future of work.” Brian and his co-authors, Sheela Subramanian and Helen Kupp, have encapsulated the findings of the forum - as well as the lessons they learned through their own experiences - in their new book, How the Future Works.

From Arrogance to Transparency Brian discusses how his perception of management evolved as his career developed. "I learned a phrase early in my profession that states ‘Seldom wrong, never in doubt’... a sort of arrogance," he recalls. He rejected his initial arrogance in the wake of Maria De Leon’s advice and observation, and realized that the greatest way to foster camaraderie and a sense of common purpose is to be open about the company's future, aspirations, and financial path. “Transparency actually creates trust,” Barry comments, “...it helps people gain clarity of what is actually happening.” Being the one with all the answers is not conducive to a healthy workplace culture, both men agree. 

The Future Forum Brian joined Slack five years ago and was immediately intrigued by the company's research team, which later became the driving force behind the Future Forum. The research-based consortium focuses on creating a better future of work that is flexible, inclusive and connected through quarterly employee experience surveys and executive working groups. Since the issues are multidisciplinary, they survey 10,000 knowledge workers from all around the world. Leaders from multiple sectors are encouraged to experiment with these solutions to champion global change.

Debunking the Myths Brian debunks five major myths about the workplace, using research from his book, How the Future Works. These include:

Return-to-Office Mandates: Top-down policies for returning to the office are a one-size-fits-all approach that ignores that each team may have a different rhythm.

Brainstorming: The whiteboard is an antiquated method of brainstorming based on groupthink. The true danger of this strategy is that it excludes under-represented groups: the person wielding the pen, usually a member of the dominant age group, culture or gender, has the power to add or eliminate ideas as they see fit.

Work Flexibility: He advocates for a shift away from the traditional 9-5 workday in favor of shorter, more efficient blocks of collaboration time when teams are available for meetings and real-time responses to one another.

Asynchronous development: Brian debunks the assumption that meetings are where fresh ideas should be presented. Instead, managers should allow their teams to think and develop asynchronously.

Classic Leadership Perspectives: If managers want to retain their high-performing personnel, they should veer away from the belief that leaders should shield their teams from difficult decisions.

Looking Ahead Brian is eager to discover more about the untapped potential of new trends such as asynchronous work models and scheduled flexibility. He's also interested in discovering strategies to safeguard a team's psychological safety by providing and encouraging skills training for frontline leaders. He's also intrigued by the concept of professional flexibility for deskless workers.

Go to BarryO'Reilly.com for full show notes.

Resources  Brian Elliott on LinkedIn | Twitter  How the Future Works by Brian Elliott, Sheela Subramanian and Helen Kupp Future Forum

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Cecelia Myers is the VP of Digital at CDW, where she leads their product management, design, demand generation, customer integration, and merchandising teams. She has a deep breadth of experience from a variety of high-profile startups and tech companies and uses that to create a culture of empowerment and openness at CDW. She is a builder of new experiences and business models from co-founding a startup to the Fortune 500, a design thinker, a survivor of lymphoma, and a voracious reader. She joins Barry O’Reilly today, to talk about how you need to bring yourself to your organization to create the kind of culture you want to build.  Following Interests and Opportunities where they Lead Cecelia left university with one of those “never land a job” majors – but she didn’t have that problem, becoming a personal archivist at a startup that managed documents for high net-worth people. This company didn’t survive the 2008 crash, but Cecelia was invited by the VC foundry that had funded the company to join them. There, she co-founded CakeStyle, leading and working in every aspect of the business. Intimate Understanding of the Problem Do you understand the problem you’re trying to solve? People often think they know, Cecelia notes, but unless you’re digging deep into the heart of things, it’s a hard thing to understand. Intimate knowledge of what is really happening at a company is hard to replace with any kind of experience or education. There’s something energizing about connecting at a visceral level to what you’re doing – it can be really fun! Unlearning Old Skills Moving into a company like Groupon, which was so new and so technology-driven was a culture shock. Politics, senior leadership, red tape – it meant having to convince finance departments and leadership that ideas were worth trying. For someone used to having control of the vision, having to work with so many other heavily involved people was a challenge, but ultimately a chance to exercise that skill of digging in deep to the business and influencing others. It was a whole new scope of managing people and leading teams. You’re not Scaling Yourself Cecelia would advise new leaders and product managers to focus on empowering teams to do the work. Leaders need to hire the right people, give them the vision, and support them in accomplishing it. They should ONLY be focusing on that, not scaling or promoting themselves. Cecelia notes that her education and passion for reading has been extremely valuable in learning to create those kinds of environments. Reading shows you a lot of different ways of communicating. Her most important tip? Start with the end and make the most important point at the beginning. Leading by Example Barry asks Cecelia what skills she has had to develop, working for a huge organization like CDW. When you don’t know everyone that you’re working with and responsible for, you have to find new ways to communicate with them. She emphasizes the importance of sharing yourself and being yourself to be more available and approachable when people need you. The key message to communicate is that we’re not really different people - we just have different roles in the business. You need to convey that it’s okay to bring yourself to work.  Looking forward Cecelia is looking forward to watching CDW evolve and go to market as a technology first, and how cool it would be to see a commercial featuring the products they are building. Seeing a company grow into being a market leader, and a place that attracts talent is inspiring. “It’s one of those gems that people don’t really know about.”

Go to Barry O'Reilly for full show notes.

Resources Cecelia Myers on the web | LinkedIn CDW

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In this episode, Barry O'Reilly talks with James Sommerville, co-founder of ATTIK, the former Vice President of Global Design for The Coca-Cola Company and today founder of KnownUnknown, an emerging Web3.0 decentralized design community. 

Sommerville talks about his entrepreneurial journey, from his early job as a street artist to co-founding ATTIK, a design studio with Simon Needham, and then becoming the Vice President of Global Design for Coca-Cola. He explains his thoughts on design, brand storytelling and existing labor structures in corporations and agencies, as well as the possibility for future advancements and new ways of working. He also discusses how these beliefs contributed to founding KnownUnknown.

The Long and Winding Road James recounts his adolescent years in Huddersfield, West Yorkshire, UK, in the midst of the collapse of the city's industrial peak. He believes that this experience led him to question society. "What led us here?” he asked. “What were the mistakes made? Maybe we need to learn what are the things we're going to do differently." His inquiring mind, and witnessing with his father's entrepreneurial spirit - he saw how much freedom his father had over his own life outside of the constraints of a regular job - strongly inspired his thoughts on business. As a result, his road to KnownUnknown was filled with entrepreneurial endeavors, but his motivation has always been "that sense of being able to do something and make people smile."

Put Yourself Out There  Putting yourself out there is the first step to success, James tells listeners. He describes his eventual employment with Coca-Cola as an unexpected reward that many people erroneously believed was an overnight success. However, ATTIK had been in existence for 20 years before Coca-Cola contacted them. He believes that their strategy of "putting [themselves] out there, putting [their] signal into the world," as Barry puts it, was the catalyst that led to such an exciting opportunity. This strategy yielded favorable results as one of their digital design publications, Noise, soon caught the attention of Coca-Cola. James remarks, "There's something to be said about if you put your work into the world and people find it in the most unexpected and surprising ways... hold on to your authentic self, put your heart and soul into these things."

Work Within Constraints “Working under constraints is one of my favorite aspects of great innovation," James tells Barry. James admits he had to overcome some initial teething challenges, transitioning from operating independently at ATTIK to working for a major global brand. He quickly discovered that the need to stay true “the Coca-Cola way" but innovate how people worked in sharing the brand with the world. In order to thrive within these new boundaries, James had to unlearn ATTIK's original mantra of thinking, looking, and acting big to "think small, act small, move like a small start-up."

Redefining the New Creative Economy  James’ reflections on the traditional design agency structure and newly available technologies led him to develop the KnownUnknown platform model - a new work environment in which gas community at the heart of the model, and regardless of geographic location, selecting the very best talents who tomorrow will have the freedom to choose their own hours and projects, free of the usual bureaucratic red tape. 

Looking Ahead  "I'm really excited for the next decade," James adds, as he prepares to “tiptoe" into the world of NFTs while experimenting with brand storytelling within metaverse and testing Web3 boundaries. He's particularly excited about the expanded opportunities for brand and talent collaborations, where current and future designers, as well as centralized brands, can explore new developments.

Read full show notes at BarryO'Reilly.com

Resources James Sommerville: Twitter| Facebook| LINKEDIN| Instagram Known Unknown

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Alison McCauley, author of Unblocked, is the Chief Advocacy Officer of Unfinished an organization focused on strengthening civic life in the digital age. She is a sought-after keynote speaker at conferences over the world and her LinkedIn Learning course about how the blockchain will change business has been taken by over 70,000 students. Alison joins Barry O’Reilly in this week's show to talk about the potential of blockchain technology for our digital lives.

The Moment of Revelation Most of us have moments when a new idea lands like a bolt of lightning and seems to change everything. Alison had been working in emerging technology for decades when she came across the idea of blockchains, and what they could mean for people and organizations. She immediately set out to generate the key questions that would help her learn exactly what experts and experimenters in the space were trying to discover.

Keeping up with Exponential Growth There is more happening, every day, in the evolution and development of blockchain technology than anyone can keep up with. Even young, energetic technologists without many outside commitments are working 17 hours a day and unable to stay on top of what is happening in their small sliver of the space. Alison shares about how learning circles in different areas create a structure for learning and sharing information that makes it possible to progress. She predicts that success is going to go to the people who can most quickly and effectively absorb and synthesize information. 

The Messy Middle Not everyone involved in emerging technologies has excellent intentions - there are nefarious actors, and even the best-intentioned projects can go off the rails. Alison makes the point that you can learn from every project, even those that go wrong, and one of the challenges is to be cautious while still being open to the learning. “If you're able to hold a healthy skepticism and an open mind in the same space… you have the most intense opportunity for learning.” 

Skin in the Game To really learn in this space, you should have skin in the game. She recommends putting skin in the game–making a small investment for the sake of learning and understanding the theories and processes involved - that kind of practical education is much richer than other types of learning, like reading an article. This isn’t financial or investment advice, but you can experiment and gain practical knowledge by getting involved through small investment in cryptocurrency, or bidding on an NFT.

Experimentation While the ultimate uses of blockchain technology are just starting to be discovered, communities are already using it to change the way people collaborate and work together. “If you’re not experimenting with it now in some kind of applied way, I think you’ll be very blindsided in three to five years,” Alison warns. Barry shares the example of Nobody Studios which is crowdfunding equity, something equally new and unfamiliar, and you can extrapolate it further and look at how people are using DAOs to change the way people can contribute and how they are compensated for doing so.

A Sense of Belonging As DAOs are being developed, communities are being formed as well. The rewards of participation aren’t only financial, and Alison shares the story of a highly paid lawyer who volunteered his time on some contracts for a DAO. He told Alison that he valued what the organization was doing and realized “I can make a contribution here. I can help.” It was the ability to contribute that drove his desire to do so. This is how many people are starting to prioritize their time and effort.

Go to Barry O'Reilly for full show notes.

Resources Alison McCauley on the Web | LinkedIn | Twitter Unblocked: How Blockchain will Change your Business (and What to Do About it) Unblocked Future

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Bill Higgins is Director of Watson Research and Development at IBM. He leads the integrated research and development team responsible for evolving the foundational IBM AI technologies powering their main products and systems. He’s especially interested in the intersection of culture in tech as it relates to increasing diverse representation and technical leadership. Bill joins Barry O’Reilly in this week’s show to discuss what is needed to innovate at scale. 

Bill’s Start Bill shares how he started in DevOps and made his way to becoming a leader in software engineering. He had always worked on software products, but after a certain point, he became disenchanted with the process of building the products, especially as it related to the methods and tools involved. He thought it could be much better than it was. In the early 2010s, he became enamored with the DevOps movement and sought to drive a DevOps culture at IBM; he was quite successful at this. His team was one of the first to be sent to the IBM design camp for product teams. He describes the experience and how it impacted his career.

Deterministic vs. Probabilistic Barry recalls how Bill shaped his perception of AI. “I still remember… being blown away by the clarity of how [Bill’s colleagues] could talk about it. I got smarter just listening to them, and so many of the notions I had of what AI could do were blown away very quickly,” Barry says. Bill responds that he realized that the field of AI is a very different paradigm from traditional programming; the latter is largely about methodically defining a set of rules to create a deterministic program. AI is the opposite, by contrast; using the example of machine learning, Bill describes how AI is probabilistic by nature.

AI Through the Years Bill and Barry explore the history and development of AI, and IBM’s role in both. “There was this really famous conference at Dartmouth University in 1956 with some of the legends of the industry… that established AI as a field of study. They adopted the term artificial intelligence as opposed to one of the competing terms like cybernetics,” Bill remarks. Throughout the ’60s and ’70s, the fundamental parts of modern AI technology - neural networks, the concept of machine learning, natural language, and speech processing - broke through, but the industry would still be considered a field of research not fit for real enterprise use up until circa 2011.

Teamwork Makes the AI Work To achieve something great with AI, you must have equally great AI algorithms made by people waist-deep in machine learning, Bill explains. They must understand the whole lifecycle of machine learning, make their algorithms available via understandable developer APIs, and run it at an internet scale. One of the biggest mistakes companies make is primarily investing millions of dollars in hiring scholars with degrees in machine learning from reputable institutions. You need both machine learning people to create the algorithm, but you also need the software developers to create the APIs and internet scale architectures.

Building Great AI Innovators face two hard problems when creating foundational AI components, Bill tells Barry. “The first one is that fusion, that synthesis of really excellent machine learning, algorithm creation and excellent software development for both creating the APIs but also creating the internet scale architectures… Number two is how do you create an innovation pipeline.” IBM’s experience has been that innovation is difficult to commercialize quickly and at scale. They found that a modular architecture helps them to add new components more readily. Extensibility is another key principle. He and Barry agree that good collaboration and composability are two additional major aspects of a good innovation pipeline.

Find full show notes a Barry O'Reilly.

Resources Bill Higgins on the Web | LinkedIn | Twitter IBM.com

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Aaron Frank is Adjunct Faculty at Singularity University, where he routinely advises large companies, startups, and governments on trends related to augmented and virtual reality and the use of virtual environments. Organizations like Twitter and FC Barcelona have benefited from his services. He is a researcher and writer whose articles have appeared in Vice, Wired, Forbes and VentureBeat. Aaron joins Barry O'Reilly in this week’s show to define the metaverse, and how to leverage it in your own business.

The First Foray Aaron talks about his thoughts when he first encountered immersive virtual reality headsets. He was tasked with doing an impromptu presentation for foreign investors and unfortunately didn’t execute it well. When he put on the VR headset, he thought about recreating the environment of the presentation as a sort of “public speaking simulator.” He went on to build a very basic version of it and was surprised by how true-to-life it felt. That was when he realized that VR wasn’t just for gaming. “This [was] a new way for people to experience anything,” he shares. “[It] can replicate almost any experience.” [Listen from 2:19]

Behind the Scenes of AR and VR The internet of the future will be immersive. Barry asks Aaron to describe his experience diving into the metaverse. “It’s important to make a distinction between augmented and virtual reality technologies,” Aaron says, “because those terms typically refer to the kinds of interfaces [necessary for each.]” An interface is a way of engaging with the digital environment, similar to how we use a mouse and a keyboard to operate our computers the way we want to. Aaron predicts that in the near future, however, we won’t need a mouse and keyboard; we’ll be using VR headsets and our arms. [Listen from 8:06]

Manipulating the Metaverse The metaverse allows you to manipulate physical space in a virtual environment and mimic social behavior to recreate real-life experiences. People are using the metaverse to train employees, Barry shares. They are put to the test in stressful situations to observe how well they respond as a team; from speaking individually to escape rooms that require cooperation and serve as a fun activity. Advancements in the metaverse are happening so quickly, he adds. “It doesn’t have to be this ‘ready player one’ experience where you put on the headset and can’t tell whether you’re in the real world or not,” Barry comments. “It can just be blocky characters.” [Listen from 17:59]

Why Game Engines are Serious Business Aaron is not advocating for a future immersed in VR. “It’s worth remembering that these are valuable tools, and it’s worth understanding what they are used for… they’re not meant to - and should not be used to - replace physical reality in any way,” he affirms. He debunks some misconceptions about the metaverse and proposes a new way of thinking about it. The metaverse is being built by game developers using game engines, but the term game is misleading; game engines are software tools that developers use to build on virtual environments. [Listen from 24:33]

The Truth About Gaming There’s a lot more to gaming than meets the eye, Barry points out. People don’t really know how much thought goes into things like simulation, incentive design, teaching people new skills, and leveling them up on their journey to mastery. “[In] any game you join, the experience is all about building skills,” he says. He talks about the skills that games teach you, like rapid experimentation, risk taking, and teamwork. “[Rather than] meaning fun and childish play, games are about coordination, incentive design and skills development.” He and Aaron explore the concept of safe-to-fail environments. [Listen from 31:17] Read full show notes at Barry O'Reilly.

Resources Aaron Frank on the Web | LinkedIn

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Ja-Naé Duane is CEO of the Revolution Factory and the bestselling author of The Startup Equation. Her mission is to make life better for one billion people. An award-winning innovator and expert on global systems, Ja-Naé helps corporations identify trends, using emerging technology such as AI and blockchain, that will help them pave the way for the future through futures forecasting and complex system building. She also loves singing opera. Currently, she is a PhD candidate focusing her research on the future of information systems as well as a research fellow at the Center of Information Systems Research at MIT. Ja-Naé joins Barry O’Reilly in this week’s show to talk about designing Distributed Autonomous Organizations (DAO). 

Everything is Interconnected John Newton’s philosophy that everything is interconnected, is one that Ja-Naé lives by. We build on everything we learn, she tells Barry. The same is true in a company: its founding principles are connected to how those tenets are manifested in interactions with customers. “All of these things - much like nature - is very much an ecosystem,” she points out. Survival depends on the dependencies and interdependencies within the ecosystem. Likewise, the systems of the future will be enabled by interconnected technology, and we have to be ready. [Listen from 2:15] 

DAO Principles Distributed Autonomous Organization (DAO) is one of the cornerstones of Web 3.0, and as Barry puts it, “the future of how the international world could become programmable.” In a DAO, business is conducted via programmable principles and smart contracts. Ja-Naé remarks that every member of a DAO has voting rights based on their level of contribution, unlike the traditional system where only a select few dictate how the organization is run; this can really move the organization forward. “With the democratization of information that comes along with that, we are seeing these pockets of erosion around centralized models,” she continues. [Listen from 4:25]

Creating Value Together DAOs transform the role of the customer from just buyer into co-creator. Ja-Naé comments, “How do we also bring customers in to co-create and really capture value with them, so that they're building not only because they like our product or they like our service, but they're aligned with the mission of where this company is headed?” It’s a massive shift in customer behavior that’s ripe for exploration and innovation, she and Barry agree. The workforce of the future - the ‘liquid workforce’ - will be one where you contribute to several companies, and you’ll be judged on credibility and your last job, Ja-Naé says. [Listen from 17:50]   How to Start Barry asks Ja-Naé to share some tips to help people get started exploring the world of Web 3.0. Try to understand blockchain and how it’s changing the world first, she urges listeners. Learn about digital twins, virtual reality and virtual worlds, as well as the metaverse. The next step is to understand crypto and NFTs; putting some ‘skin in the game’ by making a small crypto investment is a good way to learn, she comments. She gives suggestions of DAO protocols listeners can explore to learn more, including her own DAO resource. [Listen from 32:50]

Visit Barry O'Reilly for full show notes.   Resources Ja-Naé Duane on LinkedIn | Twitter | Instagram | Facebook DAO Board How to Build a DAO Revolution Factory The Startup Equation

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Barry O’Reilly welcomes David Chen to the Unlearn Podcast this week. Barry tells listeners that David’s story is nothing short of exceptional. His rapid rise at Deloitte saw him becoming one of the company’s youngest partners at the age of 34. He started the group GTIF Capital, and partners with several major businesses in the eSports, technology and healthcare sectors. David has worked with several partners and celebrities on the recent Super Bowl commercial. He sits on several boards including Mediabundance as the head of eSports, Faze Clan and the North American Collegiate League. He has brokered a deal to bring Wolves eSports gaming, a professional gaming wing of the Wolverhampton Wanderers, into the NACL via their strategic partnership with the Fosun Group.

A Happy Balance David was at the pinnacle of his career at Deloitte but his life was out of balance. He tells Barry that he had all the trappings of success, and yet he was miserable. Barry comments that successful people often feel guilty when they feel emptiness or dissatisfaction with their lives because they believe they don’t have a right to those feelings when they’ve had so much opportunity. “Nobody teaches you how to be happy,” David responds. He describes his internal struggle as the darkest journey he ever went through. “But it was the best journey that I have to go through multiple times.” The secret is to change your thought process and do things that actually matter, he posits.

A Booming Industry Gaming is the fastest-growing industry. Before the pandemic, gaming was projected to be a $3 billion industry by 2023; it’s now estimated to be worth $200 billion by 2023. This “influential shift” is because of the large population of gamers around the world. Brands trying to reach this demographic - 35 years and younger, 60% male and 40% female - have to demonstrate that they care about societal issues in a tangible way. David admonishes parents to have an open mind about gaming because it is changing the world in the same way that Amazon did with ecommerce.

Starting with eSports Barry asks David, “What are some tips you could give [people who are curious about eSports] to start experimenting and learning their way into this world because the future is going to be so connected to it?” David responds with practical steps, including:

If you’re a parent, ask your kids about their favorite games. It will help you bond with them.

Keep up with the trends as a business leader. Gaming is now mainstream, so ignoring it means ignoring the next 40 years of your client base.

Over 180 universities are giving out scholarships in gaming. If your child has the opportunity to learn, allow them to.

Building Community “Community is important in anything,” David tells listeners. Community is the people who believe in the game. The danger lies, he continues, in the business leaders who only see the dollar signs, and don’t care about young gamers’ mental health. Being sensitive to kids’ needs at such a difficult time in their lives will help you build a better brand. Also, make sure your game is great, David tells Barry. “Here's the thing: the game can't suck, and [that’s] what a lot of guys are doing wrong…Let me just put it very very simply: if it's not cool, no one's gonna do it.” He shares some common mistakes brands make in trying to influence the gaming community. 

Advice for Brands Revisit the games you enjoyed as a child, David advises listeners. It will give you the comfort level you need to start learning more about gaming. “Then start communicating with your child and understanding the trends that exist,” David says. The next step is learning the play to earn model, but understand that it has to make sense, he adds. You’re never too old to learn.

Read the full show notes at Barry O'Reilly

Resources David Chen at Website | Instagram | Twitter | LinkedIn

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Barry O’Reilly welcomes James Scott as this week’s guest on the Unlearn Podcast. James is the former Chief Digital Officer at Absa Group’s Corporate Investment Bank in South Africa. In his previous role, his focus was product design, data, and platforms, as well as new propositions. James is very passionate about building the future of digital innovation and ventures in Africa. In this week’s show, James explores his working experiences in the region, the similarities and differences in how things are done in the West, and what’s unique about Africa’s scaling venture landscape.

A New Way Forward James discovered his passion for venture building while looking for disruptive product opportunities on the continent. The last few years of working in the business end of technology, he was reluctantly involved in a massive large-scale digital transformation. “There [were] so many concurrent pieces of work,” he shares. “Organizing teams, trying to scale agile, building and transforming products and channels as well as embedding new ways of work while trying to hit regulatory deadlines… The good news from that part of the journey is that I made it out alive.” In his own journey, James found that while he loved leading and building teams within a corporate environment, he missed building products and businesses. He talks about getting back into it.

From Corporate to Entrepreneurship After being in financial services and large corporates for 21 years, James had some things to unlearn. People typically think the first thing would be the safety and security of a paycheck, but for James, it was capacity. When you’re in a large organization you don’t have to worry about machinery and funding; you focus instead on organizing internal teams. What you're really doing is mobilizing capacity, James says. “When you’re running big teams, you’re so far away from the backlog…” he adds, “part of the unlearning is [realizing] it’s quite hard to scale yourself.” He and Barry discuss creating systems to facilitate team cooperation and efficiency.

Debunking Misconceptions about Africa Africa is a bed of budding opportunities at the moment, James tells Barry. There is a common misconception that it’s just one big group of homogeneous countries but that’s not true; the diversity on the continent is phenomenal. Furthermore, the big hubs of South Africa, Kenya, Nigeria to Egypt are building amazing organizations that work exceptionally well across the continent. “It’s exciting for me because I’m starting to see the maturity of businesses emerge… when you get this right, it’s less about big, global solutions and more about local high-impact businesses creating jobs and generating value in their economies,” James comments. Localization is a key part of the game, especially on the continent, Barry adds.

How Fintech is Driving Innovation Barry asks James to talk about any recent developments that have caught his attention. “Fintech continues to dominate the investment landscape and I like some of the businesses that are providing various kinds of multi-country aggregation capability that’s not only moving traditional mechanisms of money transfer, but also plugging into the mobile networks,” James remarks. This is important because a massive part of the African financial ecosystem is mobile money. “Solutions that provide that aggregation are opening up lots of innovation; it's allowing people sitting in Nairobi to be building solutions that work in Rwanda, that may be work in Nigeria and South Africa.”

Resources James Scott on LinkedIn

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Barry O’Reilly and Sara Michelazzo know each other from their days working together at Thoughtworks. Sara is Head of Customer Experience - Tech Operations at Thoughtworks, as well as Design Advisor at Nobody Studios. Sara is an advocate for women in tech, cryptos, and NFTs. In this week’s show, she and Barry discuss human-centered technology design and making data awesome to empower users to solve real-world problems.

Empowering People with Technology “I've never been a superfan of technology for technology's sake, but more about all the opportunity that technology brings to empower people and allow them to do things that they couldn't do before and connect them in new, meaningful ways,” Sara remarks. She tells Barry that it was seeing how technology allowed her father to continue working on his passion during his illness, that drove her to pivot from her art career into tech.

Human-Centered Design Making technology simple for users is at the heart of human-centered design. Sara tells Barry that she fully grasped the power of intuitive design through her father’s experience. Technology should be easy for users to grasp and adopt, she posits. We should design for 50% of people’s attention instead of 100% because we all have so many other things going on in our lives at any moment. Barry asks her about the future of tech and what she had to unlearn regarding technology design. Humans are the same while technology is growing exponentially, she responds. As such, we need to meet people where they are and bridge the gap.

Making Data Awesome Barry and Sara discuss Thoughtworks’ journey to become data-driven. The best software or spreadsheet means little if people don’t know how to use the data, they both agree. Sara realized that her strength was in seeing the user’s perspective; she got comfortable asking questions such as, ‘Will the user understand this?’ and ‘How are they going to use it?’ 

Shifting the mindset from data and dashboards to people was a tall order, Sara says, but it was the only way forward. People don’t care about data per se; they just want to do better work. This was the principle behind their Data Awesome framework - for users to experience data delight instead of data frustration. The Data Awesome framework is made up of six simple steps including:

Understand the audience;

Define the job to be done;

Determine the questions to answer to get the job done;

Find the answers.

Looking Ahead Barry asks Sara what she is looking forward to as she looks to the future. The opportunities that NFTs bring makes her excited. “I'm learning tons about unstructured people achieving incredible results, and it's very refreshing to see how hundreds of people can contribute to an outcome without being in meetings or meeting each other very often,” she tells Barry. They talk about the value of the community of followers and creators. “The value of NFTs goes up as the popularity of the project increases. The idea is that we’re all in this together,” Sara comments. 

Read full show notes at Barry O'Reilly.

Resources Sara Michelazzo at Website | Thoughtworks | LinkedIn | Twitter Articles on Thoughtworks: Why do Data Platforms Fail? | The Data Awesome Framework | Five Tips from the Data Awesome Frontline

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Barry O’Reilly welcomes Gibson Biddle and Melissa Perri as this week’s guests on the Unlearn Podcast. Gibson is the former CPO of Netflix; he is also a speaker, teacher, writer, and author of the “Ask Gib” product newsletter. Melissa is Senior Lecturer at Harvard Business School, a member of the Board of Directors at Forsta, and host of the Product Thinking Podcast. In today’s show, Gibson, Melissa and Barry review their working experience over the past six months, discuss progress challenges in the US, and define what personal and business growth means to them in the year ahead.

The CAMP Model The CAMP model, designed by Gibson, is an evaluation of how you feel about the overall quality of your job and career. 

C is about community: do you enjoy working with your boss and your peers at your company? Do you feel a connection to the customers that you serve? 

A is about autonomy: do you feel you have the opportunity to set your own direction? 

M is about mastery: are you learning? 

P is about purpose: do you feel a connection to the work that you're trying to do? Do you feel like it will help “dent the universe” in some way? 

These questions are asked to be answered on a scale of 1 to 10. “I generally want everyone I work with to have an 8, 9, or a 10,” Gibson shares. “I can usually figure out ways to get a 6 or 7 to an 8, eventually.”

CAMP-S “I added another letter to the CAMP model,” Melissa admits. “The S is for scale. In the last board of directors meeting, I talked about how I burned out pretty hard during [the pandemic] while I was scaling [my] consultancy, so I’m trying to focus on things that scale, where it’s not me working 24/7.” Barry asks Melissa and Gibson to evaluate their experience over the past 6 months using the CAMP model.

The HBS Case Method Melissa talks about her first year doing the case method with her students. Harvard’s case method is an interactive, discussion-focused teaching approach that uses cases about true scenarios that have happened in the past to engage students in problem-solving and decision-making debates. “When the class has a discussion, they can take it anywhere, but as a teacher you have to pull them back a little,” she explains. “You make sure they take the big takeaways, but let them figure it out themselves and surface the ‘aha’ moments.”

How To Take a Break Gibson and Melissa explore ways to encourage Barry to be more disciplined in taking time off. “What I did last year when I was feeling burnout… [was] use Calendly to block out time,” Melissa says. “I don’t do anything else on Friday unless it’s something I’m gonna get joy out of… Ultimately, it’s about knowing the world’s not going to end if you’re not there.” Gibson talks about how he carves out time. “I tend to ski my age in days each year, and I’m turning 60 this year so that’s 60 days,” he adds. “[Additionally,] I always felt like it’s healthy to take a week off every quarter.”

Questions About Culture & Autonomy “You have to work to define, edit and live the values [of a world-class culture] over time; it’s a forever process,” Gibson tells Barry. “Culture is the skills and behaviors you expect from all of your employees. Frankly, the CEO and exec team have to be very invested in [the culture] because they are the role models.” Melissa shares how too much autonomy can hold you back from learning new things. “I felt like I was the only one responsible for my success, and it was never enough.”

Resources Gibson Biddle on LinkedIn | Twitter GibsonBiddle.com 

Melissa Perri on LinkedIn | Twitter MelissaPerri.com

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Barry O’Reilly welcomes Le-an Lai Lacaba to this episode of the Unlearn Podcast. Le-an is the CEO and co-founder of 2xYou, an outsourcing company that specializes in hiring, managing, and growing remote executive assistants for solopreneurs and small business owners. She has been working from home since she was 15; she published her first book at 18, and became CEO at 20. At 23 she partnered with her boss to start 2xYou Executive Services, and aims to help 10,000 entrepreneurs grow remotely, and 1 Million Filipinos to work from home. Le-an also has her own Youtube channel, where she trains Virtual Assistants on how to work from home. She and Barry talk about entrepreneurship, and she gives advice to solopreneurs and small business owners on how to scale their business.

Building Systems Le-an describes her early career as being an “outsourced CEO”, as she was running her clients’ businesses on their behalf. This was a major lesson she learned from that time, so her mission with 2xYou is “to empower executive assistants to empower the entrepreneur”. Le-an explains that she was able to develop and refine her processes over 3 years of hiring, interviewing, and training others. “There was a lot of testing and a lot of rediscovering things that I already knew, and then looking at different ways that it could be better,” she tells Barry. 

Scaling Remotely What are some key things to unlearn when you want to scale your business to working with remote teams, Barry asks Le-an. She shares three tips:

Don’t expect your team to know everything right away. Delegate the right task when you’re onboarding, so that they are not overwhelmed. 

Make sure your workers document and report what they are working on. This ensures continuity in case someone else needs to take over their task.

It’s your responsibility to build a solid relationship and clear communication with your employee. If your workers are not sure about what they need to do next, it’s your fault.

The Importance of Mentorship “I believe that you can always teach people anything, but it has to start with their character,” Le-an states. She describes the important role her mentor played in developing her leadership skills, and how she now uses what she learned to mentor her own team. She focuses on training her team to think like an entrepreneur, so it’s easier for them to help their clients. Mentorship also boosts her team’s confidence, she comments. Remote work has exploded over the last two years, she and Barry agree. She is excited about the increasing number of resources and communities now available for remote workers. What also struck her, Le-an tells Barry, is how easy it was for companies to turn remote.

Looking Ahead Barry is excited about the explosion of entrepreneurship around the world, and what it means for Nobody Studios. He asks Le-an what excites her about entrepreneurship and remote work as she looks ahead. Empowering different people to have multiple streams of income makes her happy, she responds. People now have a choice in how they want to work and how they structure their lives. Remote work has made this possible. Le-an shares tips for business owners who want to hire remotely, as well as individuals who want to find remote work. “Look for someone who can complement you,” she advises business owners. “And the only way you know how someone could complement you is by looking at what you're currently doing and then finding the pitfalls and the things that you miss, and then finding a person who won't miss that.”

Read full show notes at BarryO'Reilly.com

Resources Le-an Lai Lacaba at Website | LinkedIn 2xYou

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Barry O’Reilly is happy to welcome Dr. Sally Spencer-Thomas to this episode of the Unlearn Podcast. Sally earned international acclaim as an entrepreneur and innovator in social change, helping to establish many large-scale mental health efforts, including Man Therapy and National Action Alliance for Suicide Prevention. A trained clinical psychologist and a suicide loss survivor herself, she sees issues of suicide prevention and mental health promotion from a holistic perspective. Sally is a team member at Nobody Studios, leading the Employee Crisis Management function, where her mission is to save company-employee relationships by ensuring both sides have their needs met in times of difficulty. He and Sally discuss how we all can promote mental health in our companies, family, and community. 

The Turning Point “Many of us have these moments in our life where we had a life before and then we have life afterward,” Sally says. That pivotal moment for her was her brother’s death by suicide. She describes her deep grief and the moment in a Suicide Loss Survivors support group when she realized that she could contribute to supporting others.

Facing Down Fear “The fear around suicide is just immobilizing,” Sally tells Barry. Even trained mental health professionals feel that fear and often ‘hot potato’ clients who are struggling with suicidal feelings: they fear losing their reputation - and their license - if a client dies by suicide on their watch. If, however, we face down the fear, we can really help people, she points out.

Sally describes how fear made them reluctant to take a different approach to suicide prevention, despite data telling them that they should. In the end, they decided to face down the fear and go against the status quo. She and Barry talk about the importance of psychological safety. If people don’t feel safe to reach out for help, they won’t, and then they can’t get the help they need.

Learning From Disaster “A lot of times when we face large-scale disaster, we pull together as communities and that protects us,” Sally tells Barry. However, the Great Resignation is teaching us that people will no longer tolerate working in a toxic environment. Burnout is real, and when it reaches the point of despair, then it’s past time for companies to do something about it.

A Better Approach to Suicide Prevention  Historically, suicide prevention has been seen as an issue only medical professionals could address. This ‘only-one-path’ approach has failed. “What we learned from that is that when we force hospitalization, suicide rates go up,” Sally says. We have to broaden our view and see suicide prevention as both a public health and social justice issue.

Research shows that people who overcome suicidal despair usually fall into two categories: they related deeply with someone who went through a similar experience, or they made meaning out of their experience so they could help others. Having someone be there for you in tough times really helps, Barry and Sally agree.

Looking Ahead Sally is excited about the progress she is making advocating for mental health in male-dominated industries. 80% of people who die by suicide are male, she tells Barry, so it’s important to carry the work where it’s needed the most. It’s about creating a culture where people are excited to serve, rather than one where you are essentially a robot. She is also excited about her work at Nobody Studios, particularly the collaborative employee crisis management tool they are working on. Personally, she is unlearning that she is more than just her work. “We are the millions of decisions we make every day with the people around us,” she reminds herself and listeners.

Read full show notes at BarryO'Reilly.com

Resources Dr. Sally Spencer-Thomas on Website | LinkedIn | Facebook | Instagram

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Barry O’Reilly goes solo in this season's finale episode of the Unlearn Podcast. He answers listeners’ questions about perfectionism, permanent hybrid work, and letting go of the past, among other things.

Q: How do you deal with perfectionism in the startup you're working on at the moment?

Q: How do you get the most out of the content you create under reach?

Q: How would you summarize the insights and learnings from your podcast guests about being change agents?

Q: Given that your move towards permanent hybrid work seems to be gaining serious momentum, how will this affect founders’ efforts to scale their businesses?

Q: In the unlearning process, what encouragement do you have to counter the fear of letting go of the past?

Q: What are you most excited about at the moment?

Q: What kind of guests are you looking for for future episodes?

Q: What's the biggest lesson you've had so far in 2021?

Resources Barry O’Reilly on LinkedIn

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Barry O’Reilly is excited to welcome this week’s guest, Ryan Serhant, to the Unlearn Podcast. Ryan is founder & CEO of SERHANT., the bestselling author of Sell It Like Serhant and Big Money Energy, and is one of the most successful and well-known real estate brokers in the world. He is a producer, public speaker, and the star of multiple TV shows. In this inspiring episode, Ryan talks about how he revolutionized the traditional brokerage model and his strategies for building businesses of tomorrow.

Selling Confidence “I have never sold a house in my entire career,” Ryan tells Barry. “What I've sold is about $5 billion dollars worth of enthusiasm and confidence.” When he started out in real estate, he didn’t have the ‘right’ education, connections, or experience. What he did have in spades though, was self-confidence. Every day he would convince himself that he was the greatest real estate broker because he knew that clients were not just buying a house, they were buying into his belief that he was the very best in the business. Barry asks Ryan how he helps clients see something exciting in an otherwise ordinary property. “Facts tell, stories sell,” Ryan responds. He no longer just gives information, he deciphers it so that clients see the potential.

Diversifying Happiness “I diversify opportunities for happiness so every single day is exciting,” Ryan comments. He learned the hard way to never depend on just one “line of happiness”. As such, he used his skills to create other businesses and diversify his income sources. This led him to create his online education platform and his real estate media production company. “It’s really proven beneficial for my long-term career,” he adds. Barry comments that diversification is one of the tenets of Nobody Studios: “It's all about diversifying because you're building lots of different businesses; you're diversifying your skills, your portfolio, your investment strategy; and I think it's really important for people to see that as a skill to develop.”

People First Business books teach product, process, then people; Ryan learned that people should come first. “What I realized was you can think of the greatest product ever, …[but if people] were not part of the ideation of the products - especially in the early phases - they have no emotional connection to it, and they're just never going to care the same way you do.” Employees who are emotionally committed to your company will give their best and “will do everything possible to make sure that the company is successful,” Ryan tells Barry. He shares how this has played out in his own businesses: his team shared ideas that brought significant growth to the company. Ryan is also thinking about getting into the minds of his future customers. This is how he future-proofs his business. He says, “I want to make sure that I'm living in the future far enough, so I can predict my future.”

How to Get Started We are in the attention economy, but you can grab your customers’ attention for free. However, you have to speak to them in their language and play in their field, and their field is on their phone. Ryan's advice for anyone wanting to get started in business is to determine the story you want to sell, and why it’s better than your competitors’ story. “Get that story out there in the form of content,” he tells listeners. Barry admires that Ryan does not pretend, that he’s authentic in what he shares with the world. Ryan adds that clients come to him to interpret the facts they already know, the same reason they listen to the news. People don’t want to think, he points out. “Do the thinking for people and you can be wildly successful,” he advises listeners.

Visit Barry O'Reilly for full show notes.

Resources Ryan Serhant on Website | LinkedIn | Twitter | Instagram

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Barry O’Reilly welcomes Shiyan Koh as this week’s guest on the Unlearn Podcast. Shiyan is Managing Partner at Hustle Fund, a VC fund that invests in pre-seed software startups in the US, Canada, and Southeast Asia. What makes Hustle Funding different is that, beyond the usual criteria that VCs look for, they tend to prioritize founders that have speed of execution. In today’s show, Shiyan and Barry discuss her professional experience, from her beginnings in finance to her current role at Hustle Fund.

A Whole New World “I’ve never been one for ten-year plans, so I cannot tell you that [I knew] I was going to end up here,” Shiyan tells Barry. One major interest was policy creation and regulation, which she defines as “systems being enacted on people,” so she surprised herself when she delved into investment banking after receiving an internship in college. “I didn't really know what I was showing up for, but opened up a whole new world,” she says. The company that offered her the internship, JPMorgan, invited her to work for them as a full-time employee, which she accepted. Eventually, however, she decided that the job and the industry weren't in her long-term game plan.

Finance, to Growth Stage Venture Capital Shiyan talks about how she transitioned from investment banking, and how that experience helped her determine what to do next. “I thought [to myself], ‘I don’t want to be an investment banker anymore, but let me reflect on the things I enjoyed about the job.’ [So I] made lists… When I thought about all the different projects I've gotten to work on over the course of my time there, I realized that my favorite ones were the young companies, the ones who were just going public. And so I went ‘You know what, I want to do more of that.’”

Growing Beyond Growth It’s much easier to model growth in an Excel sheet than it is to make it happen. Shiyan recalls what she learned from her stint in growth stage venture capital. “I often felt like a fraud in those board meetings because I had never sold anything in my life… there was a huge gap between theory and practice.” Emboldened by her lack of knowledge, Shiyan resolved to attend business school to grasp a better understanding of how to build and run a business. Yet once again, she determined that this wasn’t what she wanted to do. Just because something is intellectually interesting to you, it doesn’t necessarily mean it’s a good job for you, she affirms.

NerdWallet and Takeaways Shiyan dives into her time at NerdWallet, where she was VP of Business Operations and Corporate Development. Incidentally, the founder of NerdWallet was a friend of hers. They were together for a casual meetup when she asked him if he knew of any interesting companies in New York, to which he replied with an offer to join his company. She goes on to describe her experience commuting from New York to San Francisco every few weeks. “The big takeaway from startups is that only 2 of the 100 things to do on your list are existential; you just need to let 98 things burn until they [reach that level],” Shiyan advises listeners. “You just have to focus on existing topics.”

Alignment and Action “One thing I personally struggle with is finding the balance between the appropriate amount of time to invest into getting people aligned with what you’re trying to do, and getting them to take action,” Barry shares. If you spend too much time on alignment, no action will take place, and vice versa. One thing that’s hard for a lot of people to imagine is that startups move so fast, and as human beings, we’re unaccustomed to that rate of change, according to Shiyan. We develop routines for control, but when things shift too quickly, we become stressed and emotional. You then have to investigate ways to help people continue to be productive and high-performing.

Resources Shiyan Koh on LinkedIn | Twitter Hustle Fund

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Barry O’Reilly is pleased to welcome Dr. Erik Reis to this episode of the Unlearn Podcast. Erik is a Co-Founder of Health and Wellness at Nobody Studios and has spent the last 10 years of his career helping individuals maximize their bodies, brains, and business through neuroscience and behavioral psychology. “He believes the brain is limitless,” Barry remarks, “which is why his efforts at Nobody Studios are focused on maximizing human potential and improving access to global healthcare.” In today’s show, Erik and Barry talk about the power of the brain, and how to maximize your human potential.     Maximize Your Brain “Every single one of us has the capacity to change and to improve and to adapt, and become more efficient at whatever task it is,” Erik tells listeners. He stresses that your daily actions, habits, and choices manifest in long-term outcomes. This is exciting because it means that we can achieve big goals by taking small steps every day. “I think that the brain is the final frontier. I'm thoroughly convinced that it is one of the only frontiers that we can truly try and pursue and master at some point,” Erik says.   Update Your Brain’s Software You can change your brain simply by changing your habits, Erik points out. Given the same stimulus, people make different choices based on their perceptions. As such, Erik sees it as his mission to help people change their brain, or “update their software”. This is a requirement to reach your fullest potential in life and in business, he says. One simple step anyone can take to ‘update their software’ is movement and exercise: “Movement will always be the language of the brain,” Erik says.   Small Steps, Big Impact There’s no one magic pill; rather, maximizing your potential is a matter of small actions taken consistently. Instead, keep an open mind - be open to differing opinions, perspectives, and experiences. The brain is not binary, so our mindset shouldn’t be either. He and Barry discuss the importance of diet and relationships in living a fulfilling life. What you put into your body directly affects your brain’s health. Additionally, humans are social beings, so people who have strong relationships enjoy a better quality of life.   Prevention and Habit Stacking Barry comments on the value of prehab, taking corrective action once you see a problem to prevent having to do rehab later on. Erik agrees and states that prevention is a key focus of his practice. It’s not the first cigarette or cheeseburger that kills you, he says; it’s the 1000th. Start with one small habit, and keep stacking new ones. “That's the beauty of the brain,” Erik says, “you were just laying down new neural networks, and you were just facilitating long term potential health and growth of those pathways, to now where you have just become a different person; and that's what people are striving for all around the world!”    The Infinite Game Nobody Studios’ goal is to help entrepreneurs build companies that impact the people they serve. Changing one person’s life could have exponential outcomes, Erik and Barry agree. That’s why Erik’s role at Nobody Studios is so important and bigger than himself, he says. He wants his legacy to be the people he helped change their brain and ultimately their lives. Barry asks him to advise listeners who want to change their lives about where to start. Start where you are, Erik responds. Form good foundational habits, and be willing to change your bad habits. “Take the plunge and get after it and don't be scared to ask for help,” he tells listeners. “One thing that I've realized throughout my life is the more help that I've asked for, the more help that I've gotten. More importantly too, the faster I've been able to accomplish things that I wanted to accomplish in my life.”   For full show notes, visit BarryOReilly.com   Resources Dr. Erik Reis on LinkedIn Nobody Studios

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Barry O’Reilly’s guest is Jim McKelvey, who has been everything from a glassblowing artist, to a founder of a multibillion-dollar organization. Just recently, he was appointed Chairman of the Federal Reserve Bank of St. Louis. Jim is the co-founder of Square, a leading financial services and digital payments company, and the author of The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time, where he shares the story of building Square and his philosophy for building disruptive companies. His most recent startup, Invisibly, gives consumers control of how their personal data is monetized by advertisers. Jim treats listeners to some fun facts and tips he learned from his own journey in this week’s episode.   Be Grumpy, Optimistic and Tenacious Innovation requires a “wonderful blend of grumpiness and optimism”, as well as a healthy dose of tenacity, Jim argues. Grumpiness makes you upset about a problem, and optimism inspires you to come up with a solution. Tenacity keeps you going through the tough times. “A lot of the companies that are now household names ... began with a founder who just found themselves in a really unpleasant situation and didn't quit,” Jim says. The mix of work ethic and stubbornness is often the secret sauce to your ultimate breakthrough. The most successful founders are just regular people; you just need the right tools, which Jim describes in his book.   Entertain Them Barry loves The Innovation Stack for its amusing anecdotes and contrary approaches, one of his favorites being Jim’s approach to pitching investors. “People get pitching wrong,” Jim explains. “People spend a lot of time pitching as if they are trying to sell somebody something. I pitch as if I'm trying to entertain and invite them to partner with me, and it's a subtle difference.” It’s your duty to entertain your listeners, he argues, especially if you want them to listen to you for more than 30 seconds.   Make it an Experience Your product or service should be an unforgettable experience for your customers, one they want to revisit. Jim describes thinking through the design of a new drinking glass that will invoke the users’ senses and help them see the world in a new way. These types of hidden experiences are key. “What I noticed was that immediately after an experience like that, you have this window of attention that may last 2 seconds or 5 seconds or 20 seconds,” Jim tells Barry.   Make Space in Your Head What used to work well before may stop working, and you have to be flexible enough to unlearn. “If you stick too rigidly to what has worked, you'll find that you end up one of these fossils who is so out of step with what's working that you no longer have any success,” Jim warns. “To me, unlearning is a Marie Kondo approach to your brain.” You have to get rid of the stuff that no longer works, to make space in your head for new ideas and approaches. This is a continuous process.   Looking Ahead Jim is excited about his new position as Chairman of the Federal Reserve Bank of St. Louis. He is responsible for ensuring that the right information gets to the people who need it, he says. “But it's also about gathering economic data and then going to Washington a couple times a year to make decisions on how that data gets used.” The main focus is to bring the economy back to health post-pandemic. “The key unlearning there is to just continually recognize that you don't get to copy the solution from some previous crisis because we haven't had one like this,” he tells Barry, “so just keep your mind open and be willing to listen to the person who proposes something that sounds radical, but in fact might actually be the solution.”   Read full show notes at BarryO'Reilly.com

Resources Jim McKelvey Website | LinkedIn | Twitter | Instagram The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time

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Jaime Schmidt started Schmidt’s Naturals in her kitchen and scaled it to acquisition by Unilever. In the process, she pioneered a movement of modern brands bringing naturals to the mainstream. Since then, Jaime has been empowering the next generation of consumer brands through her inclusive investment firm, Color. In 2019, she launched Supermaker, a media company that celebrates inclusive and disruptive independent brands. Her book, Supermaker: Crafting Business on Your Own Terms, on this very topic was released in 2020 and is all about turning your passion project into a thriving business. Jaime is gearing up for her starring role on Season One of Going Public airing on October 19, the first show that will enable viewers to invest in companies on screen, to help entrepreneurs take their brands to a global audience. “There's so much here that resonates with our mission at Nobody Studios about giving access to all for entrepreneurs,” host Barry O’Reilly says. 

Get Your Hands Dirty Oftentimes, you have to get your hands dirty to figure out what you want to do, Jaime discovered. She outlines her journey from college to working in HR to ultimately starting her own business. She advises listeners, try to learn something from every experience you’ve had that you can take forward: “Figure out something about that [present] job that you can take with you that will somehow make you a stronger performer in your dream job.”

Leadership Lessons Barry and Jaime talk about important lessons that Jaime learned and unlearned along the way. Some of these lessons are:

Not all leadership looks the same.

Decide how you want to show up as a boss. Emulate the good behaviors you learned from other leaders, and discard the bad behaviors.

There’s no one way to be a good leader. The best way is to just be yourself. Your leadership style is good enough.

“Don't be afraid to admit what you don't know; ask for help when you need it, and just keep that ego under control.”

Hire a good team: people you can trust who you’re proud to have representing your brand. Be transparent and let them lead sometimes.

COVID has taken a toll on leaders, but one positive effect of the pandemic is that we’re more tolerant of others than before.

Investing in People and Democratizing Entrepreneurship “In many ways,” Barry remarks, “most investors look for the people that they seem to make an investment in rather than the product.” He asks Jaime about her own philosophy for choosing investments. “As an investor today I think I have a little more openmindedness to founders that are a bit untraditional, because that was me,” she responds. She looks for more than just a good proposal on paper; it’s the passion and dedication of the founder that really helps her decide whether an investment has potential.

Two-Way Mentorship The best type of mentorship is two-way. Mentors and mentees should bring their expertise to the table, and be open to learning from each other. Leave the ego at the door though, Jaime stresses. It’s common and natural to wonder if you can add value to a business when you have no experience in that industry, but Jaime realized that many of the lessons she learned growing her own business were transferable to any business. Once you approach mentorship collaboratively, it will be successful and rewarding, she says.

Looking Ahead Jaime will continue to invest in consumer brands through Color, but she also sees an exciting opportunity in the emerging crypto and NFT space. She is learning more about this area, and feels that brands should embrace it and actually start adding these types of digital assets to their existing catalog. Brands would stay relevant, and consumers would be more inclined to buy these new products from brands they already know and trust. “The smartest hire a brand can make today is someone who is a consumer of culture” she points out.

Read the complete show notes at Barry O'Reilly.

Resources Jaime Schmidt Website | LinkedIn | Twitter

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What is a product-led organization? What does it take to build one? How can technology help solve real-world problems? These are just a few of the questions that Yi-Wei Ang has dedicated his career to answering. Yi-Wei is the Chief Product Officer at Talabat, the largest food delivery and quick commerce company in the Middle East, and is responsible for Talabat’s rapid growth in the region. He joins Barry O’Reilly to talk about what better leadership means, and what it takes to build a product-led organization.

Using Technology to Solve Human Problems “If we think about what great design is and great experiences are,” Yi-Wei tells Barry, “it's not just [that] it's beautiful - it’s how the thought process that goes behind every decision you make... is anchored on the end-user.” From an early age, Yi-Wei was fascinated with how you could create something that works using technology. He became immersed in human factors engineering in university, especially with building resilient systems that were responsive to unplanned exceptions. Ultimately, he remarks, it’s about understanding humans and building products that help them solve their problems.

Better Management Marty Cagan taught Yi-Wei that people aren’t looking for less management, they’re looking for better management. This was counterintuitive to what he believed at the time, and it was a major unlearning for him. He knew that he didn’t want a top-down micromanaged organization, so he mistakenly felt that this meant giving his teams complete autonomy to choose the problems they wanted to solve. The result from this approach was that his teams’ efforts were misaligned, and they did not deliver on several commitments because of it. Cagan’s advice opened his eyes that he needed to set constraints and provide context and direction for his teams. 

One Thing That Matters Trust the team close to the problem to solve the problem, Yi-Wei advises. Solving that problem should be their sole focus. At any given moment, there are 10 problems you could solve, and you might be inclined to tackle them all at once. This is a mistake, Yi-Wei and Barry point out. It’s more productive to pick the most important thing on the list and focus on solving that one problem. What you learn will tell you how to proceed. Leaders should help the team pick the problem. “The thing that often we don't spend enough time on - and I believe is that the crux of product leadership - is the ability for product leaders to help the team pick the one thing that actually matters,” Yi-Wei comments. 

Product Led Organizations Across Cultures  Barry asks Yi-Wei how he gives teams context and directions company-wide, while also paying attention to local differences. He replies, “The challenge with building an organization or product across all these different markets is that when you try and paint it with one brush you often just get an average product across everything.” The best approach, he finds, is to choose the most strategic problem in just one market and address that. You can go deep and find out details that you wouldn’t otherwise. Talabat’s impressive growth is due in part to taking this approach. The company sees the intersection of technology and the real world as an interesting challenge and is driven to innovate their operations to serve their customers. Yi-Wei’s definition of a product-led organization is one where you use technology and product to solve customer problems. 

Looking Ahead Barry asks Yi-Wei what he is excited about as he looks ahead. Yi-Wei responds that they are very focused on solving more problems in the food delivery space, including online and offline experiences. Scaling quick commerce is also part of their agenda, as he believes there are opportunities in so many verticals “to help enable people and bring a lot of autonomy back into their lives.” 

Read the full show notes at BarryO’Reilly.com

Resources Yi-Wei Ang Website | LinkedIn | Twitter

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Peggy Liu is on a mission to spark quantum change towards a better future faster. Hailed as the Green Goddess by the Chinese media, Peggy has been bringing people together from around the world to change the world for the better. She is the Chairperson of JUCCCE, the Joint US-China Collaboration on Clean Energy, as well as the bestselling author of Mesmerize the Media: Maximize Your Impact with More Press. She joins Barry O’Reilly on this week’s show to talk about building momentum for your change movement and how to recognize when the universe is winking at you.

From Head to Heart “The power of the intellect,” Peggy tells Barry, “is not matched at all by the magnetism of the heart.” This was an important lesson she had to learn in her own life, so everything she does now is based on tapping into emotional energy. Quantum change - societal change that’s the end goal of tornado leadership - starts with mastering emotional energy of movements, and of yourself, she argues. When you build the energetic architecture of a tornado behind the change you want to see, you bring people along with you to a better future faster.

Perception Creates Reality The books that inspired her from a young age and the influence of her grandfather, are just two of the “winks from the universe” that told Peggy what path she was meant to take. “...It begins with the perception of yourself and reality,” she remarks. “Perception is what creates reality.” You create the future by visioning that you’re already there. The emotion of euphoria of already achieving that future is what magnetizes people subconsciously.  Barry comments on the value of meditation as part of your morning routine. People who are good at leading change usually practice spending time with their thoughts, he says. Peggy shares an example of how practicing meditation helped her craft a speech for the Harvard Model UN. You have to open yourself up to transformational ideas. Allowing yourself freedom to do so is one secret to moving to quantum change.

Building Momentum Peggy helps her workshop attendees embody the future they want to see: she leads them into experiencing “the satisfaction of already living in the future that they want to create”. From there, it’s easy to reverse engineer the path to that future. Barry agrees that focusing on your vision of ‘better’ cuts through the noise and clarifies the creation process. You can choose from an infinite number of realities, Peggy comments, “but to make them come alive, you need to be excited about it and to believe that it already exists to have that satisfaction and euphoria, that love for living that life.” You then become a lightning rod to others aligned with the same vision. Barry remarks that the right people are drawn to you when you share your vision authentically.

Friction vs Flow “How successfully you create your reality is all about your level of understanding of friction versus flow,” Peggy emphasizes. Friction comes from trying to force things to go your way, flow is when things align naturally. She shares the secret of flow with listeners: “Your job is to be at the center of the tornado with a vision delivered with love; but you cannot control the tornado's path.” You have to be open to the possibilities the tornado brings. Barry shares an example of flow with founding Nobody Studios. When people are aligned you can create a bigger wave that’s like a lighthouse, Peggy adds.

Getting Started Barry asks how listeners can get started on this path. Peggy invites them to start with the questions on the Limitless Facebook page. These questions would help anyone and their community to envision the future they want to create. “Always start by being the James Cameron, creator of the Avatar world,” she advises. Believe in yourself as the creator of yourself world.

Resources Peggy Liu at Website | LinkedIn | Facebook | Instagram | Twitter  BrianTheHealer  Limitless Facebook page

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Some people just do things differently. Data analytics expert and advisor Donald Farmer is one of them. Donald works with Barry O’Reilly at Nobody Studios where he serves as the Chief Innovation Officer. With his company TreeHive, Donald advises enterprises and non-profits in emerging economies on innovation, strategy, and the uses of data. His career has taken him around the world and into a huge range of industries, from fish farming, to managing a village nursery, to being the face of business intelligence for Microsoft. He and Barry talk about creating a better world for the people who live in it through technology and innovation.

Different, not Better “I’ve never been interested in computers for their own sake. I’m really interested in what I can DO with it.” Donald tells Barry, “I see the machine as an intellectual lever that allows me to do more – that’s what’s interesting to me.” This leveraged power is important because there is a lot in the world that needs changing. A guiding principle of Donald’s work is that each individual is unique – humans can’t be aggregated into categories for whom one solution will work all the time. By moving away from the industry standards of incremental change and towards exploring alternative solutions that make things materially better for people, Donald is able to ask how a new company or idea will help change the way things are done. 

A Pivotal Moment Barry wonders about the choices Donald made that really clarified this perspective of focusing on humans above all else, and Donald shares a story about a fish farming tech startup he developed while doing some consulting work in the Scottish Highlands. He formed a company that productized the data around fish weights and measurements and aided in the complex calculations needed for transporting and exporting and so on. Eventually, they sent the product to Japan, where it was extremely well received, except for one major issue: the computer beeped when a data entry error was made. Now, in Scotland, no one cared about this, but in Japan, the public announcement of errors was intolerable. The context of the technology was different, so the product needed to be. Barry notes that you can execute an algorithm correctly, but when we’re talking about people using a product – the things that make them feel good can vary.

Don’t Solve Problems. Eliminate Barriers to Happiness. So much of software design starts from trying to understand the user problem. This sounds great, but Donald wants to start with what’s good in someone’s life – their job, their business, etc. The first step in modeling a problem is to model a positive situation, and look at how to make it easier to achieve that. Barry adds that when you’re constantly looking at the problems, you’re often overlooking better approaches: What does great look like? Problems are the obstacles in the way, so let’s design for the aspiration – you’re thinking bigger, you’re creating more options, etc. It’s an interesting way to look at the world – especially in startup space where people are always talking about the problem they’re solving, not the great world you could be creating.

Nobody Studios The vision of Nobody studios is to rapidly build a very large number of startups, but very differently from the traditional venture model, which is extremely broken. Venture startups are usually built with a financial and technical imperative – no one asks if it’s good, valuable, sustainable, or responsible. This means that a lot of ideas that might not tick those tech and finance boxes never get a chance – and that’s what is so exciting about Nobody – it’s a lighter touch focused on human, social, and personal values.

Go to BarryO'reilly.com for full show notes.

Resources: Donald Farmer: Twitter | LinkedIn TreeHive Strategy Nobody Studios

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Bill Gates is a fan of The Innovation Show, hosted by this week’s guest, Aidan McCullen. It’s also one of Barry O’Reilly’s favorites, because of the meaningful conversations Aidan has with guests, and because of Aidan himself, whose lifelong journey of reinvention is inspiring. Aidan played professional rugby for 10 years for the 2 most successful teams in Europe in Ireland and France before transitioning into the business world. He is an acclaimed consultant and advisor, with expertise in team transformation, innovation and team culture and leadership. He has also developed and delivered modules in Emerging Technology Trends at Trinity College. He and Barry talk about his recent book, Undisruptable: A Mindset of Permanent Reinvention for Individuals, Organisations and Life, as well as the mental models he learned and unlearned that helped him become who he is today.

Moments of Change “Difficult moments are always growth points,” Aidan remarks. “They’re inflection points where you can reframe them… as milestones rather than millstones.” Success is more about pushing through challenges and working hard to accomplish your goals, and less about how much talent you are born with, he tells Barry. The secret is to just keep going, and give it your all: “When I get out of this I don't want to ever turn back and go, I should have done, I could have done… I never wanted to walk away with something and have a regret.”

Discipline Is the Magic Word Aidan succeeds in rugby and in life because he just keeps showing up. “Discipline is like this force that you can use and point it at anything to use it for positive,” he tells Barry. When you do the work, Barry agrees, you set yourself up to get the best out of yourself and the situation. It’s what separates people who excel from those who are just ‘winging it’.

Lessons to Unlearn Barry asks Aidan to share some lessons he had to learn and unlearn. Some of the lessons Aidan shares include:

“There's always a high and a low at the same time. They're always coming in succession. The trick is to enjoy the highs but know there's a low coming, so prepare for it. And when you're in the low, understand that there's a high coming again [so] you'll get through this.”

For every Batman, there has to be a Joker. The anti-hero gives contrast, which you now have to manage. Someone has to play that role so you can push through your boundary. Seeing them from this viewpoint spares you from feeling angry at them; it also helps you use that energy to move on with your goal.

Don’t fall into the coconut trap. Let go of things that no longer serve you. Don’t over-identify with your jersey - you’re just its custodian for a time then you have to pass it along to the next person. 

Looking Ahead Aidan is always learning and finishing up a course in executive coaching to “add some discipline” to his existing executive coaching practice. His own workshop, The Permanent Reinvention workshop, is doing very well, he tells Barry. He is humbled to see the impact his course is having on how teams communicate and collaborate. He also coaches senior leaders on thought leadership writing and executive presence. Another project he is passionate about is Edge School, an idea he conceived and is developing in collaboration with Alexandra College and the Learnovate Centre in Trinity College. Edge School will give students the opportunity to gain real world experience in emerging fields such as AI Ethics, cybersecurity and communication skills. This is not about making money, he tells Barry; it’s a legacy that he hopes that the school will use to create a template which they can share with other schools.

For full show notes, go to BarryO'Reilly.com

Resources Aidan McCullen on LinkedIn | Twitter  Undisruptable: A Mindset of Permanent Reinvention for Individuals, Organisations and Life The Innovation Show

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Soumeya Benghanem is a product management leader at VMWare and the creator and curator of a thriving product manager and builders community on Clubhouse. Soumeya is an inspiring member of the product industry – she shows up with passion, resilience, and adaptability to everything she puts her hand to. She and Barry discuss the different kinds of cultures you run into in the tech industry, how to handle mistakes – your own and those of your team, and the value of community. What’s Different about Start-Up World Soumeya got her start at large companies and in the start-up world – this is important because what works in large companies and in smaller ones are not always the same. There are systems and values that are constant, but how they are applied in different cultures is different. The amount of risk you can take in a startup compared to a large established business is quite different, for example. Barry concurs, and notes that one of the classic traps you can fall into is that as a consultant, you can coach and guide teams towards solutions, and people will be able to take that and run with it. In a startup, you often need to get right in there and do it. Making Other People’s Mistakes It is very hard to make mistakes that you know other people have already figured out the answers to. Soumaya thinks that it is important to make them anyway, to keep the wheels moving, and to make sure you’re really learning. Barry points out that there are so many ways to do things the right way, and you just need to commit to one. It is also possible to make the same mistake over and over again without ever knowing what you’re doing. Barry notes that this is quite a common problem and shares his own repeated mistake – and the solutions he has developed to make sure there is better visibility and collaboration on small teams.  Team Retrospectives Soumeya’s team has a meeting called the Weekly Retro where they talk about what has gone on, what has been great, and what’s been difficult. This is incredible for creating awareness and taking advantage of the team memory of the big picture. Barry accuses Soumeya of mind-reading and talks about the Retrospective meetings that his start-up studio has instituted as well – something he considers the most powerful meeting you can have. They are open spaces to talk about concerns, and issues and successes, especially when working on new and innovative projects. Soumeya and Barry dig into the nuts and bolts of running retrospectives, and different ways they’ve proven themselves useful. Being the Squeaky Wheel Asking for help, when you’re in an ecosystem that’s willing to provide it, is a point of strength. It may be counterintuitive, but the teams you can trust the most are the ones who are open about saying “we’re having difficulties, here’s what’s happening and what we’re doing.” Soumeya goes on to note that even during planning, you often don’t see any disagreement or idea conflict – and that is an indication to look for two things: are people able to prepare in advance and think through different scenarios? And that there might be unhealthy team dynamics that need closer examination. Soumeya talks about the XP (Extreme Programming) methodology she uses to address these problems. Looking to the Future Soumeya is looking forward to making the jump from achieving product and market fit to scaling – and getting through the awkward and painful canyon that is often in between them. It is this gap that Soumeya finds fascinating right now, and wants to work in.

Read full show notes at BarryOReilly.com

Resources: Soumeya Benghanem on Twitter | LinkedIn VMWare Clubhouse

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“If there's one thing we love on this show,” Barry O’Reilly tells this week’s guest, “is people just speaking from their heart and what really matters and what they believe in; and I can't think of anyone who better exemplifies that than you.” JeVon McCormick's story is certainly a testament to the value of believing in yourself and taking consistent action despite the odds. JeVon persevered through every setback, vowing to never stop until he achieved his goals. He and Barry talk about his inspirational journey and how to keep going even when the decks are stacked against you.

Possibility Opens Your Eyes You can only aspire to what you see and know is possible, JeVon tells Barry. He shares that a drive through an affluent community as a child was the beginning of his mindset shift. “It showed me possibility, and that was very key,” he comments. A big problem in lower economic communities is that many people there don’t know all the options that exist. “When I was shown possibility, that was game-changing for me; even though I didn't know how I was going to get there, it showed me possibility, and it was up to me to go figure out [how to] make that happen,” he says. [Listen from 2:00]

Be Consistent In a society of instant gratification, the importance of consistency is often downplayed. However, JeVon tells Barry, what helped him improve his circumstances and his life overall was his commitment to never stop trying. “The biggest thing was I was always consistent,” he remarks. He kept learning from his mistakes and improving on his strengths. He posits, “I truly believe you only fail if you stop trying.” Barry adds that society rarely talks about the hard part of consistency: getting back up after getting knocked down, or holding on when it seems more sensible to let go. [Listen from 8:35]

How Conscious Capitalism Can Change Lives Barry sees JeVon’s work in conscious capitalism as a great juncture of his ethics, mindset, and entrepreneurialism. He asks him what inspired him to get involved in the space. Society demonizes capitalism, JeVon replies, but it has tremendous power to change lives: “Capitalism has provided me with the life that I have right now, and I truly believe that if more people from the lower economic communities that I come from knew the power of capitalism, that it could also change their lives.” Conscious capitalism is about taking capitalism to the communities where it can really make a positive impact. He shares an example about how retailers like Whole Foods could help change generational poverty by opening stores in lower-income neighborhoods. More than just creating jobs in these communities, they would be creating possibility, so younger generations would now have more to aspire to. [Listen from 22:20]

Looking Ahead JeVon is excited about doing his part in making a racially just society. He explains why he now goes by JeVon instead of JT. “I made the decision for every kid named RayVontae, Martavias, Lawanda, Lacresha; and I did it with the intent - in the belief - that one day when they hit corporate America, that maybe they can work next to a JeVon and not just a JT.” He’s about creating real, tangible change: not just attracting diverse persons, but creating a culture of belonging so everyone feels welcome and respected in the workplace. Barry comments that we have to call out inequality, talk about it, so we can start the change. [Listen from 33:55]

Find complete show notes at BarryO'Reilly.com

Resources JeVon McCormick Website | LinkedIn | Twitter  Charles Marohn Jr - Strong Towns: A Bottom-Up Revolution to Rebuild American Prosperity

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Casey Rosenthal is the co-founder and CEO of Verica and the former Engineering Manager of the Chaos Engineering team at Netflix. He is an author and thought leader in chaos engineering, “a discipline of experimenting with software systems in production in order to build confidence in the system's capability to withstand unexpected and turbulent conditions.” Casey was an early engineer and champion of chaos engineering, bringing together people from companies like Netflix, Google, Facebook, and Amazon to explore the field. In this week’s Unlearned Podcast, Casey and Barry O’Reilly talk about the chaos engineering domain and how to apply its principles to build high-performance teams and businesses.

Origins of Chaos Engineering Netflix’s migration to the cloud, in particular the sudden outages and service disruptions that would occur, spurred the creation of a program they called Chaos Monkey. “So Chaos Monkey would for each service inside Netflix, every day it would randomly choose an instance and turn it off,” Casey tells Barry. The underlying principle was that once engineers knew a problem existed, they would fix it. “It changed their behavior by aligning the organization around the business problem that needed to be solved,” he remarks. He shares the early Chaos Community Days, bringing colleagues together from leading tech companies to build the discipline they would call chaos engineering.

Navigating Complexity Chaos engineering assumes that you already have complexity in your system. “This is engineering to navigate it, or to surface it so that you’re aware of it,” Casey explains. Once you’re aware a problem exists, you can take steps to fix it. It’s a proactive approach to improving availability and security, which improves your system overall. He shares an example of how United Health Group was able to discover a system vulnerability they didn’t know they had, and allocate appropriate resources to strengthen their position. Barry comments, “The thing that’s very contrary with this is that it's not about people trying to predict the future, it's about them having the data to understand how the systems are performing and then taking action based on that.”

Relearning Leadership “Unlearning management is relearning leadership”, Barry says. He asks Casey to share lessons he learned that he is bringing to his new company. Managers are creatures of habit, and that holds them back, Casey responds. “Most of us think we're making decisions when we're not; we're just following habit.” He tries to formulate his own management principles and strategies in his company, instead of following traditional ideas. He believes a manager’s job is to ensure their team has the context they need to make the right decisions. His litmus test is this: if your employees can explain why what they’re working on is the most important thing they could be working on for the company right now, then you are a successful manager.

Read the full show notes at BarryOReilly.com

Resources Casey Rosenthal on LinkedIn | Twitter  Verica.io

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Sejal Thakkar is on a mission to educate and empower others to create a world where everyone is treated with dignity and respect. She is a former employment law attorney, a TEDx speaker, and the founder and Chief Civility Officer at TrainXtra, where she helps her clients create positive, safe, and respectful workplaces through customized training and coaching. She also recently joined Nobody Studios as Chief Culture Officer. Barry O’Reilly welcomes her on this week’s Unlearned Podcast to share her story of unlearning how to shift her own biases and beliefs.

Check Your Biases It’s difficult to acknowledge your biases because they often portray a vision of you that is the opposite of what you believe of yourself. Sejal had to check her own biases in order to do her job as an attorney, representing persons accused of discrimination and harassment. “I had to do a lot of my own inner work to recognize my own bias so that I can do my job because there's no way that I can represent people unless I checked my own biases,” she remarks. Our biases often stem from our experiences, and they don’t make us bad people. The key is to slow down and recognize when we’re letting our unconscious biases affect our decisions and use strategies to combat them. She has changed her language: she no longer refers to them as biases, but beliefs. She shares an online tool listeners can use to discover their unconscious beliefs. She also advises leaders to have an accountability partner who will tell them honestly if they’re letting unconscious beliefs influence their decisions.

Unlearning Preconceived Notions Practice active listening, Sejal advises, and you’ll start picking up on your own preconceptions and judgments. Barry reminds listeners that we’re all programmed to have automatic responses in some situations. However, we can reprogram our brains once we become aware of our negative hidden beliefs. He and Sejal discuss their own blind spots and the importance of being humble and willing to learn and grow. “I've spent my whole life up to this point learning, and now the rest of life is unlearning,” Sejal comments. It’s about taking small steps in the right direction; eventually “everything else will start to roll”. “The ability to adapt is so powerful,” Barry agrees; “...just do small steps and learn your way through it.”

Where Culture Starts  “Your culture starts the moment you hire the first person,” Sejal tells her clients. Building a healthy, respectful, and diverse culture means maximizing the skills, talents, and contributions of every employee. You have to know what your employees want: ask them and listen to their feedback. “If you're too afraid to know about what problems are going on, how can you fix them?” she argues. Nurture an environment where people feel safe to speak up so that you can deal with problems before they become a lawsuit.

Looking Ahead Sejal is excited about being part of Nobody Studios and helping to build the company culture from the ground up. “The key is the learning is never gonna stop,” she tells Barry, “so I'm excited about the fact that I get to learn about and challenge myself in ways that I never have.”

Read full show notes at Barry O'Reilly.com

Resources Sejal Thakkar on LinkedIn | Twitter  Implicit Association Test

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Rich Sheridan, world-renowned entrepreneur and bestselling author of Joy, Inc. and Chief Joy Officer, is on a mission to inspire organizations to create joyful cultures. He is the CEO and Chief Storyteller at Menlo Innovations, recognized by Inc Magazine as the Most Joyful Company in America. People from all over the world have visited Menlo to see firsthand the unique culture and systems at the company. Barry O’Reilly welcomes Rich to this week’s Unlearn Podcast to talk about how leaders can inspire joy at work.

Listen to Your Intuition Rich’s experience at “one of the highest-flying entrepreneurial tech firms” motivated him to listen to his instincts. He tells Barry that they were so far removed from what their customers wanted, that he knew instinctively they would not survive. His intuition proved correct. “They weren’t learning anything,” he remarks; “...they were only applying what they learned from years past.” He vowed to do things differently in his own company so that they didn’t make the same mistake. “All of us have that little place in our guts when something goes wrong… I just learned to pay attention to that signal,” he tells Barry.

Look For the Opportunity When things aren’t going well, that’s where the opportunity is. Many systems exist because they helped you get to where you are, but “there are bits that calcify”, Barry says; leaders need to be true to themselves and see where changes need to be made. Rich points out that when things are going wrong, the leader must become a student again. He recommends going to books first: read the first 30-40 pages, and if it resonates with you, keep reading. You may discover a new idea or an opportunity that will help your company grow.

Experiments Over Meetings “Let’s try it before we defeat it.” This simple change of approach has inspired dramatic change in many organizations, Rich says. Ideas need a chance to be proven before being discarded, because only then would you really know if they work. “I think that word ‘try’ is probably one of the most underutilized but most important behaviors for companies to do innovation,” Barry argues. “Take an approach that says take action versus take a meeting,” Rich agrees. He and Barry discuss the benefits of doing small experiments. When you create a culture of experimentation, your systems will always evolve. The leader’s job is to foster that culture by driving out fear: “My role as a leader [is] to pump fear out of the room,” Rich emphasizes. He shares how his daughter inspired him to unlearn leading through fear. It takes self-awareness and a good dose of humility to acknowledge where you’re going wrong and to course correct, Barry comments. He tells Rich that he has learned to be more intentional about who he chooses as role models because our own leadership behavior is conditioned by our models.

Looking Ahead The biggest challenge of the pandemic is loneliness and isolation, Rich says. However, coming back together will likely be as difficult as the separation was, and it will take a while to get over the anxiety. He believes we will continue to embrace the new ways of working we learned during the pandemic. He and Barry agree that we see each other as whole persons now, because of this experience. As such, we will continue to be more empathetic and see each other’s humanity, building deeper relationships and a stronger culture. The past year has also reinvigorated his entrepreneurial spirit, Rich says.

Full show notes can be found at BarryO'Reilly.com

Resources Rich Sheridan on LinkedIn | Twitter  Rich Sheridan books Menlo Innovations

Chatter by Ethan Cross

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Margaret Molloy and Barry O’Reilly connected by following each other’s podcasts and work. Margaret grew up in Ireland, and attended Harvard in the US. She currently serves as Chief Marketing Officer at Siegel+Gale, a leading brand strategy and design experience agency. She is a recognized leader in diversity and inclusion, and has built a global community around her How CMOs Commit podcast, as well the popular panels she regularly convenes.

Simple is Smart “I study topics deeply to understand them profoundly, to be able to communicate them simply,” Margaret tells Barry. Being able to distill a brand to its essence and then communicate that in clear, simple language is very compelling, she argues. COVID-19 has only amplified the value of simplicity as it removes “cognitive tax” during this stressful time. “I believe the buying public will reward brands who truly appreciate the opportunity to remove that cognitive tax... Simplicity is just another way to say removing friction,” she remarks. Barry adds, “When you can create these simple, clearly understood messages, that's what connects with people.”

Illuminating Blind Spots It’s an act of courage and grace for someone to show you your blind spot. Understandably, it’s common for your first reaction to be defensiveness. This was certainly Margaret’s initial reaction to being told by an attendee that her gender-equal panel did not reflect ‘The Future of Branding’ as the name promised since it was not racially diverse. The experience challenged her view of herself and showed her that race was her blind spot. “Shortly after that I caught myself, and I realized I had just received probably the most constructive feedback I had ever received in my career,” she says. She had to unlearn her mental model of being color blind: she needed to be color brave. “Ever since that day I have worked to build my network and extend myself to make sure that I have diverse representation on our panels,” she points out. Interestingly, it was because someone else illuminated his own blindspot, and he learned from the experience, that the attendee felt inspired to pay it forward to Margaret.

From Defensiveness to Curiosity It takes courage to listen to and accept feedback that’s “contrary to what you believe to be true of yourself”, Barry comments. He asks Margaret how she is able to get past defensiveness in those moments. “The heart and soul of it is curiosity, and what I've learned over the years is that curiosity and judgment can't coexist,” she responds. Taking a posture of curiosity helps you move from judging yourself or defending your position, to growth. It’s really hard to take criticism in areas where you feel accomplished, she says, but being curious helps. “The older I've become, I've actually become more curious... The unlearning for me is that you don't have to have all the answers. In fact, your impact is much more a function of your ability to frame good questions.”

Looking Ahead Margaret believes that the evolution of brand as customer experience will continue to play out in the future. An aspect of this evolution will include how companies demonstrate their purpose and how customers discern their authenticity. She believes that forward-thinking marketers will shift focus from buyers to users in order to build community and ultimately, customer loyalty. She advises listeners to “look out for companies who build products out loud…” Barry agrees that the traditional paradigm of secrecy about upcoming product features and releases should be changed. It’s one of the reasons they founded Nobody Studios, he says.

Read the full show notes at BarryO'Reilly.com

Resources Margaret Molloy on LinkedIn | Twitter Siegel+Gale How CMOs Commit with Margaret Molloy

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Mark McNally has seen the upside and downside of new company ventures. He has been involved in 14 startups, as a senior executive or CEO each one building on the lessons he learned from the one before. Barry O’Reilly describes him as a “radical thinker, venture innovator, founder and Chief Nobody at Nobody Studios.” Mark’s bold vision to create 100 compelling companies over the next 5 years was so intriguing to Barry that he jumped at the opportunity to join Mark on the boldest bet of their careers. In this week’s show, they discuss the vision for Nobody Studios, as well as their lessons learned and unlearned over the years as entrepreneurs. And why now is the moment for the missing piece of the venture ecosystem .

The Bold Vision For Venture  “...What we're about to do next is launch a venture studio together with an amazing collection of diverse innovators, entrepreneurs, and creators who want to change the way new companies are created, sourced, explored, and scaled to sustainable businesses,” Barry tells listeners. “But not only that, we're going to be the first company to make venture investing accessible to the masses by crowdfunding the company to enable anyone to own equity in the studio and every single company we create in the future forever.” 

Missing out on making simultaneously exploring companies of the future frustrated Mark. “I decided I really wanted to create a vehicle that allowed people to be more involved and more aggressive in making bets on things that aligned with their vision of the future,” the result is Nobody Studios.

People First Nobody Studios’ founding principle is people first. If you have ideas and talent, no matter where you are in the world, the company invites you to join them on their journey. “I'm a big believer that if we focus on building up people around us, then our journey will be just fine,” Mark remarks. 

Making people part of something bigger is in the company’s DNA, he tells listeners. Transparency is another of their key tenets. “We're giving them [people who get involved] this kind of really open access to how this grows,” Mark says. Another powerful principle is learning from one another: “As much as we're mentoring people that recognize their gaps, we're also letting them mentor us.” To achieve their goal of building 100 companies in five years, Barry says that they have to build a system to get ideas to market as quickly as possible. He is excited about the unique incentive structure, where you’re rewarded for your contribution across the company’s portfolio.

Why Venture Capital Needs Venture Studios Our purpose at Nobody Studios will be to de-risk pre-seed stage business ideas. We’ll do this by minimizing the time, speed, and capital involved in validating truly repeatable, scalable business models before significant venture investment. 

Venture capital investors usually wish they could:

Stop an investment;

Split one company into multiple companies;

Merge several companies into one company; 

Pause companies when the timing isn’t right;

Optimize talent by putting players in their best positions over time.

Making Wealth Creation Accessible To All For Nobody Studios to accomplish the goal of 100 companies, we’ll need a tremendous amount of talent, capital, influence, and ideas. 

There's a whole array of opportunities for you to get involved:

Becoming part of the effort in some capacity, whether part-time or freelance, joining Nobody Studios itself, or one of the companies that we create. 

Investing. We're actually going to be the first venture company to offer equity in the studio through crowdfunding. 

The potential upside is pretty fantastic for anyone involved, because the equity will be spread across the whole portfolio of businesses.  Meaning you wouldn’t be betting on just one company—you’ll have a stake in every company we create, forever! 

Resources NobodyStudios.com  Nobody Studios on LinkedIn | Instagram | Facebook

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Kai Haley is the Head of UX Methods and Practice at Google and the founder and leader of the Google Sprint Leadership Academy. She is an expert at leading change, creating movements and creating high performance teams. Barry O’Reilly says of her, “She was one of the first people to embrace design sprints at Google and helped formulate that practice, codify it, and has coached hundreds - if not thousands - of people how to use these tools to identify product visions, drive successful user-centered products, and build cultures of innovation all across Google and outside.” She joins Barry in this week’s show to talk about how design sprints started, lessons she unlearned along the way, and the importance of designing for people first.

Looking Outside Look for patterns and inspiration outside of your field, Kai advises. “I do gravitate towards looking outside of wherever I'm focused right now to how are people solving things over here, or what inspiration could we gain from something else?” she says. Her undergraduate study in anthropology helps her to keep the human and cultural connection top of mind in any design project. “When I'm looking outside of the discipline of design I'm keeping my eyes on the people and who this is for and who are we trying to solve these problems for,” she tells Barry.

Origin of Design Sprints Creating a high performance cross-functional team requires a shared language and a shared idea of success. Getting design sprints off the ground meant that Kai and her team needed to bring together elements of design thinking, user research, business methods and psychology. The term ‘sprint’ was used to get the engineering team to buy in, as they were already used to ‘agile sprints’. Kai tells Barry that the first sprints were just four hours long, while other people were running longer sessions. Starting small gained her buy-in as everyone praised how impactful the exercise was, and asked for more. Her manager soon asked her to have one every two weeks. “In a very small and quick way I was able to get what we needed as a team, which was shared vocabulary, shared understanding of success, ideation, and then we could choose a direction together and then send people off to start executing against it,” she comments.

Key Lessons Barry asks Kai to share the key lessons from her design sprint journey. She explains that every design sprint would be different, so when she trains people she doesn’t use a rigid framework. Instead she wants them to focus on the goal to accomplish; she wants them to use the tools she teaches and modify them for their unique circumstances. “How are you going to get alignment and buy in before you even get people into the room? And then once you get them into the room, how do you make sure you don't waste their time?” she asks leaders to consider. 

She and Barry discuss other key lessons, including:

It takes attention and focus to help people learn how to learn.

Nurture a culture that encourages people to try things.

Think about the humans you are designing for. Kai advocates for an inclusive co-creation approach.

“Movements are really important because they give people something to believe in.”

Share a common vision and metric of success.

Start where you can show the impact.

Focus on the people who want to change.

Read the full show notes at BarryOReilly.com

Resources Kai Haley on LinkedIn | Twitter

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Nancy Householder Hauge is the Chief HR Officer at Automation Everywhere, one of the fastest-growing companies in the world. She sees herself as Chief People Officer because she believes in putting people first even in the midst of disruption. Nancy has won the Stevie Award for women in hi-tech and is considered one of the most influential women in Silicon Valley. 

Barry O’Reilly admires her talent for spotting winners and her sense of humor. Nancy has coached future female leaders and truly understands the challenges that organizations face when they are transforming. She joins Barry to talk about how she spots future disruptors, the importance of thinking time, and why automating human jobs should be celebrated rather than feared.

Spotting Future Disruptors Nancy credits her time at Sun Microsystems with giving her an appetite for companies that disrupt. She believes that getting ready for the future means unlearning the past and being open to something new and different. Three things get her intuition buzzing that a company may be a future disruptor, she says:

The people are smart;

They are good, as people, and at their mission;

They are passionate about what they can achieve.

She tells Barry that she joined Automation Everywhere because the CEO asked her a provocative question that made her want to help solve it. Barry comments, “People that are smart and passionate and deeply ingrained in something new seem to be able to ask those provocative questions; and great teams are good at asking those provocative questions of one another... to actually tease out some of the real meaning, the real value, the real things that matter to folks.” [Listen from 2:50]

Automation is Good Automating repetitive manual tasks frees humans up to do the work our brain was made to do. It uncovers talents in us that we couldn’t explore because we were bogged down with “arcane processes and mundane work”. “The really wonderful discovery I've had around bots,” Nancy tells Barry: “One is I've never met anybody who wants to go back to manual after they've automated something. And the second thing is we've never built a bot... that didn't promote a human being. In other words, they got to do something more interesting.” Because Automation Everywhere robotized many repetitive tasks, they were able to use the data generated to create individual development plans for their employees, which helps ensure each employee is getting what they need to thrive. This is something that could not have been developed without automation, Nancy proudly emphasizes. Barry comments, “...bots are here to unleash people to do highly complex, creative work and take away the menial tasks that are holding them back from blooming…” “Automation has given me access to my ‘if only’ list,” Nancy continues. [Listen from 9:40]

Read the rest of the show notes on BarryOReilly.com

Resources Nancy Householder Hauge on LinkedIn

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Barry O’Reilly and this week’s guest, Zhamak Dehghani met 10 years ago when they worked together at ThoughtWorks. Zhamak is currently the Director of Emerging Technologies at ThoughtWorks and the creator of Data Mesh, which Barry describes as “one of the most exciting paradigm shifts in how we manage data at scale.” He and Zhamak discuss why traditional data architecture models are failing and how applying product thinking principles to data management is a way to harvest the data’s full potential. “This show,” Barry remarks, “is for those who are curious to understand how to bring the convergence of product thinking, data management, and distributed systems development together to create platforms and products of the future.”

Early Values Zhamak has always believed in distribution of responsibility and decentralization of ownership. She finds that these design principles are more compatible with real life. Colleagues taught her the Unix philosophy early in her career which now forms the basis of her data management approach. “They taught me those wonderful ideas to build systems and programs that do one thing and one thing really well. But most importantly they work together really well,” Zhamak says. “‘Simple is beautiful and beauty is the truth’... Reduce systems to their simple principles; then together can emerge complex behaviors.” She saw an opportunity to bring the UNIX principles to data.

Challenging Assumptions It often takes someone new to a system to point out obvious flaws to long-time practitioners. Zhamak says that when she came into the world of big data, she was agnostic to the accepted assumptions, so she felt free to challenge them and conceive a different paradigm. For some reason when it comes to data, people eschew UNIX principles and see it as something to be centralized. Unsurprisingly, a data lake becomes monolithic and departments become siloed. Reimagining the world of data requires a new language, she points out: “The moment you need to imagine something different you need to use a very different language.” Instead of seeing data as an asset - which you want to hoard and get more of - Zhamak advocates that data can be seen as a product which should be used to serve internal and external customers. Barry adds that the idea of the single source of golden data makes companies unable to move as they get bigger.

Move to Product Thinking Barry comments that the shift towards product thinking started with Amazon. Their monolithic database was preventing them from scaling. “They realized that they needed to create these smaller, more autonomous units that had the capabilities to build things just like product teams. This is where this notion started to emerge from changing the organizational design... both technically and just how teams would work together,” Barry says. In this new way of working, teams could experiment and own outcomes. They could make small, quick changes and see the effects.   What is Data Mesh? Instead of trying to fit data into a mold, Zhamak feels that its dynamism should be embraced. “Create an architecture and ownership of data that starts with the assumption that data can be useful and shareable and trustworthy right at the point of origin; and then allow for different domains and different aggregations, different projections to get created as a mesh picture,” she posits. She explains how this new view of data impacts ways of working and the type of platform a company would create. The four principles of the Data Mesh philosophy are, “domain ownership of the data; data as a product; self serve data platform to enable autonomous teams; and a federated computational governance to balance the interoperability of a decentralized world with the trust and security built-in.”

Read the rest of the show notes on BarryO'Reilly.com

Resources Zhamak Dehghani on LinkedIn | Twitter Data Monolith to Data Mesh article Data Mesh Principles article

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On reading Lean Enterprise, this week’s guest, Chris Goddard, reached out to Barry O’Reilly several years ago to help implement its principles and practices at his company, G-Research. Chris has been with G-Research, a leading quantitative research and technology company in the algorithmic investment space, for almost 20 years. He is currently the Chief Technology Officer there. Barry says of G-Research, “Working with the team has really helped me evolve my thesis on the power of gathering and synthesizing data to inform your products and business model investments, much of which is actually captured in my latest article, Precision Product Creation…” 

Becoming a Leader Being thrown into a job that he didn’t sign up for turned out to be a blessing in disguise for Chris. “What it really taught me was how the ecosystem of everything hung together;” he says, “how you needed to think about the building blocks as being bigger than just lines of code…” That experience set him up to progress to more strategic roles over his 20-year career at G-Research. He says that it’s important for leaders to ask good questions and to look for inspiration outside their field. Also, you have to accept that you will be wrong sometimes and face up to your mistakes. 

Signals of Change and a Culture Shift At a certain point, the strategies that brought you success in the past no longer suffice. At that point, a leader needs to move in another - often counterintuitive - direction. G-Research’s founder asked Chris, “Why does it feel like it's not working? Like we were adding more resources and that the business was doing well, but it felt like it was getting harder.” Chris tells Barry about the changes happening in the company, as well as how he realized that the company needed to shift their focus from functionality to developing their craft. With Barry’s help, Chris says, the company underwent a culture change. He jokes about the ‘Barry Post-Its’ that now decorated the previously bare walls. “It felt like it just cracked open the creativity that was in the business,” he comments.

Becoming More Open The transition from developing all their own software to embracing open source is just one of the culture changes G-Research adopted. Barry comments that he admires the spirit of the team - he loves how they see ideas as hypotheses that they openly challenge. Chris remarks that they also started measuring more: they wanted to see how the new methods were impacting the company. He and Barry talk about the risk metric that G-Research used to measure speed to market. Interestingly, the team itself also grew more close-knit. They each wanted to learn about what their colleagues were doing, and took pride in being part of the team.

The Power of 10,000 Using open-source software is like getting “the power of 10,000 engineers when you only have a few hundred,” Chris argues. He tells Barry that it comes down to what you’re contributing to open source. You don’t have to expose your IP, but if you can solve general problems that many people have and put the code out there for them to use and modify, it will benefit everyone. You’re also showing the quality work you do, he says. 

Looking Ahead and Top Tips Chris is thinking more about what could be around the corner technology-wise, particularly exploring how best to use the public cloud even while investing in private data centers. Barry asks him to give advice to a leader who senses that their future success is being limited by their present actions. Chris advises such leaders to keep in touch with the people doing the job, keep abreast of technology trends and read a lot. He stresses that sometimes you just need to “stew on it.” He remarks, “Actually if you sometimes just let your mind tell you the answer you'll find it's there. You just have to kind of quiet down a bit.”

Resources Chris Goddard on LinkedIn

Thinking, Fast and Slow by Daniel Kahneman

Download Barry’s latest article: Precision Product Creation

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“Amy Farrow [is] a seasoned executive who lives at the center of customer-focused product and technology innovation,” Barry O'Reilly says. Amy is a collaborator, team builder, and problem solver at heart, traits that she brought to her former roles at Salesforce and Twitter, and which she continues to champion as the current Chief Information Officer of Lyft. Amy and Barry talk about the value of reflection and how to leverage learning to build a better organization, including what not to do in times of challenge or crisis. As Barry points out, this episode “is a fantastic podcast to understand the convergence of customer insights, technology, and product to create great experiences.”

Learning From Customers “There’s what you see and then there’s what you don’t see. And often what you don’t see is more impactful than what you do see,” Amy remarks. She and Barry discuss the importance of learning about and directly from customers. In her early career, Amy didn’t really understand why this was so important. Her time at Salesforce in particular gave her a new perspective. Barry comments that customer discovery is part of building great products and delivering great service. If a customer has a problem, help them to solve it as best as you can and bring back what you learned to the team so you can improve the product. Building this type of culture ultimately becomes a competitive advantage, as it did for Salesforce.

Keep Moving Forward Leveraging your team’s expertise in a crisis is critical; to do that you first have to bring people together and build trust in one another. Barry comments that high-performance teams feel free to make mistakes and to discuss them openly without laying blame. In this healthy culture, teams respond quicker and learn faster than the competition, he says. In a challenge or crisis, keep going forward, Amy adds. Take small steps toward solving the problem. She says that she tries to understand why the problem arose without laying blame. Instead, her focus is on studying the problem and finding ways to solve it with the help of her team.

The Value of Reflection  Reflecting is hard work: Amy describes it as ‘cognitive load’ to constantly think about your actions. However, it’s critical work as it helps you to understand what is working and what you should do differently. “One bad pattern I see is this belief that you retrospect at the end... Why would you wait?” she remarks. You should reflect multiple times, including at the start of the year. Last year was tough for everyone, so she chose to reflect on her team’s accomplishments instead of the negatives. “We definitely learned from it, but I also just felt like people needed to let it go and move on from it more than any other year,” she tells Barry. Barry also shares an uplifting story about celebrating small wins. These small acts have a “profound impact on building team, on building trust, on role modeling ... just upping the bar in terms of the culture you want to create in the company,” he comments. Amy emphasizes that it’s important for leaders to take action on what they learn from these reflective exercises.

Looking Ahead Barry asks Amy what she is excited about for the future. She describes two ongoing unlearning events in her personal life. Overall, she believes that the end of this year will be much better than the start. Her advice to listeners is to “Keep learning forward”. Take what we learned about work and life and apply them to make work better in the future.

Read the rest of the show notes on BarryOReilly.com

Resources Amy Farrow on LinkedIn

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Quincy Caroll has a passion for delighting users, fans, and communities through world-class mobile, web, and computer applications and services. Quincy is this week’s guest on the Unlearn Podcast. He and host Barry O’Reilly discuss the bold product decisions he experienced while working on initiatives such as GarageBand at Apple, pivoting eBay’s search algorithm to scaling Crunchyroll, the world-leading Manga streaming platform from 300,000 to 3 million users. 

A Product Person Quincy changed careers several times throughout his professional life. What he learned along the way helped him to become a “product person”. Barry asks him to explain some of the things he learned about himself during this period. Quincy responds that being a product person allowed him to work with all kinds of people. The diverse perspectives and experiences are invaluable in developing products, he comments. He is happy that the focus is now on group mentality and fostering team success. “Now it’s about the actual function of the role as it is, like either mentoring other people or setting up the team in such a way that the chemistry is right.”

Getting The Timing Right Companies, products, and projects are all about the right timing. How they come to be and how they ultimately develop depends on the time spent on them and what concepts and disciplines are used to create them. Barry comments that craft discipline is a concept that is still forming even now. He remarks on Quincy’s time at eBay. Quincy adds that during his time there, he worked on, and was able to complete, significant platform-level projects within eBay’s system. However, he also faced the challenge of convincing the company not to end certain projects. Many organizations face this same challenge, Quincy comments: they either end projects too quickly, or let them run for too long.

Quality over Quantity Quincy and Barry discuss the challenges of business owners who are rigid regarding product development. Barry comments that many people have challenges getting their ideas launched and supported due to these owners. “Companies need to look at different variables to create quality rather than quantity,” Quincy says. One such variable is an employee’s working process. Employees may structure their entire working process around a particular method to get a desired outcome. He warns that changing their structures in hopes of improving company profitability may have adverse effects. He advises that these kinds of issues can be resolved by testing new technologies and analyzing the resulting data to decide what methods work.

Cultural Crystallization Cultural crystallization is unraveling an original framework into its components and deviating from the established norm. For companies to develop, they need to crystallize the culture of not only the company but also the industry and the product. They need to unravel the cultural framework around promotion. To do this, product developers need to be heard. Quincy gives an anecdote of presenting a product to the heads of department through the use of comic books. Through this innovative way, he was able to keep the board members actively engaged while informing them about his product. Barry comments that the conventional ways of promotion and pitches through slides are boring and outdated and that we need to keep things fresh and engaging.

The Age of Information We live in the age of readily accessible information. Quincy talks about being able to liaise and engage in product development with people around the world. Leaders need to capitalize on that to help build production. The tools are there and we must use them, he emphasizes. 

Resources Quincy Caroll | LinkedIn

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Diana Kander is a New York Times Bestselling Author, an entrepreneur, and keynote speaker. Barry O’Reilly likes to reference her Ted Talk and $1 experiment in many of his videos. Diana has spent her career challenging assumptions and asking thought-provoking questions. Barry welcomes her to this week’s show as they discuss tips and tricks that lead to innovation.

The Road to Innovation Her parents’ ability to essentially create something from nothing fed Diana’s urge to get into entrepreneurship and innovation. Her immigrant parents had to work hard to provide for the family. Through their hard work, they were able to build their own business. 

New Mindset, New Growth One of Diana’s biggest unlearning experiences happened while starting up her own business. She gives an anecdote of her interaction with a high growth program leader. She talks about having to change her mindset and approach to business due to that interaction and how it grew her company 1000% in one year! Barry adds that breaking free of existing behaviors within that frame and thinking big but starting small can help a business grow.

Saying No and Letting Go “Good strategy means you say no, even to customers you know,” Barry says. Customers you go after are the customers you will get, Diana emphasizes. Sales from larger companies will take longer to get, but the return is worth it. She says that you should say no to companies that can prevent you from going after the kind of business you really want. She cites her experience of letting go 90% of her own customers so she could have more growth and profitability. Barry iterates that being serious about your business growth means sometimes letting go of existing customers.

Quality Decision-Making Making decisions on a 1 to 10 scale allows you to make higher quality decisions. Diana says that many people are misguided on how to say yes to things because they think about decisions as a yes or no binary, rather than on a scale of one to ten. In the business decision-making process, it’s important to have people around you who can help you find ways to work through hard decisions.

Pivot Indicators Diana calls the things we monitor to inform our decisions, ‘pivot indicators.’ There should be systems in place - such as a decision-making rubric - that monitor the outcomes of our decisions and help people make progress in uncertain situations. Diana says that your decision-making rubric is a living document that will evolve as you do new things and experience what works. She adds that she has a decision diary for when she’s making tough decisions, with a checklist for those decisions. “50% of decisions are probably wrong because you have limited information,” Diana expresses.

Looking Ahead Diana is currently focused on leading people through innovation, creating an environment that helps them get through an innovation project, and big transformation within a company. Diana’s tips to managers are to create pivot points within their work environment, give employees their space to do their tasks, and trust their employees to achieve the business’ desired outcomes.

Resources Diana Kander | Twitter, LinkedIn, Instagram, Website

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This week’s guest, Annette Gabriel, is enthusiastic about helping leaders and teams adopt higher performance practices. Annette is a former Senior Director of Human Resources at Pepsico. Barry O’Reilly describes her as “one of the people who just shines when you hear her stories.” Annette and Barry discuss the framework of agility, and how to let teams lead.

Agility Mindset Leaders who adopt an agility mindset are eager to explore the world around them. Annette says that she views each job as a learning opportunity and a new experience whether she ends up liking it or not. Barry comments that trying and even failing is part of the process: you just have to recalibrate when things don’t go as you planned. If more people adopted an agility mindset, they would be open to trying new ways of working. 

Unlearning Moments Barry asks Annette to relate some of the mistakes she made along the way, and what she had to unlearn. “Trying to do too much at once whilst still trying to influence the leadership layer of the company,” she begins. She gives an anecdote of going at the leadership layer with working programs that failed because they were too complicated. She was still learning the programs while trying to share and develop them, so she should have taken more time to fully understand them before presenting to company leaders. Barry comments that leaders often find it hard to just get out of the way and let front line staff have more authority. However, when they start to see the values and principles come to life and the positive outcomes of them, it becomes easier for them to trust the process.

Being Agile “There is no one way to be agile,” Annette remarks. “Being agile is actually pivoting and adjusting for what you need at that moment, at that time based upon what you've learned, what information you've gathered and what you've learned from testing,” she continues. It’s a common misconception that processes have to be standardized to be successful, Barry comments. A better approach is a localized one: focus on equipping teams to adapt based on the context.

First Follower Concept “A champion can bring [the team] along a lot more quickly if you give that champion the license to take the team through [training],” Annette says. She advocates the importance of ‘first followers’. “A first follower,” Annette explains, “is that champion who is going to make the extra time investment and go deeper on things, when they try to pull a group into an exercise or facilitate a discussion.” She reiterates that these individuals are influential in reaching more people and bringing them onto the new plans and directions the organization may take.

The Team Leads The Way Barry expresses that at times senior level management believe that they have all the answers and that this can create challenges within the organization. He adds that processes designed to make things work often keeps progress back because those processes rely on one or two people signing off a document. It is better to empower the hundreds of frontline workers - who deal with the issues and know what exactly the problems are - to come up with the solutions. Annette agrees and adds that a well-constructed team with all the right capabilities will be experts at resolving issues.

Looking Ahead Not knowing what’s ahead is what excites Annette the most. She’s looking forward to her ‘next great learning experience.’ Her advice to leaders who may be struggling with unlearning: play along and see what happens, you may not always like the result but it will always be a learning experience.

Resources Annette Gabriel on LinkedIn

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Welcome to the Unlearn Podcast’s second Ask Me Anything, something that is fast becoming an annual tradition. This episode is a kind of retrospective, a chance to not only answer questions from listeners all over the world but a chance to reflect on the year that has happened - the challenges as well as the opportunities.  Here’s to 2021 – and now, 10 answers to 10 questions. ·    What has been the most important characteristic that has helped you lead through COVID? ·    As a leader, what advice would you give your younger self for managing such an accelerated period of change? ·    What was the biggest shift for you personally in your approach to leadership this year? ·    What are the key traits and habits that leaders need to adopt to lead in this new world of work? ·    You often talk about collaboration fit — can you elaborate on it? ·    What’s been your most interesting video conference experience in 2020? ·    What are your principles of work? ·    What one change have you made to help you for 2021 and beyond? ·    What’s the most interesting research you’ve discovered this year? ·    What’s your favorite book you read this year?

Further Listening: Role Modeling Culture Transformation with Christian Metzner Product Management For Large Scale Innovation with Secil Tabli Watson Help Others Win with Steven Leist Resources: How to be an Anti-Racist Strong Towns

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Steven Leist is the Vice President for Customer Technology at American Airlines, the world’s largest airline. He is a technology leader who is intentional about creating a culture that cares for his team members. Barry and Steven discuss building employee relationships, becoming better leaders, and developing culture within organizations in this week’s Unlearn Podcast.

Helping Others Win at Work Over time, Steven has adopted the concept of helping others win at work. He tells Barry that it comes down to people within an organization, and stresses the importance of culture as the driving force behind his leadership. Helping others win changes people's mindset. "I think some of the challenges we hear at times are that folks feel constrained by policies, and so we worked really hard to try to listen to our frontline employees and really try to put them in a situation where they can actually help the customer," Steven comments. He tells Barry that he had to unlearn how to let go as a leader, and that he did not have to be the smartest person in the room.

Thinking Big and Starting Small One of the challenges many companies have is that they think big but don’t start small. Steven shares an example where he and his team became frustrated with a project at work because they thought big and started big to complete it faster. He expresses that this is a common management issue "because they have to see the big picture and they've got to get the revenue results". The pandemic allowed American Airlines to pivot and start attacking the new problems presented by it, within the parameters of thinking big and starting small. "I think this capability and mindset - and behavior really - you've built of thinking big but starting small, means teams are constituting small things, and there's opportunities for leaders to see small progress, small steps, small mistakes and then course correct and grow into these bigger solutions that have profound impact across your company," Barry remarks.

Trust Culture Barry asks Steven to give some advice to persons wishing to embark on the journey of building culture within an organization. "You have to have a culture that's built on trust," Steven answers. It’s important to have leaders who are willing to step up and advocate for the team, he adds. Leaders should also be humble enough to let the team figure out their own way of handling problems such as including them in decision making and helping them build camaraderie. Another key factor is having the right relationship with the right business partners. Taking all these steps can develop the trust culture within the organization.

Looking Ahead American Airlines is moving towards better product management and building a stewardship concept in terms of how product management is done. Steven believes it is vital to continue the dialogue on diversity and inclusion and bring in new perspectives to enrich the company’s culture. He wants employees to be better connected to their customers and have direct feedback with them.

Resources Steven Leist on LinkedIn  Steven Leist on Twitter

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Sara Wood is the CEO of Kaluza. She is a product leader, non-executive board member and a “builder at heart” who has even helped the UK with its Covid systems. Barry O’Reilly welcomes Sara to this week’s show as they discuss changing technology and the effects of the pandemic on the energy sector.

Transitioning Across Domains Sara’s wide-ranging experience has enabled her to go from place to place through the lens of “what is interesting here, what’s interesting about the technology there”. She is essentially “a builder at heart”, she says. Barry asks her what advice she would give to someone who wants to transition from one domain to another. She responds,  “I think the combination of really being curious about the world around you, about where technology is going, and adaptable to what you find on the other side of that.”

The Platform Play and Supply Chain Sara learned supply chain in the fashion industry at Gap. She moved to Farfetch because she was impressed with that company’s platform play, particularly the impact it would have on supply chain. At Kaluza, she sees technology and data as the platform that would enable the transition in the energy industry. What we do now with regard to the climate crisis will inform the future, she points out. She laments that the existing data and technology is not being put to use as they should be. To her, she tells Barry, a platform approach is about “how do we empower people in their homes who are just living a normal life to both understand how they participate in the energy ecosystem and adapt behavior?” She finds that using the technology and data to empower customers and give them more choices is fueling demand for sustainable energy.

Platform Thinking Trends and data that exists within the teams she works with, are all information Sara pools together into her platform. Barry applauds this “platform thinking.” Sara says that she jumps into a new industry with a fair amount of curiosity. She believes that product leaders who adopt this mental model are the “CEOs of the future” and are building a system to “create conditions for success.” Her teams have since adopted her approach.

Going Remote As a platform technology company, going remote due to the pandemic was relatively easy for Kaluza. The company’s pace of growth has continued. Additionally, during the lockdown, Kaluza was able to fully migrate one of its customers into its newly updated platform.

Pride of Work People need to feel connected to the job that they’re doing. For example, Barry says, the workers at Tesco light up when they see how they’re able to help customers. Small acts of kindness and recognition can have a great effect, and leaders should ensure that their teams are able to see the benefits of their hard work.

Looking Ahead  Sara is looking forward to applying her skills and experience to making energy simple, cheap and safe. She is anticipating that the world would rely less on things that are damaging to the environment.

Resources Sara Wood on LinkedIn

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Barry O’Reilly welcomes Rick Weil onto this week’s show. Rick Weil is a Head of Global Product and Analytics at Amazon. He started off as an officer in the U.S. Marine Corps, then worked at General Dynamics and Microsoft before his current position at Amazon. Rick and Barry discuss key human-centered approaches to unlocking team motivation and performance. [Listen from 00:34]

A Positive Culture “When you can create this culture where everybody wants to help each other towards a shared goal, you've unlocked some incredible opportunities for performance,” Rick comments. He is focused on creating a positive culture in his working environment where peers selflessly help each other excel versus competing with each other. He stresses taking time to listen to his employees and their concerns, as well as deliberately stepping back at times to let team members address challenges on their own. This is especially important when managing ‘managers of managers’ and dealing with internal conflict. [Listen from 6:51]

360° Feedback Barry asks Rick some of the things he noticed about himself that have evolved over time. One of the many things Rick has learned at Amazon is the power of “taking check x-rays” and using 360° feedback to identify leadership patterns to pay attention to. This helps us know what levers to pull to improve team culture and performance. Rick also talks about the importance and power of genuinely caring for people in the workplace over following scripted leadership behaviors. “Just because I can read all these books on leadership and follow the recipe doesn't make me a good leader,” Rick comments. As a leader you need to find ways to effectively sense how your teams are doing at the human level and connect the personal needs and motivations of your team to business goals to drive organizational change. “Mission First, People Always”, Rick says. [Listen from 14:00]

Leadership and Relationships Being a transformational leader is rooted in building strong relationships with the people you lead and work with. One way to do this is through intentional question asking. We often use questioning to assess the health of work operations, yet the true power (and intrinsic leadership fulfillment) comes from getting to know people at the human level, teaching, developing, and being part of your teams’ career journeys. Ask how your team members are doing (and mean it). Get to know about their aspirations and what’s important to them. And for leaders where this genuine, human-centered approach may not come natural, Rick urges them to give caring a try. “Care about people. That will change your perspective, it'll impact your mindset,” Rick expresses. When you look at leadership as a platform for positive human impact and not as a position of individual power, it changes the way that you think about life and work, and directly correlates with the performance of your team. [Listen from 21:00]

Looking Ahead Barry asks Rick what he’s looking forward to. He responds that he is looking forward to his partnership with the Project Management Institute (PMI) and developing a product, called Kickoff, which is an intuitive, web-based guide to project management. There are so many resources available for project and program management practitioners, but few for non-PMs who need to know how to better get project work done, essentially to know PM “as a skill”. Kickoff starts with basics, includes helpful templates and examples, and is aimed at helping individuals get acquainted with the fundamentals of project management. This product has the potential to fundamentally enhance how work gets done for millions of people, from students putting together class projects to start-ups creating new products and support functions tenured PMs who need project support from other, non-PM team members [Listen from 33:58].

Resources Rick Weil on LinkedIn

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Barry O’Reilly is pleased to welcome Secil Tabli Watson, Executive Vice President for Digital Solutions for Business at Wells Fargo. In this week’s show, Barry chats with Secil about the techniques she uses to drive innovation in both retail and business banking environments. She shares the lessons she unlearned in the process and how to bring product management principles into a large organization in a way that drives innovation.

First Lesson: Speak The Customer’s Language Secil’s first assignment as a digital channel manager 18 years ago was to make Wellsfargo.com into a buying site. She focused on language that was customer-focused, rather than the bank-centric. “We brought in the capabilities and the competency of doing user research and understanding customer tasks and understanding their behaviors and motivators and really putting that into the language,” she says. In addition, they transformed the architecture of the website so that it was more customer driven. [Listen from 1:55]

Staff People to Outcomes Not Products If you’re struggling to move from project-based teams to outcome-based ones, Secil advises that you reframe how you think. This was a critical unlearning for her, she remarks. She shares an example of how she recast her thinking about a project from product to outcome, as a result of which her team was able to see themselves as responsible for a broader outcome, and partner with other departments to make it happen. She advises listeners to break the project into phases with quick wins, and gives insight into how to create cross-functional teams with as little awkwardness as possible. “If you ask a little bit at a time from people, they're more willing to help,” she points out. [Listen from 6:50]

B2B Customer Relationships Are Deeper Businesses with B2B customers can develop deeper relationships with them. Because their B2B customers are fewer in number, Secil says, they are able to communicate on a more intimate level over a longer period of time. She asks her B2B customers, “How do you feel?” because it elicits deeper answers. “And I'm also then able to ask the question, Why?” Secil remarks. “I can ask the question as many times as I want to try to get down to a deeper meaning and a deeper need or a desire or a business problem that the customer may be having.” She and Barry discuss why co-creating with your customers - as counterintuitive as the idea appears - is their favored approach. “It builds more trust and actually derisks more of your relationship,” Barry comments. [Listen from 15:20]

It Only Takes 10 “...it doesn't take more than 10 people to do things but you have to get the right 10 people,” Secil argues. Her job, as she sees it, is to figure out what to do differently so she can identify those 10 people quickly in her large organization environment. Barry comments that if more companies adopt this approach they would see greater success. [Listen from 29:35]

OKRs are not for Compensation Secil and Barry agree that while measuring performance is important, performance metrics should not be tied to compensation, as pay for performance inhibits innovation. Secil believes that the team should win together and learn together; they should not compete against one another. “There is nothing more we could do to make a better team other than enable them to learn,” she says. [Listen from 36:00]

Looking Ahead Secil is excited about the current trend to apply product management principles and skills in atypical areas, such as for thinking through outcomes and tactics for diversity and inclusion efforts. Barry comments, “I think everybody can take these principles and methods and apply them to build better experiences for people.” [Listen from 43:35]

Resources Secil Tabli Watson on LinkedIn

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This week’s guest is a leader who role models change. Christian Metzner is Chief Information Officer (CIO) at Volkswagen Financial Services UK. Barry O’Reilly describes him as someone who is “constantly staying curious and getting outside his comfort zone; and you only have to spend time with him and his team to realize how much his actions inspire others.” Christian and Barry discuss the role of leadership in inspiring organizational culture.   Initiating Change Christian has learned to step out of his comfort zone and reflect on what other leaders and cultures are doing better. Emphasizing that the one with power needs to initiate the change, he says, “If you are the one in the position with the power, then you need to open up first. You can’t expect others to change if you’re not leading the way.”

Hacking Culture Innovation is often the result of challenging yourself and pushing your boundaries. “You don't come to innovation if you only go one mile faster every day,” Christian points out. “You have to push boundaries... Try to find the 5% to 10% where you can challenge your behaviors, where you can challenge people who might be stuck in their thinking.” He advocates using cultural hacks - low effort steps that can be implemented quickly, but which have high emotional impact - and shares examples of cultural hacks that he successfully implemented. Barry comments that these small changes often create ripple effects throughout an organization.

Being a Leader “My simple understanding of leadership is... to remove your blockers and to make you better on a day-to-day basis.” Christian sees learning from competitors and his team as key to creating a culture of innovation: an environment where everyone is on the same playing field. “IT is - next to the capital market - the single biggest threat to an organization like ours,” he points out. “And we need to get our job... absolutely right to enable our commercial colleagues to come up with great products and services for our real end customers.”

Trade-offs in Decision-Making Barry commends Christian’s ability to take “a little bit of information and make a decision and then getting more information…” He asks Christian to describe his process and the trade-offs of this approach. Christian responds that transparency, engagement, and iterating in short cycles are the key elements in this approach. The current crisis demands different behaviors, he argues. “We’re not playing the game big fish against small fish anymore,” he says. “We're playing big fish against fast fish, and that requires a different behavior.” 

Build Systems Around People “It's less the individual [than] the systems and the structures that are in place to help them succeed,” Barry comments. “If more companies started to recognize that they’re designing systems around people to make them successful… that’s a massive transformation that... would have a huge impact on their company.” “Let's bring people into a role where they can flourish, where they are allowed to bring in their strengths,” Christian adds.

Looking Ahead Christian says that he wrote a framework in the early days of the COVID crisis that has guided the company’s decision-making. The framework focuses on three dimensions: decisiveness, simple communication, and taking care of one another. He speaks of dealing with the pandemic in phases: they are entering the phase of renewing the company, so they are using what they learned in the previous phases to inform their approach. In particular, he is excited about how the company will maintain pace and flexibility so that they can provide the best possible customer experience.

Resources Christian Metzner on LinkedIn

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Katie Anderson is a leadership coach consultant and author, best known for inspiring individuals and organizations. She started off in public health research then moved to Japan in 2015. Barry O’Reilly welcomes her to the show as she shares the lessons she learned in Japan on how to deepen your leadership skill.

Learning Lean at the Source Her life in Japan inspired Katie to learn lean at the source as she had already been applying Toyota production principles in the healthcare system. Moving away from academia and research was her big pivot as she transitioned from public health into her own consulting practice. [Listen from 2:30]

Leading With Intention Katie advocates leading with intention and orienting your actions in the direction of the behaviour that will achieve your desired purpose. Now that she was in a position where she had to help other people solve problems, she realized that her mindset and approach needed to shift. She needed to show up in a different capacity: she had to be a model and guide instead of simply going in and doing it all on her own. [Listen from 6:25]

Effective Leadership Role People need alignment: they need to know what the target of the organization is in order to meet that target. If leaders don’t have clarity on what the target is, it is unlikely that the employees will. Barry comments that if employees don’t know what direction has been set by leaders, that’s a failure of the leadership team. You can have activity without vision, but not in a meaningful direction. [Listen from 13:00]

Hoshin As a Tool Hoshin is about identifying the top strategies in the organization, and how the next level down contributes to achieving those strategies. It is anchored in the scientific method, and a deep process of reflection. It provides the organization with the real data, whether positive or negative and allows for the leadership team to make better and accurate decisions based on that data. [Listen from 21:45]

Looking Ahead Katie is looking forward to hearing listeners’ reflections on her stories and experiences. She is excited to continue to amplify her message. She is also committed to continue helping individuals connect with their intention and their purpose, in order to achieve their desired goals. [Listen from 34:25]

Resources KBJAnderson.com

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Daniel Elizalde is the VP and head of IoT for North America at Ericsson. He’s spent more than 20 years working in industries, from manufacturing to aerospace and energy. Today, Daniel also teaches courses on the decision framework that he’s created. Barry O’Reilly welcomes Daniel to this week’s show to discuss how much the concepts of IoT have changed, and the impact of technology on the current world.

The Evolution of IoT Once Daniel learnt of the IoT concept and recognized it in the way he did his work, he started cataloguing and creating frameworks and approaches. With the advancement of technology, you can now plot a system of sensor data points on a graph, which would have taken a year to put together previously. The advancement of technology also led to the scaling back of employees and time. Daniel encourages adapting the product psyche and learning what you can do today so that you can take advantage of the technological curve in the future. [Listen from 1:50]

Looking the Other Way Around “Building relationships is the most important part to get things done,” Daniel says. Barry parallels the IoT system with the people working in a well-functioning unit: the technological idea and the people idea is what drives the performance. Daniel talks about introducing new ways of application to Ericsson, and helping the company to unlearn some of its long held strategies to adapt to the current times. Daniel says he’s always looking the other way around to determine feasibility and what the customers really want. [Listen from 15:00]

Building Capability Driving results, for Daniel, involves discovery and getting more projects from other units in order to apply their concepts to Ericsson. Daniel describes what has worked for him in terms of expanding technology in the company. He discusses monetizing 5G networks as they emerge, focusing on customers’ problems and adding value. “Your capability is the knowledge you’re accumulating in your organization, and making good decisions based on what you’re learning,” Barry comments. [Listen from 23:25]

Looking Ahead Daniel is excited to see how 5G is applied in the coming years and how it will level the technological playing field. He is looking forward to individuals being able to build on 5G just like the Internet. He is also looking forward to seeing the things people had talked about ten years ago becoming a reality in the not too distant future. [Listen from 41:05]

Resources Daniel Elizalde on LinkedIn Daniel’s blog & podcast: danielelizalde.com  D-15 IoT Studio at Ericsson: https://www.ericsson.com/en/about-us/experience-centers/d-fifteen/d-15-iot-studio

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Diana Stepner is the VP for Product Management of Innovative Learning Solutions at Pearson. She enjoys building product experiences that customers love as well as weaving innovation, experimentation, and technology into actionable product visions and roadmaps that accelerate growth. Barry O’Reilly welcomes Diana to this week’s show as they discuss finding her voice and why a product management approach to leadership is valuable in these times.

Finding Her Voice Barry comments, “We often figure out what we want to do as we do things and learn our way through them.” Diana explains that she had to unlearn the notion that a leader must be the loudest person in the room and know all the answers. A point from an article she read - that great leaders spend more time listening and asking questions than talking and giving answers - helped her realize that her natural leadership style was indeed valid. Encouraging others to contribute, bringing people into the conversation who might not have felt comfortable to speak before, was the right way for her.

The Power of Pausing Pausing to think, to process and analyze information before responding, helps you make better decisions. Diana says that she had to unlearn making snap decisions and jumping to conclusions. “What I've had to do,” she says, “is take a step back when I've got a lot of information that I need to synthesize; to open up more towards other ways of addressing an approach; think about a more broad perspective; and then evaluate a couple of different opportunities initially, test them out and then be able to determine what's the right way to proceed.” Pauses are ok, Barry emphasizes, and we should make more space for them in communication.

A Period of Unlearning Many companies are going through a sense of unlearning, Diana says. She and Barry discuss the changes that are happening in companies currently: they are realizing the power of having diverse representation so they are listening more. Diana remarks that those companies that make the effort to have these changes stick will benefit in the long run. “If you don't define the outcome, if you don't make the data available, if you don't look at the reality of what's happening and make changes to move towards the direction you want, nothing is going to change,” Barry adds. While change may be difficult and uncomfortable, good can come from it.

Advice for Leaders Barry asks Diana to share advice for leaders who want to adopt her leadership approach. She gives several tips including:

Expect change.

Learn from those around you.

Find ways to empower those you work with.

“I think it’s by the creation of a space where people feel comfortable to speak up and to share their voice, where you can truly have a tremendous amount of impact,” she says.

Looking Ahead Diana says that she tries to find the good in everything that is happening right now. She is excited to see the acceleration of trends: things that we thought would happen in the future are happening today. More companies are encouraging a culture of experimentation now to get an insight into the future, she says. Barry comments that he is glad that more people are realizing that no one person has all the answers, and that our best bet moving forward is to learn our way through together. Diana hopes that we continue to normalize remote working as the pandemic has proven that we can be productive outside of the workplace.

Resources Diana Stepner on LinkedIn

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Barry O’Reilly is delighted to welcome Alexander Osterwalder, famed author of The Business Model Canvas, The Value Proposition Canvas and most recently The Invincible Company. Alex is also an entrepreneur and speaker, and one of the world’s leading experts on innovation and entrepreneurship. In this exciting episode, they discuss some of the aspects that help innovation and entrepreneurship flourish, including how business leaders can identify what they have to unlearn to be successful in the future. 

Failure is a Door to Opportunity Oftentimes we overstate failure, and we don’t look for the opportunities that come out of it. Alex relates how failure often turned out to be a door to new opportunities for him. “I think you just have to be ready to embrace the surprises that life gives you and learn from every failure,” he says. He advises listeners to own their failures and don’t blame others. “If you focus on the positive, all of a sudden you know how to instrumentalize failure.” Entrepreneurs distinguish between reversible and non-reversible decisions, so they can make calculated bets. While failure is never the goal, it is an inevitable consequence and a good thing. You can become more dispassionate about failure if you view it as experimentation, Alex posits.

You Get Better Over Time You get better at innovation and entrepreneurship over time. Most successful entrepreneurs are 40 years and over, and have been through several startups. They learn what not to do through practical experience. However, Alex says, you also need to learn the technical aspects of entrepreneurship and innovation.

Stay Humble “No company is invincible,” says Alex, “but companies that constantly reinvent themselves because they don’t believe they’re invincible, those are the ones who are going to stay ahead.” Staying humble and keeping the mindset that there is always something new to learn, some new way to reinvent your company, is the difference between growth and stagnation. Barry adds, and Alex agrees, that successful leaders are always creating scenarios that take them out of their comfort zone. Alex shares an exercise he does with leadership teams to help them visualize their current state, and recognize what they need to do differently.

Create the Environment for Innovation “As a leader you don’t pick the winning ideas; you create the conditions for the winning ideas and the winning teams to emerge,” Alex remarks. Research shows that only four out of every 1000 projects will succeed, so leaders need to foster an ecosystem for those winning ideas to surface. He describes a practical system companies can adopt to incrementally fund winning ideas. He emphasizes that innovation and execution must work in harmony to enable each other. Barry comments that entrepreneurs should ask, “How quickly can we get these ideas in front of people to see? Should we build it and then test? Can we execute it?”

Alex and Barry discuss why innovation is a moral obligation for companies. “My belief is innovation is almost a moral obligation - not to create more money but actually to create more stable jobs,” Alex says. 

Looking Ahead Alex is excited about the boost of distributed work that the pandemic has accelerated. He loves that the software tools being adopted are leveraging human creativity, and sees huge opportunities coming out of this difficult period.

Resources AlexOsterwalder.com The Invincible Company: How to Constantly Reinvent Your Organization with Inspiration From the World’s Best Business Models

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Barry O’Reilly welcomes authors Alexandra Jamieson and Bob Gower to this week’s Unlearn Podcast. They are the co-authors of a new book which details their practical system to have difficult conversations in a productive manner. The book is entitled Radical Alignment: How to Have Game-Changing Conversations That Will Transform Your Business and Your Life. 

How the System Originated Alex and Bob describe how the Radical Alignment system started. It was a tool they used in their own relationship and that they taught to others. Often people would reach out to them afterwards about implementing the tool in other contexts. It soon became apparent that they had something valuable that they could share with the world.

Four Simple Steps The heart of the Radical Alignment system is four simple steps, Alex points out. “As a couple, or even as an individual or as a team, you share your intentions, concerns, boundaries and dreams.” Bob explains that they usually constrain the system to a topic and he illustrates how the system would work in the context of the current pandemic. Barry comments that he finds the system practical and applicable. “I felt like it was very explicit about what things matter, what was I going to do, and I could act on it straight away,” he says.

How To Have Difficult Conversations Conflict often develops because there’s a missing conversation, according to Fernando Flores. “More often than not,” Bob adds, “the missing conversation is just some key little piece of context that you don't have, that really explains the person's behavior.” He shares an example of how context changed his perception from annoyance with his neighbor to acceptance. Alex remarks that this system brings structure and ease to her communication. “For me the most valuable thing about this structured conversation is that it gives me a way to organize my emotions and my thoughts and my desires.” 

The Goal is Binding People Together Radical alignment essentially is about binding people together. Although the first three steps are vital, they can be somewhat utilitarian, Bob comments. The fourth step - talking about your dreams - is inspirational. He describes the physiological effects of sharing dreams, which results in binding people together as a group. Alex emphasizes that there are important rules for having these conversations: no cross-talk, no arguing points, you must listen to each other. The objective is to develop tactical empathy, which is simply understanding where each person is coming from.

Other Important Lessons Barry, Alex and Bob share some important learnings and unlearnings about being radically aligned:

People want to have difficult conversations but don’t have the tools to do so.

Alex says, “Don't talk about anything important when either of you are hungry, angry, lonely or tired. We adapted that to be AHA - angry, hungry or alcohol.”

Reason and emotions are intimately intertwined.

“Teams fall apart because people can’t get along, because people don’t understand each other,” Bob comments. “...The big lesson of the last few years is how much I need to actually listen and to take on somebody else’s perspective before I have an opinion about it.”

People may not understand how useful a tool is unless they use it.

Trust is a lubricant that helps diverse people work together.

Looking Ahead Alex is excited about how their tool is helping mom entrepreneurs. Bob wants to see people bring their whole selves to work. He hopes that this tool, that has been so impactful in their lives, can impact many others.

Resources Radical Alignment: How to Have Game-Changing Conversations That Will Transform Your Business and Your Life

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Susan O’Malley is an expert at building high performance teams and culture. This is the passion that influenced her work at Google, as well as her current position of Senior Director at IDEO. She joins Barry O’Reilly on this week’s show to share her inspiring story.

Being Open to Following Your Heart Few people approach new opportunities with the openness that Susan displays, Barry comments. She credits her mindset to a love of learning and the ‘harmonizer’ role she embodied as a middle child. It deepened when she joined Google in its early years. “I literally saw the product changing the world and changing people’s business models,” she says. “…And it gave me this tremendous sense of optimism around what technology can do, not just for the big guys, but actually for the little guys and the guys in the middle. That was a really, really inspiring thing.” 

What Makes Great Leaders Susan looked to the great leaders around her for traits she could cultivate in her own life. From her observations, great leaders were charismatic, fair, intentional and they succeeded at whatever they put their hand to. Barry adds about great leaders, “...they all seem to be working in a different field than they originally trained, and yet they really cultivated this capability to continuously adapt to changing circumstances. And they build systems that allow them to explore uncertainty very intentionally; they build a lot of fast feedback mechanisms into things. They're very curious to get outside their comfort zone.”

The Value of Authenticity Authenticity is about being yourself. Susan says, “It helps other people be attracted to what you’re trying to do. It helps us communicate. It helps us produce amazing results in other people… Our job is to cultivate companies and teams where we have a great mix of people, and where people can really be themselves so that we can all find this energy and find this collaboration that's gonna take us to the next level.” Barry comments that being inauthentic demands energy, while just being your true self gives you energy.

Living Your Values Performing at your highest level as an organization demands living out your values. Susan relates that she had to unlearn several ideas when she joined IDEO, including how to embrace ambiguity and how to work with designers. She now teaches these lessons to her coaching clients. “It’s not about your performance, and it’s not about what you know,” she tells her clients. “It’s about the things that everybody can make together.” Creating this kind of high performance environment means knowing your culture, she points out. She describes how leaders and teams can create the culture they aspire to.

Focus on the Process Not the Outcome High performance is more about perfecting the process rather than the outcome, according to Susan. Barry adds, “The result is secondary to figuring out what's the real problem here and having a good process to explore it. And if we do that well, we're gonna be taken to the direction that we should go, that's probably not where we thought we would be at the start.” Susan shares practical tips including the Hierarchy of W’s and having Torque Partners.

Looking Ahead Susan is coming to understand more and more how important culture change is in building an organization that will succeed. She is delving into talent design: helping organizations identify, retain and develop the talent they need to win.

Resources Susan O’Malley on LinkedIn IDEO.com 

Books referenced: Nine Lies About Work - Marcus Buckingham and Ashley Goodall Dying for a Paycheck - Jeffrey Pfeffer Building Microservices - Sam Newman Unleashed - Frances Frei and Anne Morriss

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This week’s guest, Tendayi Viki, is an Associate Partner at Strategyzer. A prolific author, he has written three books and is a regular contributor to Forbes magazine. His most recent book, Pirates in the Navy: How Innovators Lead Transformation, is a manifesto on how to drive corporate innovation in large organisations. He and Barry O’Reilly chat about how he helped organizations drive and scale innovation, including key unlearning moments along the way.   Good Enough Is Better Than Perfect In an interesting twist of fate, Tendayi ended up in Stanford’s Graduate School of Business under the tutelage and mentorship of innovators like Steve Blank. He says that this was the turning point for him to converge his psychology training with entrepreneurship and innovation. He recounts two major unlearning moments, the major one of which was his tendency to over-edit. Barry describes this as a classic trap: we want our product to be perfect before we publish, but the better approach is to make it good enough, put it out there and start the conversation. In the academic world, Tendayi points out, your ideas evolve in private; but the innovation world is the opposite as your ideas evolve in public. This makes you vulnerable and takes courage, but the feedback you receive makes your product better.

Earn the Right to Criticize You have to earn the right to criticize, according to Tendayi. People will only follow you when they see you as a partner on their journey, when they feel that you understand their struggle and have their best interests at heart.

Helping Successful Ideas Evolve There’s no way to tell which of your ideas will succeed, so invest in many ideas and see which ones pan out. Tendayi remarks, “The fundamental theory of innovation is the theory of an entrepreneurship ecosystem… and in that ecosystem the evolution of successful ideas is actually pretty random. We don't know what's going to succeed and what’s not going to succeed. What we do is just throw things at the wall: we invest in a whole bunch of stuff and then we see what succeeds and what fails.” He emphasizes that you cannot choose winning ideas yourself on day one. He tells leaders that they have to provide the context for the best ideas to bubble up. Double down once you see what works.

Coaching the Team Training is not enough: build organizational habits that allow the training to become a repeatable process within your organization. Tendayi explains why he uses this approach when working with large organizations. Coaching the team - both the leaders and employees - involves helping them incorporate this new mindset into their daily routine. Leaders in particular need to be deliberate about what they say and the questions they ask. Their questions should help to bring out the best in the team.

What Lean Startup Is Not Lean startup is not a way to make any idea you have work. In fact, the majority of times it will tell you what doesn’t work. “What lean startup does is it allows you to find things that don't work, quicker and cheaper, so you can stop working on that stuff and double down on the things that work,” Tendayi says. He shares practical tips for incorporating the lean startup culture into a large organization, including creating artificial scarcity, which instills the discipline of focusing on what you need to do to be successful.

Looking Ahead Tendayi is working on completing ongoing projects, including the Insight Strategyzer tool and a new book entitled Right Question Right Time. His next step, he says, is to return to his academic roots to research the psychology of uncomplacency.

Resources TendayiViki.com Pirates In The Navy: How Innovators Lead Transformation

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Barry O’Reilly talks with social scientist and author of Tiny Habits, Dr. BJ Fogg on this week’s Unlearn Podcast. BJ is a Research Associate at Stanford University and creator of the Fogg Behavior Model in which he teaches people how to adapt their behavior based on the challenges they want to solve. His students include the co-founder of Instagram, as well as several other product, app, and service developers who create solutions using the models and methods he teaches.

A Natural Experimenter “There’s a real skill about recognizing different patterns and seeing a trend and bringing it all together to create a new field,” Barry comments. He describes BJ as a natural experimenter, as he was able to converge his love of rhetoric with scientific study to create the new field of persuasive technology. BJ points out that it’s not a straight path: “You kind of stumble into learning and unlearning moments—you find what works and what doesn't; and certainly do by being curious to explore new paths, design experiments and get insights through research.”

How To Make Change Sustainable Lasting change has these two characteristics, according to Fogg: Will it help you do what you already want to do? Will it help you feel successful? These two maxims are foundational to Fogg's systematic approach, Behavior Design, that helps people make the sustainable changes they are aiming towards. BJ describes how he discovered this new domain by setting himself up to be free to pursue his goals in the way he felt was best. Once you have a little support to independently sustain yourself for a while, he says, you realize that you can take more risks than you thought before. Barry adds, “Our ability to continuously adapt our behavior and thinking to changing circumstances is probably the most important skill we may need.”

Just Get It Out There “Design the experiment. Crank it out. The first you're gonna mess up on. So just do it, learn, change and then do the next one,” BJ advises. Instead of trying to get it perfect, just get it done and put it out. The market will tell you what you need to improve and how to iterate. This is a key tenet of Behavior Design, BJ says. He illustrates this idea with an interesting story about how he forced his students to create a Facebook app in a seemingly impossible deadline. An important lesson he took away from that experience, he says, is that simplicity is key. It was the simple apps that really took off: “10 weeks later it engaged over 24 million people on the Facebook platform and some of them were making lots of money.”

Looking Ahead As BJ looks to the future, he comments that now is the critical time for behavior change. He feels a responsibility to help people get through the current pandemic and social justice issues using his behavior change system. It’s a system that you can apply to any problem, so he wants to teach people to use the system to tackle these challenges. He also talks about the focus mapping tool that he is launching to help users match themselves with new habits or behavior changes that are right for them.

Resources BJFogg.com TinyHabits.com

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Barry O’Reilly and Jeff Gothelf have been best friends ever since Jeff reviewed Barry’s first draft of Lean Enterprise and told him it sucked. They have worked together as co-authors of the Lean series, and as consultants to Fortune 50 clients. Jeff joins Barry on the Unlearn Podcast this week to talk about his new book, Forever Employable: How to Stop Looking for Work and Let Your Next Job Find You. 

Push vs Pull The higher up the corporate ladder you climb, the fewer the jobs and the fiercer the competition. You have to constantly push your way through. Jeff woke up on his 35th birthday and made the unsettling realization that he would soon be battling younger, better-skilled people for a job. He understood that this was untenable, so he vowed that he wouldn’t look for jobs anymore, rather he would have jobs look for him. He tells Barry that pulling job opportunities means telling the world explicitly who you are, where you could help them, where people can find you and what problems you can solve for them.

First Steps Why do you exist? How can you help people become successful? Being forever employable involves self-assessment. Jeff says that the first step he took was to examine what he was good at and what value he had provided up to that point. Then he thought about his audience and where the market was trending. “...if you're going to plant a flag somewhere you want to plant it in a growing market rather than ... one that's shrinking,” he points out.

Your Personal Brand You have a story to tell that no-one else has: storytelling is how you differentiate yourself. Jeff tells listeners that we all have a unique perspective, and it’s how we build our personal brand. He and Barry talk about sharing their stories and fighting the impostor syndrome. “People massively underestimate themselves,” Jeff says. He coaches people how to find the self-confidence to pursue their goals, a trait that is critical if you want to be successful. Barry says that doing something you enjoy gives you confidence because your passion shines through.

Catching The Wave Recognizing a problem, tracking the trends, then adopting a position and sharing it, orients you to catch the wave of new opportunities. Jeff describes how sharing his ideas attracted many unforeseen opportunities. “All of a sudden this conversation goes global and that begins the pull,” he shares. “All of a sudden I start to attract new opportunities because the story and the conversation and the sharing has become so powerful. Giving all this stuff away starts to attract all these new opportunities my way.” He shares how each new opportunity gave him the confidence to take another step, until he could confidently transition into full-time entrepreneurship. Barry comments, “One of the things people also need to unlearn is this isn't like from 0 to 100% overnight.” It takes small, continuous steps and a constant process of experimenting, evolving and reinventing and growing the things you already do.

Counterintuitive Leadership A great leader does not purport to have all the answers, Barry says. Instead, it’s someone who is authentic and vulnerable and willing to learn. Jeff says that he is unlearning the fear of becoming vulnerable in public. He finds that his personal struggles resonate with people. He is becoming comfortable with being uncomfortable, which Barry notes is the mark of a successful leader. Jeff is driven by enthusiastic skepticism as coined by Astro Teller: there’s always a better way to do something the next time around.

Looking Forward Jeff is looking forward to the launch of Forever Employable and the new opportunities it brings his way.

Resources

JeffGothelf.com Forever Employable: How to Stop Looking for Work and Let Your Next Job Find You

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Barry O’Reilly welcomes Kanika Tolver to this week’s Unlearn Podcast. Kanika is the bestselling author of Career Rehab and founder of a consultancy business of the same name. She has coached hundreds of clients, helping them discover opportunities to do their best work and to find higher performance roles that are better suited to them.

How To Break Up With Your Job Despite fear and anxiety about job security, especially in this COVID-19 pandemic, Kanika says, that you shouldn't be afraid to seek the right job or to break up with the wrong one. She and Barry discuss practical advice: 

Turn your anxiety into accomplishments. For example, you can upskill by getting a new certification, and expand your network. Connect with recruiters or hiring managers who can help you get a new position.

Join a new online community. Apart from learning new skills, you may be able to connect with experts.

Fearlessly resign when you know you’re prepared. To prepare, think about what you need to do to get ready, what you can learn, and who you can connect with or who you know that can refer you. Taking these small steps builds your confidence to fearlessly resign.

You Are The MVP Whether you're thinking of changing careers or starting a business, think of yourself as the product. The first step is a Career Rehab Diagnosis, a self-assessment of what is and isn't working in your career. Make adjustments based on what you discover. Next, Kanika says, list your career, education and personal goals. The next step is to think about financial goals and culture fit.

Barry comments that it takes so much unlearning for people to recognize that they deserve to have a fulfilling career in a place where they’re recognized for who they are and what they bring to the table. Kanika cites Barry’s book about reevaluating past behaviors. We need to stop thinking that we should conform to fit the company culture. Instead we must recognize that we’re the MVP (minimum viable product), and negotiate job offers with this mindset. She remarks, “They should be just as happy to have you as you are to have them. So I think when we shift our mindset to looking at ourselves as products and services - we have unique offerings - then it changes the direction of the conversation. Instead of you just praising the company, no - praise yourself and then get with the right company.”

Divorcing The Job For The Dream Innovating your behavior is imperative to live your dream. Incorporate continuous feedback as it helps you to continuously improve. Another key point is that you should never settle in your career or your business. You have to be resilient in order to be successful.

Kanika also shares the following advice:

You have knowledge and skills from your job that you can transfer into your new business.

Start creating your personal brand: you need a track record before you can divorce your job and marry your dream.

Don’t overthink it. Just do it.

Consistency is all it takes.

Looking Ahead  Kanika is excited about the future of the workplace. The current crisis has proven that workers can still add value working remotely, so she expects more companies to transition into remote. She is also looking forward to more virtual events so new speakers can get an opportunity to spread their message. Information sharing and online networking is being normalized, she believes, and she is looking forward to seeing how businesses and careers pivot during this period, as people develop new communication skills.

Resources Website: KanikaTolver.com  Book: https://www.amazon.com/Career-Rehab/dp/1599186519/

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Michael Bungay Stanier is the bestselling author of The Coaching Habit. He is part of the Thinkers 50 and has been named the number one Thought Leader in Coaching this year. Michael joins Barry O’Reilly on the Unlearn Podcast this week to share insights, including how to measure success and pivotal lessons that shaped him.

An Unconventional Career Path There is a saying that inspiration is when your past suddenly makes sense. Certainly, several experiences in his early career showed Michael that he needed to work for himself in order to be at his best. He recounts that the turning point for him was 20 years ago when he was fired from the last company he worked with. That’s when he started his own business.

Three Memorable Lessons Barry asks Michael about the lessons he’s learned over the years. Michael responds with the three pivotal lessons that he remembers to this day:

You need to understand who you work best with. He is a great leader to his ideal clients, Michael says. “I'm great at having people's backs; I'm great with people who take responsibility and accountability; I'm great with people who have just been waiting... for the wind beneath their wings… In terms of figuring out who influences and nudges and helps shape people's journeys, you’ve got to get the right match between the right people.”

The power of No. “Part of what I've learned is that the more courageous I can be about what I say no to and the fewer things that I say yes to, the more likely it is I'm going to make a difference in the world.” A lesson that stands out for Barry from The Coaching Habit is that if you’re going to say yes to something, that means you have to say no to something else. There’s great discipline in being able to say no.

Be careful about what you measure as success. Barry and Michael talk about the insidiousness of vanity metrics: sometimes the metric becomes the target and you do anything to achieve it, oftentimes destroying the bigger win that you’re looking for. Michael says that how he measures success is to constantly keep in mind “the bigger game.” He describes how he used this principle with his book. 

Serendipity or Intention? Is success intentional or serendipitous? How do we create success? Barry posits that it starts with systems: when you have big aspirations you need to think big but start small. Michael agrees that “intentionality is what allows serendipity.” Taking steps towards your goal is what prepares you to notice opportunities that you can capitalize on.

Advice That Has Shaped Michael’s Life A question from his Latin teacher helped Michael decide to become a Rhodes Scholar. Commendation from a past employer helped him see himself as a force for good. And a frustrated directive from his friend to focus helps him “find the focal point that allows [me] to play but also creates the boundaries in which [I] play so that there's a coherence to the stuff that [I] do.” Barry adds that we all need to have a system for who gives us feedback and helps us become aware of our blind spots. Michael comments that the deepest level of feedback is to speak to a person’s being rather than their doing. “To speak to somebody's inherent qualities as to how you see them and how you experience them is a very powerful active leadership,” he remarks.

Looking Ahead Michael has launched a podcast called We Will Get Through This, where he talks with interesting people about building resilience at the personal, team and organizational levels. He says that he is still figuring out how he will serve next, but he is disciplining himself to say yes less so that he has the space to see what emerges.

Resources MBS.works TEDx Talk: How To Tame Your Advice Monster  

Michael’s new book The Advice Trap is out, and it's pretty good. Don’t forget to get his international bestseller, The Coaching Habit.

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Barry O’Reilly is excited to welcome Amy Jo Kim to this week’s Unlearn Podcast. Amy is a game designer, startup coach, and author of Game Thinking. She has worked on the early design teams of games such as Rock Band and The Sims, and has helped many companies, including Netflix and eBay, find their customers to help them scale.

A Cooperative Designer Amy describes herself as a social game designer. She is enthusiastic about teamwork, having learned many lessons about creating a collaborative environment from working in music bands and modeling great bandleaders. One of those lessons that she now teaches in her Team Accelerator program is how to “make everything gel so we don't even remember whose idea it was… just getting the work done in a really focused yet creative way.”

Many opportunities opened up for her Amy when she found a tribe of like-minded people. She tells Barry that she found mentors that she could click with and saw a way that she could contribute immediately to a much larger team.

Go After The Early Beachhead “...If you're innovating you can't just go after your average customer in that market,” Amy posits. “You have to capture this narrow early beachhead market first.” As early as 1961, Everett Rogers of Bell Labs found that innovations always start by capturing the early market before going into the early and later mainstream. Amy has taken these insights from innovators like Rogers, Jeffrey Moore, and Will Wright, and made them accessible through a step-by-step program. She shares how these principles were lived out in building out The Sims, and in companies such as eBay and Netflix. “...There's so much you can learn and get out of iterating ideas with [your early beachhead] that it gets you to a point where you can get a vector in the direction and build out for the next layer of people around them,”Amy adds.

Early adopters or beachheads have these three characteristics:

They actually have the problem that your product solves;

They know they have the problem and are willing to try anything that might help;

They're taking actions that demonstrate they're trying to solve the problem.

Game Design Is About Customer Journey The best game designers create a customer journey and then use mechanics such as gamification to deliver that journey. While shaping behavior with rewards - the basis of gamification - may deliver short-term lift, it does not provide long-term engagement. Barry comments that tapping into intrinsic motivation is a delineation towards game thinking. Step one in designing for intrinsic motivation, Amy says, “is understanding that the best use of any game mechanics or progression mechanics is to support a journey.”

The framework Amy details in her book gives a synthesized approach to building an engaging customer journey. The core, she says, is how your product transforms the user into the person they want to be. “If you think about creating a product that gets better as the customer becomes more skilled, you'll be really getting to the heart of it.” Barry comments that Amy’s work is about helping the person to be the best they can be, realizing that struggle is part of the journey. “All the best things we do in life,” Barry says, “requires to test our character, to cultivate skills and behaviors in ourselves that we don't have, to grow as individuals.”

The mental model - the story that’s unfolding in the customer’s head - is at the heart of intrinsic motivation, Amy points out. She advises mapping out the story building up in the customer’s mind to understand their point of view. This will drive retention, she says.

Looking Ahead Amy is excited about the explosion of creativity that’s being unleashed because of the pandemic. She says that it’s “so much good that’s happening for the planet.”

Resources GameThinking.io  https://amyjokim.com/  https://twitter.com/amyjokim  https://www.linkedin.com/in/amyjokim/ https://www.youtube.com/channel/UC9jS5pCo5v8MoF6GjpGiXBw

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Barry O’Reilly is excited to welcome Temi Ofong to the Unlearn Podcast. Temi is the Chief Operating Officer for Corporate Investment Banking at Absa, South Africa’s most influential bank and one of the largest banks on the African continent. Temi describes his journey to his present role as an incredible learning curve. He shares the lessons he learned and unlearned throughout his career, in particular, the importance of putting people first to achieve success.

Empathy As A Superpower “If you're not able to connect with the person's journey and history and context, it's very difficult to get the best out of them because you don't really understand what motivates them,” Temi points out. Barry calls empathy a superpower. People who develop empathy always get the best information which informs how they behave and helps them to be successful in different environments. “Ultimately business is about people,” Temi adds. “Life is about people… The biggest thing you’ve got to unlearn or learn… is people and what motivates people, what makes them tick…” He illustrates how this principle helped him in the build out of their corporate banking business.

Unlearning A Common Leadership Myth  One of the most common myths about leadership is that a good leader does it all on his or her own. However, Temi points out that his biggest breakthrough actually came as a result of his coach. Many times the attitudes and behaviors that brought you success thus far, are not the same ones that will take you further. The right coach, he argues, can lead you on a journey of unlearning which will help you enhance your performance. Barry says that getting a coach helped him accelerate exponentially. 

Leaders also need to unlearn:

How to be vulnerable;

How to harness EQ;

What motivates their people.

The Notion of Collective Success A leader’s job is to create the environment for other people to succeed. “Ultimately it comes down to the notion of collective success,” Temi adds. People need to feel that they are part of the team, that their work is contributing to the success of the organization. “It’s about trying to create as many points of connection and collaboration where everybody feels that together they can achieve more,” Temi says.

Temi shares insights about what led to his bank’s successful multi-year transformation program:

It was a bank wide effort.

There was a specific deadline.

The team was willing to use a new approach.

They trusted one another.

They revamped how they tracked success and how they dealt with failure.

They started with one project, then iterated.

They invested in training colleagues.

Frequent Evidence of Success Nothing builds trust faster than seeing evidence of a new way of working, Barry says. When they see regular progress, leaders feel more confident about new methods. This kind of collaboration builds trust, momentum and rapport. “That’s where you see real transformation in organizations, where people go through an experience together and deliver something beyond their expectations,” Barry comments.

Looking Ahead Temi says the next step is to take what they learned in this project and implement it throughout the bank. Now that they are emerging from this multi-year project where they were focused internally, they have to make up any ground they lost in the market and accelerate past the competition. “The pieces that I focus on are the human parts,” he says. “I see my job as being to help them think through problems but without diminishing their accountability… it's a team sport and in that team we all play our part and I think that's a very important perspective to have as a leader.”

Resources Temi Ofong on LinkedIn

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Karen Tay, Smart Nation Director for the Prime Minister's Office of Singapore, is on a mission to transform Singapore into the world’s leading smart nation, where technology is used for maximum public good. 

She chats with Barry O’Reilly about how she is helping to modernize government by applying product development thinking to policy, organizational and talent development. She shares how this is changing the way the Singaporean government works. 

[note: this was recorded before the coronavirus outbreak in the US. If you want to chat about how these insights pertain to Government management of the coronavirus, Karen is happy to chat]

User-Driven Design

In charting directions for a country, being responsive to citizen sentiments is important, but there is also a place for Governments to exercise leadership in decision-making, eg. the decision that investing in preschool education is critical to social mobility, decisions on how to manage crises such as the coronavirus.

Regardless, how the central government implements their decisions should be driven by user behavior. Karen points out that using an iterative process is beneficial in many cases. She relates that they combined user research and iterative testing for policies in the Ministry of Education and found that stakeholders felt more engagement and ownership of the new policies. You have to be willing to listen to what your educators need and want from your product, and change it to something they are willing to implement, Karen says. Barry agrees that you should use user data to reframe your problem, then look at ways to improve.

Make Customers Feel Valued Karen and Barry discuss several unlearning moments in Karen’s career. She points out that in government it’s not about what ideas you have, rather whether you can execute them. She says that she was surprised by how little she needed to get something done. She found that it was often as simple as listening to her potential customers’ needs and designing around them, instead of feeding into prevailing assumptions. “You want to make [your customers] feel that you thought about them when you designed the product,” Karen says.

Go Deep First When you’re trying to build a policy or product, you must “go deep first,” Karen says. “You need to really get to know the people you're trying to serve… Focus on building that relationship and that trust with the community. Everything else - the dividends - come later.” As you respond to those needs, you learn more about how to scale later on. Barry agrees. He argues that a one-size-fits-all solution never works because each company and culture is different. “The way to scale innovation is actually to descale it, to start with a small group of people. Go very deep with a narrow focus and demonstrate new behaviors. Show what works and doesn't work in your context,” Barry emphasizes.

It’s All Relational Building talent pipelines and communities is all relational. Magic happens when you get to know people as human beings, Karen says. You achieve outcomes by connecting on a human level: people feel inspired to change when they have an emotional connection to the change you’re trying to make. Barry comments that the most successful leaders role model the behaviors they want their employees to adopt.

Looking Ahead Karen outlines several differences between engineering culture and management culture. She wishes that more hierarchical organizations would adopt the hands-on approach of engineering culture. This is the experience economy, she argues: people want to feel that your company is thinking about them, that they are valued. In fact, you should see all your customers and your employees as ambassadors. As such, you should treat them well and create an amazing experience for them.

Resources Karen Tay on LinkedIn

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This week’s guest on the Unlearn Podcast is Eric McNulty, head of the National Preparedness Leadership Initiative at Harvard. Eric is a crisis leadership expert who has worked on crises such as the Boston Marathon bombing, Hurricane Sandy and Deepwater Horizon, the BP oil spill off the coast of Mexico. He offers valuable insights about making decisions in crisis situations, in light of the Coronavirus pandemic that has gripped the world.

A Helpful Decision-Making Tool The leaders who respond best to a crisis are those who can weave several disciplines together to see three-dimensional patterns others miss. Such leaders see what’s missing, and can make connections between different domains to come up with a new solution. Host Barry O’Reilly says that it’s important to recognize the effects of your decisions. He asks Eric about tools to discover potential obstacles when implementing decisions during a crisis. Eric says his colleague, Peter Neffenger, created the Situation Connectivity Map for this very purpose. This tool helps you map out secondary situations that may arise, and allows you to connect the dots and get a richer picture of the overall impact. He says, “You think you're solving for problem X, but around that are different stakeholders, different aspects of that, and the extent you can map them... and to say What's gonna play off in this? How are they connected? Who are the stakeholders? Then you begin to really figure out where you need to put your attention.”

How Can We Be Our Best? This is a time to be aspirational, Eric says. Your old bureaucratic process will keep you from innovating, and actually prevents you from doing right by your customers. Ask yourself, “How can we be at our absolute best right now?” He encourages leaders to make changes, to rise above the situation to come out better and stronger. Barry adds that when you empower people to be their best, you will be amazed by what you can achieve together. Eric shares some interesting stories of resilience and innovation that he saw during crises.

It’s About Creating Order In a crisis, Eric says that he is “completely uninhibited about asking stupid questions.” He wants to understand why things are done in a certain way. Sometimes, his questions help others open up to doing things differently. He always asks these questions first:

Who or what has suffered here? Are they being taken care of?

Who should we have helping us who’s not here?

He says that failure often happens when you try to control everything. However, the very nature of a crisis is that it’s partly beyond your control. As such, you should aim to create order, not control. You only impose control when it brings more order, he says. He advises leaders to trust their people and delegate as much as possible. That’s how you give yourself space to contemplate the bigger decisions and understand the potential unintended consequences. 

Looking Around the Corner “If you're looking around the corner what's coming next actually is pretty obvious,” Eric says. He gives some practical tips to help leaders look ahead during a crisis:

Think about what’s likely to happen and the future consequences, based on the evidence you have;

Micro-journal your decisions and the information that led to them.

Resources Eric McNulty on LinkedIn

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Alberto Savoia had a successful career as Chief Technology Officer in major companies such as Sun Microsystems, SunLabs, and was Google’s first Engineering Manager. As an entrepreneur, however, he realized that building the right thing was more important than building things right. He chats with Barry O’Reilly about the pivotal unlearning moments in his life and his new approach to product development.

The Beast of Failure You work hard to create a great product, you launch it and the market rejects it. That’s one of the most painful experiences for any software developer. Alberto relates his first experience with ‘the beast of failure’: even though the market told them “if you build it, we will buy”, they did not actually buy. Alberto says that this failure felt as if someone had pulled the rug from under him.

However, it was also a seminal unlearning moment for him. The first lesson he took away was that if you’re building the right ‘it’, you will find a way to succeed in the market. The second lesson was that you have to own your failures before you can move forward.

Unlearning Market Research There is an 80% chance that the original version of any idea will fail. As such, Alberto now goes into a venture expecting failure, and the market has to prove him wrong. Optimizing to be wrong rather than to be right, flips traditional market research on its head. Barry comments that it’s at the heart of the scientific method since you have to conduct experiments to invalidate your hypothesis; if you can’t invalidate it, then it’s probably a good hypothesis.

Alberto’s most important experiment to test his ideas is his ‘skin in the game meter’. Asking the market if they will buy if you build is due negligence, he argues; that’s just promises and opinions. Instead, he tells them, “If you buy, we will build.” The ultimate demonstration that someone wants a product is when they put down a deposit. Money is the ultimate skin in the game, as Elon Musk’s example proves.

Pretotyping Engineers usually know whether a product can be built. The uncertainty lies in whether it should be built. Alberto says that when he looked at how creators approached this problem, he saw many examples of pretotyping. A pretotype is something you build before you start to build something that works; for example, how Jeff Hawkins developed the Palm Pilot. The only data that is valuable, Alberto says, is YODa - Your Own Data. Just as Hawkins did, Alberto only counts YODa that is backed up with skin in the game. Barry adds that YODa has the ability to shift mindsets. He has found that the people who own their results, and are continuously learning and unlearning to enhance their product, get exceptional results.

Change Takes Time Logic does not convince people to change their age-old thinking. It takes time and dedication to get people to buy in to new ideas and methods. Start with one project, Alberto advises, and incorporate some traditional techniques. Let them experience the results firsthand: that will start to open their minds up to a different way of thinking and acting. Barry agrees that logic is not enough to change minds or behavior. “You have to act your way to a new culture,” he says. “You start to see the world differently when you do things differently, and that’s what challenges your mental model and shifts it.”

Looking Forward Alberto has written a book to teach entrepreneurs and innovators about pretotyping, so they work on ideas that are likely to succeed. He advises them not to depend on luck and to assume failure. If you iterate enough, however, you will find the idea that succeeds, he says. That is how to play in a systematic way. “Unlearning is learning. It just takes courage to flip it around.” 

Resources AlbertoSavoia.com

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For 20 years, Jen Grace Baron has sought to discover the secrets of sustaining inspiration. Her findings are the subject of a book which she co-authored with Allison Holzer and Sandra Spataro, entitled Dare To Inspire: Sustain the Fire of Inspiration In Work and Life. She chats with Barry O’Reilly about his interesting topic in this week’s show.

What makes it worthwhile? In entrepreneurship, as in life, there are going to be tough days. Jen says that she and her co-authors asked each other, “What is the difference that we want to make that will make bad days worthwhile?”

Inspiration is a muscle and a resource Jen’s research proved that the traditional view of inspiration is erroneous. Inspiration isn’t something that happens to you. In fact, it can be generated: inspiration is a muscle that you can build and it’s a resource that organizations should manage. She outlines three ways we get inspired: 

We inspire ourselves;

We are inspired through, with and by others, mainly in relationships;

We’re inspired through situations. 

Jen adds that there are predictable pathways, or engines, that people use to inspire themselves.

Rituals and culture Barry and Jen talk about how simple ‘reset rituals’ spark inspiration and prepare us for success. Systematized rituals are essentially the building blocks of great culture. Culture, Jen says, is the hardest thing you’ll ever build in your company, but it’s the most precious. Barry adds that exceptional leaders role model the behaviors they want their people to adopt. Sustained change does depend on leaders, Jen agrees, which often means unlearning past beliefs and behaviors. The desire for the change has to be stronger than the fear of changing, she says.

Am I inspiring? Many leaders believe that they are not inspiring, or that being inspiring is the same as being charismatic. Jen describes the strategies and tools she uses to help her clients see their strengths and uniqueness. Barry comments that our capabilities are often our blind spots because they come so naturally to us. However, we inspire others just by being ourselves. Inspiration is about being authentic; it’s about knowing our strengths and how to use them, Jen adds. Situational leadership is also an essential element of inspiration as leaders today must be agile. Some engines of inspiration We’re inspired by people who share their fallibility and vulnerability with us. Jen comments that just needing other people, and expressing that, is magnetic and inspiring. She shares an important unlearning story from her own life. It was humbling, difficult and uncomfortable, she says, but it taught her how to be a better leader. Another engine of inspiration is overcoming adversity. Past constraints have motivated and inspired many people to succeed. Jen explains that a surprising engine of inspiration is failure, loss and grief. She shares the story of Dr. Joe Kasper to illustrate that grief can be a deep source of inspiration and can be channeled for good.

Finding your inspiration If you can reflect on traumatic events, failure, loss or grief, Jen says, and find ways they can serve you, you will grow stronger. This is called Post-Traumatic Growth. Barry asks the best way someone can figure out what will inspire them. Jen responds that inspiration helps you have your best days more often. As such, write down what your best day looks like for you, and why.

What’s next for Jen Jen wants to work with companies to measure inspiration and build inspiring partnerships to increase it.

Resources Dare To Inspire: Sustain the Fire of Inspiration In Work and Life

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Testing Business Ideas with David J. Bland

David Bland’s work includes the product death cycle, a classic anti-pattern innovators and entrepreneurs fall into when trying to create a new product. He highlights that building what customers say they want is not the way to be successful; instead, ideas need to be tested to see what they need to succeed. In this week’s show, Barry O’Reilly and David discuss his new book, Testing Business Ideas: A Field Guide for Rapid Experimentation, including what it takes to do experimentation right.

Stick To Your Vision or Walk Away? “It doesn’t matter how beautiful something looks, or who you think your customer is, if they don’t want it they don’t want it.” His early experience in a financial services startup taught David this valuable lesson. He says that at some point you have to decide whether to stick to your vision and pivot to another segment, or walk away. Having the market reject your hard work is humbling because you personally attach yourself to what you’re creating. However, David comments that the way to move forward is to listen to the data.

Being Open To Being Wrong Your vision may need to be tweaked in some way for you to be successful, David says. As such, leaders should adopt the mindset that they’re testing their vision against reality and that they might be wrong.

Unlearning Ideas About Experimentation Barry asks David to comment on what organizations need to unlearn about experimentation. David responds that much of it boils down to leadership mindset. People usually become leaders because they are experts in some area and have proven that they can produce results. It’s an ego-driven path, David says. If you’re not careful, you can become a CEO who still thinks that it’s all about you. Building a culture of experimentation means however, that you have to create more leaders around you. Barry adds that so many leaders are used to managing to output-based measures of success. Asking them to measure outcomes seems an alien concept, so they are resistant to the idea.

David says funding is another area organizations need to unlearn. He contrasts the traditional method of annual budgeting for projects with the concept of internal VC funding, and explains why the latter is better suited to experimentation.

Big Leadership Questions Technology is changing the world so quickly that organizations need to be able to adapt. The static business model that can run for years without change cannot survive in today’s market and economy, David comments. A very important question leaders need to consider is, What would happen if a startup is created today that would make us obsolete? Barry adds that another question leaders should ask is, What would stop us investing in this idea? It’s not enough to optimize only for the happy path; pairing it with metrics that tell you when to kill an initiative creates a clearer picture of what success would look like.

Start Manually David shares the story of an SMS dating app to illustrate that you can use manual processes to test the validity of a business idea without building sophisticated features. You can use what you learn to find a strategy or automate a process to scale. It also de-risks the process, Barry comments, as you find out if anyone cares about your product, if anyone would use it, and if you should build it. Starting manually makes for safe experimentation since you’re only investing your time, but you learn so much.

Looking Ahead David hopes to influence change in funding startups, as he believes that it should be based on evidence rather than emotion.

Resources Testing Business Ideas book David Bland on Twitter

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Dr. Gail Lebovic is a surgeon and entrepreneur whose work has made a great impact on the healthcare space, particularly by devising innovative surgical techniques and developing medical devices aimed at improving the lives of women with breast cancer. Host Barry O’Reilly describes her as a world leader with a passion for problem-solving and for thinking outside the box, which makes her unique in the highly structured field of surgery.  Challenging The Accepted Culture Surgical thinking is founded on achieving good outcomes and avoiding risk. Very few surgeons would think about trying a different procedure if the accepted way is working. Gail, however, knew that there had to be a better way to do breast cancer surgery. She felt that when a surgeon performs a mastectomy, he or she should also be doing a reconstruction. This was a radical idea at the time. Eventually, she sought out Dr. Donald Laub as her mentor and together they explored how to make this idea happen. Barry comments that everything pushes against you when you’re trying to innovate, especially in highly regulated, high consequence scenarios.  Breakthrough Even with a sought-after practice, and data to support her methods, Dr. Gail still found herself marginalized by the mainstream surgical community. Nevertheless, she focused on helping her patients and became involved in medical technology. She realized that she could impact many more people by creating technology and teaching others how to use it. Her MammoPad invention has now been used by over 100 million women. Another step she took was teaching surgeons her techniques. One surgeon can impact more than 250 cancer patients a year, she points out. To date, she has trained over 1000 surgeons around the world, escalating the opportunity to impact many more women than one on one. She created a post-graduate course that has hosted more than 18 conferences thanks in part to a grant from the Mary Kay foundation. Recognizing Opportunity  Barry asks Gail to describe how she recognizes an opportunity, including the steps she takes to determine if it’s worth pursuing. He quips that most Silicon Valley entrepreneurs start with a solution that’s looking for a problem! For Gail, it’s just the opposite – it begins by recognizing a problem or a basic need - for example, how to help more women get life-saving mammograms. Then you have to diligently research many different aspects of the problem as well as the potential solutions you may have. Then you can start prototyping. Ultimately, choosing the right prototype is a complex problem, but in the end you have to rely on gut instinct, she says. “That’s the key moment that ultimately will drive adoption.” Critical Thinking Skills People tend to optimize for the happy path, and very rarely do they think about unintended consequences, Barry comments. He finds that critical thinking is often a missing component in product development. Gail says that successful product development takes a cohesive team. You can’t get married to an idea just because you like it. The objective is to keep critiquing your designs and anticipating the risks until you have a prototype that you feel confident in. Barry adds that leaders should role-model accepting criticism of their own ideas; it's one of the most powerful things you can do, he says. The Value of Empathy Automating manual processes is great, but technology cannot replace the human touch. The medical process is both an art and a skill, Gail points out. Empathy is what drives the identification of needs, which inspires creation of technology products that save people’s lives and provides an avenue for compassionate care along the way.

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Barry O’Reilly opens Season 2 of the UnLearn Podcast by commemorating the 50th anniversary of the Apollo moon landing. He welcomes special guest Dr. Ed Hoffman, NASA’s first ever Chief Knowledge Officer. Ed is a Senior Lecturer at Columbia University School or Professional Studies, and serves as Strategic Advisor for the Project Management Institutue. In these roles he works with industry leaders to develop capabilities in leadership, projects, teaming, and future of work dynamics. He is a sought-after consultant and speaker, and the co-author of Shared Voyage: Learning and Unlearning from Remarkable Projects. 

Knowing Why Knowing what you’re doing is important, but it’s also critical to know why. Ed has always believed that NASA’s work contributes to the good of humankind. His thoughtful response to the interesting test Deputy Administrator Dr. Hans Mark put him through during his internship, proved that he knew why he was there. Barry comments that we can achieve amazing outcomes when we are connected to mission, when we know why we’re doing what we’re doing.

It Starts With The People The best organizations have thoughtful, effective leaders; they build teams who are themselves leaders; and they share a common mission. Ed says that when you work with people that you respect and care about, when you have a sense of purpose, and you feel that your skills are being utilized, then work feels like a special place. Barry asks how leaders can build such high-performance teams. Ed responds that the best leaders create - and are part of! - the best teams. “It starts with the people aspect,” he says. A sense of pride, appreciation and gratitude, and commitment to the dream are components of the best teams. Only then should the management part come in, Ed says.

A Lack of Communication Leads to Tragedy Ed relates how a lack of communication and collaboration at NASA led to the 2003 Columbia tragedy. When you’ve had a period of success, it’s common to feel pressure to produce faster results. Communication between teams often suffers and that’s when danger happens, Ed says. The Discovery mission six years later was successful because of the high level of communication and collaboration. The psychological safety to talk about anything is the most important ingredient in teamwork, Ed insists. Barry adds that information-sharing is crucial because making good decisions depends on having high quality information.

A Process of Unlearning  Putting yourself in an uncomfortable environment, where you have to actively learn, synthesize information and present it back for feedback, is a form of iterating, and a powerful mechanism for personal and team growth, Barry says. Ed had to go through this process of unlearning when he assumed the leadership of NASA’s Program Project Management Initiative. What he had in his favor, he says, was that he knew what he didn’t know. He has learned that knowledge is profoundly social: the answers are out there in the community, so the best teams learn from each other. Ed says that he is in awe of his technical and engineering colleagues because they’re doing work that he can’t understand. Enjoying the people you work with, appreciating them and the work you do together helps the whole team grow. Be in tap with what you enjoy, Ed advises. “It’s not work when you love something,” he says.

A meaningful interaction with a mentor was another powerful unlearning moment for Ed. Thanks to his mentor, his approach to finding solutions now involves setting up boundaries to know whether something is working, as well as the tools to recover. All of this has to do with an emphasis and commitment to building reflective leadership skills for learning and unlearning.

Resources Dr. Ed Hoffman

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In this finale episode of Season 1, Barry O’Reilly takes the time to answer questions posed by listeners. He reached out via social media and allowed his followers to ask him anything about himself, the podcast, or things they might want to learn and unlearn. Here are several of the questions posed and Barry’s answers:

Q: What takes up too much of your time? (Helen, Melbourne AUS) A: Noisy notifications. Non-specific interruptions that disrupt my flow are frustrating for me. I don’t like interruptions or context switching because it limits my progress.

Q: How do you measure success for the podcast? (Caroline, New York USA) A: I’m more interested in outcome-based measures of success. I know it’s going to be a great show when a guest says “I’ve never shared this story before,” or “I never thought of it like that.” Those authentic conversations, and getting feedback from listeners that they feel they’re part of them, are really powerful for me. 

Q: What has been the single best day of 2019, and why? (Prithi, Bangalore IND) A: Being sent a photo of Serena Williams reading Unlearn. It was especially poignant because watching her story on TV was a major unlearning moment for me. It forced me to acknowledge that there were things I needed to adapt in myself to achieve the outcomes I wanted. Seeing her reading my book was inspiring and felt like a closed feedback loop.

Q: What’s the most counterintuitive skill to unlearn? (Simon, San Francisco USA) A: Definitely the concept of coaching. We seem to think that only people who are underperforming need coaching. However, the highest performing persons have and actively seek out coaches to help them improve. Coaching has certainly been one of the best investments I’ve ever made in myself.

Q: Getting comfortable with being uncomfortable is nearly impossible for me. What do you do to actively get uncomfortable? (Kirstie, Helsinki FIN) A: Actually, I feel uncomfortable if I’m not doing something uncomfortable! Trying new things, embracing counterintuitive ideas challenges your thinking and your belief systems, but it also gives you evidence that either supports your original beliefs or the new idea. I encourage you to think about one small step you can take on the edge of your comfort zone. How can you improve by even half a point? Get someone you trust to rate you in that area at the beginning, then at the end of one week.

Q: It’s often said that the biggest blocker to success is fear? How do you unlearn fear? (Adrian, Johannesburg, SA) A: By thinking big but starting small. Taking small steps lets you find out what works and what doesn’t. You being to feel successful. As you continue to take those small steps, you improve and gain momentum. You start to see change happening. This is the antidote to fear: small wins create belief, show evidence and make it safe to fail.

Q: What’s the best piece of advice you have been given? (Yuko, Tokyo JPN) A: That you don’t only get one shot at success, there are actually many. Entrepreneurship for me is about life and life is about growth through learning experiences. When things don’t go the way you want, the trick is to pick yourself up, dust yourself off and get ready for your next shot. As my cousin Phillip would say: “if you’re still breathing you haven’t failed. Make sure you learn something for the next spin and go get inspired and do it again.”

What To Expect in 2020  Barry says that in the next iteration of the Unlearn Podcast, he will be interviewing guests from a broader range of industries, not just technology. He’s excited to hear about their journey to unlearn.

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Tanya Cordrey started her career as a journalist for a road haulage magazine. Today she serves on several boards and consults with many leading organizations. She has led teams and international expansions in companies such as BBC and eBay, and oversaw the transformation from print to digital media at The Guardian Media Group in her role as Chief Digital Officer. She joins host Barry O’Reilly to discuss her role in leading difficult change in often very traditional organizations.

Doing Something Different Doing something different can lead to new and wonderful opportunities. Tanya’s unconventional decision to do an MBA to pair and contrast with her literary arts degree resulted in creating the opportunity for her to lead a strategy team at the BBC and later to be recruited as part of the European executive team for BabyCenter. Barry comments that many people don’t realize the challenges involved when you’re trying to do something different. Tanya says that she seeks out high-paced environments. She takes calculated risks that she believes will yield good results, like the MBA and working with technology. Both decisions gave her in-demand skills and an advantage in the market.

Identifying Scalable Opportunities Convincing stakeholders to grasp new opportunities is often a difficult task. However, being clear on your vision and giving them a taste of the expected results makes the task easier. A little survival anxiety can help as well! 

Tanya and her colleagues wanted to convince eBay to introduce fixed price selling—her data supported it. They were turned down initially but were later told that if other countries wanted it, they could give it a try. The international partners were all interested. At the time, Amazon was talking about launching its marketplace, which spurred the decision-makers to see fixed price selling as a defensive maneuver. The project was eventually rolled out, to phenomenal success. Within a few days of seeing the results around the world, eBay US also rolled out fixed price selling. This experience taught Tanya to think big, and use data to support her beliefs. She says that it was the first time one of her ideas led to such a huge impact on revenue. By leveraging external competitors to accelerate action, and collaborating with many different stakeholders, she was able to cause a huge transformation.

Shaking Off Existing Paradigms Leading change, especially in traditional companies, involves unlearning your tried and true methods and learning what works in the current context. Having spent several years in purely digital companies that were largely data-driven, Tanya found that using charts and logical arguments derived from the data didn’t really work at The Guardian. 

Tanya learned that she had to appeal to hearts as well as heads in order to persuade the media giant. Barry agrees that you need a well-constructed value hypothesis grounded in evidence and data, as well as an aspirational vision and mission to show people where you want to go.

Three Phases of Change Tanya’s says The Guardian’s transformation fell into three phases:

Phase 1: Changing as much as possible, as quickly as possible.

Phase 2: Communication.

Phase 3: Cross-functionality.

Resources Tanya Cordrey on LinkedIn | Twitter

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Stephen Orban found an old TI-99 in his uncle’s attic when he was eight years old. The first thing he did, he says, was take it apart to learn how it worked. Soon he was writing programs to make things move around on the screen. He knew since then that he wanted to work with computers. Throughout his career he has brought exponential technology to many traditional organizations, such as Bloomberg and Dow Jones. He is now leading a new initiative in Data Analytics at AWS. 

Killed by Traditional Technology It was during his tenure at Bloomberg that Stephen became infatuated with cloud computing. He relates to Barry O’Reilly that they were experimenting to create new businesses. However, the traditional method of trying to build best-in-class technology was making the process slow and expensive. We were building too much into disaster recovery and business continuity for things that might not even be there tomorrow, he says. He recognized that cloud computing would allow them to test and scale on demand, only using the resources they needed. When he moved to Dow Jones he pushed towards using cloud technology and dev-ops methodology, which allowed them to create a more agile organization.

Unlearning Leadership Massive technology changes come with people changes. Stephen soon realized that the way he led at Bloomberg would not work at Dow Jones. Barry comments that it’s almost a reflex to use the behaviors that brought us success in the past. However, those same behaviors may not yield success in a new context. Stephen says that he failed as a leader for the first six months. His advisor told him that there’s no glory in being the only one at the finish line. From that day, he says, he learned to be more empathetic and open instead of the top-down leader he previously was. He wanted his team to buy in to his vision.

In order to share their wins, he increased communication with employees from quarterly to monthly town hall meetings. Team members were invited to share what they were doing and how it was aligned to the broader vision. Barry says that when you recognize that you’re not driving the outcomes you want, the first step is to acknowledge it. He commends Stephen for the subtle but impactful changes he made.

Building Cross-Functional Teams When Stephen decided to change the siloed IT functions into two cross-functional teams, he expected everyone to be as excited as he was. Each team was responsible for a measurable customer outcome. This required unlearning silos and learning cross-functional team behaviors. Stephen relates that the engineers were not pleased. It was hard for them to understand this new paradigm, and Stephen comments that it was hard for him to lead through the change. Barry comments that a first step is to help people feel successful as fast as possible. If they have some quick wins, they would be more willing to embrace the new behaviors.

To reinforce the paradigm shift, the IT department was renamed Dow Jones Technology. Respected persons in the company started to share positive stories about the impact of the new changes, and the metrics showed that the new methods were working. Barry agrees that metrics paired with local success stories leads to breakthroughs.

Looking Forward Stephen now works at Amazon, an organization that has a very high performing, well-prescribed culture and operating model. He is excited about the pace of innovation that’s going to happen. Those who can’t move fast enough will feel the impact on their profitability, he says. Don’t be stuck in analysis paralysis, he advises; there are lots of opportunities to start and learn what works and what doesn’t for your organization. You can’t think your way to a new culture, Barry adds, you have to act your way there.

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As a trained occupational psychologist, Kim Atherton has worked with leaders and organizations to understand how they create high-performance teams. She joined Ovo Energy - a green energy tech company in the UK - when it was just 50 people in a barn, and helped to scale the company to 2,500 employees. During her time at Ovo, she recognized that misalignment was a problem for companies, which inspired her to found Just3Things, a startup that helps organizations improve alignment at scale. 

Alignment With The Vision In 2012 Kim was in the final interview stage at a large bank. It was a great career move on paper, but the thought of getting out of bed every day to do succession planning for a big bank just didn’t excite her. About that time she met the founder of Ovo Energy, who told her that he needed someone to help him build the world’s best company, someone who would be willing to unlearn traditional HR practices. Kim jumped at the opportunity to help scale Ovo as she believed in its vision. [Listen from 1:45]

The mission and values of a company are more important than the compensation and prestige, Barry comments. A transformative purpose pulls people together: you’re willing to put up with more when you know it’s for the greater good. It keeps you going through the tough times. [Listen from 3:45]

Aligning Values With Behavior Human beings pick up on behavioral cues almost unconsciously. Creating a company culture that aligns with your vision often means unlearning traditional practices, and being intentional about using processes that result in desired behaviors. Ovo knew their success depended on being nimble and agile, so they eschewed traditional competency-based interview practices in favor of interviewing based on learning agility. Kim says that you can always upskill an employee if they don’t have a certain programming ability, but you can’t train learning agility - you either have it or you don’t. [Listen from 6:50]

In the fast-paced world of a startup company, full transparency and good communication are vital. You want to create an environment of psychological safety to empower your team to experiment and learn. Reiterate the vision often and embed activities around values to remind your team that we’re all part of a bigger purpose, Kim advises. [Listen from 12:15]

Learning and Unlearning Employee Incentives Barry finds that the highest performing companies are those who experiment and figure out the right practices for their context. Kim agrees that experimentation and an efficient feedback loop enabled Ovo to learn what works best for them. For example, their experiment with removing the holiday policy taught them that, trendy though it was, it wasn’t ideal for them. We need guardrails, they learned, otherwise it’s really hard to do our jobs. At Just3Things, Kim finds that they’re unlearning all the time. Feedback from customers often challenges their assumptions and they have to rethink some aspect of the product. [Listen from 19:55]  

A Golden Thread Just3Things was inspired by the need for a goal-setting tool for cross-functional teams. Kim describes it as a simple and transparent tool where teams could see how the outcomes they are working on align with company strategy, then link their day to day tasks to the outcomes, forming a golden thread through the entire process. It started as a manual process at Ovo, but was developed into a digital tool when the concept proved useful in recouping lost productivity time. Kim describes how she discovered the need in the market for her product, and how she founded Just3Things to answer that market need. Barry comments that when you understand how your effort is aligning to positive customer outcomes, its an unending tap of motivation and experimentation. [Listen from 30:00]

Resources Just3Things.com

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Barry O’Reilly is pleased to welcome Martin Eriksson to the Unlearn Podcast. Martin is the co-founder of ProductTank and the Mind the Product conferences that have scaled and sustained themselves around the world. 

Learning From One Another When he started ProductTank in the back of a London pub, Martin never imagined that his small meetup of 25 product managers would be the genesis of a community over 150,000 strong from 180 cities, or that they would be hosting 5 conferences around the world. Their goal was simply to learn from one another so they could be better at their jobs.

That initial meetup took on a life of its own because many others had the same need. All of their growth has been inbound, Martin relates: people come to them for help in setting up local ProductTank chapters. Martin embraced those opportunities, seeing that the more the community expanded, the more people they could meet and learn from.

Recognizing Opportunities and Gaining Momentum When you recognize that you’ve built something of value that your customers love and want more of, naturally, you want to grow. Martin’s approach was to think about the next step and move in that direction. ProductTank was continuing to expand to more cities and countries, so they decided to launch a conference to get big names from the US to share their expertise.

Barry remarks that the power of momentum is often underrated. As you continue to do reps, you build momentum and eventually a movement. In the case of ProductTank, they were learning valuable lessons as they continued to meet and grow, such as how to work together and get the best out of one another. Soon Martin recognized the global potential of their fledgling company.

Making A Great Experience for Everyone A successful conference prioritizes great experiences for everyone. The needs of attendees, speakers and vendors have to be catered for, and ample time must be given for people to learn and network. Barry asks how Martin ensures that these great experiences are part of every conference, especially as the company scales. It’s really all about people, Martin responds. They closely screen people who want to organize local ProductTank chapters or conferences to make sure that they share the same purpose. This is what has driven the strength of this community, he says. If you have the right people you can trust them to build on that experience.

Mission and Shared Values One of the hallmarks of great business is that your mission statement centers around your customer as opposed to your business. Mind the Product encapsulates this in its mission statement: “Our mission is to make other people more successful by coming together to further our craft.”  Barry notes that these principles should be codified as you grow to not only attract the right people, but so that they behave in a way that protects the community and the essence of what you're trying to create. Some of the team values that guide Martin’s company are:

We are an empowered and autonomous team;

We should be excellent to each other;

If we’re not winning, we’re learning;

Hard work should be rewarding.

Unlearning and Next Steps Two important lessons Martin would unlearn if he had the chance to start over would be to think bigger and embrace the opportunity sooner and to understand his brand and the market better. Building connections among regional and international communities is a powerful part of their mission going forward. There is a wealth of talent all over the world and we can learn so much from each other, Martin says. He sees it as his personal mission to reach out into his network and lift up stories and different ideas and ways of working. That sense of curiosity and willingness to learn empowers and motivates him.

Resources MartinEriksson.com  mindtheproduct.com

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This week’s guest is Thaniya Keereepart, Head of Product, International at Patreon. Thaniya joined Patreon after working with Major League Baseball (MLB) and TED, moving into the digital space. Raising Your Hand Some people gravitate towards structure, but people like Thaniya thrive on unstructured paths. She says, “The through-line of all of my turning points has been that I have a habit of raising my hand to volunteer to do things I don't really know how to do.” She credits her bravery to learning through doing: she understands how to iterate so she puts guardrails in place to learn what works and be flexible and adaptive when unintended consequences occur. She relates how her Game Day program crashed in the opening MLB game, with four million users online. That scary moment taught her how to handle live events. Something admirable about that environment, however, is that when anything broke, everyone came together to fix it. Barry notes that high-performance cultures focus on solving the problem and improving the system, rather than blaming an individual. This allows everyone to feel comfortable and give their best. Building an Inclusive Team When you’re building products for the masses, you want your team to reflect the diversity of your consumers. The best performing teams are usually the most diverse. Both Barry and Thaniya had to unlearn a great deal when they started working in diverse environments. Thaniya was used to working largely with males in college and at MLB, so there was a culture shock when she started at TED, but it opened her eyes to what it’s like to work in an environment with people of various backgrounds, cultures and genders. Barry says that he never saw the problem of a lack of diversity and inclusion until he started to work in San Francisco. He was in a bubble of sorts at Thought Works, his previous workplace since it was the norm to have a diverse workforce. He felt a call to action to share the values he learned at Thought Works in his new, male-dominated workplace. Sharing a Beautiful Vision of the Future It’s important to share a vision of the future. Thaniya believes in creating big change in small chunks, creating value that can be seen and felt immediately. She involves the teams that will benefit from the change in the product development phase. These teams then become champions of the new product. When you start small, Barry adds, you create evidence of the future you’re trying to build; you build trust and confidence that your big vision can come to life. It’s also important to anchor the big change with a beautiful narrative, says Thaniya. Engaging Customers Part of re-platforming includes building a change management system to set customer expectations. It’s unwise to have big changes foisted on your customers suddenly. Thaniya’s strategy at TED was to create excitement around the coming changes by inviting customers to be part of a beta program. They felt that they were helping to build TED’s new platform, which engaged them and made them champions of the coming change. Resources Thaniya Keereepart on LinkedIn Why Diverse Teams are Smarter - Harvard Business Review Diversity + Inclusion = Better Decision Making at Work

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Barry O’Reilly is excited to welcome Eric Ries to the Unlearn Podcast. Eric is an entrepreneur who currently heads the Long Term Stock Exchange. He is best known, however, as the author of the international bestseller: The Lean Startup. The principles of Lean Startup were birthed from seeing many startups and Silicon Valley companies fail for lack of customer engagement, slow iteration, and long feedback cycles—experiences that inspired Eric to think about different ways to work. He shares how he discovered, and subsequently helped people unlearn many of the methods that were holding them back, and relearn counterintuitive methods to help them succeed in situations of high uncertainty. Pioneering ChangeIn his early days at IMVU, Eric found himself constantly explaining why his new methods had merit. At one point he had to decide whether to continue to advocate for his ideas or agree to work the conventional way. He chose to advocate for what he believed in. He reflects that had he not had the courage of his convictions he would never have found out who his ideas resonated with. Counterintuitive ideas cause frustration and difficulty for people. If counterintuitive thinking is key to the success of your business culture, then you need to help people rewire their brains. To have reform, and move people to the next steps, you must find the sweet spot between familiarity and novelty: you can't be too radical, or too conservative. Principles and Long-Term VisionBusiness strategy must be guided by principles in the context of a long-term vision. Barry commends Eric for the iterations he made to his business over time, which were guided by a continuous loop of customer feedback and testing new features in small batches. Eric shares the many pivots he had to make noting that you can always change strategy, but keep the vision. Opening Minds Through EmpathyEric says that he has spent years trying to understand what would it take to change public companies from being short-term focused on multi-stakeholder long-term focused organizations. He would often face vehement opposition from officials when he promoted his ideas. He notes that when people vehemently oppose an idea, method or technique but their reasons are poor, it’s usually a signal that they’re reacting emotionally, trying to protect the status quo. Barry adds this is a behavior he also sees a lot when people don’t deeply understand why they’re doing what they are doing, missing underlying principles instead of sticking to the only practice they know. Eric is sympathetic because he understands: they’re trying to do a difficult, often thankless job, using the tools and techniques they’ve refined over years. He represents a threat to their comfort zone. He tries to understand what they care about so that his plans and ideas are compatible with their values. They appreciate his respectful approach and work with him to find a comfortable compromise. Empathy, he finds, is the path to greater effectiveness. Barry agrees that empathy is key. It leads to mutual understanding. If you are willing to listen to people and they feel that they're being heard, the quality of information that you get just skyrockets. When you have high-quality information and a good decision-making process, you have a better chance of getting the results you want. Changing the WorldOur grandparents built the institutions that were needed in their world, with the institutional infrastructure that their time demanded. Our world today is very different, and those institutions - hotels, hospitals, unions, schools and universities - are all collapsing at the same time. Eric says that we need to establish the institutional infrastructure that our time demands. If we fail in our responsibility to confront these problems on our society’s behalf, we will soon be replaced. ResourcesEric Ries

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Snehal Kundalkar, Senior Director of Engineering at Reddit, grew up in a world of dualities. On the one hand she was taught that her place as a woman was between the kitchen and the kids, but on the other hand she was encouraged to embrace uncertainty to solve complex problems. She was naturally attracted to engineering and she channeled her anger at the injustice of her situation into creativity. She didn’t see herself in the expected role of home provider, so after completing her Bachelor's degree in Computer Engineering, she left her home country to pursue her Masters in the US. She longed to find the adventure she needed in her adopted country. Celebrating Failure After a little bit of success, failure feels unwelcome”. Don’t let that be you. Embrace it as a natural yin yang of the journey. It takes a lot of patience and grit, but you have to learn to expect and even embrace that some of your efforts will fail. Innovating, building things that have never been built before, is a highly unpredictable situation with loads of unknowns. What Snehal learned from her time at Apple was to break down your big vision into smaller sets: make small things that are almost as good as the big thing, then combine them together to build momentum. Failure is good information: it tells you what didn’t work. It's regrettable that our culture stigmatizes failure as bad instead of focusing on what you learned and how that’s going to help you move forward. Barry points out that in reality, you’ll never be able to predict the future, so you need to test the future: you need to fail as much and as quickly as possible to learn what works and what doesn't. Make Decisions Quickly. It’s natural to be scared when making decisions in a high-stakes, uncertain environment, but the trick is to make decisions fast and stick to them. If your strategy doesn't work, then make another decision fast. Soon enough you'll have a successful process. Encourage all members of the team to come up with their best solution within a limited timeframe. Bring them all to the table and choose the best idea/solution. Unlearning Is Not Forgetting Barry reminds us that unlearning does not mean forgetting everything you know. Your experience stays with you but you recognize that the behaviors that work in one context may not work in another. This is what Snehal experienced when she transitioned from the Apple ecosystem which she knew, into Reddit whose culture was totally different. At the same time, however, she was able to successfully introduce some of the behaviors she learned at Apple. A leader needs to be flexible when introducing a new culture. You may have big aspirations, but you can’t force culture, you have to be patient. Consider your previous knowledge and experience as tools in your toolbox: you don't necessarily have to use all of them at the same time, just the ones that work in your present context. This is what learning and unlearning means to Barry: helping people adapt to their particular context and find the right methods to achieve their desired outcomes. What’s Next for Snehal? Role models like her 71-year-old father, who recently completed his degree in music, inspire Snehal’s unlearning journey. She says that no one is born great, you continuously develop your skills into greatness. She's excited about being part of Reddit’s foray into conversation AI, as well as the company’s expansion into new international markets. Snehal Kundalkar on: LinkedIn, Medium

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Creativity can come in a variety of forms, and for Jake Knapp, author of Sprint and Make Time, it was a mixture of painting, artistry and old school programming. Jake finds creative satisfaction in trying to figure out how to design, optimize and improve everything from the default settings in his own life, to how people run meetings and design products. Sometimes, having an outsider’s view can be quite useful. What’s holding us back? We’ve all had times when we feel like we haven’t gotten enough done, or we haven’t gotten done the one thing that would have helped us make real progress. Jake talks about how experiencing moments of intensity helped him understand and prioritize the outcomes from his life he really wanted. Looking at and thinking about the outcomes he wants, and then gathering data that allows him to review his behavior in light of these outcomes is one of the keys to Jake’s success – and perhaps one that can be replicated, even by people who don’t see the world as he does—as code. Listen from 6:15 Failure actually… sucks. You’d think that tech startup founders are handed a script before being interviewed, outlining how they should mention that they absolutely love failure. It doesn’t bother them in the slightest. Most of us don’t feel quite that way about it. Unlike the popular ideology would have you believe – screwing something up sucks. It hurts, it’s embarrassing, it impacts other people and it can feel terrible. The thing to do with failure isn't to pretend you like it, but to actively and intentionally learn from it as part of the coping process. Listen from 12:00 Principles have to be learned to be unlearned. There are certain assumptions we make when we start to gain experience and expertise in our fields, especially when we’re leaders. One of the most critical things Jake had to learn was that other people’s ideas and contributions were as likely to be the best ones as his own. The idea of not selling or pitching your idea to your team goes against most of what we’ve been taught about working in companies. It's a skill set that can be totally unrelated to the problem you’re trying to solve, and it’s better for the best idea to win, not the loudest or most popular person. Jake shares a story about the development of what would eventually become Google Hangouts – and what it taught him about collaboration. Listen from 21:00  The value of the supporting the Decider role. There are people whose job it is to come into a situation and make the call—the deciders. It’s important to have some empathy for that role – even though it may not result in the decisions you personally would make. You can support leaders and decision-makers by giving them the tools and resources they need to make the best possible decision. It’s not always a democracy, but if you do the groundwork to minimize the possibilities of bad options, then great things can happen. Listen from 28:45 What’s next for Jake? Something helping Jake learn and unlearn right now is writing a science fiction novel. He’s not sure when it will be finished, but creating it and using the process he’s refined in other areas of his life, gathering and analyzing data to help optimize for outcomes, is playing a role in how he writes. Listen from 33:00

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You always want to look back on your life and say that your path from point A to point B was linear. It almost never really is. Today’s guest on the Unlearn Podcast is Mark Graban, author of Lean Hospitals and Measures of Success, who started out as an engineer for General Motors. It’s been quite a journey. Today, he and Barry O’Reilly will be talking about how that kind of a shift can happen, and what he learned and unlearned along the way. Clashes of Culture You might not think that the worlds of manufacturing and healthcare have much in common, but having worked in both, Mark thinks they have plenty in common - especially when it comes to culture. People aren’t machines, but the culture of many hospitals and clinics echoes what you’ll find on the factory floor - especially in institutions that haven’t done much to modernize the way they manage and lead people. Barry points out that there are similarities in tech as well: every industry thinks it’s unique, but it’s all human systems and people working together to drive outcomes.  Unlearning Your Whole Career When you’ve invested years or decades into a career, you often feel like you need to stay in it. Having made a major career transition, Mark knows that doing so allows you to bring fresh insight into an organization that may not be expecting it, and when you’re in a wholly new environment, you’re in a better position to avoid the curse of expertise. Looking back, Mark wishes he’d unlearned top-down style management earlier - the benefits of engaging people in change are so many and so valuable.   Seeking and Finding Clarity Before you start optimizing for, or worse, applying a solution, you have to be exceptionally clear on what the problem really is, and what outcome you want to achieve. Mark and Barry discuss the ways this can manifest in different kinds of organizations, and the framework for problem-solving that Mark uses to help healthcare providers make changes to their operations with input from people working at all levels. The process is one that listeners will be familiar with: unlearn, re-learn and breakthrough!   The Courage to Change It’s easy to tell when something isn’t right, but it's harder to create a moment where people are open to truly unlearning and making changes. Mark notes that looking outside of your area of expertise takes a fair amount of courage - but many people are highly skilled in their specific profession and not in the other areas of running a business or managing a team. This is often problematic because when we’re faced with things we don’t know, or feel scared and threatened - our higher-order brains shut down. There is never going to be a ‘perfect’ time for a major change, so you might as well just get started.  What are the Top 3 Reasons to Do This? Management from the top-down usually doesn’t usually provide the results companies are looking for. It’s much more effective to lead as if you had no authority - by seeking input and finding out what makes people tick, and why they think the way they do. Something that Mark had to unlearn over the course of his career was that you can’t just tell people what to do, even if you’re wildly excited about helping them. Change has to be based on feedback and engagement with the people it affects. Mark has some insights on what makes people more open and receptive to change and leaves us with the thought that it’s okay to struggle with change. It doesn’t make you a bad person or a bad manager - it’s just something to figure out.  Resources Lean Hospitals  Measures of Success

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Entrepreneurs tend to talk about the success, the fun and excitement of running a company. Fewer talk about struggles. Today, on the Unlearn Podcast, Barry O’Reilly talks to Teresa Torres, Product Discovery Coach at Product Talk. They get into what’s hard about the path to success, and at the end of the day, what really matters. No One Has All The Answers Like many young CEOs and founders, Teresa found herself working with people who were older, more experienced, and with access to more resources than she did as a leader. She shares a key unlearn moment about discovering that no one really has all the answers - and how that gave her the confidence to start trying things to see what worked. Barry points out that trying is a learned behavior, and Teresa discusses how education and experience in design-thinking instilled in her the idea that your first attempt won’t always work: iteration is the key to achieving your goals. A Process for Decision-Making Very little about being a CEO is black and white - and coming from an environment where situations were more granular was a challenge for Teresa. She says sales is a lot like product development and gives us some insight on the similarities, and how she brought an outcome-based focus into her work as a product leader and later as a CEO. Every process has parts, and those parts can be modeled, measured and optimized. Our Defaults Can Be Unhelpful When people are working under stress, they tend to revert to the skills, strategies, and habits that they are the best at - it feels good, and more importantly, it feels productive. Barry and Teresa talk about how this tendency can actually work against people whose roles are less about producing, and more about helping other people produce, or taking a bigger picture view of the growth and direction of a company. This is especially challenging when every situation feels extremely high stakes. Letting Other People Help You Teresa recalls the scenario her company was navigating through during the economic downturn, and how critical it was to let her team play to their own strengths and be responsible for their outcomes - and importantly, create a space for them to be transparent with her about her work and responsibilities. During a particularly fraught time, Teresa wasn’t going to make payroll and ended up offering team members the option to become owners in the company. This had several beneficial outcomes and ended up giving her employees a unique learning experience, as well as company stock.   Defining Success on Multiple Levels After being a CEO, Teresa had to decide what came next. She experimented with different projects and determined that what she wanted to tackle was the waste of time and talent endemic in many startups, founding a new company to do so—Product Talk. Barry brings up how, as a solopreneur, it can be difficult to handle loss-aversion, and constantly feeling like you have to take every opportunity that comes along. Teresa’s answer to this is to try and make sure you have only awesome options to choose from and shares some examples of how she’s made that a part of her working life. What Feels Fun That Helps? Teresa used what she calls a divergent-convergent process to try many different options to help weed out what she didn’t want to do. Barry and she discuss how this applies to both business and to life, and why embracing an abundance mindset can help you identify and create many amazing options for yourself—therefore improving the options you end up selecting to succeed. Resources: Product Talk| LinkedIn

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CEO School and The Future of Work with Stephane Kasriel In this episode of the Unlearn Podcast, Barry O'Reilly speaks with Stephane Kasriel, the CEO of Upwork—the world’s largest freelancing platform where businesses and independent professionals connect and collaborate remotely. Upwork is driving the future of work conversation, and discovering what it really means along the way. Creating Capability To Continuously Change Stephane feels one of the most exciting aspects of the tech industry is how quickly it changes— a key competency he believes people must develop is adapting to that change, learning continuously, and unlearning what is no longer useful. He talks through two specific changes Upwork has experienced: the switch from traditional waterfall development to remote agile teams, and sourcing and clarifying Upwork’s values from within. Secrets To Distributed Agility Several years ago, no one believed that agile could work in teams that weren’t co-located, but Upwork—along with other companies like GitHub and Automatic—has demonstrated it can. It takes an open mind, strong culture of feedback and honest personal evaluation to understand if working remotely is a fit for you. Making this clear during hiring is crucial. Not everyone will be passionate about or motivated to work in a distributed manner—and that’s okay. It’s better to discover it as quickly as possible because it means the people who join your organization are aligned with the opportunities and affordances of distributed work. They’re happier, more productive and stay longer. Challenges Transiting To The Top Transitioning from one role to another can be challenging, but the transition to CEO is unique. There’s no CEO school. Stephane shares how he found his way by applying many of the strategies that made him successful as a product and engineering leader. Actively learning from the people around him—wherever they are in the hierarchy—helped guide this approach to lead the company forward. In the tech industry, where so many founders are CEOs, knowing where to step up and step back is key in creating a healthy culture within leadership teams. Stephane shows how he’s tried to let the smart people bring their skills to bear. Unlearning At The Global Level There are a handful of things reshaping the economy: automation technologies, the acceleration of the rate of technological change and innovation, and the geographic mismatch between where jobs are being lost and where they’re being created. Stephane talks about how these forces are causing changes in the labor market and how you need to approach learning to stay current. It’s the people who can be in the habit of doing new things, and consistently adding new small skills who are ultimately going to be successful. Stephane adds that if we can’t embrace change, we’re doomed. We’re part of the future that’s coming; we can be a part of making it happen, or let it happen to us. The Power of Remote Work Upwork is focused on making remote work possible, and that’s not just about profitability. When the cost of living becomes unbearable in the big tech centers, but other towns are dying for a lack of good jobs—the best solution can’t be for everyone to move to expensive cities. Responsible tech leaders need to abandon the idea of having their entire workforce in a single building in a big city. Many jobs do not need to be on-site, and they shouldn’t be. Society as a whole will be better when we start making growth and success inclusive of more people. It’s not a good outcome for the world to have a huge part of the population unemployed or underemployed. One of our most precious resources is the human mind, and we shouldn’t be wasting it.

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Barry O’Reilly has had many mentors over the years, and among them, Mary and Tom Poppendieck have been some of the most inspirational. In today’s conversation, they talk about challenges the Agile community faces, debunk the myths of scaling agility, and finally, Mary and Tom reveal how they have stayed relevant for decades as they continue to coach, mentor, and help others. About Mary and Tom Neither Mary nor Tom started with software. Mary was an engineer who worked with problems that had life and death ramifications, and Tom was a physics teacher whose students contact him decades later to say ‘thank you - you made a big difference.’ They’ve written many of the seminal books and contributed much to the Lean and Agile movement and have seen fads and trends come and go. Barry asks them what has been their key insights over the years. When did you discover agile? Agile developed as a reaction to what was happening in the software industry in the late 1990s. Agile has to grow up, to no longer be reactionary when bad things happen, but to determine how to create GOOD software engineering from the start. She draws on her experience as a traditional engineer and shares a lesson about how proxies between engineers and people with problems are a bad idea. It’s a matter of trusting professional judgment. Tom observes that, too often, Agile tries to solve problems with processes. But the problem isn’t usually the process; it’s architectural. He talks about the different structures, from software to the leadership teams, that can lead to dysfunctional situations. If you want to solve a problem, you need to fix the structure. How Agile Can Grow There’s no simple answer to this, Mary points out because it depends on where you’re at. You can understand all the fundamental steps needed but if your team isn’t well-integrated, it will get you nowhere. She shares an experience with a company who had accepted a big contract they weren’t ready for. Mary recommended the ‘sync and stabilize' method and taught them how to use it. It didn’t just save their contract; it changed how they looked at their whole company. Tom highlights the non-technology component of software, the ‘wetware,’ or what happens with people. He points out that money isn’t the issue; it’s the shortage of passionate, creative people - especially in isolated IT departments that are treated as cost centers. Tom believes you should give them challenging problems and get out of their way. Teams Tailored to Problems Mary loves to talk about how organizations such as AWS and T-Mobile handle their organizational structure and customers. When there is a customer problem, a team is brought together to solve it and integrate it into the rest of the services so everything works. That team is given a lot of autonomy, including trading immediate profits for better customer experience AND have accountability to ensure they are also adhering to operational excellence and profitability of their service. Ultimately, better customer experiences drive bigger profits. Tom makes an important point: scaling isn’t possible after a certain point. At some point, complexity dominates future gains and wipes them out, so you have to descale. In other words, you have to do things in ‘little chunks’ that are independent and don’t require strict coordination. Tom uses the example of a city and how it functions. Final Thoughts Part of what helps Tom and Mary stay current is that they are truly agile. Mary points out that she’s never seen anything in technology last two decades and remain current. Agile has been around for about that long, but has it been changing and adapting? Resources https://twitter.com/mpoppendieck http://www.poppendieck.com/

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Joe Norena is the Managing Director at HSBC and the Global Markets Americas COO. From corporations to startups to corporate digital, his experience has run the gamut of organization. Joe has led a life of unlearning, and every new thing he learned he has applied to the next situation. In this episode, Joe and Barry talk about the pivotal moments in his career that brought him where he is today. Unlearning Starts Early... From the beginning of his life, Joe has been surrounded by people who modeled the type of behavior that would shape his success. His father, an immigrant who didn’t speak the language, began work in the mailroom of Citibank and retired as the Vice President. His mother always encouraged him to ‘just go and try it.’ Joe shares a funny story about nearly drowning when he tried out for the swim team in grade school. ...And Continues Through Life During his time at Citibank, Joe continued to have powerful role models. First among them was Michael, a senior trade manager. Michael was willing to sit down with the most junior of employees - even graduates - and open his mind to new ways of thinking, doing things, and techniques. He was a true ‘unlearner’ who modeled that behavior for everyone around him. Joe’s time at Bridgewater taught him another very important lesson: having a voice based on principles rather than the desire to be right. Understanding that success might be revealed through another lens, or way of thinking, helps a company grow and remain sustainable. The debate then becomes about what the real issue or problem is, and what is the right thing to do. Unlearning Moments You need to be comfortable with being uncomfortable; it’s the hallmark of a life-long unlearner. Joe experienced this several times during his career. First among those was the huge mind-shift he had to make when moving from being a trader to a COO. A trader knows whether he was an asset to the company at the end of the day; he only needed to look at profit/loss. But when Joe became COO, it wasn’t that obvious. It took 3-6 months before he knew if he was succeeding or not. The second unlearning experience for Joe was at the hedge fund startup. Every day he had to deal with and make decisions about situations he had no experience in. He was also used to having many people to help him, but in the startup, he only had himself. In the end, they had to close the startup, but Joe brought all the new learning with him. Joe’s time at the startup taught him about the need for lean startup principles, and he was able to apply that learning at HSBC. In effect, while leading a team of 30 people on a limited budget Joe looked at an experiment as being successful if it failed because he learned something. From those ‘failures’ came some of the greatest successes. Organizational Learning Learning comes from the bottom up, but if you don’t have support from the top, it becomes very difficult. The message from the top should be ‘we want to change, we want to try this out, and it’s okay.’ This doesn’t mean that C Suite managers need to know exactly how the change will occur or be a daily part of it; the tone they set will be the change maker or breaker. A Principle for Business In any decision that you make, it has to be about building a sustainable business model, which means it goes far beyond your own career. Joe admits it’s not easy, especially when you don’t know if you’re making the right decision for the future. He likens it to raising children. Another is that if you don’t speak, you lose an opportunity for teaching and learning. Joe shares how his office is set up to mirror that belief. Resources LinkedIn

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Have you ever felt boxed in based on your job description? Join us today as Katri Harra-Salonen, the Chief Digital Officer of Finnair Oyj, shares what she’s learned and unlearned throughout her career of mixing industries, mixing roles, and being comfortable with being uncomfortable. The Un-comfort Zone: By design, Katri actively puts herself in situations where she has to grow, and calls this being in the Un-comfort Zone. When you put yourself in a place that challenges you, you become energized, you’re able to be curious and explore, and you learn new things, not just about the situation, but about yourself as well. Katri has gone from the consultancy world into the airline world, which has meant a lot of discomfort, learning, and unlearning. But there is so much that the two worlds - consultancy and airline - can learn from the other, so she believes in building bridges between different kinds of companies and different kinds of thinking. That’s where creativity stems from. Inspiration: Working with other countries is strategic. But for Katri, there are intangible benefits as well. For example, they work with a lot of exciting Asian companies, which gives them insight into how mobile services are developing, what’s happening in the digital world, and how they can possibly incorporate this into a European country. For example, many cities in Asia are cashless societies, whereas Europe has been slow to adapt to digital money. But studying Asia, you can see how people behave and what it means, and insights like these can help embrace development. Best of both worlds: Katri is a third-generation engineer, and at one point in her career, she worked for a design company. How did she bring those two worlds together? Don’t put people in boxes. “Boxes are for dead people.” You need to be able to change perspectives in order to be creative, so don’t limit yourself to the box that’s been given to you. Just because you’re an engineer by profession, that’s not all you are and all you can do. Thinking you’re locked in does nothing to help you move forward. Katri believes in lifelong learning and unlearning. You want that exchange of disciplines and perspectives. Collaboration and building bridges: Katri shares about an experiment they conducted where the employees themselves designed their office space instead of hiring a design firm. It was done in five batches, and the teams were a mix of people from different departments. People collaborated, learned about how different teams work, and were learning and unlearning at the same time. Structures: Structure follows strategy. And when the strategy changes — as it does, because it needs to be agile — it’s so important that the structures are alive as well. Be aware of the structures you create, and think of them when you think of serving your talent best. For example: how can you build collaboration into the structure of your organization? Many departments are siloed from one another, but to innovate and move things forward, people need to be able to work together across disciplines. The future of technology: Technology is everywhere, and Katri is looking forward to it solving the big issues today. What do we need to do so we can create a setting where technology is working for the benefit of the world? Resources: Katri Harra-Salonen (LinkedIn)| https://twitter.com/KinStockholm

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How do you figure out what works? On this episode, we have Gibson Biddle, a speaker, advisor, and teacher who is the former Vice President of Product Management at Netflix. He’s been involved with many startup companies to help them develop products, and today we’re talking about consumer science, metrics, and experimenting our way through work and life. Data and consumer science: “I don’t care what they said, I don’t care what it looks like, I just want to see the data.” These were a former boss’s words to Gibson and a moment of great insight for him. Consumer science is about forming hypotheses quickly, putting them into A/B tests to see which ones move the metrics, and then create a system where you can test and discover what consumers love. And though he worked for people who said they didn’t care what a focus group said (“launch it, get it out there, and see if it moves the metrics or not”), speaking to people was still important for Gibson because it gave him great ideas. It kept the voice of the customer top of mind when he generated new hypotheses. Top line metrics and proxy metrics: Being able to measure whether you’re successful are critical. At Netflix, Gibson’s top line metric was to improve retention. But the key thing is to also develop proxy metrics to help you achieve your top line metric. One of their proxy metrics was the percentage of members who watched at least 15 minutes in a month. These proxy metrics work on a local level to impact your top line metric and define success. They also help build in a system of accountability — that ties in with freedom and responsibility — for people on the front lines. Context not control: Inventing the future is really hard, and to build and teams that can figure things out for themselves, the idea is context, not control. Success relies on testing and the willingness to experiment with ideas to discover what works. Strategy meetings would discuss hypotheses to hit proxy metrics, and while there is a certain discipline to all that, it wasn’t about telling people what to do. Things to think about: One of the most effective tactics Gibson has for learning new things is to teach. For years, he would teach a topic of the week on Friday mornings, and having to codify his thoughts and share them with others was an amazing way for him to learn. Another nugget: building a career is a lot like building a product. You have theories, hypotheses, and metrics, and you can test and learn and experiment your way to discover what works. Gibson also has a personal Board of Directors: a collection of peers, people he’s worked with, and mentors, who care about him and give him insight about the things he’s trying to explore — while being candid and giving him the hard truth when he needs it. “Treat me like I’m stupid” is one of Gibson’s catchprases. It’s simply daring to acknowledge that you’re at the beginning of your learning curve, and that there are no stupid questions. Resources Gibson Biddle (LinkedIn)

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Kent Beck is a third-generation geek. His grandfather was a radio geek, his father, an electrical engineer, moved to Silicon Valley in the 60s, and Kent and his father built their first personal computer together. He’s the creator of Extreme Programming, alphabetically the first signer of the Agile Manifesto and most recently helped Facebook scale their engineering organization from 700 to 5,000 people. Helping geeks feel safe in the world. This is one of Kent’s creeds, and as a third-generation geek, he’s looking to help the fourth generation. As a mentor, he encourages younger programmers not to worry so much about finding their purpose from the beginning; instead, they need to get out there and try things, investing in new experiences, then connect the dots later. And feeling scared has two sides: some situations feel scarier than they need to feel, and others should feel scary. Knowing the difference – and how to handle each – is key. Kent shares the story of how, on a consulting gig, he realized that one small tweak—rearranging furniture—was more important than sharing his virtuoso programming skills. The corner office executives were literally sitting in the wrong place. This lesson, Kent recalls, was the beginning of the course change that led to Extreme Programming. Extreme Programming. Kent started by considering a conventional belief: programmers couldn’t be trusted to test their own code. So he began experimenting with ways to challenge that belief with automated testing. But there was a deeper disruption Kent had in mind: programmers being responsible for their own mistakes and for fixing them in real time. He and Barry dive deeper into what that really means, and how it resulted in the Extreme Programming framework and more. The truth about courage and innovation Despite what people say to and about him, Kent doesn’t believe he’s courageous or innovative. Instead, he feels that he’s just doing what he senses needs to be done. Instead of over-analyzing and worrying if he’s got a perfectly formed idea, he starts trying it out. This is what Barry calls a ‘bias of action,’ and they dive into Kent’s way of behaving that makes him stand out. He has several habits to help him learn, and unlearn—fast; the first of those is to reverse and test any sentence that starts with ‘obviously.’ The second is to ask, “Can we try this?” Kent shares some practical applications of how he works and a few more habits and systems you can use in your own work.  Cycling through ideas. Cycling through ideas as quickly as possible is another strategy Kent uses to innovate, and he shares how he tends to make small changes quickly to see how effective they’ll be. And more importantly, how easy they will be to roll back if they don’t work. He explains his latest concept of, Test & Commit || Revert. And Barry and Kent talk about how this principle applies not just to programming but can be used to launch new products, improve systems of work and entire organizations. What’s next for Kent? The impossible: he’s setting out to discover how to scale software collaboration beyond what people believe is sensible. Specifically, how to have software application with 100,000 engineerings, each deploying over a 1,000 deployments times a day. Resources for Kent Beck: Website | LinkedIn | Twitter | Books on Amazon | Agile Manifesto | Test && Committ || Revert

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Melissa Perri is a champion for product management who’s built her business around helping others understand it. She now teaches product thinking for product management to all types of companies and excels at experimenting small and fast for big results. Unlearning Business Analysis and relearning Product Management. Starting out, Melissa had no idea what she wanted to do but she knew she wanted to work with people, code and design together. After passing on Wall Street and developer jobs, Melissa found her first gig as a business analyst at Capital IQ. After numerous roles trailing developing and business analyst, Melissa landed at Open Sky, which served as a pivotal moment in her professional life. She discovered the term that truly represented what she was doing—product management. Melissa’s manager at Open Sky pushed her into teaching her personal type of product management thinking. This led to successful talks and workshops, and eventually, consulting. However, the employees she worked with weren’t allowed to execute what she was teaching, so she taught her way up to the C Suite, innovating product management into product transformation. Recognizing and solving problems. One skill that sets Melissa apart is her natural ability to recognize, address, and fix problems within organizations. Her mantra is ‘what’s the bigger problem?’ and she follows it to the source. Melissa shares a story about working at a startup and how she had to unlearn everything that had made her successful before. It started with karaoke in Nashville and ended up with Scrum. Melissa’s next unlearning moment came after she and her product team found major success working together to figure out how to ship products sooner. They were more productive than ever before, but that came to a screeching halt when no one used a product she and her team developed. After a weekend conference for startups, Melissa was inspired and began to experiment more freely. She shares the story of how she overcame her fear of failure that enabled her to breakthrough. How Melissa experiments. One of the keys to Melissa’s experimentation strategies is to implement small changes that can be iterated quickly. It all comes down to this: How do I learn a little more about what works and what doesn’t? She reveals a huge mistake that many organizations make when they consider an experiment ‘one and done.’ Instead, she recommends starting with the vision and the outcome, taking the next small step that will lead you to your vision, and the importance of learning as you go. This strategy isn’t fiction, as Melissa shows how she used it to launch her own rapid scaling business of today. Innovating the product management industry. The product management field as a whole is still quite immature and Melissa believes there is much that can be learned. She speaks in terms of two types of companies: those who have scaled through people growth, and those that scale using software. For both types, the cycle of unlearning must begin in the C Suite. Melissa explains why product thinking is the critical component that ties everything together. And the question these companies need to ask is “How do we evolve our businesses to embrace product thinking for scaling product management?” Resources for Melissa Website | LinkedIn | Product Institute | Escaping The Build Trap: How Effective Product Management Creates Real Value

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Over 2,000 years ago, the Roman Empire rose to heights previously unseen, occupying more than 2 million square miles and ruling 20 percent of the world's population. Was that success due to visionary leaders? The prime location of the Tiber River? Engineering feats of roads and aqueducts? Maybe the laws of governance? The truth is, it was none of those. The Roman Empire's tactic of abandoning old practices in favor of new ones that worked better, often taken from those they conquered, is what gave them the flexibility to scale to such a massive level. My inspiration to create the Unlearn podcast came from what I frequently find to be a significant inhibitor when helping high-performance individuals get better—not the ability to learn new things but the inability to unlearn mindsets, behaviors, and methods that were once effective but now limit their success. In this podcast, we’ll dig deep into the practice of unlearning—what it is, why you should adopt it, and how you can leverage its tremendous power for yourself, your teams, and your organization. If you already feel you’ve unlearned before, great—I’ll teach you how to do it intentionally. If not, I’ll teach you to practice it deliberately. I’ll show you how to think big but start small, and why choosing courage over comfort can take you to places you never imagined possible.