Discussing Stupid: A byte-sized podcast on stupid UX

Season 3 of the Intentional AI series started with a simple premise: AI is a powerful tool, but the way it gets marketed and the way most people actually use it are two very different things. Eighteen episodes later, that premise has held up. In this finale, Virgil and Cole take stock of what the season actually taught them. Not the hype, not the headlines - what they observed firsthand through te...

Near the end of Season 3, Virgil and Cole sit down to look back at the prompts used throughout the Intentional AI series, what worked, what did not, and what that gap says about how most people approach AI. The conversation starts with a simple premise: the prompt itself is not really the point. The words you type are just the output of a more important process, which is knowing clearly what you w...

If there is one thing AI should be genuinely good at, it is analytics. Pattern recognition across large data sets is more or less what it was built for. But just because AI can look at your data does not mean it knows what you are actually trying to learn from it. That is the part most people skip. In this episode, Cole brings in a framework from a LinkedIn post by Tim Stoddart that puts the probl...

AI-generated social media content is everywhere right now. The question is not whether you should use AI for it. The question is whether what you are producing is actually worth putting out there. In this episode, Cole and Virgil get into the honest version of this conversation. Social media is already oversaturated. The algorithm rewards activity, but activity without a message is just noise at s...

Agentic AI has been one of the most repeated phrases in marketing and technology for the past year. Most people using it cannot tell you what it means. Virgil and Cole bring in Sean Wright, Lead Product Evangelist at Kentico, to cut through the noise and talk about what agentic AI actually does inside a content management workflow. The starting point is a distinction that gets lost in the hype. St...

Conversational search changes the fundamental contract of how users interact with a website. Instead of returning links, it returns answers. That sounds like a clean upgrade. What it actually does is make the quality of everything sitting underneath the AI impossible to ignore. In this episode, Virgil and Cole bring in their first-ever guest for the series, Will Noble from Squiz, who has spent ove...

Most of the Intentional AI series has tested AI in areas where judgment, creativity, and context matter a lot. This episode is a little different. Virgil, Cole, and returning guest Chad take a look at AI and web development, a domain where patterns, repetition, and known best practices are the whole point. On paper, that should be where AI shines. Chad makes clear that for working developers, AI i...

AI video tools promise fast, cheap production. But what you get back depends entirely on how much thinking you did before you hit enter. In Episode 11 of Season 3's Intentional AI series, Virgil and Cole take on AI video generation, arguably the most complex and most hyped area of AI content creation. Video production has always been expensive, often running thousands of dollars per minute through...

In Episode 10 of Intentional AI, we are taking a short detour in our Intentional AI series to talk about the Super Bowl. Not the game. The ads. A noticeable chunk of them leaned hard into AI. On the surface, it felt like a big moment for the industry. But when you look closer, it raises a different question. Are we watching real progress, or just very expensive hype? We unpack what was actually be...

In Episode 9 of the Intentional AI series, Cole and Virgil take on one of the most common and misunderstood uses of AI today: image and graphic generation. From social media visuals to promotional graphics, AI images are fast, easy, and everywhere. The conversation focuses on why images became the public on ramp to AI and why that familiarity creates risk. Visuals feel harmless, but the moment AI...

In Episode 8 of the Intentional AI series, Cole, Virgil, and Chad explore one of the most tempting uses of AI in digital work: wireframing and page layout. With AI now able to generate full wireframes in minutes or even seconds, the promise of speed is undeniable. But speed alone is not the point. The conversation focuses on where AI genuinely helps in the wireframing process and where it introduc...

In Episode 7 of the Intentional AI series, Cole and Virgil focus on content personalization and why it is one of the most overpromised areas of AI. While personalization is often positioned as simple and automated, doing it well requires far more clarity and intent than most tools suggest. They break personalization into two main approaches. Role based personalization tailors messages for specific...

In Episode 6 of the Intentional AI series, Cole, Virgil, and Seth move into the visibility stage of the content lifecycle and tackle a common mistake they see everywhere. Teams keep treating SEO, GEO, and AEO as optimization problems, when in reality they are content quality, structure, and clarity problems. Search engines andgenerative models have both gotten smarter. Keyword tricks, shortcuts, a...

In Episode 5 of the Intentional AI series, Cole, Virgil, and Seth shift into another part of the content lifecycle. This time, they focus on accessibility and how AI fits into that work. Accessibility is more than code checks. It is making sure people can actually use and understand what you create. The team walks through what happened when they ran the High Monkey website through an AI accessibil...

In Episode 4 of the Intentional AI series, Cole and Virgil move further into the content lifecycle and this time they are focusing on content management. Once your content’s written, the real work begins. Editing, organizing, translating, tagging, all the behind-the-scenes steps that keep content consistent and usable. In this episode, the team looks at how AI can help streamline those tasks and w...

In Episode 3 of the Intentional AI series, Cole and Virgil move into the next stage of the content lifecycle: content creation. AI can write faster than ever, but that doesn’t mean it writes well. From prompting and editing to maintaining voice and originality, AI-generated content still requires human effort and judgment. In this episode, the team explores where AI can help streamline production...

In Episode 2 of the Intentional AI series, Cole and Virgil dive into the first real stage of the content lifecycle: research and analysis. From brainstorming ideas to verifying data sources, AI is being used everywhere in the early stages of content creation. But how much of that information can you actually trust? In this episode, the team unpacks where AI helps, where it hurts, and why you still...

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 episo...

“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...

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, includi...

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...

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 d...

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 lik...

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 desi...

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-wo...