Discussing Stupid: Talking Digital Customer Experience

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In the Season 3 premiere of Discussing Stupid, Cole and Virgil kick off the new series Intentional AI: a season-long dive into how AI fits (and sometimes doesn’t even fit) into the stages of the content lifecycle.

Organizations are rushing to hand entire workflows over to AI… but without a clear plan, the results are messy at best and risky at worst. Instead of asking “what can AI do?”, this episode flips the question to “where does AI actually help?” by breaking down the real process first.

This first episode sets the foundation for the whole series. In the weeks ahead, each stage of the content lifecycle gets its own dedicated episode with real examples of where AI shines, where it fails, and how to use it responsibly. By following the series, you’ll walk away with a complete picture of how to maximize AI in your digital workflows without falling into the common traps.

In this episode, they explore:

Why you should map your workflow without AI before adding automation
The 5 stages of the content lifecycle where AI could be useful (research & analysis, content creation, content management & accessibility, SEO/GEO/AEO, & content personalization)
How to spot which stages AI supports well and which it doesn’t
Why teaching AI and understanding your process are inseparable
The dangers of unchecked automation, from bad content to legal risk

Upcoming episodes in the Intentional AI series:

Oct 14, 2025 — Research & Analysis
Oct 28, 2025 — Content Creation
Nov 11, 2025 — Content Management & Accessibility
Dec 2, 2025 — SEO / AEO / GEO
Dec 16, 2025 — Content Personalization
Jan 6, 2026 — Front End Development & Wireframing
Jan 20, 2026— Design & Media
Feb 3, 2026 — Back End Development
Feb 17, 2026 — Conversational Search (with special guest!)
Mar 3, 2026 — Chatbots & Agentic AI
Mar 17, 2026 — Series Finale & Tool Review

Whether you’re a marketer, strategist, or developer, this conversation is about making AI adoption practical, intentional, and less stupid.

Season 3 of Discussing Stupid is here! New episodes every other Tuesday starting now.

For more conversations about AI, digital strategy, and all the ways we get it wrong (and how to get it right), visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro

(1:17) - Organizations are rushing into AI without strategy

(3:25) - Effective AI requires training & process clarity

(4:37) - Series focus: Maximizing AI in your content process

(5:50) - Stage 1: Research & Analysis

(8:27) - Stage 2: Content Creation

(11:05) - Stage 3: Content Management & Accessibility

(13:10) - Stage 4: SEO, AEO, GEO

(16:10) - Stage 5: Content Personalization

(17:20) - Closing takeaways

(17:58) - Outro

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“Stupid is as stupid does.” Forrest Gump said it best... and you don't have to look far in the digital world to see just how much stupid is out there.

Whether you're lost in the layers of a bloated website, juggling 5 different collaboration tools just to get ONE project done, or searching for a document you know exists but still can't find... we've all been there.

That’s why we started Discussing Stupid. This podcast is our way of calling out the bad digital practices we see every day - and giving you practical advice to fix them.

We are BACK for Season 3, building on the foundation we set last season. In Season 2, we tackled search, UX, accessibility, websites, and collaboration systems. This time around, we’re taking those same topics further - unpacking the details, workflows, and decisions that can make or break your digital experiences.

We’re kicking things off with a series called Intentional AI, and it is all about using artificial intelligence (AI) more purposefully in your workflow. Too many orgs are throwing it into their workflows without a plan - wasting money, tanking productivity, and getting frustrated when the tech doesn’t deliver.

To flip that script, we’re using the content lifecycle as our case study. It’s a process every digital team touches, from research and analysis, to content creation, to management, SEO, accessibility, and personalization - and it’s a perfect way to show how AI can actually work for you instead of against you.

In Episode 1, we’ll zoom out with a quick look at how AI could play a role in each stage, then go deep into the first part of the cycle: research and analysis. We’ll break down the good, the bad, and the ugly of AI in that stage, and how to avoid the traps we see so many orgs falling into.

If you work in digital experiences, this podcast will put you ahead of the curve - whether that's making smarter use of AI, cleaning up your search strategy, or building digital spaces that actually make sense for people.

Season 3 drops September 30th. Subscribe, share this with your team, and let’s make the digital world a little less stupid, one episode at a time.

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In the Season 2 finale of Discussing Stupid, Virgil and Cole are joined by Ali Gillberg, a senior developer at High Monkey, to talk about one of the most broken (and misunderstood) parts of UX: form accessibility.

Using a real-world PowerApps project for the Minnesota Office of Accessibility, the team breaks down the invisible complexity of building forms that actually work for all users, including those using screen readers or assistive tech. Spoiler: most “accessible” forms aren’t.

In this episode, they dig into:

The most common accessibility fails in forms (labeling, tab order, cryptic errors)
Why Microsoft tools like PowerApps and SharePoint often work against accessibility
How poor form validation breaks user experience and trust
What it really takes to make dynamic forms work properly
The tedious but necessary work behind making forms usable for everyone

Whether you’re designing a public-facing form or managing internal workflows, this episode will change how you think about accessibility, and show why most tools still fall short.

This wraps up Season 2 of Discussing Stupid. We’ll be back in September with new episodes, fresh rants, and more stupid digital decisions to unpack. Thanks for listening!

For more conversations about digital strategy, UX, accessibility, and all the ways we get it wrong (and how to get it right), visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro

(3:13) - The form looks fine… but is it usable?

(4:57) - The false promise of built in accessibility

(6:08) - Inside a real accessible PowerApps build

(10:15) - What screen readers see (that you don't)

(12:12) - The workarounds nobody talks about

(16:33) - Why this problem isn't just Microsoft's fault

(17:38) - Outro

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In this episode of Discussing Stupid, Virgil and Cole tackle a quiet killer of user experience: layout inconsistency.

From university websites that feel like ten different brands stitched together to internal systems that change button locations with every page, inconsistent layouts confuse users, break trust, and derail digital goals. This episode dives into why it happens, what it costs, and how to start fixing it.

They also explore:

Why inconsistent layouts are often a sign of deeper organizational problems
How users feel bad design before they can explain it
The difference between visual theming and layout consistency
What a consistent structure looks like across homepage, sections, and detail pages
Why a style guide is your most underrated asset

Whether you’re building a public-facing site or an internal portal, this episode will help you recognize the hidden ways layout chaos is holding you back—and how to clean it up.

(0:00) - Intro

(2:22) - Where layour inconsistency happens the most

(4:57) - The difference between theming and consistency

(7:24) - Structuring consistency in layers

(10:57) - Why inconsistency hurts your organization

(13:12) - Layout chaos as a symptom of deeper issues

(15:22) - How to start fixing this issue

(16:51) - Outro

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In this episode of Discussing Stupid, Virgil sits down with High Monkey’s Senior Developer, Chad Heinle, to break down one of the most debated choices in modern digital strategy: headless vs traditional CMS.

While flashy features and buzzwords like “omnichannel” dominate vendor pitches, the real decision comes down to your organization’s resources, structure, and long-term goals. Chad and Virgil dive into the practical realities of each approach, helping you cut through the hype and avoid the biggest mistakes teams make when choosing a CMS.

They also explore:

Why your internal team structure matters more than the CMS features
The rise (and reality) of content hubs and static site generators
What “freedom” really means in a headless setup
How traditional and headless CMSs are merging in unexpected ways
Why reuse and omnichannel content sound good—but rarely happen

Whether you’re in IT, marketing, or somewhere in between, this episode will help you make smarter, more grounded tech decisions.

(0:00) - Intro

(2:10) - It's not about the CMS, it's about your team

(4:44) - Headless gives you freedom - if you're ready for it

(6:36) - Traditional & headless are starting to look alike

(9:56) - Don't choose a CMS based on buzzwords

(12:00) - There's no perfect CMS - just the right one for you

(15:00) - Outro

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In this episode of Discussing Stupid, Virgil and Cole are joined by a new guest—High Monkey’s Project Manager and QA specialist, Seth Moline. Together, they dig into the often-overlooked world of quality assurance (QA) and why it can make or break a digital project.

From accessibility issues to ripple effects caused by last-minute code changes, Seth walks us through what great QA really looks like—and why it’s not just a checklist you run through before launch. The team discusses how QA needs to be methodical, repeatable, and fully integrated into your build process—not an afterthought.

They also explore:

Why QA isn’t just testing—it’s marketing
How staging environments save you from public embarrassment
The value of fresh eyes and non-developer perspectives
Common QA mistakes and how to avoid them
Why accessibility should never be separated from quality

Whether you’re a developer, content manager, strategist, or digital lead, this episode will change the way you think about testing and quality.

(0:00) - Intro

(3:04) - Seth's QA role at high monkey

(4:45) - Quality testing is best done by a fresh set of eyes

(6:47) - QA is about systems, not spot checks

(11:06) - Why you need a staging environment

(14:18) - How to stay methodical with your testing

(16:36) - Baking accessibility into your QA process

(18:06) - A quality site = top tier marketing

(19:52) - Outro

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In Episode 14, host Virgil Carroll and co-host Cole dig into a core truth behind most UX mistakes: people don’t pay attention. From sending a message to the wrong person to confusing web forms, today’s digital missteps often stem from one thing—poorly designed experiences that expect users to be careful, focused, or even logical.

But here’s the hard truth: they’re not.

That’s why UX exists—to design for inattention, not perfection. In this episode, Virgil and Cole explore how small misjudgments in interface design can lead to big problems, and why it’s time to stop blaming the user and start designing smarter.

They dig into key lessons and takeaways, including:

Why assuming users will “just pay attention” is a guaranteed way to fail
The danger of designing tools for internal teams instead of real users
How AI and other tools can mislead teams if used without critical thinking
Why user feedback beats assumptions—every single time
What it really means to design for the lowest common denominator

From confusing buttons and abandoned carts to real-world usability failures, Virgil shares insights from decades of experience that highlight how easy it is to get digital experiences wrong when we ignore how people actually behave.

If you’ve ever wondered why people keep screwing up your carefully planned interface—or if you’re trying to build something that works for all humans, not just ideal ones—this episode’s for you.

(0:00) - Intro

(2:10) - People don't pay attention

(4:41) - Are people bad at browsing or is tech too complex?

(6:49) - Will AI shape the future of UX?

(10:50) - The gap between internal assumptions and real user needs

(14:27) - Build for the lowest common denominator

(17:40) - Outro

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In Episode 13.1, host Virgil Carroll is joined by co-host Cole and developer Chad to talk about something deceptively complicated: color. Specifically, the intersection of color palettes, visual design, and accessibility—and why getting it wrong can tank your user experience.

While color choices often get made in design tools or branding meetings, they don’t always translate well to real-world implementation. The crew breaks down why the prettiest colors can create the ugliest accessibility problems once they hit the web.

They dig into key challenges and lessons, including:

Why accessible design isn’t just about having the right colors—it's about using them correctly
How contrast ratios break down across devices and screen sizes
Why bright and “fun” color palettes often fail accessibility testing
How to bring visual flair to a site without sacrificing inclusivity
The difference between decorative vs. purposeful color use—and why it matters

From failed color combinations to misused font sizing, Virgil, Cole, and Chad share their own battle scars from High Monkey’s recent site redesign—and explain how inclusive design forces teams to think functionally, not just aesthetically.

If you’ve ever struggled to make your brand colors work on the web—or if you're tired of your site failing contrast tests but you still want some color pop—this episode’s for you.

(0:00) - Intro

(2:43) - Accessibility and your brand's color palette

(6:03) - Factoring in font sizes

(7:54) - I still want color pop on my website!!

(11:36) - The approach we took with our new site's color scheme

(15:13) - Outro

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In Episode 12, host Virgil Carroll is joined by co-host Cole from High Monkey to dig into a deceptively tricky topic: metadata—what it is, how it works, and why getting it right is more about balance than perfection.

Metadata plays a huge role in findability, search accuracy, and content structure. But when it comes to tagging your content, more isn’t always better—and less definitely isn’t enough. That’s where the concept of the “metadata Goldilocks zone” comes in.

They unpack the most common metadata mistakes and what to do instead, including:

Why under-tagging leaves your site relying on search engine guesswork
How over-tagging renders metadata meaningless
What makes a tag actually useful (and when it’s just noise)
How to approach metadata as an evolving strategy—not a one-time fix

Virgil shares hard-won lessons from consulting across industries, explaining why metadata success depends on both the structure and the context of your content. From internal file systems to public websites, they explore how to build better tagging frameworks without falling into analysis paralysis.

To wrap things up, they offer a practical rule of thumb for anyone managing metadata: optimize for the 80% of user needs first—and let real usage data guide the rest.

For more conversations about digital strategy, search, UX, and all the ways we get it wrong (and how to get it right), visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro

(2:27) - What even is metadata?

(4:10) - Metadata is not one-size-fits-all

(7:20) - The dangers of under tagging

(10:00) - The dangers of over tagging

(12:43) - Finding the “Goldilocks” zone with metadata

(15:30) - Virgil’s verdict: Follow the 80/20 rule

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Discussing Stupid has a new look! This episode marks the beginning of our refreshed brand—featuring a brand new website, sleek color scheme, updated album cover, and a restructured intro sequence. While our look has evolved, our mission remains the same: breaking down the biggest digital mistakes so you don’t have to make them.

In Episode 11, host Virgil Carroll is joined by co-host Cole from High Monkey, along with developer Chad, to tackle a common but frustrating issue—why web designs that look perfect in Figma often fall apart when built for real-world use.

They explore the biggest challenges of translating static designs into fully responsive websites, including:

The problem with designing for just one screen size
Why text, images, and layouts often break in development
What developers wish designers knew about responsive design
Lessons learned from their own website redesign mistakes

Chad shares a developer’s perspective on why rigid, pixel-perfect designs don’t always work and how to approach layouts with flexibility in mind. Through real-world experiences—including High Monkey’s own site rebuild—the team discusses the need for good communication between design and development and how to avoid the most common headaches.

To close things out, they share practical tips on designing for multiple screen sizes, working more effectively with developers, and ensuring that your website doesn’t just look great—it actually functions for all the devices browsing your website.

New intro, new look, new website, same crew ready to help you avoid dumb digital mistakes! Join us every two weeks for fresh episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

(0:00) - Intro

(2:06) Design is checkers… development is chess

(4:53) Common responsive design fails

(7:18) Unfortunately we are speaking from experience.

(11:09) How many breakpoints do you design for???

(15:40) Designers & developers need to talk

(18:07) - Outro

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In Episode 10 of Discussing Stupid, host Virgil Carroll is joined by co-host Cole from High Monkey to reflect on reaching episode 10 and the ongoing journey of digital marketing beyond just launching a project. As they celebrate this milestone, they dive into why the launch is only the beginning of a much longer journey in the digital world.

Virgil and Cole discuss the continuous effort required to maintain and grow digital projects like blogs, podcasts, websites, and more. They share personal experiences and lessons learned about adapting strategies based on analytics and listener feedback. The conversation highlights how even successful launches need follow-up actions to keep the momentum going and ensure long-term engagement.

As the episode progresses, they explore the importance of constantly evolving digital marketing tactics to meet changing audience needs. Insights are shared on how they are in the process of tweaking their podcast's format and content to prevent listener drop-off, especially during the intro.

To wrap up, practical tips are offered on how to effectively use analytics to drive content improvements and audience retention strategies. Listeners will gain a better understanding of the necessity for resilience in digital marketing and how to make incremental changes that significantly impact their projects' success.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

(0:00) - Intro

(0:47) - Let's hear it for Episode 10!!!

(1:56) - The work starts POST launch

(3:30) - Change is in the air for Discussing Stupid

(5:18) - Our takeaways after 10 episodes

(7:10) - Establish value RIGHT AWAY

(8:45) - Analytics. Analytics. Analytics.

(10:55) - A message for those who made it this far

(11:36) - Digital marketing is not just social media

(13:45) - Time to eat our own dog food

(14:40) - Cole is moving into a penthouse

(15:20) - Be intentional with your analytics & engagement

(17:00) - Discussing Stupid is now a live case study

(18:30) - Outro

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In Episode 9 of Discussing Stupid, host Virgil Carroll is joined by co-host Cole from High Monkey to break down a frustrating reality of modern work: the overwhelming number of collaboration tools that don’t actually improve teamwork. With so many platforms—Slack, Teams, ClickUp, Figma, email, and more—why does collaboration feel more chaotic than ever?

Virgil and Cole explore how the abundance of tools often leads to scattered conversations, lost information, and inefficiency, rather than better collaboration. They discuss real-world examples of how context gets lost in endless message threads, how teams juggle disconnected platforms, and why no single tool seems to solve the problem.

As the conversation unfolds, they dig into why the issue isn’t just the tools, but also the processes behind them. They explore what effective workplace collaboration really looks like, sharing insights on how teams can reduce tool overload, set clear communication guidelines, and establish a single source of truth to prevent chaos.

To close, they offer practical takeaways on improving collaboration—whether through better workflows, tool integration, or just picking a platform and sticking to it. Listeners will walk away with a clearer understanding of why collaboration is broken and what steps can actually make it better.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com

(0:00) - Intro

(1:24) - Modern collaboration: Many tools, little clarity

(4:00) - Why the "perfect collaboration tool" is a false promise

(7:30) - The path to streamlining collaboration

(12:00) - It's about strategy, not just software

(15:00) - Outro

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In Episode 8 of Discussing Stupid, host Virgil Carroll is joined by co-hosts Chad and Cole from High Monkey to tackle a common yet overlooked frustration: poor mobile button design. The trio dissects why mobile usability remains such a challenge and explores how bad design impacts user experience on mobile devices.

Virgil, Chad, and Cole highlight the pitfalls of prioritizing aesthetics over functionality, sharing real-life examples of frustrating mobile experiences—like accidentally disliking articles in Apple News due to poorly placed buttons. They dive into the broader challenges of mobile-first design, discussing how designers often fail to account for varying finger sizes, touch accuracy, and real-world usage patterns.

As the discussion unfolds, the team offers actionable insights for improving mobile usability. From creating larger, well-spaced buttons to understanding mobile interaction patterns, they outline best practices to ensure users can navigate and interact with apps and websites effortlessly.

To close, the team reflects on the importance of practical testing and design iteration to deliver seamless mobile experiences. Listeners will leave with practical tips and a deeper appreciation for the role of thoughtful design in modern digital experiences.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

(0:00) - Intro

(1:57) - Calling out poor mobile button design

(3:46) - Some real life frustrations

(6:07) - Challenges of mobile first design

(9:11) - Optimizing mobile separately from desktop

(12:17) - Think about how people operate

(14:35) - Practical tips for better mobile buttons

(17:00) - Outro

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In Episode 7 of Discussing Stupid, host Virgil Carroll and co-host Cole Schlotthauer from High Monkey tackle the buzz surrounding artificial intelligence (AI) and its implications for technology, marketing, and content management. This episode explores the reality behind AI’s hype, focusing on the importance of high-quality content and structure to make AI truly effective.

Virgil and Cole delve into the nuances of AI’s capabilities, examining the gap between its marketing promises and practical limitations. They discuss tools like schema.org and highlight the challenges organizations face in defining content effectively for AI and search engines. Drawing from years of experience, Virgil emphasizes that AI is only as good as the content it analyzes, echoing the need for robust content governance and thoughtful strategy.

To wrap up, the duo discusses the potential applications of AI in areas like coding and keyword generation while cautioning against viewing it as a quick fix for deeper organizational issues. Listeners will leave with a clear understanding of how to prepare their content and strategies for success in an AI-driven world.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

(0:00) - Intro

(1:38) - Safe to say AI is the buzz right now

(3:10) - Practical capabilities VS marketing hype

(3:55) - Schema.org and AI

(5:50) - AI is not a silver bullet

(9:40) - Staying ahead in the transition to AI search

(11:21) - AI will only be as good as your content

(12:40) - End

Link to the CMSWire Article mentioned: https://www.cmswire.com/digital-experience/the-growing-importance-of-schemaorg-in-the-ai-era/?utm_campaign=cm&utm_content=all-articles-rss&utm_medium=web&utm_source=cmswire.com

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In Episode 6 of Discussing Stupid, host Virgil Carroll and co-host Cole from High Monkey reflect on the evolution of web design and discuss how websites have grown increasingly complex over the years. This episode delves into the challenges of balancing form and function in web design, examining how trends have influenced modern websites—often at the expense of user experience.

Virgil and Cole explore the history of web design, from the simplicity of early 2000s websites to the rise of stylistic trends like Flash, hero images, and parallax scrolling. They discuss how the pursuit of flashy, modern designs can overshadow usability, creating obstacles for users trying to complete tasks. Drawing on decades of experience, Virgil shares insights into the “form vs. function” debate, emphasizing that good design prioritizes purpose and user needs.

To wrap up, the duo highlights the growing trend toward simplicity in web design and the importance of finding a balance between aesthetics and practicality. Listeners will leave with a deeper understanding of how to create websites that are both visually engaging and user-friendly.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

(0:00) - Intro

(1:26) - Websites have gotten too complicated

(3:13) - Evolution of web design trends

(4:43) - Form vs Function: An age old battle

(6:59) - When did style over substance get big?

(8:53) - The pressure to keep up with trends

(10:15) - It's about balancing form and function

(13:55) - Outro

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In Episode 5 of Discussing Stupid, host Virgil Carroll and co-hosts Chad and Cole from High Monkey explore the often-overlooked mistakes organizations make with typography and the significant impact it can have on user experience and performance. From excessive font usage to unreadable design choices, this episode dives into the dos and don’ts of effective typography.

The team discusses:

Why using too many fonts on a website creates confusion and slows down performance.
The importance of keeping fonts readable and how font size and weight affect usability.
Real-world examples of font mistakes, including when and where decorative fonts can work—and when they don’t.
How poor typography choices can kill website performance, particularly through improper font loading.

To wrap up, they discuss actionable best practices, including limiting font selections, optimizing font files for performance, and always keeping your audience in mind when choosing typography.

By the end of this episode, you’ll gain practical insights to help your website achieve both aesthetic appeal and functional clarity—without sacrificing performance.

This marks the final episode of 2024, and we want to thank all of you for joining us this year! We’ll be taking a short break for the holidays but will return in 2025 with more episodes, more “stupid,” and more expert advice to help you avoid common digital mistakes.

Until then, like, review, and subscribe on your favorite podcast platform, and visit www.discussingstupid.com for updates and resources.

Happy holidays, and see you in the new year!

(0:00) - Intro & holiday spirit

(1:44) - Welcome back, Chad

(2:20) - Too many fonts = chaos

(4:05) - Learning from print design

(5:25) - Typography as Art vs. Function

(6:23) - The hidden cost of fancy fonts

(8:04) - Should some fonts be banned?

(10:11) - Know your audience and the context

(12:06) - With fonts, less is more

(14:28) - Outro & happy holidays!

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In Episode 4 of Discussing Stupid, host Virgil Carroll and co-host Cole from High Monkey dive into the complex world of search systems and the importance of semantics in delivering relevant results. This episode explores the frustrations users often face when search systems fail to recognize variations in spelling, synonyms, and context, which can drastically impact user experience.

Virgil and Cole discuss common issues with search systems, such as treating every search term the same and ignoring common phrases and alternative names. They share real-world examples, like a bank where users searched for one name in numerous ways, illustrating the need for search systems to recognize and account for these variations. The team also emphasizes that improving search functionality requires more than just turning it on—it involves continuous work, testing, and understanding of user behavior.

To wrap up, Virgil highlights best practices, including using “push search” technology to guide users to the right results and leveraging search analytics to understand how people are searching. By the end of the episode, listeners will gain practical insights into making search more intuitive and user-friendly.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

(0:00) - Intro

(1:26) - A lot of search systems suck

(1:57) - Search needs semantics

(3:04) - Search with VS without semantics

(4:48) - When AB&T meets AB and T

(6:14) - The English language is funny

(8:00) - The power of curated results

(10:50) - Virgil's biggest piece of advice

(12:41) - Outro

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In Episode 3 of Discussing Stupid Season 2, host Virgil Carroll, along with Cole from High Monkey, dives into the topic of content readability. They focus on how overly complex or technical language can turn users away and make it harder for people to understand.

The team discusses common readability mistakes like using too much jargon, confusing sentence structure, and not keeping the audience in mind. Virgil shares examples from government and education where content wasn’t simple enough. They explain why it’s important to know your audience and keep language clear, especially for government websites that need to be at an 8th-grade reading level.

The episode also includes a demo using Readable.com, where Virgil and Cole show how to take a sentence and make sure it is clear and easy to read. This example shows why keeping content simple helps people understand and stay engaged.

By the end of this episode, you’ll have tips to make your content easy to read and understand, reaching a wider audience.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

LINKS

Readable.com: https://www.readable.com/

Watch a clip of Virgil and Cole using Readable.com to enhance content clarity:

https://youtu.be/5NW1A2ZSD4E

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In Episode 2 of Discussing Stupid Season 2, host Virgil Carroll, along with Chad and Cole from High Monkey, dives into the topic of page performance and SEO, specifically focusing on how oversized images can slow down your website.

They discuss common mistakes people make with large images—like shrinking images in HTML without optimizing file size—and how these errors can negatively impact both the user experience and SEO rankings. The team shares insights into how to avoid these pitfalls and explores how tools like RIOT (Radical Image Optimization Tool) can help reduce file sizes without sacrificing image quality.

You'll also hear about the often overlooked balance between mobile and desktop optimization. The team highlights why simply resizing images for mobile isn’t enough and explains how poor image handling can lead to sluggish performance on mobile devices, frustrating users and hurting your site's overall effectiveness.

By the end of this episode, you'll walk away with actionable tips on optimizing images for both performance and SEO, ultimately improving your site’s speed and user experience.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

LINKS

Riot (Radical Image Optimization Tool): https://riot-optimizer.com/

Riot demo clip from this episode: https://youtu.be/kL3nu5Mj8VA

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Welcome to the first episode of Discussing Stupid Season 2, where your host Virgil Carroll, along with Chad and Cole from High Monkey, dive into the importance of inclusive design. In this episode, they focus on the often overlooked but crucial aspect of alt text for images.

Virgil, Chad, and Cole discuss the significance of alt text in creating an inclusive digital experience. They emphasize that alt text is not merely about ticking boxes for WCAG or ADA compliance. Instead, it plays a crucial role in enhancing accessibility and inclusivity for individuals who rely on screen readers. The discussion covers the various types of images—decorative, practical, and informative—and offers insights on how to accurately describe them to improve the digital experience for everyone.

The episode also explores the limitations of relying solely on AI to generate alt text, underscoring the importance of human-crafted, meaningful descriptions that can profoundly impact users who depend on assistive technologies. Furthermore, the team shares practical tips on integrating inclusive design practices into your content creation process, ensuring that your digital content is accessible and understandable to all users.

Throughout the episode, you'll gain valuable knowledge on how to implement best practices for alt text and learn why it's essential to consider inclusivity at every stage of your content lifecycle. By the end of the discussion, you'll be equipped with the tools and insights needed to make your digital content more accessible and inclusive.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

LINKS

Tools mentioned:

Wave: https://wave.webaim.org/

Lighthouse: https://developer.chrome.com/docs/lighthouse/overview/

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In this highly anticipated return of the Discussing Stupid podcast, host Virgil Carroll welcomes new co-host Cole Schlotthauer to kick off Season 2. After a five-year hiatus, they're back with a fresh approach, focusing on shorter, more targeted episodes that delve into specific UX and digital practices.

Virgil and Cole discuss the shift from long-form interviews to concise, 10-15 minute episodes designed to provide actionable insights. This season will cover a range of topics, from alt text best practices to the pitfalls of relying too heavily on AI for accessibility. The goal is to offer practical advice that listeners can immediately apply in their own work.

In addition to audio, the podcast will now include video episodes, allowing for more dynamic content and visual examples. For those who prefer audio-only, detailed show notes will ensure no one misses out on the valuable information shared.

Don't miss out on the latest updates and exclusive content—subscribe to Discussing Stupid on their website, and follow them on YouTube, Apple Podcasts, Spotify, or Soundcloud. Get ready for a season packed with insightful discussions on UX and digital best practices!

Links:

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In this episode of the Discussing Stupid podcast your host Virgil Carroll has a conversation with Brett Matson, the Managing Director of Funnelback Search Technology, about search, semantic search, knowledge graphs, artificial intelligence in search, and the related leverages and pitfalls.

Brett shares that there are several big things coming in the area of search, after reaching a plateau and stagnation for a few years. Some of these are paradigmatic (understanding the search has multiple purposes, not just page rankings,) and some include changing the approach (i.e. modifying queries,) changing presentation of results (modules,) knowledge graphs, semantic search (detecting the intent of the query,) and many more.

Brett explores how some of these new technologies are intrinsically more attractive to people. For example, knowledge graphs are (or can be) visual and show relations between entities in them. Thus, they are much more intuitive in contrast to being faced with a wall of data to choose from. The point is, of course, making content a lot more intelligent and hence more useful, by treating it as a product and perfecting its delivery.

In Brett’s opinion, during the next decade we will see a real proliferation of smart tools that will help users and companies perform a significantly better search. Virgil and Brett also discuss how it is very important to avoid making too many connections when using a new, powerful technology that can do that. This can bog down the whole organization, its data servers, employees, and finally, users.

Virgil’s conversation with Brett is very rich and diverse, so make sure to listen to the whole episode and pay close attention to what he had to share.

Links:

Episode mentioned:
Future-proofing your experience delivery strategy with Intelligent Content by Kate Skinner.

Siraj Raval's YouTube channel is full of short, fun videos that teach all different aspects of machine learning and AI.

Coursera's Machine Learning course, one of the original online machine learning courses, delivered by leading AI researcher Andrew Ng.

A great article by Sebastien Dery discussing the challenges of knowledge graphs.

Connect with Funnelback:
https://www.funnelback.com/

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In this episode of the Discussing Stupid podcast, your host Virgil Carroll has a conversation with Kanwal Khipple about successful and consistent user experience (UX) across multiple channels. The question is how to design consistent user experience for people across different interfaces developed by different companies to provide different experiences. Kanwal is the CEO at 2toLEAD, and great UX innovation is his passion. Virgil and Kanwal dive deep into the past and recent trends of tools, the challenges that user experience design faces across tools, and offer advice on the best approaches to cultivate successful cross-app user experience.

One of the major challenges of UX is adopting a tool (or tools) that can sometimes be too complex and can feel burdensome. For UX design to be successful, it is important to understand the users themselves and how they utilize your services or business’s tools. For that reason, it’s important to note and map how consumers find your tools and how they use the tools. Another important aspect of UX design is to not overwhelm users. For example, one common error is overloading them with notifications that they cannot manage or turn off. Building a road map where the whole process will help the users and the company as well.

There are 3 facets of UX – navigation, search, and the actual content. The best approach is to focus on one of these, excel at it, gather feedback, and continuously improve.

Buzzword for this episode: seamlessness

Links:

Connect with Kanwal on LinkedIn

Follow Kanwal on Twitter (@kkhipple)

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In this episode of the Discussing Stupid podcast, the first in 2019, host Virgil Carroll and Principal Solutions Architect at High Monkey, has a conversation with Chad Heinle and Joel Baglien about how technology has changed due to people’s needs changing and how certain technology has been recycled to reflect a market that’s now ready to utilize it. Chad Heinle and Joel Baglien are both VPs at High Monkey. Chad heads the production team and Joel, co-founder of High Monkey with Virgil, heads the sales and marketing team. Both Chad and Joel briefly discuss how they became interested in web work and got to where they are now in their careers.

Virgil starts the discussion by highlighting the developments and changes in web design. While previously a web developer was essential to program and put together a website, today with advanced CMSs almost anyone can build a website and almost everyone does. Chad voices his concern of a current issue that was not present before – now people who are not well versed in web development have tools at their disposal to create websites; however, many of these non-developers tend to make subpar websites. Chad believes, however, that people are coming to realize that for the sake of efficiency and ease of use, more consideration is going into who makes a website. Virgil also shares his take on user-friendly website development and its correlation with technology growth. Joel brings to light the fact though many years have passed; yet for many organizations, institutions, and companies, their websites are still inaccessible to certain site visitors. Joel suggests that this can be rectified with proper design, development, and content role allocation. With the recent push for more simplistic, accessible sites the need for knowledgeable web developers and programmers has returned.

This trend has also changed things in the domain of search engine design. Search engines have become better at finding and displaying information. However, if a user is drowned in information and is not able to quickly find the information he needs, he will most likely not use the search engine or the website that he happens to be on again. There’s the simple truth that some companies and messages resonate with visitors and potential customers, while others don’t. In order for your message to resonate, you need to be efficient. One should also aim to use the platforms that fit your company, message, and brand – for instance, don’t focus on Twitter if you are a visually oriented company.

Another trend that contributed to the recent strive towards simplicity is that the everyday activities of people have become digital. This digital-centeredness can be overwhelming and socially stressful for some people with having to deal with different media sources, information, platforms, and passwords on a daily basis. Hence, the desire to have more simplified search capability and user-ability, since having to navigate the daily digital landscape is complicated already. The difference between today and a decade ago is that things that are done now need to have a purpose – rarely are elements on websites there just to have them there (Macromedia/Adobe Flash anyone?).

Developments in various markets and niches are cyclical, as can be attested by the recent renaissance of the muscle car. The recent trend towards simplicity might develop towards complexity when it has run its course. Virgil, Chad, and Joel’s advice to you is that it pays to follow trend developments and not forget that things happening now, probably happened before at one point in time in the past.

Buzz words for this episode: digital workplace

LINKS

https://www.highmonkey.com/

https://contentstrategyalliance.com/resources/csa-handbook/

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In this episode of the Discussing Stupid podcast, host Virgil Carroll sits down with Martin MacCulloch from Kentico Cloud. Martin is a product manager at Kentico Cloud. Kentico Cloud is a cloud-based environment for content management and delivery. Martin joins Virgil to discuss content friction, common workflow problems, and how Kentico Cloud is harnessing technology to improve content efficiency and cohesiveness. After their interview, Virgil shares his frustration with a new buzzword in the Stupid Buzz section of the show.

As the conversation unfolds, Martin defines content friction as everything that causes inefficiency or damage throughout the content lifecycle. Martin breaks down some of the friction his teams experienced around new product launches. Namely, how they found it difficult to decide who would write the content, how to craft a cohesive message, and how to collaborate efficiently as a team. Martin and Virgil talk about how to build beneficial workflow systems and avoid perpetuating the problems you’re trying to fix.

Next, Martin shared numerous technological and workflow issues that he has witnessed throughout his career. Some of these issues include inefficient file storage where hundreds of emails are exchanged, failing to work on the most recent version of a file in collaborative projects, bottlenecked team structures where a plethora of decisions have to be made by a single person, and more. Virgil then asks Martin about how Kentico Cloud is working to streamline the collaborative content-creation process, help brands craft a cohesive message, and improve the journey from ideation to execution.

After the conversation winds down, Virgil dives into Stupid Buzz, where he talks about a buzzword that gets on his nerves. This week’s buzzword is “omnichannel.” Virgil shares his concerns about the way that people use the term incorrectly and points back to its legitimate meaning, which implies understanding your content on a microscopic and big-picture level as it relates to the various platforms it’s being published on. In short, omnichannel content is far more complex and specific than many people suggest through their inaccurate use of the term.

LINKSLearn more about Kentico Cloud
https://www.kentico.com/

Download a free handbook of templates and best-practices from the Content Strategy Alliance
https://contentstrategyalliance.com/resources/csa-handbook/

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The digital world of today challenges marketers to carefully craft their messaging or risk causing the type of public relations nightmare most don’t want to think about. Now, digital marketers have to not only appreciate the power of the words and imagery they use (or choose not to), but also recognize the need to elevate their messaging to tell a much broader, more diverse story around our brands and products. To help shed some light on some of these challenges, Virgil is joined by the always delightful Heather Newman from Creative Maven. Heather is not only an experience marketer, but is also known for her endeavors in the promotion of better diversity and inclusion in the workplace, especially in the field of technology.

During the discussion, Virgil and Heather ‘get real’ on how the conversation around diversity is changing the digital marketing landscape and share some big (and sometimes funny) screw-ups and successes along the way. In the end, the conversation explores the complex topic, pokes fun at many of our predisposed ideas about how diversity in messaging works (its not just about your person count in images) and gives real world examples on the dos and donts we should all try to follow.

Resources discussed:

https://www.creativemaven.com/ - Heather's marketing agency
https://storybrand.com/ - Story Brand
https://www.microsoft.com/en-us/diversity/ - Microsoft Global Diversity and Inclusion
https://www.womeninsharepoint.com/ - Women in SharePoint
https://www.womenintechnology.org/ - Women in Technology
https://www.womenshistory.org/ - National Women's History Museum

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In today’s digital world, creating an inclusive visitor experience is often discussed but never really implemented. One of the biggest challenges facing successful implementation is taming the behaviors of a large base of content contributors. In this episode, Virgil is joined by Doug Burgett of the University of Illinois, to discuss his first-hand experience with this topic. Doug is the Creative Director for Marketing Communications for Enrollment Management (translation: he markets for admissions). In this role, Doug has primary responsibility for the most important areas of the University of Illinois website and must ‘wrangle’ a diverse population of contributors who possess a variety of skill levels.

During the podcast, Virgil and Doug discuss the challenges we all face keeping our digital properties accessible. Add to the mix that we have to train our contributors to use the tools at our disposal in an educated way. According to Burgett, “When content editors use WYSIWYG editors they don’t realize that as the enter content into the editor, code is actually being created in the back end. Knowing this helps content editors to Realize the power they have at their fingertips.” Once consistency among content editors has been achieved, Virgil and Doug discuss bad practices to avoid, look at some of the monitoring tools and techniques you can employ, and explore how to provide your customers with all-inclusive digital experiences.

Resources discussed:

https://developers.google.com/amp/ - Google’s mobile first development methodology
https://www.w3.org/TR/wai-aria-practices-1.1/ - Understanding the use of ARIA tags
https://fae.disability.illinois.edu/anonymous/?Anonymous%20Report=/ - University of Illinois’s Functional Accessibility Evaluator
https://webaim.org/ - Online accessibility compliance auditor
https://www.paciellogroup.com/resources/contrastanalyser - Accessibility color contrast tester

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Join Virgil Carroll for Monkey Byte 3.5. Follow along as Virgil digs through some of the more popular tools in the world of customer experience and see how well these companies are prepared for the European Union's General Data Protection Regulation (GDPR). Virgil digs through tools like Facebook, LinkedIn, Hootsuite and even Mail Chimp to see what steps they are taking to comply with the new regulation.

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Since Virgil knew you couldn’t get enough about good data practice regulations, he decided to do another episode on GDPR . . . yay! Where Episode 2 dealt with the collection of private data, this Episode focuses on how you handle your customer’s private data after you collect it. To assist him in telling this exciting story, Virgil recruited his long-time friend Liam Cleary. Liam is a well-respected data security expert. Liam applies his expertise in both his own consultancy, SharePlicity, and as the Security Product Owner for Rencore. Liam also spends a significant amount of time in the world of hacking . . . teaching people how to protect their own data from being hacked (wink, wink).

During this enlightening discussion, Virgil and Liam discuss the bigger problem in the way we handle customer data, that is, do we actually know where it goes? According to Liam, "One of the key things to focus on regarding GDPR is to make sure you understand how the data moves around and really how it integrates in other applications and systems that you might utilize it in." Take a customer's email as one example; you can forward it in an email, add it to a CRM, put it in an order tracking system, or add it to your email subscription list. But, can you find all of that customer's data and know how to remove it if you receive a request to do so? Virgil and Liam also discuss the importance of good processes and procedures and some of the realities around the effort it takes to be compliant.

If you care about your customer's private data once you have it, then you might want to give a listen.

Resources discussed:

https://www.eugdpr.org/ - European Union GDPR regulations
https://www.marketo.com/ - Online marketing automation system
https://techcommunity.microsoft.com/t5/Security-Privacy-and-Compliance/Compliance-Manager-Preview-is-now-available/ba-p/124662 - Microsoft’s Compliance Manager
https://ec.europa.eu/eurostat/cros/ - European Commission official stats site

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Join Virgil Carroll, in the second 'MonkeyByte' episode of the series, as he talks more about GDPR and more specifically containing consent. It is important when using user’s information that you've collected that you receive specific consent for the types of activities in which you plan to use their information. Whether that be newsletters, email campaigns and or any other type of activities.

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Join Virgil Carroll as he hashes over what has been one of the most over-talked about changes in global digital marketing in a very long time - the implementation of GDPR. The European Union’s General Data Protection Regulation rewrites the book on digital personal privacy and creates a new mandate for how organizations need to respect and protect individual’s data. While this topic has been talked about in a million different ways, today’s podcast offers a different angle. We focus on how difficult GDPR is to implement as part of your digital strategy while exposing some of the myths and overreactions around these new regulations. You might not think you should care about regulations from the European Union, but GDPR compliance is a huge step in the direction of showing your customers that their privacy really matters to you!

To help gain a better perspective on GDPR, Virgil is joined by David Komárek, the Content Management Product Owner at Kentico Software. David led the charge at his organization to make Kentico CMS software to be one of the first fully GDPR-compliant Content Management Software solutions on the market. During the discussion, David will share the complex journey Kentico had to take and what they learned about their own data practices as well as those of their customers. David recommends "First, try to learn as much as you can about GDPR . . . use somebody who is informed in GDPR and who can educate your internal staff . . . then look at the data and what you're doing with it". Virgil and David also discuss how to understand what is important to do in managing your customer’s privacy and give some good real-world advice on how to start your compliance journey.

Resources discussed:

https://www.kentico.com/product/all-features/marketing/gdpr-and-data-protection - About Kentico’s GDPR readiness
https://www.kentico.com/product/resources/whitepapers/gdpr-compliance-and-your-cms/gdpr-compliance-and-your-cms.pdf - Whitepaper on being GDPR compliant
https://www.eugdpr.org/ - European Union GDPR regulations

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Join Virgil, in his first 'MonkeyByte', as he dives a bit deeper into the concept of machine learning and discusses how it can be used and how it can be helpful and hurtful to your customer experiences.

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On our very first podcast (episode 1 YEAH!!!), Virgil is joined by Ben Tilley from Funnelback, an Australian-based search company, to break through all the hype around the use of artificial intelligence in search and talk about real world implementations and pitfalls.

Listening to this discussion, you will discover that implementing AI in search is not all that easy (shocker!!) and still requires you to follow good content and search practices. Where AI has many practical applications in search, effort is still needed and fundamentals need to be followed. In the end, AI cannot fix your search if your content still sucks.

There is reason to hope, good AI can be very helpful. According to Ben, "Being able to use some form of natural language processing to extract information out of your written text and turn that back into structure is a great way you can start to improve search."

Throughout this episode, Virgil and Ben will share the challenges you will face while giving you thoughts on how you can get your content and search ready to be able to use AI to its full potential.

Resources discussed:

https://www.wolframalpha.com/ - one of the first search engines to use AI
https://www.westpac.com.au/ - example organization using AI in their search

Helpful articles from Funnelback:

https://www.funnelback.com/blog/artificial-intelligence-why-the-farmer-killed-the-fox
https://www.funnelback.com/blog/intelligent-question-answering
https://www.funnelback.com/blog/is-the-future-of-search-proactive

Discussing Stupid: Talking Digital Customer Experience: Recent Episodes

Virgil Carroll