Discussing Stupid: A byte-sized podcast on stupid UX

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.

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.

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.

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 lifecycle
• The major risks of using AI for research, including accuracy, bias, and misinformation
• Why trust, verification, and validation are now part of your job
• Security and legal concerns around AI scraping and data usage
• How different tools handle citations, transparency, and usability
• Why 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.

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 automation
• The 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’t
• Why teaching AI and understanding your process are inseparable
• The dangers of unchecked automation, from bad content to legal risk

Upcoming episodes in the Intentional AI series:

• Oct 14, 2025 — Research & Analysis
• Oct 28, 2025 — Content Creation
• Nov 11, 2025 — Content Management & Accessibility
• Dec 2, 2025 — SEO / AEO / GEO
• Dec 16, 2025 — Content Personalization
• Jan 6, 2026 — Front End Development & Wireframing
• Jan 20, 2026— Design & Media
• Feb 3, 2026 — Back End Development
• Feb 17, 2026 — Conversational Search (with special guest!)
• Mar 3, 2026 — Chatbots & Agentic AI
• Mar 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: