Primarily Context Based: Recent Episodes
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Primarily Context Based is the Tech Leader's Guide to questions with more than one right answer, from the creators of CTO Craft and Skiller Whale. We talk about what needs to be considered when you're tackling tech decision topics like: "should we use Kubernetes?", or management topics like "how do I address diversity in my team?" or process topics like "are daily stand-ups a total waste of time?"
Zoe Cunningham is one of the first members of the Softwire team, joining as a developer and working her way up to Director level. She was Hywel's first manager (!) and has lots of opinions on tech hiring! Zoe also has a career as an actor, has published three books, recently won an award for her portfolio career.
In this episode, Hywel and Zoe discuss what 'best' and 'for the job' really mean in the tech landscape, how they're often interpreted alongside the benefits and pitfalls of different hiring practices.
Hywel is joined by Abi Noda - a programmer, researcher, and entrepreneur focused on helping leaders measure and improve developer productivity. Abi is currently the CEO and Co-Founder of DX, a platform that helps organisations improve the productivity of their developers.
In addition to DX, Abi runs the Engineering Enablement newsletter and podcast which cover the latest research and perspectives on developer productivity. Prior to DX, Abi held CTO roles at several companies and was the founder and CEO of Pull Panda, which was acquired by GitHub in 2019.
In this episode, Abi talks about the shortcomings of DORA and SPACE. Abi has worked very closely with two lead authors of those frameworks - Dr Nicole Forsegren and Dr Margaret Ann-Storey - and recently published a new research paper alongside those authors, which focuses on the developer experience. Access the paper here.
We’re delighted to have our very own Head of Engineering Marco Risi on this week’s episode of The Pod. Marco is the ex-CTO of Everli, the European marketplace for online grocery shopping that started in Italy. He built the engineering ladder at Everli and scaled the team from 1 - 70, after joining as the first full stack developer.
Career ladders allow leaders to communicate across a business what a role looks like, and what good looks like in that role. Marco and Hywel consider when you might need to implement an engineering career ladder, technical vs management paths, abilities and responsibilities and how to quantify technical and non-technical skills.
Jonathan Lister Parsons co-founded PensionBee with Romi Savova in 2014 and has since held the role of CTO. He champions a tech-forward culture within the business, aiming to raise the level of technology literacy among employees. Prior to co-founding PensionBee, Jonathan founded a digital consultancy, Penrose, and worked at British Telecom. Jonathan also holds an MSci in Experimental and Theoretical Physics from the University of Cambridge.
This week we’re releasing an episode that was recorded with Jonathan last year, just after Pension Bee IPO’d. Tune in to hear how you aim for and think about IPO, and how you can structure your organisation to be ready for it. Hywel and Jonathan cover early decision points, building up credibility and consumer trust, investing time in growing a strong board and technology due diligence.
Hywel is joined by leadership and executive coach, Lena Reinhard. Lena has dedicated her career to building successful, high-performing, globally distributed engineering organisations, and helping teams thrive in times of high change. She now offers transformational leadership coaching and consulting for leaders. Previously, Lena has served as VP Engineering with CircleCI and Travis CI, been a CEO and co-founded a startup, and through her cross-functional background and experience, she brings a unique perspective on systems of technology, business, and people.
In this episode Hywel and Lena take a deep dive into the distinctions between strategy and tactics and encourage leaders to define the peak they’re aiming for. We cover dopamine triggering activities and when to complete them, the mental capacity for + essentiality of strategic work and as ever, context.
Find Lena’s writing on leadership and more about her work at lenareinhard.com. And follow these links directly to see the articles discussed on today’s show:
https://www.lenareinhard.com/articles/what-is-strategic-leadership-and-why-does-it-matter
https://www.lenareinhard.com/articles/how-to-lead-strategically-every-day
This week our host Hywel Carver is joined by Mathias Meyer, an executive coach for CTOs and VP Engs and a founding partner at The Intentional Organization, he is also the co-author of a forthcoming book of the same title.
Mathias supports engineering executives and founders in their personal and professional growth as they scale their business and teams. While starting his career as an engineer, he founded Travis CI, which empowers people to build and ship great software. Mathias then found his calling in management, leadership, as a CEO and CTO, and now as a coach.
In this episode, Hywel and Mathias cover the issue of time management as a leader, how to make work in progress visible, and the pain of inefficient meetings.
Hywel is joined by Josh Goldberg who is the author of Learning TypeScript, and a full-time open-source maintainer of projects in the Typescript ecosystem.Throughout this discussion, which delves into a perpetual question faced by tech leaders, Hywel and Josh discuss the difference between a re-factor and a restructure, while considering the pains and gains of each.
What are your alternatives to restructuring and how do you avoid stopping the world? Find out now.If you're interested in finding out more about and supporting Josh's work, see the links below:
- learningtypescript.com: to learn more about Learning TypeScript
- typescript-eslint.io: homepage for typescript-eslint, the tooling that enables running ESLint and Prettier on TypeScript code and provides many static analysis rules to improve TypeScript codebases.
- joshuakgoldberg.com: Josh's personal homepage, with links to his blog, social media sites, and conference talk resources.
- github.com/sponsors/JoshuaKGoldberg: how to sponsor Josh to work on open source projects improving the TypeScript experience for everyone.
This week Hywel is joined by the brilliant Nick Rogers, VP of Engineering at Wagestream, for a fast-paced debate-style episode! Hywel plays devils advocate and challenges Nick on his ideas about what’s wrong with the software engineering industry, in order for the two leaders to really tease out the answers to common and pertinent industry questions. Nick and Hywel talk software engineering as a team sport, the rarity of startups turning a profit, having a healthy skepticism towards hype and a lot more.
Our guest this week is Sally Lait, a highly experienced tech leader who is currently working as the VP of Engineering at Farewill. Sally has previously led engineering teams and served as the web disciple lead at Monzo, been the Head of Technology at a global digital agency and has founded her own digital transformation consultancy.
In this episode, Hywel and Sally take a Skiller Whale-approved ‘deep dive’ into one of the most critical questions facing tech leaders today.
Tune in to find out what you can do to integrate your team, hear about the risk management considerations you might need to consider and listen to some great stories from Sally on her work with the F1 Manor Racing team.
This is a special episode recorded in the month of ‘Movember’, as we are keen to contribute to the movement raising awareness of mental health. If you or someone you know is struggling, it's really important to get the right help. You can find a link to some organisations that offer support in our LinkedIn post here.
In this show, Hywel is joined by Omar Reid, CTO at mental health start-up Alena, to discuss how to support your team, and still hit deadlines. Hywel and Omar discuss the mental health issues that can often arise in tech teams, and what tools you can implement as a leader to help”.
This week Hywel is joined by Lewis Moore, who previously helped carve a new category in hospitality operational software as CTO of Trailapp, and is now part of the early engineering team at Evidenced, an interview intelligence platform.
In this discussion, Lewis shares his experience in pivoting from an extremely sales-led growth approach, to a much more product-led one at Trailapp.
This episode features VP of Engineering and Product at Healx, Ryan Tomlinson. Ryan has previously led engineerings teams at OpenTable, Salesforce and GSK and this week, he joins our host Hywel to discuss what makes a good leader, and leans on his vast experience to address how you can drive change in a high performing organisation.
Ryan and Hywel bond over being context-based advocates, talk the ‘30,000 foot view’ and slowing down to speed up.
‘Digital transformation’ on your mind? Hear Ryan’s insights on how people often play fast and loose with key terms in the tech industry, and what they really mean in practice.
Erynn Peterson- ex-CTO of Drizly and current CTO of Simple Health joins Hywel in a discussion on the benefits and drawbacks of being agile and having a roadmap, and when each might be the better method to use.
If you want to hear a fresh take on a topic every tech leader has considered, this one’s for you.
This week we’re delighted to have Omnipresent’s Director of Engineering, Matt Belanger joining us. Matt has scaled the engineering team from 2 to almost 90 over the last year or so and is an expert on fast growth.
In a recent blog post, Hywel presented the discovery that it takes on average, 62 days to hire for senior roles in tech. Tune in to find out if you can beat that and have an effective tech team up and running at pace.
Part 2 of last episode’s discussion sees Hywel Carver and Meri Williams focus on feedback and its relationship to empowerment. Tune in for useful tips on how- to, (and how- not- to) give and receive it.
If this is a topic you’re interested in, here’s a link to a Meri-approved resource we think all leaders - tech or other, will find useful: Thanks for the Feedback - By Douglas Stone and Sheila Heen.
In the first of a brilliant two-part discussion, Hywel is joined by Meri Williams. Meri is an experienced CTO and leader of technology organisations. She has led teams ranging in size from 30 to 300, in a range of organisations from Procter and Gamble, to the Government Digital Service, to Monzo and AI-driven rare disease treatment discovery company Healx, amongst others. A published author and international speaker, she is the chair of The Lead Developer conference. In her spare time she enjoys building complex Lego, board & video gaming, snorkelling and underwater photography.
In this episode, Meri and Hywel address the growing need for a culture of empowerment in work spaces. How do you create one? How does that help you with scaling, as a business and as a leader? Why is it important?
Simon Andrews is the Head of Engineering at Hubble, London's largest online marketplace for renting flexible office space, and the world's first hybrid workplace platform.
Simon has been coding since he was 10 and is now a people-focused leader, striving to build an engineering environment where everyone can thrive.
In this episode, Hywel and Simon reflect on how Hubble navigated a period of economic pressure and uncertainty, and emerged from it successfully.
In this episode, Hywel and Chris discuss the challenges of growing quickly. Is it people or processes that you should scale first? How should you structure your teams to maximize scaling? What happens if you have enough people but not the right processes in place and how important is consistency?
Chris is a self-described "passionate technology leader" with over a decade's experience leading teams at some of London's most well-known scale-ups. He's currently the Director of Software Engineering at Gousto and helping shape the rapid growth of the Tech team there as the company consistently outperforms its expectations and sets the ambition ever higher.
Hywel Carver is the Co-Founder and CEO of Skiller Whale, a SaaS company enabling development for developers. Hywel was a CTO for a variety of VC-backed companies for over 10 years, ran Tech Leader Dinners, and coached other CTOs. He’s a published curriculum author and avid blogger.
Dave, Hywel, and Hayley created Skiller Whale out of the frustration that learning for developers is broken; Learn more about the company and sign-up for a free trial here.
In this episode, Laura and Hywel discuss diversity in tech teams, as well as some of the common mistakes companies make when trying to improve diversity in an existing team.
They delve into questions such as: What’s the difference between diversity and inclusion? Why is a neutral interview process sometimes anti inclusive? Do you prioritise candidates who are a culture ‘add’, as opposed to a culture ‘fit’? And, what are the implications of having a founding team that lacks diversity?
Laura Tacho is a product development leader with a successful track record leading cross-functional product development teams — engineering, product management, design, and data — through different stages of growth and transition. She's a former VP of Engineering for an edtech startup, and previously worked as a Senior Director of Engineering at CloudBees after joining the company through the acquisition of Codeship, a CI/CD tool. She became involved in the cloud native container ecosystem during the very early days of Docker, when she worked on some of the first open-source developer tools for Docker. Since then, she's been awarded the title of Docker Captain, has spoken at dozens of development conferences across the globe, and enjoys jumping in to help teams and companies solve big engineering problems.
Hywel Carver is the Co-Founder and CEO of Skiller Whale, a SaaS company enabling development for developers. Hywel was a CTO for a variety of VC-backed companies for over 10 years, ran Tech Leader Dinners, and coached other CTOs. He’s a published curriculum author and avid blogger.
Dave, Hywel, and Hayley created Skiller Whale out of the frustration that learning for developers is broken; Learn more about the company and sign-up for a free trial here.
In this episode, Hywel and Ted discuss ethical hacking - what it is, when it is appropriate, and how widely the concept is misunderstood. What really is a hacker in the context of security and why are there so many misconceptions around securing software? Listen to this episode of Primarily Context-Based for answers to these questions and many more.
Ted Harrington is the #1 best-selling author of HACKABLE: How to Do Application Security Right, and the Executive Partner at Independent Security Evaluators (ISE), the company of ethical hackers famous for hacking cars, medical devices, web applications, and password managers. He’s helped hundreds of companies fix tens of thousands of security vulnerabilities, including Google, Amazon, and Netflix. Ted has been featured in more than 100 media outlets, including The Wall Street Journal, Financial Times, and Forbes. His team founded and organizes IoT Village, an event whose hacking contest is a three-time DEF CON Black Badge winner. He also hosts the Tech Done Different podcast.
Hywel Carver is the Co-Founder and CEO of Skiller Whale, a SaaS company enabling development for developers. Hywel was a CTO for a variety of VC-backed companies for over 10 years, ran Tech Leader Dinners, and coached other CTOs. He’s a published curriculum author and avid blogger.
Dave, Hywel, and Hayley created Skiller Whale out of the frustration that learning for developers is broken; Learn more about the company and sign-up for a free trial here.
In this Episode, Hywel and Rob evaluate the pros and cons of using the Spotify model in your organization, when it is appropriate, and how. Should you have a front-end team, a back-end team, and a mobile team? Or should you really just have squads, guilds, tribes, and chapters? Listen to this episode to find out what you should be aiming for when introducing the model, and why that’s crucial to your success.
Rob Elkin is the Co-Founder and CTO at Churnly, a customer behavior software. Having been in technology for over 15 years, Rob started out as a developer for front-end and back-end tech, DevOps before it was DevOps, and then moved into leadership roles. He ran tech at Just Eats before moving on as CTO at Busuu. Today, he’s a consulting CTO, advisor, and entrepreneur. Read more about his work here.
Hywel Carver is the Co-Founder and CEO of Skiller Whale, a SaaS company enabling development for developers. Hywel was a CTO for a variety of VC-backed companies for over 10 years, ran Tech Leader Dinners, and coached other CTOs. He’s a published curriculum author and avid blogger.
Dave, Hywel, and Hayley created Skiller Whale out of the frustration that learning for developers is broken; Learn more about the company and sign-up for a free trial here.
Is ‘legacy’ always a bad thing? In this episode, Hywel and Rich discuss whether re-platforming is really worth it, and how you know if, and when it is. They discuss the cost of re-platforming and how to prepare for its impact.
Rich Kershaw is an experienced, multi-disciplined creative technologist with 20 years of experience, 17 of which are as a CTO. Over the years, Rich has covered an enormous range of different projects; from payments and UX to mobile app and website development, IoT and transit. Today, he combines due diligence consultancy for investors with working as a consulting CTO for companies in need of a long-term processing strategy. Specializing in technology strategy and mentoring, Rich works with startups, scale-ups, and mid-market companies on scaling tech, UX & product road mapping, and streamlining development processes to build sustainable growth and funding. Read more about him here.
Hywel Carver is the Co-Founder and CEO of Skiller Whale, a SaaS company enabling development for developers. Hywel was a CTO for a variety of VC-backed companies for over 10 years, ran Tech Leader Dinners, and coached other CTOs. He’s a published curriculum author and avid blogger.
Dave, Hywel, and Hayley created Skiller Whale out of the frustration that learning for developers is broken; Learn more about the company and sign-up for a free trial here.
In this episode of Primarily Context-Based, Hywel is joined by Emanuele Blanco to discuss the role of coding in leadership technology positions. Is it true that “if you’re coding, you’re not truly a CTO”? They discuss different versions of the CTO position, and how the choice to code or not to code impacts strategy and leadership, as well as the ownership, trust, and accountability of the development team.
Emanuele Blanco is a technology leader with over 10 years of experience helping businesses in sectors such as government, finance, and e-commerce to deliver value to their customers via modern technology practices. Originally from Italy, Emanuele started his career as a software engineer in the UK before moving into consulting. He worked with companies such as Klarna, HMRC, and Sky before rising up the ranks at Moneyfarm, a pan-European digital wealth manager, where he is now the CTO. Learn more about his approach to leadership on this Digital Innovation Chat podcast episode and in the following articles:
CTO Craft Con - ‘From Zero to CTO’ FinTech Magazine - (interview)
Hywel Carver is the Co-Founder and CEO of Skiller Whale, a SaaS company enabling development for developers. Hywel was a CTO for a variety of VC-backed companies for over 10 years, ran Tech Leader Dinners, and coached other CTOs. He’s a published curriculum author and avid blogger.
Dave, Hywel, and Hayley created Skiller Whale out of the frustration that learning for developers is broken; Learn more about the company and sign-up for a free trial here.
In this episode, Hywel and Dave discuss everything data - why pure data is not always as it seems, why modeling data will not always make your predictions more accurate, and why data is contextual. They discuss examples from Sony, Ferrari, and Netflix and share anecdotes of how they learned that quantitative data is not relevant without qualitative data.
Together with Hywel, Dave Millican is the Co-Founder and CTO at Skiller Whale. He has managed data science teams and projects since 2012, including developing data-driven race simulation tools for the Ferrari F1 team and as the Lead Data Scientist for BridgeU.
Hywel Carver is the Co-Founder and CEO of Skiller Whale, a SaaS company enabling development for developers. Hywel was a CTO for a variety of VC-backed companies for over 10 years, ran Tech Leader Dinners, and coached other CTOs. He’s a published curriculum author and avid blogger.
Dave, Hywel, and Hayley created Skiller Whale out of the frustration that learning for developers is broken; Learn more about the company and sign-up for a free trial here.
In this episode, Hywel and Squirrel talk about the right way to do Agile. Having recently published a book called 'Agile Conversations', Squirrel offers interesting viewpoints on what has or has not worked for tech teams in the past. To read more about his book, go to https://www.douglassquirrel.com/index.html or listen to Squirrel's own podcast, Troubleshooting Agile, at https://podcasts.apple.com/us/podcast/troubleshooting-agile/id1327456890
Hywel Carver is the Co-Founder and CEO of Skiller Whale, a SaaS company enabling development for developers. Hywel was a CTO for a variety of VC-backed companies for over 10 years, ran Tech Leader Dinners, and coached other CTOs. He’s a published curriculum author and avid blogger.
Dave, Hywel, and Hayley created Skiller Whale out of the frustration that learning for developers is broken; Learn more about the company and sign-up for a free trial here.
In this episode, Hywel and Jon discuss which contexts are best for adopting Kubernetes (and which aren’t). They discuss the benefits and disadvantages, share experiences and evaluate the challenges of using Kubernetes.
Prior to launching The Scale Factory in 2009, Jon Topper worked as a developer and lead systems administrator at mobile messaging startup Trutap. There he built an infrastructure around practices that would later be referred to as “DevOps”. Having cut his teeth on physical hardware and networks in the data centers – he started his career at Designer Servers (DSVR), one of the first UK companies to offer virtual server hosting – Jon finds the ease and speed of cloud services a joy.
Jon was awarded DevOps Leader of the Year at the 2017 DevOps Excellence Awards. He’s currently recognized as an AWS Partner Network Ambassador.
Hywel Carver is the Co-Founder and CEO of Skiller Whale, a SaaS company enabling development for developers. Hywel was a CTO for a variety of VC-backed companies for over 10 years, ran Tech Leader Dinners, and coached other CTOs. He’s a published curriculum author and avid blogger.
Dave, Hywel, and Hayley created Skiller Whale out of the frustration that learning for developers is broken; Learn more about the company and sign-up for a free trial here.
In this episode, Hywel and Andy discuss the pros and cons of different approaches to measuring tech team efficiency. They share horror stories about poor incentive strategies, as well as approaches that have worked for them.
Andy Skipper has led startup engineering teams as a CTO since 2006, including Made.com, and was the first CTO at Comic Relief, one of the largest charities in the UK.
He now runs CTO Craft, a mentoring community and coaching practice focussed on CTOs and technology leaders, numbering 1100 and spanning the globe, where he helps technologists get to grips with senior leadership and management, culture, and operations alongside a number of other experienced CTO mentors and strategists.
He also curates the Tech Manager Weekly newsletter for technology leaders.
Hywel Carver is the Co-Founder and CEO of Skiller Whale, a SaaS company enabling development for developers. Hywel was a CTO for a variety of VC-backed companies for over 10 years, ran Tech Leader Dinners, and coached other CTOs. He’s a published curriculum author and avid blogger.
Dave, Hywel, and Hayley created Skiller Whale out of the frustration that learning for developers is broken; Learn more about the company and sign-up for a free trial here.