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 website
	• Where AI tools give useful insights and where they misinterpret content
	• Why conversational explanations can help non technical teams
	• How to prompt AI to look for the issues you actually care about
	• The importance of plain language and readable writing in accessibility
	• A readability comparison using Copilot, Perplexity, and Grammarly
	• Why 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.

https://links.discussingstupid.com/s3e5companion

Upcoming episodes in the Intentional AI series:
	• Dec 16, 2025 - SEO / AEO / GEO
	• Jan 6, 2026 - Content Personalization
	• Jan 20, 2026 - Front End Development and Wireframing
	• Feb 3, 2026 - Design and Media
	• Feb 17, 2026 - Back End Development
	• Mar 3, 2026 - Conversational Search (with special guest)
	• Mar 17, 2026 - Chatbots and Agentic AI
	• Mar 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


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

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.