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.

DS-S3-E5-CompanionDoc.pdf

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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https://www.discussingstupid.com/

Watch us on YouTube:

https://www.youtube.com/@discussingstupid

Listen on Apple Podcasts, Spotify, or Soundcloud:

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 lifecycle
• Common use cases like translation, auto-summary fields, and accessibility checks
• Where automation makes sense and where it doesn’t
• The biggest risks of AI content management, from oversimplification to data privacy
• Why good input (clear, readable content) still determines good output
• How 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 — 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 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,...

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 lifecycle
• Why AI-generated content often takes just as much time as writing from scratch
• The key risks of AI content creation, including accuracy, effort, and authenticity
• How to maintain your voice, tone, and originality when using AI tools
• Why humans are still responsible for quality control and credibility
• What 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