Discussing Stupid: A byte-sized podcast on stupid UX

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Weighing AI tools, one practical use at a time.

The gist

Discussing Stupid takes a practical, business-minded look at digital tools, and its third season turns that lens on AI across wireframes, images, video, code and conversational search. The talk is openly skeptical of the hype without being closed to it, and the speakers rate building with code as the use with the most potential.

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About Discussing Stupid: A byte-sized podcast on stupid UX

Discussing Stupid is built on a simple instinct: point at the digital practices that go wrong and talk through why. Its third season turns that instinct on artificial intelligence. The episodes carry an 'Intentional AI' label, and the series has run long enough that one speaker jokes it must be up to 400 parts. The approach is one use per episode, judged by what it actually does for a website, a marketing team or a business. Wireframing is a good example. The discussion grants that a single prompt can generate full wireframes that look impressive at first, then moves to what the output forgot or misunderstood. It concludes that expertise is still required. Someone has to apply best practices and confirm that the design can be built within a real timeline and budget, and one speaker notes that the tool was working from a blog post supplied as source material. The image episode weighs ethics, trust and ownership, the questions that come up once AI images enter a marketing workflow. It stops short of a blanket rejection. One voice concedes that an AI collage can be good enough for a social post most people only glance at, while insisting that there are still lines. Video is framed partly around creativity versus speed, with a skeptical look at ads promising a whole product from one typed sentence. The series also stops for an interlude on AI companies' Super Bowl commercials. The speakers find those ads selling savings in time and effort that the tools do not deliver, and they wonder aloud what that says about how tired people are. The tone turns with coding. Having spent many episodes, by their own account, bashing AI, the speakers call building with code the use with the most potential, and they run the same prompt through three different tools. They set code quality aside for now and wonder whether a second run of the same prompt would produce different code. For conversational search, the show departs from its usual lineup and brings in an outside guest, Will Noble of Squiz. That conversation covers the new facelift for the site search bar, sprawling sites with hundreds or thousands of pages nobody has curated for a long time, and why the old trick of excluding weak content does not carry over neatly to language models. Chad and Cole recur across episodes, with a lead voice who routinely hands Cole the topic introduction and jokes that people must be sick of it. Each episode opens with a short setup that ends in an invitation to start discussing stupid. The talk is loose and self-deprecating, with fumbled sayings left in and a passing worry from one speaker about becoming like the AI. What a listener gets is a grounded, hype-resistant sense of where AI helps with digital work and where a person still has to finish the job.

Made for: Suits a listener who is responsible for a website, marketing content or internal systems and wants a candid, conversational take on which AI tools are worth bringing into that work. It also fits someone who is wary of AI advertising but still wants to find the useful parts.

What sets it apart: It works through AI one practical use per episode, from wireframes and images to code and site search, asking what each one saves and what still needs a person. Because its skepticism is stated outright, the praise it does give, notably for AI-assisted coding, carries weight.

In their own words

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

Why you'd press play

The AI wireframe looks great; your development budget would like a word.

Press play if you want

  • a second opinion before you let AI-generated layouts dictate what your team builds
  • help deciding when an AI image is useful and when it puts trust at risk
Read the full recommendation in PlayNext →
AI-generated wireframesethics and ownership of AI imagesAI video for businessAI-assisted coding toolsconversational and site searchAI advertising hypehuman expertise alongside AI

Talks about

Best episodes of Discussing Stupid: A byte-sized podcast on stupid UX

Short reviews from the PlayNext desk, based on the episodes we processed.

S3E13.1 - Intentional AI: What the rise of conversational search means for your websiteApr 7, 2026

A practical look at why conversational search starts with content discipline.

Conversational search gets its real test on websites too large to navigate with confidence. Discussing Stupid brings in Will Noble of Squiz, the show's first outside guest, to look at what changes when a search bar that may have accounted for roughly 9 to 12 percent of website…

S3E12 - Intentional AI: AI might struggle with creativity, but coding isn't creativeMar 24, 2026

A grounded test of AI-generated accordion code, accessibility constraints, and the consistency questions developers still have to answer.

AI gets a more credible workout here than in recent talk about videos, images, and the Super Bowl. Colt and Chad narrow the frame to web development, asking whether pattern-based work, like building an accessible accordion component, is where the technology can do useful labor.

S3E11 - Intentional AI: AI video rewards planning, not your ideasMar 10, 2026

A grounded reminder that useful AI video starts with business purpose, not just a prompt.

This episode treats AI video less as a novelty and more as a planning discipline. Before anyone starts generating clips, the discussion keeps returning to the business question: what is the piece supposed to do?

S3E10 - Intentional AI: The Super Bowl didn't sell AI, it exposed itFeb 24, 2026

A Super Bowl wave of AI ads leads to a sharper test of what the technology actually improves.

Super Bowl advertising turns into a referendum on AI's public sales pitch in Discussing Stupid, as the hosts weigh a night full of big promises against the smaller question of what the technology actually improves.

S3E9 - Intentional AI: Just because AI can create images doesn't mean you should use themFeb 10, 2026

A grounded look at when AI image generation saves time and when it raises trust and ownership concerns.

Discussing Stupid gives AI image generation a grounded pressure test, moving past wireframes and layouts into static visuals such as imagery, graphics, and logos.

Podcasts like Discussing Stupid: A byte-sized podcast on stupid UX

Episodes

  1. 1

    S3E13.1 - Intentional AI: What the rise of conversational search means for your website

    Hidden gem

    ["\"Discussing Stupid\" brings in Will Noble from Squiz to talk with Virgil and Colt about conversational search on websites and internal systems.", "Will frames the shift as moving from link retrieval to answer retrieval, using the librarian-and-encyclopedias analogy to explain why it changes user experience.", "The episode focuses on the risk side too: old PDFs, buried policy pages, and content that an LLM can surface as confident but wrong answers.", "The most concrete rollout advice is to start with one narrow slice, like a 50-page student-life area inside a 250,000-page university site, and let unrelated questions fall back to keyword search."]

    Apr 7, 2026·27m·1 clip
  2. 2

    S3E12 - Intentional AI: AI might struggle with creativity, but coding isn't creative

    Hidden gem

    Discussing Stupid's S3E12, "Intentional AI: AI might struggle with creativity, but coding isn't creative," argues that web development is the clearest use case for AI.

    Mar 24, 2026·26m·1 clip
  3. 3

    S3E11 - Intentional AI: AI video rewards planning, not your ideas

    Hidden gem

    Discussing Stupid S3E11 looks at intentional AI in video and tests three tools against the show's accessibility article.

    Mar 10, 2026·23m·1 clip
  4. 4

    S3E10 - Intentional AI: The Super Bowl didn't sell AI, it exposed it

    Discussing Stupid examines Super Bowl advertising for AI, including the hosts' estimate that 23% of 66 commercials involved AI and that a 30-second spot cost $8–10 million.

    Feb 24, 2026·20m·1 clip
  5. 5

    S3E9 - Intentional AI: Just because AI can create images doesn't mean you should use them

    Hidden gem

    Discussing Stupid S3E9, "Intentional AI: Just because AI can create images doesn't mean you should use them," weighs AI image generation against trust, ownership, and deepfake-style risk.

    Feb 10, 2026·29m·2 clips
  6. 6

    S3E8 - Intentional AI: The real value of AI wireframes is NOT the wireframes

    Hidden gem

    Discussing Stupid S3E8 examines whether AI wireframe generation helps UX work or merely creates more material to fix.

    Jan 28, 2026·29m·2 clips
  7. 7

    S3E7 - Intentional AI: Why AI can make your content personalization worse

    Hidden gem

    Discussing Stupid: A byte-sized podcast on stupid UX examines why AI-driven personalization can make audience targeting more complex than sales pitches suggest.

    Jan 13, 2026·26m·1 clip
  8. 8

    S3E6 - Intentional AI: You’re asking AI to solve the wrong problems for SEO/GEO/AEO

    Virgil, Cole, and Seth compare SEO, AEO, and GEO, arguing that AI optimization still depends on good content, structure, accessibility, and plain language.

    Dec 16, 2025·26m·1 clip
  9. 9

    S3E5 - Intentional AI: How much can you trust AI for accessibility?

    Virgil ran the company's expertise page through AI for an accessibility review and found it flagged metaphors and tab-order problems but wrongly reported missing alt text on alternate images.

    Dec 2, 2025·23m·1 clip
  10. 10

    S3E4 - Intentional AI: The role of AI in content management

    Nov 11, 2025·21m
  11. 11

    S3E3 - Intentional AI: Smarter content creation with AI

    Oct 28, 2025·20m
  12. 12

    S3E2 - Intentional AI: Maximizing AI for research & analysis

    Oct 14, 2025·22m
  13. 13

    S3E1 - Intentional AI: Applying AI across the content lifecycle

    Sep 30, 2025·19m
  14. 14

    Season 3: The Teaser

    Sep 9, 2025·3m
  15. 15

    S2E18: What it really takes to build accessible forms

    Jun 24, 2025·19m
  16. 16

    S2E17: Why inconsistent layouts wreck your UX

    Jun 10, 2025·18m
  17. 17

    S2E16: Headless vs traditional CMS: Which one fits your organization?

    May 27, 2025·16m
  18. 18

    Headless vs traditional CMS: Which one fits your organization?

    May 27, 2025·16m
  19. 19

    S2E15: What separates good projects from great ones? Proper testing.

    May 13, 2025·22m
  20. 20

    S2E14: Want good UX? Expect less from your audience.

    Apr 29, 2025·19m
  21. 21

    S2E13.1: Keys to balancing aesthetics and accessibility in web design

    Apr 15, 2025·16m
  22. 22

    S2E12: Finding the metadata "Goldilocks zone"

    Apr 1, 2025·18m
  23. 23

    S2E11: The challenges of translating design into a responsive website build

    Mar 18, 2025·19m
  24. 24

    S2E10: The real work starts AFTER your project launches

    Mar 4, 2025·20m
  25. 25

    S2E9: The chaos of modern workplace collaboration

    Feb 18, 2025·17m
  26. 26

    S2E8: Bad mobile button design is driving us crazy

    Feb 4, 2025·18m
  27. 27

    S2E7: AI alone won't fix your crappy content

    Jan 21, 2025·14m
  28. 28

    S2E6: Are websites evolving or devolving?

    Jan 7, 2025·15m
  29. 29

    S2E5: Font mistakes that are costing you big time

    Dec 17, 2024·16m
  30. 30

    S2E4: Why search systems fail without semantics

    Dec 3, 2024·14m
  31. 31

    S2E3: If you want people to read your content, make your content readable!!

    Nov 12, 2024·17m
  32. 32

    S2E2: Big images, slow loading

    Oct 29, 2024·17m
  33. 33

    S2E1: Your poorly written alt text doesn't go unnoticed...

    Oct 15, 2024·16m
  34. 34

    Season 2: The Teaser

    Oct 1, 2024·5m
  35. 35

    The Semantics of Search | Brett Matson, Funnelback

    May 15, 2019·46m
  36. 36

    Consistent UX across multiple channels | Kanwal Khipple, 2toLEAD

    A podcast discussing stupid UX practices and how to improve digital experiences across websites and Microsoft tools.

    Mar 13, 2019·45m
  37. 37

    What's Old is New Again | Chad Heinle & Joel Baglien, High Monkey

    Host Virgil Carroll returns to discuss outdated tech practices that are becoming relevant again, with guests Chad Heinle and Joel Bagley.

    Jan 30, 2019·45m
  38. 38

    Reducing friction in your digital content creation | Martin Michalik, Kentico

    Oct 24, 2018·44m
  39. 39

    Making sense of diversity in digital messaging | Heather Newman, Creative Maven

    Sep 19, 2018·51m
  40. 40

    Creating inclusive digital experiences – getting your content contributors onboard | Doug Burgett, University of Illinois

    May 23, 2018·38m
  41. 41

    MonkeyByte 3.5: GDPR Readiness Scorecard

    May 16, 2018·8m
  42. 42

    Being a HERO with your customer’s data (and understanding what you have) | Liam Cleary, SharePlicity & Rencore

    The episode discusses GDPR compliance from a UX perspective, focusing on handling personal data behind the scenes.

    May 9, 2018·36m
  43. 43

    GDPR and Your Consent

    May 2, 2018·6m
  44. 44

    Preparing your website for GDPR (or just because privacy matters) | David Komarek, Kentico

    Apr 25, 2018·30m
  45. 45

    AI & Machine Learning

    Apr 18, 2018·6m
  46. 46

    The hype and sensibility of Artificial Intelligence in Search | Ben Tilley, Funnelback

    Host Virgil Carroll interviews Ben Tilley about integrating AI into search engines to improve digital customer experience.

    Apr 11, 2018·35m