Discussing Stupid: A byte-sized podcast on stupid UX

High Monkey
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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

  1. DEC 2

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

    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 accessibility review, where the tool gave helpful guidance, and where it completely misread the page. They also talk about the pieces of accessibility that AI handles surprisingly well, especially language, metaphors, and readability, and why these areas are often missed by standard scanners. In the second half of the episode, they continue the ongoing experiment from earlier episodes. Using the same AI written article from before, they test how three tools handle rewriting it to an adult eighth grade reading level, then compare the results with a readability checker. The differences across models show why simple writing, clear prompts, and human review are still necessary. In this episode, they explore: How AI evaluates accessibility on a real websiteWhere AI tools give useful insights and where they misinterpret contentWhy conversational explanations can help non technical teamsHow to prompt AI to look for the issues you actually care aboutThe importance of plain language and readable writing in accessibilityA readability comparison using Copilot, Perplexity, and GrammarlyWhy simple content supports both accessibility and AI performance A downloadable Episode Companion Guide is available below. It includes key takeaways, tool notes, prompt examples, and practical advice for using AI in accessibility work. DS-S3-E5-CompanionDoc.pdf Upcoming episodes in the Intentional AI series: Dec 16, 2025 - SEO / AEO / GEOJan 6, 2026 - Content PersonalizationJan 20, 2026 - Front End Development and WireframingFeb 3, 2026 - Design and MediaFeb 17, 2026 - Back End DevelopmentMar 3, 2026 - Conversational Search (with special guest)Mar 17, 2026 - Chatbots and Agentic AIMar 31, 2026 - Series Finale and Tool Review Whether you work on websites, content workflows, or internal digital tools, this conversation is about using AI with care. The goal is to work smarter, keep content readable, and avoid handing all of your judgment over to automation. New episodes every other Tuesday. 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. Chapters (0:00) - Intro (0:46) - Today’s focus: Accessibility with AI (1:20) - We let AI audit HighMonkey.com (4:00) - Finding the human value in AI feedback (6:25) - The power of strategic prompting (12:33) - We tested 3 AI tools for accessibility (14:49) - AI Tool findings (18:17) - Keep all your readers in mind (20:50) - Next episode preview Subscribe for email updates on our website: https://www.discussingstupid.com/ Watch us on YouTube: https://www.youtube.com/@discussingstupid Listen on Apple Podcasts, Spotify, or Soundcloud: a href="https://links.discussingstupid.com/applepodcasts" rel="noopener...

    23 min

  2. NOV 11

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

    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 where it still creates new challenges. Joined by returning guest Chad, they break down where AI fits, where it fails, and what happens when you trust it to translate complex content on its own. In this episode, they explore: How AI supports the content management stage of the lifecycleCommon use cases like translation, auto-summary fields, and accessibility checksWhere automation makes sense and where it doesn’tThe biggest risks of AI content management, from oversimplification to data privacyWhy good input (clear, readable content) still determines good outputHow readable, accessible writing improves both human and AI understanding This episode also continues the real-world experiment from previous episodes. Using the accessibility article originally created with Writesonic, the team tests how well three AI tools: Google Translate, DeepL, and ChatGPT, handle translating the piece into Spanish. The results reveal major differences in accuracy, tone, and overall usability across each model. A downloadable Episode Companion Guide is available below. It includes key takeaways, tool comparisons, and practical advice for using AI in the content management stage. DS-S3-E4-CompanionDoc.pdf 🦃 Note: We’re taking a short Thanksgiving break, the next episode will drop on December 2, 2025. Upcoming episodes in the Intentional AI series: Dec 2, 2025 — AccessibilityDec 16, 2025 — SEO / AEO / GEOJan 6, 2026 — Content PersonalizationJan 20, 2026 — Front End Development & WireframingFeb 3, 2026 — Design & MediaFeb 17, 2026 — Back End DevelopmentMar 3, 2026 — Conversational Search (with special guest!)Mar 17, 2026 — Chatbots & Agentic AIMar 31, 2026 — Series Finale & Tool Review Whether you’re managing websites, content workflows, or entire digital ecosystems, this conversation is about using AI intentionally, to work smarter without losing the human judgment that keeps content trustworthy. New episodes every other Tuesday. 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. Chapters (0:00) - Intro (0:50) - Today's focus: Content management with AI (1:58) - Content management opportunities with AI (6:18) - Recurring series theme: Trust (8:34) - Refine your process one step at a time (9:53) - Better content = better everything (10:22) - We tested 3 AI translation tools (12:02) - Cole's "elephant in the room" test (14:28) - Poor content = poor translations (16:58) - True translation happens between people (18:45) - Closing takeaways Subscribe for email updates on our website: https://www.discussingstupid.com/ Watch us on YouTube: https://www.youtube.com/@discussingstupid Listen on Apple Podcasts,...

    21 min

  3. OCT 28

    S3E3 - Intentional AI: Smarter content creation with AI

    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 and where it can’t replace the creative process. In this episode, they explore: How AI fits into the content creation stage of the lifecycleWhy AI-generated content often takes just as much time as writing from scratchThe key risks of AI content creation, including accuracy, effort, and authenticityHow to maintain your voice, tone, and originality when using AI toolsWhy humans are still responsible for quality control and credibilityWhat happens when you test the same research prompt across three writing tools This episode also continues the real-world experiment from Episode 2. Using the research compiled with Perplexity, the team tests how three content-generation tools—Jenni AI, Perplexity Pro, and Writesonic—handle the same writing task. The results reveal just how differently each model performs when asked to create original, publishable content. A downloadable Episode Companion Guide is available below. It includes key takeaways, tool comparisons, and practical advice for using AI in the content creation stage. DS-S3-E3-CompanionDoc.pdf Upcoming episodes in the Intentional AI series: • Nov 11, 2025 — Content Management • Dec 2, 2025 — Accessibility • Dec 16, 2025 — SEO / AEO / GEO • Jan 6, 2026 — Content Personalization • Jan 20, 2026 — Front End Development & Wireframing • Feb 3, 2026 — Design & Media • Feb 17, 2026 — Back End Development • Mar 3, 2026 — Conversational Search (with special guest!) • Mar 17, 2026 — Chatbots & Agentic AI • Mar 31, 2026 — Series Finale & Tool Review Whether you’re a marketer, strategist, or developer, this conversation is about creating content intentionally and keeping your human voice at the center of it all. New episodes every other Tuesday. 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. Chapters (0:00) - Intro (0:30) - Smarter content creation with AI (1:00) - Effort doesn't go away (3:20) - Tool / LLM differences (5:34) - Audience fit & voice (7:44) - We tested 3 tools for AI content creation (10:08) - Testing Jenni AI (13:23) - Testing Perplexity (14:55) - Testing Writesonic (16:55) - Key Takeaways Subscribe for email updates on our website: https://www.discussingstupid.com/ Watch us on YouTube: https://www.youtube.com/@discussingstupid Listen on Apple Podcasts, Spotify, or Soundcloud: https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024 https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0 a...

    20 min

  4. OCT 14

    S3E2 - Intentional AI: Maximizing AI for research & analysis

    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 need to be the researcher of the research. In this episode, they explore: How AI fits into the research and analysis stage of the content lifecycleThe major risks of using AI for research, including accuracy, bias, and misinformationWhy trust, verification, and validation are now part of your jobSecurity and legal concerns around AI scraping and data usageHow different tools handle citations, transparency, and usabilityWhy you can’t skip the human role in confirming, editing, and contextualizing AI outputs This episode also features the first step in a real experiment: researching a blog topic on digital accessibility using the tools Perplexity, ChatGPT, and Copilot. The results of that research will directly fuel the next episode on content creation. A downloadable Episode Companion Guide is available below. It includes key episode takeaways, tool comparisons, and practical guidance on how to use AI responsibly during the research stage. DS-S3-E2-CompanionDoc.pdf Upcoming episodes in the Intentional AI series: Oct 28, 2025 — Content CreationNov 11, 2025 — Content ManagementDec 2, 2025 — AccessibilityDec 16, 2025 — SEO / AEO / GEOJan 6, 2026 — Content PersonalizationJan 20, 2026 — Front End Development & WireframingFeb 3, 2026 — Design & MediaFeb 17, 2026 — Back End DevelopmentMar 3, 2026 — Conversational Search (with special guest!)Mar 17, 2026 — Chatbots & Agentic AIMar 31, 2026 — Series Finale & Tool Review Whether you’re a marketer, strategist, or developer, this conversation is about making AI adoption intentional and keeping your critical thinking sharp. New episodes every other Tuesday. 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 (1:44) - Better research with AI (3:46) - Risk: Trust & reliability (5:29) - Risk: Security/legal concerns (7:04) - Risk: Hallucinations (9:17) - We tested 3 tools for AI research (11:03) - Testing Perplexity (14:38) - Testing ChatGPT (17:45) - Testing Copilot (19:54) - Comparing the tools and key takeaways (20:52) - Outro Subscribe for email updates on our website: https://www.discussingstupid.com/ Watch us on YouTube: https://www.youtube.com/@discussingstupid Listen on Apple Podcasts, Spotify, or Soundcloud: https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024 https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0 a href="https://links.discussingstupid.com/soundcloud" rel="noopener noreferrer"...

    22 min

  5. SEP 30

    S3E1 - Intentional AI: Applying AI across the content lifecycle

    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 automationThe 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’tWhy teaching AI and understanding your process are inseparableThe dangers of unchecked automation, from bad content to legal risk Upcoming episodes in the Intentional AI series: Oct 14, 2025 — Research & AnalysisOct 28, 2025 — Content CreationNov 11, 2025 — Content Management & AccessibilityDec 2, 2025 — SEO / AEO / GEODec 16, 2025 — Content Personalization Jan 6, 2026 — Front End Development & WireframingJan 20, 2026— Design & Media Feb 3, 2026 — Back End DevelopmentFeb 17, 2026 — Conversational Search (with special guest!)Mar 3, 2026 — Chatbots & Agentic AIMar 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 Subscribe for email updates on our website: https://www.discussingstupid.com/ Watch us on YouTube: https://www.youtube.com/@discussingstupid Listen on Apple Podcasts, Spotify, or Soundcloud: https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024 https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0 a href="https://links.discussingstupid.com/soundcloud" rel="noopener noreferrer"...

    19 min

  6. SEP 9

    Season 3: The Teaser

    “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. Subscribe for email updates on our website: https://www.discussingstupid.com/ Watch us on YouTube: https://www.youtube.com/@discussingstupid Listen on Apple Podcasts, Spotify, or Soundcloud: https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024 https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0 https://soundcloud.com/discussing-stupid Check Us Out on Socials: https://www.linkedin.com/company/discussing-stupid https://www.instagram.com/discussingstupid/ https://www.facebook.com/discussingstupid https://x.com/DiscussStupid

    3 min

  7. JUN 24

    S2E18: What it really takes to build accessible forms

    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 accessibilityHow poor form validation breaks user experience and trustWhat it really takes to make dynamic forms work properlyThe 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 Subscribe for email updates on our website: https://www.discussingstupid.com/ Watch us on YouTube: https://www.youtube.com/@discussingstupid Listen on Apple Podcasts, Spotify, or Soundcloud: https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024 https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0 https://soundcloud.com/discussing-stupid Check Us Out on Socials: https://www.linkedin.com/company/discussing-stupid https://www.instagram.com/discussingstupid/ https://www.facebook.com/discussingstupid https://x.com/DiscussStupid

    19 min

  8. JUN 10

    S2E17: Why inconsistent layouts wreck your UX

    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 problemsHow users feel bad design before they can explain itThe difference between visual theming and layout consistencyWhat a consistent structure looks like across homepage, sections, and detail pagesWhy 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. 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 (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 Subscribe for email updates on our website: https://www.discussingstupid.com/ Watch us on YouTube: https://www.youtube.com/@discussingstupid Listen on Apple Podcasts, Spotify, or Soundcloud: https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024 https://open.spotify.com/show/0c47grVFmXk1cco63QioHp?si=87dbb37a4ca441c0 https://soundcloud.com/discussing-stupid Check Us Out on Socials: https://www.linkedin.com/company/discussing-stupid https://www.instagram.com/discussingstupid/ https://www.facebook.com/discussingstupid https://x.com/DiscussStupid

    18 min
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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

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