Discussing Stupid: A byte-sized podcast on stupid UX cover art

Discussing Stupid: A byte-sized podcast on stupid UX

Discussing Stupid: A byte-sized podcast on stupid UX

By: High Monkey
Listen for free

About this listen

 Discussing Stupid returns to the airwaves to transform digital facepalms into teachable moments—all in the time it takes to enjoy your coffee break! Sponsored by High Monkey, this podcast dives into ‘stupid’ practices across websites and Microsoft collaboration tools, among other digital realms. Our "byte-sized" bi-weekly episodes are packed with expert insights and a healthy dose of humor. Discussions focus on five key areas: Business Process & Collaboration, UX/IA, Inclusive Design, Content & Search, and Performance & SEO. Join us and let’s start making the digital world a bit less stupid, one episode at a time. Visit our website at https://www.discussingstupid.com© 2025 Discussing Stupid: A byte-sized podcast on stupid UX Economics Marketing Marketing & Sales
Episodes
  • S3E14 - Intentional AI: AI agents are only as good as your workflow

    S3E14 - Intentional AI: AI agents are only as good as your workflow
    Apr 21 2026
    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. Standard AI chat requires you to keep driving it. You ask, it answers, it stops. Agents do not stop when you do. They make decisions, take action, and iterate toward a goal using whatever tools and data they have access to. Sean makes the case that this shift in behavior is significant, but only if the agent has something real to work with. Context is the deciding factor every time.Sean walks through two areas where Kentico's built-in AI engine, AIRA (AI Recommendations and Assistance), is already handling real workflow tasks. The first is image management - optimization, cropping, focal point detection, alt text generation, and taxonomy tagging, all happening in the background without the marketer stepping in. The second is a content strategist agent that evaluates web content against your organization's content strategy document, checking for consistency in tone, style, and voice before anything goes live.The conversation closes on evals, a concept that does not get enough attention outside of product development circles. As models change and context evolves, teams need a way to verify that output quality is holding steady. Sean makes the case that this applies to individual marketers and marketing teams, not just vendors. If you rely on a repeatable AI-assisted workflow, you should have a way to know when something has quietly shifted.Previously in the Intentional AI series:Episode 1: Intentional AI and the Content LifecycleEpisode 2: Maximizing AI for Research and AnalysisEpisode 3: Smarter Content Creation with AIEpisode 4: The role of AI in content managementEpisode 5: How much can you trust AI for accessibilityEpisode 6: You’re asking AI to solve the wrong problems for SEO, GEO, and AEOEpisode 7: Why AI can make your content personalization worseEpisode 8: The real value of AI wireframes is NOT the wireframesEpisode 9: Just because AI can create images doesn't mean you should use themEpisode 10: The Super Bowl didn't sell AI, it exposed itEpisode 11: AI video rewards planning, not your ideasEpisode 12: AI might struggle with creativity, but coding isn't creativeEpisode 13.1: What the rise of conversational search means for your websiteNew episodes every other Tuesday.For more conversations about AI, design, and digital strategy, visit https://www.highmonkey.com/podcast and subscribe on your favorite podcast platform.(0:00) - Intro(0:44) - Meet Sean Wright from Kentico(1:45) - What does "agentic" actually mean?(3:13) - The agent doesn't stop when you do(4:11) - It all depends on the tools(5:49) - AI output is non-deterministic. Plan for it.(8:11) - What AIRA handles behind the scenes(11:17) - Where AI works best: logic over creativity(12:17) - Evaluating content against your own strategy(15:24) - Consistency is harder than creation(16:03) - AI still requires planning(16:58) - Tools that can help across the content lifecycle(18:48) - Cognitive load and the 80/20 rule(20:16) - Will AI replace your job?(21:45) - The Wall-E chair question(23:19) - Agentic AI is intentional AI(24:17) - What are evals and why do they matter?(27:01) - Wrapping up(28:00) - OutroSubscribe for email updates on our website:https://www.discussingstupid.com/Watch us on YouTube:https://www.youtube.com/@discussingstupidListen on Apple Podcasts, Spotify, or Soundcloud:https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0https://soundcloud.com/discussing-stupidCheck Us Out on Socials:https://www.linkedin.com/company/discussing-stupidhttps://www.instagram.com/discussingstupid/https://www.facebook.com/discussingstupidhttps://x.com/DiscussStupid
    Show More Show Less
    29 mins
  • S3E13.1 - Intentional AI: What the rise of conversational search means for your website

    S3E13.1 - Intentional AI: What the rise of conversational search means for your website
    Apr 7 2026
    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 over a decade working in the information discovery space for large enterprise organizations.Will explains the shift with a clean analogy early in the episode. Traditional search is like asking a librarian for help and getting handed a stack of encyclopedias. Conversational search is that same librarian reading every book in the library and handing you a direct answer. The user experience improvement is real. But so is what it depends on, because the AI reads everything, including the outdated policy documents buried in a subdomain that nobody has touched in a decade. When dormant content gets surfaced as a confident answer, the gap between what was published and what is actually true becomes a reputational and legal problem.The practical guidance that emerges from the conversation is to start with a defined slice of content you know is solid. Will walks through a real example of a university with 250,000 pieces of content that scoped its initial conversational search implementation to 50 pages focused on student life. Questions related to that area got clean, accurate answers. Everything else defaulted to traditional keyword search. That controlled scope is what allowed the project to prove value before expanding, and it is what kept stakeholders from pulling the plug the moment a bad result surfaced.The garbage-in, garbage-out principle has always been true in search. What this episode makes clear is that it has never carried higher stakes. LLMs do not skip the bad content. They find it, surface it, and present it with confidence. The first step toward getting conversational search right is the same step the rest of this series keeps coming back to: know what you are working with before you deploy.Previously in the Intentional AI series:Episode 1: Intentional AI and the Content LifecycleEpisode 2: Maximizing AI for Research and AnalysisEpisode 3: Smarter Content Creation with AIEpisode 4: The role of AI in content managementEpisode 5: How much can you trust AI for accessibilityEpisode 6: You’re asking AI to solve the wrong problems for SEO, GEO, and AEOEpisode 7: Why AI can make your content personalization worseEpisode 8: The real value of AI wireframes is NOT the wireframesEpisode 9: Just because AI can create images doesn't mean you should use themEpisode 10: The Super Bowl didn't sell AI, it exposed itEpisode 11: AI video rewards planning, not your ideasEpisode 12: AI might struggle with creativity, but coding isn't creativeNew episodes every other Tuesday.For more conversations about AI, design, and digital strategy, visit https://www.highmonkey.com/podcast and subscribe on your favorite podcast platform.(0:00) - Intro(0:51) - Meet Will Noble from Squiz(2:14) - Today's topic: Conversational search(4:14) - Welcome to the new era of information seeking(7:10) - The dormant content problem(9:48) - You can ignore the problem, but it won't ignore you(11:45) - Where do you start with thousands of pages?(14:36) - Start small, don't go big(17:14) - AI's opportunity as a content auditing tool(20:39) - Search is the foundation of everything AI does(22:13) - How do you keep up when AI moves this fast?(25:43) - OutroSubscribe for email updates on our website:https://www.discussingstupid.com/Watch us on YouTube:https://www.youtube.com/@discussingstupidListen on Apple Podcasts, Spotify, or Soundcloud:https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0https://soundcloud.com/discussing-stupidCheck Us Out on Socials:https://www.linkedin.com/company/discussing-stupidhttps://www.instagram.com/discussingstupid/https://www.facebook.com/discussingstupidhttps://x.com/DiscussStupid
    Show More Show Less
    27 mins
  • S3E12 - Intentional AI: AI might struggle with creativity, but coding isn't creative

    S3E12 - Intentional AI: AI might struggle with creativity, but coding isn't creative
    Mar 24 2026
    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 is already genuinely useful. Generating boilerplate, producing code blocks for well-understood functionality, and cutting down on time spent typing out repetitive structures. These are real wins. The catch is that getting value out of AI-generated code still requires knowing what you're looking at. If you can't read the output, you can't catch the errors, and you can't fix what's wrong.That gap becomes more visible when you consider who these tools are being marketed to. The pitch is often aimed at business users and non-developers, promising a fast path from idea to working product. The episode digs into why that gap -- between what gets generated and what is actually usable -- is harder to close in code than it is in content or images. A piece of writing that's 80% there can be polished. Code that's 80% there can be a liability, especially if the person using it doesn't know what the other 20% is.Virgil tested Claude, ChatGPT, and GenSpark against the same prompt: build a visually appealing, fully accessible accordion web component using the series source article. All three produced something workable. None were perfect. Claude handled screen reader accessibility well but had a JavaScript bug that prevented the drawers from opening and used a low-contrast color scheme. ChatGPT produced the most functional but visually flat result, with the worst screen reader compliance. GenSpark produced the most polished visual, with the most helpful follow-up prompts, and landed in the middle on accessibility. As Virgil put it, these were the least failures the series has generated, which is saying something.Previously in the Intentional AI series:Episode 1: Intentional AI and the Content LifecycleEpisode 2: Maximizing AI for Research and AnalysisEpisode 3: Smarter Content Creation with AIEpisode 4: The role of AI in content managementEpisode 5: How much can you trust AI for accessibilityEpisode 6: You’re asking AI to solve the wrong problems for SEO, GEO, and AEOEpisode 7: Why AI can make your content personalization worseEpisode 8: The real value of AI wireframes is NOT the wireframesEpisode 9: Just because AI can create images doesn't mean you should use themEpisode 10: The Super Bowl didn't sell AI, it exposed itEpisode 11: AI video rewards planning, not your ideasNew episodes every other Tuesday.For more conversations about AI, design, and digital strategy, visit https://www.highmonkey.com/podcast and subscribe on your favorite podcast platform.(0:00) - Intro(0:44) - Today's topic: Intersection of AI & coding(2:46) - The "just type and get a website" myth(3:44) - Where AI actually helps with coding(6:08) - When "good enough" works and when it doesn't(8:13) - The real win: Using AI as a developer(11:06) - Tool test: building an accordion with AI(13:14) - Testing Claude(16:23) - Testing ChatGPT (Codex)(18:25) - Testing GenSpark(20:25) - Using AI to fix AI code(23:11) - Tons of opportunity with AI and coding(24:16) - OutroSubscribe for email updates on our website:https://www.discussingstupid.com/Watch us on YouTube:https://www.youtube.com/@discussingstupidListen on Apple Podcasts, Spotify, or Soundcloud:https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0https://soundcloud.com/discussing-stupidCheck Us Out on Socials:https://www.linkedin.com/company/discussing-stupidhttps://www.instagram.com/discussingstupid/https://www.facebook.com/discussingstupidhttps://x.com/DiscussStupid
    Show More Show Less
    26 mins
No reviews yet
In the spirit of reconciliation, Audible acknowledges the Traditional Custodians of country throughout Australia and their connections to land, sea and community. We pay our respect to their elders past and present and extend that respect to all Aboriginal and Torres Strait Islander peoples today.