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 performanceA 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.pdfUpcoming 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 ReviewWhether 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 previewSubscribe 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:

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