Will explains the shift with a clean analogy early in the episode. Traditional search is like asking a librarian for help and getting handed a stack of encyclopedias. Conversational search is that same librarian reading every book in the library and handing you a direct answer. The user experience improvement is real. But so is what it depends on, because the AI reads everything, including the outdated policy documents buried in a subdomain that nobody has touched in a decade. When dormant content gets surfaced as a confident answer, the gap between what was published and what is actually true becomes a reputational and legal problem.

The practical guidance that emerges from the conversation is to start with a defined slice of content you know is solid. Will walks through a real example of a university with 250,000 pieces of content that scoped its initial conversational search implementation to 50 pages focused on student life. Questions related to that area got clean, accurate answers. Everything else defaulted to traditional keyword search. That controlled scope is what allowed the project to prove value before expanding, and it is what kept stakeholders from pulling the plug the moment a bad result surfaced.

The garbage-in, garbage-out principle has always been true in search. What this episode makes clear is that it has never carried higher stakes. LLMs do not skip the bad content. They find it, surface it, and present it with confidence. The first step toward getting conversational search right is the same step the rest of this series keeps coming back to: know what you are working with before you deploy.

Previously in the Intentional AI series:

• Episode 1: Intentional AI and the Content Lifecycle
• Episode 2: Maximizing AI for Research and Analysis
• Episode 3: Smarter Content Creation with AI
• Episode 4: The role of AI in content management
• Episode 5: How much can you trust AI for accessibility
• Episode 6: You’re asking AI to solve the wrong problems for SEO, GEO, and AEO
• Episode 7: Why AI can make your content personalization worse
• Episode 8: The real value of AI wireframes is NOT the wireframes
• Episode 9: Just because AI can create images doesn't mean you should use them
• Episode 10: The Super Bowl didn't sell AI, it exposed it
• Episode 11: AI video rewards planning, not your ideas
• Episode 12: AI might struggle with creativity, but coding isn't creative

New episodes every other Tuesday.

For more conversations about AI, design, and digital strategy, visit https://www.highmonkey.com/podcast and subscribe on your favorite podcast platform.

(0:00) - Intro

(0:51) - Meet Will Noble from Squiz

(2:14) - Today's topic: Conversational search

(4:14) - Welcome to the new era of information seeking

(7:10) - The dormant content problem

(9:48) - You can ignore the problem, but it won't ignore you

(11:45) - Where do you start with thousands of pages?

(14:36) - Start small, don't go big

(17:14) - AI's opportunity as a content auditing tool

(20:39) - Search is the foundation of everything AI does

(22:13) - How do you keep up when AI moves this fast?

(25:43) - Outro

Subscribe for email updates on our website:

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Chad makes clear that for working developers, AI is already genuinely useful. Generating boilerplate, producing code blocks for well-understood functionality, and cutting down on time spent typing out repetitive structures. These are real wins. The catch is that getting value out of AI-generated code still requires knowing what you're looking at. If you can't read the output, you can't catch the errors, and you can't fix what's wrong.

That gap becomes more visible when you consider who these tools are being marketed to. The pitch is often aimed at business users and non-developers, promising a fast path from idea to working product. The episode digs into why that gap -- between what gets generated and what is actually usable -- is harder to close in code than it is in content or images. A piece of writing that's 80% there can be polished. Code that's 80% there can be a liability, especially if the person using it doesn't know what the other 20% is.

Virgil tested Claude, ChatGPT, and GenSpark against the same prompt: build a visually appealing, fully accessible accordion web component using the series source article. All three produced something workable. None were perfect. Claude handled screen reader accessibility well but had a JavaScript bug that prevented the drawers from opening and used a low-contrast color scheme. ChatGPT produced the most functional but visually flat result, with the worst screen reader compliance. GenSpark produced the most polished visual, with the most helpful follow-up prompts, and landed in the middle on accessibility. As Virgil put it, these were the least failures the series has generated, which is saying something.

Previously in the Intentional AI series:

Episode 1: Intentional AI and the Content Lifecycle

Episode 2: Maximizing AI for Research and Analysis

Episode 3: Smarter Content Creation with AI

Episode 4: The role of AI in content management

Episode 5: How much can you trust AI for accessibility

Episode 6: You’re asking AI to solve the wrong problems for SEO, GEO, and AEO

Episode 7: Why AI can make your content personalization worse

Episode 8: The real value of AI wireframes is NOT the wireframes

Episode 9: Just because AI can create images doesn't mean you should use them

Episode 10: The Super Bowl didn't sell AI, it exposed it

Episode 11: AI video rewards planning, not your ideas

New episodes every other Tuesday.

For more conversations about AI, design, and digital strategy, visit https://www.highmonkey.com/podcast and subscribe on your favorite podcast platform.

(0:00) - Intro

(0:44) - Today's topic: Intersection of AI & coding

(2:46) - The "just type and get a website" myth

(3:44) - Where AI actually helps with coding

(6:08) - When "good enough" works and when it doesn't

(8:13) - The real win: Using AI as a developer

(11:06) - Tool test: building an accordion with AI

(13:14) - Testing Claude

(16:23) - Testing ChatGPT (Codex)

(18:25) - Testing GenSpark

(20:25) - Using AI to fix AI code

(23:11) - Tons of opportunity with AI and coding

(24:16) - Outro

Subscribe for email updates on our website:

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In Episode 11 of Season 3's Intentional AI series, Virgil and Cole take on AI video generation, arguably the most complex and most hyped area of AI content creation. Video production has always been expensive, often running thousands of dollars per minute through traditional workflows. AI tools are pitched as the solution to that cost. The reality is more complicated.

The core question Cole raises early: are you using AI for speed, or for creativity? With video, that matters even more than with text or images, because the ability to edit what AI generates is extremely limited. You are largely working with what comes back.

Virgil tested three tools, Claude, Artlist, and Sora, using the same prompt and the same source article the series has been following. The results varied wildly. Some tools produced clean, factually grounded output that could serve as a foundation with additional editing. Others burned through resources quickly and delivered results that raised more questions than they answered (to put it lightly). Each tool had tradeoffs between creative quality, turnaround time, cost, and practical usability.

The pattern held across the board: AI video does not reward vague ideas. It rewards storyboarding, defined objectives, and clear constraints. The most realistic use case is not generating entire videos from scratch, but using AI for individual pieces -- a specific animation, a graphic element, a rough draft to react to.

AI video is getting better. But better does not mean ready.

Previously in the Intentional AI series:

Episode 1: Intentional AI and the Content Lifecycle

Episode 2: Maximizing AI for Research and Analysis

Episode 3: Smarter Content Creation with AI

Episode 4: The role of AI in content management

Episode 5: How much can you trust AI for accessibility

Episode 6: You’re asking AI to solve the wrong problems for SEO, GEO, and AEO

Episode 7: Why AI can make your content personalization worse

Episode 8: The real value of AI wireframes is NOT the wireframes

Episode 9: Just because AI can create images doesn't mean you should use them

Episode 10: The Super Bowl didn't sell AI, it exposed it

New episodes every other Tuesday.

For more conversations about AI, design, and digital strategy, visit https://www.highmonkey.com/podcast and subscribe on your favorite podcast platform.

(0:00) - Intro

(1:04) - The good & bad of AI video generation

(1:30) - Are you using AI for speed or creativity?

(3:56) - Structure up front = your best friend

(7:28) - How Coinbase used simplicity to stand out

(8:42) - More Super Bowl AI narrative unpacking

(10:20) - We tested 3 tools for AI video generation

(11:47) - Testing Claude

(14:24) - Testing Artlist

(16:32) - Testing Sora

(19:03) - Closing thoughts & takeaways

(21:40) - 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

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We unpack what was actually being sold, what was implied, and what gets left out when AI is positioned as effortless.

AI has value. We are not arguing that it does not. But it works best when it is used intentionally and within clear boundaries. When it is marketed as a replacement for thinking, planning, or strategy, that is where things fall apart.

If you are trying to separate signal from noise, this one is for you.

Previously in the Intentional AI series:

1. Episode 1: Intentional AI and the Content Lifecycle
2. Episode 2: Maximizing AI for Research and Analysis
3. Episode 3: Smarter Content Creation with AI
4. Episode 4: The role of AI in content management
5. Episode 5: How much can you trust AI for accessibility
6. Episode 6: You’re asking AI to solve the wrong problems for SEO, GEO, and AEO
7. Episode 7: Why AI can make your content personalization worse
8. Episode 8: The real value of AI wireframes is NOT the wireframes
9. Episode 9: Just because AI can create images doesn't mean you should use them

New episodes every other Tuesday.

For more conversations about AI, design, and digital strategy, visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro

(0:42) - We had to talk about the Super Bowl

(2:05) - The numbers behind AI in the Super Bowl

(3:55) - How AI is marketed vs reality of AI

(7:30) - This is why we started Intentional AI

(8:30) - Reflections on the current realities of AI

(13:20) - Where does AI make the most sense?

(15:30) - Our reaction to the AI generated ads

(17:30) - Join us and learn to be responsible with AI

(19:00) - Outro

**Also disclaimer: there is a math error at 18:15 - the correct calculation is closer to $100-150 million.**

Subscribe for email updates on our website:

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The conversation focuses on why images became the public on ramp to AI and why that familiarity creates risk. Visuals feel harmless, but the moment AI starts generating finished looking images, teams inherit decisions around ownership, ethics, and trust that they are often unprepared to make.

A central theme of the episode is responsibility escalation. As AI reduces the effort required to create images, the importance of human judgment increases. Treating AI generated visuals as final work can quickly introduce legal, ethical, and reputational problems.

Virgil shares a practical experiment where he used a simple prompt to generate three social media promotional graphics from an existing article and tested the results across three tools: Canva, Claude, and Artlist.

Canva produced the most generic and repetitive designs. Claude delivered cleaner structure and stronger messaging but struggled with fonts, formats, and variation. Artlist created the most visually interesting outputs, though it introduced workflow limitations and cost concerns.

The episode reinforces a consistent conclusion across the series. AI can help jumpstart visual work, but it cannot replace judgment, intent, or responsibility.

In this episode, they explore:

1. Why AI images are so tempting to use
2. Where AI generated graphics actually help
3. Why most AI visuals fall flat
4. Ethical and ownership risks teams overlook
5. A comparison of Canva, Claude, and Artlist

A downloadable Episode Companion Guide is available below with example outputs and tool takeaways.

https://links.discussingstupid.com/s3e9companion

Previously in the Intentional AI series:

1. Episode 1: Intentional AI and the Content Lifecycle
2. Episode 2: Maximizing AI for Research and Analysis
3. Episode 3: Smarter Content Creation with AI
4. Episode 4: The role of AI in content management
5. Episode 5: How much can you trust AI for accessibility
6. Episode 6: You’re asking AI to solve the wrong problems for SEO, GEO, and AEO
7. Episode 7: Why AI can make your content personalization worse
8. Episode 8: The real value of AI wireframes is NOT the wireframes

New episodes every other Tuesday.

For more conversations about AI, design, and digital strategy, visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro

(1:40) - You can’t escape AI imagery

(3:18) - Why AI images are risky

(4:40) - The legal and ethical line

(6:15) - Creativity vs time and cost

(9:28) - Every tool has hopped on the AI bandwagon

(13:20) - The slippery slope of AI visuals

(15:35) - We tested 3 tools for AI visuals

(17:30) - Testing Canva

(20:40) - Testing Claude (Opus)

(22:15) - Testing Artlist

(24:15) - Tool testing takeaways

(26:45) - Closing thoughts

(28:00) - Outro

Subscribe for email updates on our website:

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Listen on Apple Podcasts, Spotify, or Soundcloud:

https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024

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The conversation focuses on where AI genuinely helps in the wireframing process and where it introduces new risks. Wireframes are meant to establish structure, hierarchy, and intent, not just visual output. While AI can quickly generate layouts, components, and patterns, it still requires strong human judgment to evaluate what is correct, what is missing, and what could cause problems downstream.

A key theme of the episode is escalation of responsibility. As AI reduces the time required to create wireframes, the importance of human review, direction, and decision making increases. Treating AI generated wireframes as finished work can introduce serious risks, especially around accessibility, content fidelity, maintainability, and overall project direction.

Virgil shares an experiment where he used AI to first generate a detailed prompt for wireframing, then tested that prompt across three tools: Claude, Google Gemini 3, and Figma Make. The results reveal clear differences in layout quality, accessibility handling, content retention, and how easily the outputs could be integrated into real workflows.

Claude produced the strongest layout and structural patterns but failed badly on accessibility and removed large portions of content. Gemini generated simpler wireframes with clearer structure, but used even less content and still struggled with accessibility. Figma Make stood out for workflow integration, retaining all content and allowing direct editing inside Figma, though it also failed accessibility requirements and relied heavily on generic styling and placeholder imagery.

Throughout the episode, the group returns to the same conclusion. AI is extremely effective at getting the first portion of wireframing done quickly. It is far less effective at making judgment calls, enforcing standards, or understanding context without guidance.

In this episode, they explore:

1. How wireframing fits into the content lifecycle
2. Why speed changes the risk profile of design work
3. Using AI to generate prompts instead of starting from scratch
4. Where AI wireframes succeed and where they fail
5. Accessibility and content risks in AI generated layouts
6. A wireframing comparison of Claude, Gemini 3, and Figma Make

A downloadable Episode Companion Guide is available below with tool comparisons and key takeaways.

DS-S3-E8-CompanionDoc.pdf

Previously in the Intentional AI series:

1. Episode 1: Intentional AI and the Content Lifecycle
2. Episode 2: Maximizing AI for Research & Analysis
3. Episode 3: Smarter Content Creation with AI
4. Episode 4: The role of AI in content management
5. Episode 5: How much can you trust AI for accessibility?
6. Episode 6: You’re asking AI to solve the wrong problems for SEO/GEO/AEO
7. Episode 7: Why AI can make your content personalization worse

New episodes every other Tuesday.

For more conversations about AI, design, and digital strategy, visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro

(1:12) - Why wireframing belongs in the content lifecycle

(2:24) - Wireframing is hard / The appeal of AI here

(4:08) - Using AI to create the prompt for wireframing

(5:27) - Why prompt creation unlocks the real value

(7:15) - AI wireframing = filling in blanks & reacting

(10:34) - Risks for teams without wireframing expertise

(12:21) - Using AI to ask better questions, not skip thinking

(13:57) - Iterating prompts and adding constraints

(15:24) - We tested 3 AI tools for wireframing

(15:56) - Testing Claude

(19:41) - Testing Gemini

(21:05) - Testing Figma Make

(24:56) - Practical takeaways and best use cases

(26:50) - Outro

Subscribe for email updates on our website:

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Listen on Apple Podcasts, Spotify, or Soundcloud:

https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024

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They break personalization into two main approaches. Role based personalization tailors messages for specific audiences or job functions, while behavioral personalization adapts experiences based on how people interact with content over time. The conversation also touches on predictive analysis and where AI may eventually help interpret patterns across analytics data.

A central theme of the episode is trust. Using AI for personalization assumes the system understands audience priorities and pain points. Without clear direction, AI fills in the gaps with assumptions. Cole and Virgil explain why personalization has always been difficult to implement, why adoption remains low, and why AI does not remove the need for strategy, measurement, or human judgment.

The episode also addresses the risks of personalization. Messages that are too generic get ignored, while messages that feel overly personal can cross into uncomfortable territory. Finding the right balance is still a human responsibility.

In the second half of the episode, they continue their ongoing experiment using the same AI written accessibility article from earlier episodes. This time, they test three tools by asking them to generate role based promotional emails for a head of web marketing, a director of information technology, and a C level executive. The results highlight meaningful differences in tone, structure, and assumptions across tools.

The takeaway is consistent with the Intentional AI series. AI can support personalization, but only when you define goals, outcomes, and boundaries first.

In this episode, they explore:

1. What content personalization actually means
2. Role based versus behavioral personalization
3. Why personalization adoption remains low
4. The balance between relevance and creepiness
5. How AI supports personalization without replacing strategy
6. A role based email comparison of Perplexity, Copilot, and Claude

A downloadable Episode Companion Guide is available below with tool comparisons and practical takeaways.

DS-S3-E7-CompanionDoc.pdf

Previously in the Intentional AI series:

1. Episode 1: Intentional AI and the Content Lifecycle
2. Episode 2: Using AI for Research and Analysis
3. Episode 3: AI and Content Creation
4. Episode 4: Content Management and AI
5. Episode 5: How much can you trust AI for accessibility?
6. Episode 6: You’re asking AI to solve the wrong problems for SEO, GEO, and AEO

New episodes every other Tuesday.

For more conversations about AI and digital strategy, visit www.discussingstupid.com and subscribe on your favorite podcast platform.

(0:00) - Intro

(0:56) - Delivering tailored content with AI

(1:30) - Different kinds of AI personalization

(4:10) - Why personalization can be tricky

(5:00) - The need for measurement and outcomes

(7:45) - The Personalization Pendulum™

(10:00) - The work doesn’t go away!

(13:10) - We tested 3 AI tools for personalization

(16:10) - Testing Perplexity

(18:10) - Testing Copilot & Claude

(19:20) - Explaining our prompting process

(21:25) - The topic of AI replacing human labor

(24:30) - Outro

Subscribe for email updates on our website:

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Listen on Apple Podcasts, Spotify, or Soundcloud:

https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024

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Search engines andgenerative models have both gotten smarter. Keyword tricks, shortcuts, and “secret sauce” tactics no longer work the way they once did. Instead, visibility now depends on clear intent, strong structure, accessible language, and content that actually helps people. The group looks at how SEO history is repeating itself, why organizations keep chasing hacks, and how that mindset actively works against long-term discoverability.

They also dig into how SEO, GEO, and AEO overlap, where they differ, and why writing exclusively for AI can backfire by alienating human readers. The conversation covers content modeling, headless-style structures, and why these approaches help machines understand relationships without sacrificing usability.

A major focus of the episode is schema. The team explains why schema is becoming increasingly important for generative engines, why it is difficult and error-prone to manage at scale, and where AI can help draft complex schema structures without fully understanding context. This leads to a broader point. AI can accelerate specific tasks, but it cannot replace judgment, prioritization, or review.

In the second half of the episode, they continue their ongoing experiment using the same AI-written accessibility article from earlier episodes. They test how three tools approach GEO-focused improvements. Each tool surfaces different insights, none of them are complete on their own, and all of them require human decision-making to be useful. The takeaway is consistent with the theme of the series. AI is powerful when you ask it to solve the right problems, and dangerous when you expect it to fix foundational issues for you.

In this episode, they explore:

• Why SEO, GEO, and AEO fail when treated as optimization tricks
• How search has shifted from keywords to clarity, structure, and intent
• Where SEO and GEO overlap and where they meaningfully diverge
• The risk of writing for AI instead of for people
• Why content modeling supports both search engines and generative engines
• How AI can assist with schema creation and where humans must intervene
• Why repeating the same schema everywhere weakens its value
• A GEO-focused comparison of Writesonic, Grammarly, and Claude
• Why broad prompts underperform and targeted prompts lead to better outcomes

A downloadable Episode Companion Guide is available below. It includes tool notes, schema examples, prompt guidance, and practical takeaways for applying AI to search without losing clarity or control.

DS-S3-E6-CompanionDoc.pdf

Previously in the Intentional AI series:

• Episode 1: Applying AI to the content lifecycle
• Episode 2: Maximizing AI for research and analysis
• Episode 3: Smarter content creation with AI
• Episode 4: The role of AI in content management AI
• Episode 5: How much can you trust AI for accessibility?

Upcoming episodes in the Intentional AI series:

• Jan 6, 2026 – Content Personalization
• Jan 20, 2026 – Wireframing and Layout
• 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

Holiday break notice

Discussing Stupid will be taking a short break for the holidays. The next new episode will be released on January 6th.

Whether you work on websites, structured content, or digital strategy, this episode is about recognizing when AI is being asked to solve the wrong problems. The goal is not more optimization. It is clearer intent, better structure, and content that actually deserves to be found.

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

(0:37) - Boosting your SEO, GEO & AEO with AI

(1:10) - Virgil on how SEO history is repeating itself

(4:08) - Defining SEO & GEO overlaps

(7:04) - Is a headless CMS better for GEO?

(8:27) - Schema generation is awesome with AI

(13:54) - If you tag everything, you’ve tagged nothing

(15:18) - We tested 3 AI tools for SEO/GEO/AEO

(16:39) - Testing Writesonic

(18:16) - Testing Grammarly

(19:33) - Testing Claude

(20:54) - Every AI tool has gaps & you’re the filler

(23:49) - Next episode preview…

(24:55) - Outro

Subscribe for email updates on our website:

https://www.discussingstupid.com/

Watch us on YouTube:

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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

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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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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:

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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:

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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.

DS-S3-E2-CompanionDoc.pdf

Upcoming episodes in the Intentional AI series:

• Oct 28, 2025 — Content Creation
• 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 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:

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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:

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Watch us on YouTube:

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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:

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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 accessibility
• How poor form validation breaks user experience and trust
• What it really takes to make dynamic forms work properly
• The 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:

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https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024

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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 problems
• How users feel bad design before they can explain it
• The difference between visual theming and layout consistency
• What a consistent structure looks like across homepage, sections, and detail pages
• Why 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

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While flashy features and buzzwords like “omnichannel” dominate vendor pitches, the real decision comes down to your organization’s resources, structure, and long-term goals. Chad and Virgil dive into the practical realities of each approach, helping you cut through the hype and avoid the biggest mistakes teams make when choosing a CMS.

They also explore:

• Why your internal team structure matters more than the CMS features
• The rise (and reality) of content hubs and static site generators
• What “freedom” really means in a headless setup
• How traditional and headless CMSs are merging in unexpected ways
• Why reuse and omnichannel content sound good—but rarely happen

Whether you’re in IT, marketing, or somewhere in between, this episode will help you make smarter, more grounded tech decisions.

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

(2:10) - It's not about the CMS, it's about your team

(4:44) - Headless gives you freedom - if you're ready for it

(6:36) - Traditional & headless are starting to look alike

(9:56) - Don't choose a CMS based on buzzwords

(12:00) - There's no perfect CMS - just the right one for you

(15:00) - Outro

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From accessibility issues to ripple effects caused by last-minute code changes, Seth walks us through what great QA really looks like—and why it’s not just a checklist you run through before launch. The team discusses how QA needs to be methodical, repeatable, and fully integrated into your build process—not an afterthought.

They also explore:

• Why QA isn’t just testing—it’s marketing
• How staging environments save you from public embarrassment
• The value of fresh eyes and non-developer perspectives
• Common QA mistakes and how to avoid them
• Why accessibility should never be separated from quality

Whether you’re a developer, content manager, strategist, or digital lead, this episode will change the way you think about testing and quality.

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

(3:04) - Seth's QA role at high monkey

(4:45) - Quality testing is best done by a fresh set of eyes

(6:47) - QA is about systems, not spot checks

(11:06) - Why you need a staging environment

(14:18) - How to stay methodical with your testing

(16:36) - Baking accessibility into your QA process

(18:06) - A quality site = top tier marketing

(19:52) - Outro

Subscribe for email updates on our website:

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https://podcasts.apple.com/us/podcast/discussing-stupid-a-byte-sized-podcast-on-stupid-ux/id1428145024

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But here’s the hard truth: they’re not.

That’s why UX exists—to design for inattention, not perfection. In this episode, Virgil and Cole explore how small misjudgments in interface design can lead to big problems, and why it’s time to stop blaming the user and start designing smarter.

They dig into key lessons and takeaways, including:

• Why assuming users will “just pay attention” is a guaranteed way to fail
• The danger of designing tools for internal teams instead of real users
• How AI and other tools can mislead teams if used without critical thinking
• Why user feedback beats assumptions—every single time
• What it really means to design for the lowest common denominator

From confusing buttons and abandoned carts to real-world usability failures, Virgil shares insights from decades of experience that highlight how easy it is to get digital experiences wrong when we ignore how people actually behave.

If you’ve ever wondered why people keep screwing up your carefully planned interface—or if you’re trying to build something that works for all humans, not just ideal ones—this episode’s for you.

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

(2:10) - People don't pay attention

(4:41) - Are people bad at browsing or is tech too complex?

(6:49) - Will AI shape the future of UX?

(10:50) - The gap between internal assumptions and real user needs

(14:27) - Build for the lowest common denominator

(17:40) - Outro

Subscribe for email updates on our website:

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While color choices often get made in design tools or branding meetings, they don’t always translate well to real-world implementation. The crew breaks down why the prettiest colors can create the ugliest accessibility problems once they hit the web.

They dig into key challenges and lessons, including:

• Why accessible design isn’t just about having the right colors—it's about using them correctly
• How contrast ratios break down across devices and screen sizes
• Why bright and “fun” color palettes often fail accessibility testing
• How to bring visual flair to a site without sacrificing inclusivity
• The difference between decorative vs. purposeful color use—and why it matters

From failed color combinations to misused font sizing, Virgil, Cole, and Chad share their own battle scars from High Monkey’s recent site redesign—and explain how inclusive design forces teams to think functionally, not just aesthetically.

If you’ve ever struggled to make your brand colors work on the web—or if you're tired of your site failing contrast tests but you still want some color pop—this episode’s for you.

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

(2:43) - Accessibility and your brand's color palette

(6:03) - Factoring in font sizes

(7:54) - I still want color pop on my website!!

(11:36) - The approach we took with our new site's color scheme

(15:13) - Outro

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Metadata plays a huge role in findability, search accuracy, and content structure. But when it comes to tagging your content, more isn’t always better—and less definitely isn’t enough. That’s where the concept of the “metadata Goldilocks zone” comes in.

They unpack the most common metadata mistakes and what to do instead, including:

• Why under-tagging leaves your site relying on search engine guesswork
• How over-tagging renders metadata meaningless
• What makes a tag actually useful (and when it’s just noise)
• How to approach metadata as an evolving strategy—not a one-time fix

Virgil shares hard-won lessons from consulting across industries, explaining why metadata success depends on both the structure and the context of your content. From internal file systems to public websites, they explore how to build better tagging frameworks without falling into analysis paralysis.

To wrap things up, they offer a practical rule of thumb for anyone managing metadata: optimize for the 80% of user needs first—and let real usage data guide the rest.

For more conversations about digital strategy, search, UX, 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

(2:27) - What even is metadata?

(4:10) - Metadata is not one-size-fits-all 

(7:20) - The dangers of under tagging

(10:00) - The dangers of over tagging

(12:43) - Finding the “Goldilocks” zone with metadata

(15:30) - Virgil’s verdict: Follow the 80/20 rule

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In Episode 11, host Virgil Carroll is joined by co-host Cole from High Monkey, along with developer Chad, to tackle a common but frustrating issue—why web designs that look perfect in Figma often fall apart when built for real-world use.

They explore the biggest challenges of translating static designs into fully responsive websites, including:

• The problem with designing for just one screen size
• Why text, images, and layouts often break in development
• What developers wish designers knew about responsive design
• Lessons learned from their own website redesign mistakes

Chad shares a developer’s perspective on why rigid, pixel-perfect designs don’t always work and how to approach layouts with flexibility in mind. Through real-world experiences—including High Monkey’s own site rebuild—the team discusses the need for good communication between design and development and how to avoid the most common headaches.

To close things out, they share practical tips on designing for multiple screen sizes, working more effectively with developers, and ensuring that your website doesn’t just look great—it actually functions for all the devices browsing your website.

New intro, new look, new website, same crew ready to help you avoid dumb digital mistakes! Join us every two weeks for fresh episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

(0:00) - Intro

(2:06) Design is checkers… development is chess

(4:53) Common responsive design fails

(7:18) Unfortunately we are speaking from experience.

(11:09) How many breakpoints do you design for???

(15:40) Designers & developers need to talk

(18:07) - Outro

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Virgil and Cole discuss the continuous effort required to maintain and grow digital projects like blogs, podcasts, websites, and more. They share personal experiences and lessons learned about adapting strategies based on analytics and listener feedback. The conversation highlights how even successful launches need follow-up actions to keep the momentum going and ensure long-term engagement.

As the episode progresses, they explore the importance of constantly evolving digital marketing tactics to meet changing audience needs. Insights are shared on how they are in the process of tweaking their podcast's format and content to prevent listener drop-off, especially during the intro.

To wrap up, practical tips are offered on how to effectively use analytics to drive content improvements and audience retention strategies. Listeners will gain a better understanding of the necessity for resilience in digital marketing and how to make incremental changes that significantly impact their projects' success.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

(0:00) - Intro

(0:47) - Let's hear it for Episode 10!!!

(1:56) - The work starts POST launch

(3:30) - Change is in the air for Discussing Stupid

(5:18) - Our takeaways after 10 episodes

(7:10) - Establish value RIGHT AWAY

(8:45) - Analytics. Analytics. Analytics.

(10:55) - A message for those who made it this far

(11:36) - Digital marketing is not just social media

(13:45) - Time to eat our own dog food

(14:40) - Cole is moving into a penthouse

(15:20) - Be intentional with your analytics & engagement

(17:00) - Discussing Stupid is now a live case study

(18:30) - Outro

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Virgil and Cole explore how the abundance of tools often leads to scattered conversations, lost information, and inefficiency, rather than better collaboration. They discuss real-world examples of how context gets lost in endless message threads, how teams juggle disconnected platforms, and why no single tool seems to solve the problem.

As the conversation unfolds, they dig into why the issue isn’t just the tools, but also the processes behind them. They explore what effective workplace collaboration really looks like, sharing insights on how teams can reduce tool overload, set clear communication guidelines, and establish a single source of truth to prevent chaos.

To close, they offer practical takeaways on improving collaboration—whether through better workflows, tool integration, or just picking a platform and sticking to it. Listeners will walk away with a clearer understanding of why collaboration is broken and what steps can actually make it better.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com 

(0:00) - Intro

(1:24) - Modern collaboration: Many tools, little clarity

(4:00) - Why the "perfect collaboration tool" is a false promise

(7:30) - The path to streamlining collaboration

(12:00) - It's about strategy, not just software

(15:00) - Outro

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Virgil, Chad, and Cole highlight the pitfalls of prioritizing aesthetics over functionality, sharing real-life examples of frustrating mobile experiences—like accidentally disliking articles in Apple News due to poorly placed buttons. They dive into the broader challenges of mobile-first design, discussing how designers often fail to account for varying finger sizes, touch accuracy, and real-world usage patterns.

As the discussion unfolds, the team offers actionable insights for improving mobile usability. From creating larger, well-spaced buttons to understanding mobile interaction patterns, they outline best practices to ensure users can navigate and interact with apps and websites effortlessly.

To close, the team reflects on the importance of practical testing and design iteration to deliver seamless mobile experiences. Listeners will leave with practical tips and a deeper appreciation for the role of thoughtful design in modern digital experiences.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

(0:00) - Intro

(1:57) - Calling out poor mobile button design

(3:46) - Some real life frustrations

(6:07) - Challenges of mobile first design

(9:11) - Optimizing mobile separately from desktop

(12:17) - Think about how people operate

(14:35) - Practical tips for better mobile buttons

(17:00) - Outro

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Virgil and Cole delve into the nuances of AI’s capabilities, examining the gap between its marketing promises and practical limitations. They discuss tools like schema.org and highlight the challenges organizations face in defining content effectively for AI and search engines. Drawing from years of experience, Virgil emphasizes that AI is only as good as the content it analyzes, echoing the need for robust content governance and thoughtful strategy.

To wrap up, the duo discusses the potential applications of AI in areas like coding and keyword generation while cautioning against viewing it as a quick fix for deeper organizational issues. Listeners will leave with a clear understanding of how to prepare their content and strategies for success in an AI-driven world.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

(0:00) - Intro

(1:38) - Safe to say AI is the buzz right now

(3:10) - Practical capabilities VS marketing hype

(3:55) - Schema.org and AI

(5:50) - AI is not a silver bullet

(9:40) - Staying ahead in the transition to AI search

(11:21) - AI will only be as good as your content

(12:40) - End

Link to the CMSWire Article mentioned: https://www.cmswire.com/digital-experience/the-growing-importance-of-schemaorg-in-the-ai-era/?utm_campaign=cm&utm_content=all-articles-rss&utm_medium=web&utm_source=cmswire.com

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Virgil and Cole explore the history of web design, from the simplicity of early 2000s websites to the rise of stylistic trends like Flash, hero images, and parallax scrolling. They discuss how the pursuit of flashy, modern designs can overshadow usability, creating obstacles for users trying to complete tasks. Drawing on decades of experience, Virgil shares insights into the “form vs. function” debate, emphasizing that good design prioritizes purpose and user needs.

To wrap up, the duo highlights the growing trend toward simplicity in web design and the importance of finding a balance between aesthetics and practicality. Listeners will leave with a deeper understanding of how to create websites that are both visually engaging and user-friendly.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

(0:00) - Intro

(1:26) - Websites have gotten too complicated

(3:13) - Evolution of web design trends

(4:43) - Form vs Function: An age old battle

(6:59) - When did style over substance get big?

(8:53) - The pressure to keep up with trends

(10:15) - It's about balancing form and function

(13:55) - Outro

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The team discusses:

• Why using too many fonts on a website creates confusion and slows down performance.
• The importance of keeping fonts readable and how font size and weight affect usability.
• Real-world examples of font mistakes, including when and where decorative fonts can work—and when they don’t.
• How poor typography choices can kill website performance, particularly through improper font loading.

To wrap up, they discuss actionable best practices, including limiting font selections, optimizing font files for performance, and always keeping your audience in mind when choosing typography.

By the end of this episode, you’ll gain practical insights to help your website achieve both aesthetic appeal and functional clarity—without sacrificing performance.

This marks the final episode of 2024, and we want to thank all of you for joining us this year! We’ll be taking a short break for the holidays but will return in 2025 with more episodes, more “stupid,” and more expert advice to help you avoid common digital mistakes.

Until then, like, review, and subscribe on your favorite podcast platform, and visit www.discussingstupid.com for updates and resources.

Happy holidays, and see you in the new year!

(0:00) - Intro & holiday spirit

(1:44) - Welcome back, Chad

(2:20) - Too many fonts = chaos

(4:05) - Learning from print design

(5:25) - Typography as Art vs. Function

(6:23) - The hidden cost of fancy fonts

(8:04) - Should some fonts be banned?

(10:11) - Know your audience and the context

(12:06) - With fonts, less is more 

(14:28) - Outro & happy holidays!

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Virgil and Cole discuss common issues with search systems, such as treating every search term the same and ignoring common phrases and alternative names. They share real-world examples, like a bank where users searched for one name in numerous ways, illustrating the need for search systems to recognize and account for these variations. The team also emphasizes that improving search functionality requires more than just turning it on—it involves continuous work, testing, and understanding of user behavior.

To wrap up, Virgil highlights best practices, including using “push search” technology to guide users to the right results and leveraging search analytics to understand how people are searching. By the end of the episode, listeners will gain practical insights into making search more intuitive and user-friendly. 

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

(0:00) - Intro

(1:26) - A lot of search systems suck

(1:57) - Search needs semantics

(3:04) - Search with VS without semantics 

(4:48) - When AB&T meets AB and T

(6:14) - The English language is funny

(8:00) - The power of curated results

(10:50) - Virgil's biggest piece of advice

(12:41) - Outro

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The team discusses common readability mistakes like using too much jargon, confusing sentence structure, and not keeping the audience in mind. Virgil shares examples from government and education where content wasn’t simple enough. They explain why it’s important to know your audience and keep language clear, especially for government websites that need to be at an 8th-grade reading level.

The episode also includes a demo using Readable.com, where Virgil and Cole show how to take a sentence and make sure it is clear and easy to read. This example shows why keeping content simple helps people understand and stay engaged.

By the end of this episode, you’ll have tips to make your content easy to read and understand, reaching a wider audience.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

LINKS

Readable.com: https://www.readable.com/

Watch a clip of Virgil and Cole using Readable.com to enhance content clarity:

https://youtu.be/5NW1A2ZSD4E

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They discuss common mistakes people make with large images—like shrinking images in HTML without optimizing file size—and how these errors can negatively impact both the user experience and SEO rankings. The team shares insights into how to avoid these pitfalls and explores how tools like RIOT (Radical Image Optimization Tool) can help reduce file sizes without sacrificing image quality.

You'll also hear about the often overlooked balance between mobile and desktop optimization. The team highlights why simply resizing images for mobile isn’t enough and explains how poor image handling can lead to sluggish performance on mobile devices, frustrating users and hurting your site's overall effectiveness.

By the end of this episode, you'll walk away with actionable tips on optimizing images for both performance and SEO, ultimately improving your site’s speed and user experience.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

LINKS

Riot (Radical Image Optimization Tool): https://riot-optimizer.com/

Riot demo clip from this episode: https://youtu.be/kL3nu5Mj8VA

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Virgil, Chad, and Cole discuss the significance of alt text in creating an inclusive digital experience. They emphasize that alt text is not merely about ticking boxes for WCAG or ADA compliance. Instead, it plays a crucial role in enhancing accessibility and inclusivity for individuals who rely on screen readers. The discussion covers the various types of images—decorative, practical, and informative—and offers insights on how to accurately describe them to improve the digital experience for everyone.

The episode also explores the limitations of relying solely on AI to generate alt text, underscoring the importance of human-crafted, meaningful descriptions that can profoundly impact users who depend on assistive technologies. Furthermore, the team shares practical tips on integrating inclusive design practices into your content creation process, ensuring that your digital content is accessible and understandable to all users.

Throughout the episode, you'll gain valuable knowledge on how to implement best practices for alt text and learn why it's essential to consider inclusivity at every stage of your content lifecycle. By the end of the discussion, you'll be equipped with the tools and insights needed to make your digital content more accessible and inclusive.

Join us every two weeks for new episodes, and don’t forget to like, review, and subscribe on your favorite podcast platform. For more resources and updates, visit www.discussingstupid.com.

LINKS

Tools mentioned:

Wave: https://wave.webaim.org/

Lighthouse: https://developer.chrome.com/docs/lighthouse/overview/

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Virgil and Cole discuss the shift from long-form interviews to concise, 10-15 minute episodes designed to provide actionable insights. This season will cover a range of topics, from alt text best practices to the pitfalls of relying too heavily on AI for accessibility. The goal is to offer practical advice that listeners can immediately apply in their own work.

In addition to audio, the podcast will now include video episodes, allowing for more dynamic content and visual examples. For those who prefer audio-only, detailed show notes will ensure no one misses out on the valuable information shared.

Don't miss out on the latest updates and exclusive content—subscribe to Discussing Stupid on their website, and follow them on YouTube, Apple Podcasts, Spotify, or Soundcloud. Get ready for a season packed with insightful discussions on UX and digital best practices!

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Brett shares that there are several big things coming in the area of search, after reaching a plateau and stagnation for a few years. Some of these are paradigmatic (understanding the search has multiple purposes, not just page rankings,) and some include changing the approach (i.e. modifying queries,) changing presentation of results (modules,) knowledge graphs, semantic search (detecting the intent of the query,) and many more. 

Brett explores how some of these new technologies are intrinsically more attractive to people. For example, knowledge graphs are (or can be) visual and show relations between entities in them. Thus, they are much more intuitive in contrast to being faced with a wall of data to choose from. The point is, of course, making content a lot more intelligent and hence more useful, by treating it as a product and perfecting its delivery. 

In Brett’s opinion, during the next decade we will see a real proliferation of smart tools that will help users and companies perform a significantly better search. Virgil and Brett also discuss how it is very important to avoid making too many connections when using a new, powerful technology that can do that. This can bog down the whole organization, its data servers, employees, and finally, users.

Virgil’s conversation with Brett is very rich and diverse, so make sure to listen to the whole episode and pay close attention to what he had to share. 

Links:

Episode mentioned:

Future-proofing your experience delivery strategy with Intelligent Content by Kate Skinner.

Siraj Raval's YouTube channel is full of short, fun videos that teach all different aspects of machine learning and AI.

Coursera's Machine Learning course, one of the original online machine learning courses, delivered by leading AI researcher Andrew Ng.

A great article by Sebastien Dery discussing the challenges of knowledge graphs. 

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One of the major challenges of UX is adopting a tool (or tools) that can sometimes be too complex and can feel burdensome. For UX design to be successful, it is important to understand the users themselves and how they utilize your services or business’s tools. For that reason, it’s important to note and map how consumers find your tools and how they use the tools. Another important aspect of UX design is to not overwhelm users. For example, one common error is overloading them with notifications that they cannot manage or turn off.  Building a road map where the whole process will help the users and the company as well.

There are 3 facets of UX – navigation, search, and the actual content. The best approach is to focus on one of these, excel at it, gather feedback, and continuously improve.

Buzzword for this episode: seamlessness

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Virgil starts the discussion by highlighting the developments and changes in web design. While previously a web developer was essential to program and put together a website, today with advanced CMSs almost anyone can build a website and almost everyone does. Chad voices his concern of a current issue that was not present before – now people who are not well versed in web development have tools at their disposal to create websites; however, many of these non-developers tend to make subpar websites. Chad believes, however, that people are coming to realize that for the sake of efficiency and ease of use, more consideration is going into who makes a website. Virgil also shares his take on user-friendly website development and its correlation with technology growth. Joel brings to light the fact though many years have passed; yet for many organizations, institutions, and companies, their websites are still inaccessible to certain site visitors. Joel suggests that this can be rectified with proper design, development, and content role allocation. With the recent push for more simplistic, accessible sites the need for knowledgeable web developers and programmers has returned. 

This trend has also changed things in the domain of search engine design. Search engines have become better at finding and displaying information. However, if a user is drowned in information and is not able to quickly find the information he needs, he will most likely not use the search engine or the website that he happens to be on again. There’s the simple truth that some companies and messages resonate with visitors and potential customers, while others don’t. In order for your message to resonate, you need to be efficient. One should also aim to use the platforms that fit your company, message, and brand – for instance, don’t focus on Twitter if you are a visually oriented company. 

Another trend that contributed to the recent strive towards simplicity is that the everyday activities of people have become digital. This digital-centeredness can be overwhelming and socially stressful for some people with having to deal with different media sources, information, platforms, and passwords on a daily basis. Hence, the desire to have more simplified search capability and user-ability, since having to navigate the daily digital landscape is complicated already. The difference between today and a decade ago is that things that are done now need to have a purpose – rarely are elements on websites there just to have them there.

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As the conversation unfolds, Martin defines content friction as everything that causes inefficiency or damage throughout the content lifecycle. Martin breaks down some of the friction his teams experienced around new product launches. Namely, how they found it difficult to decide who would write the content, how to craft a cohesive message, and how to collaborate efficiently as a team. Martin and Virgil talk about how to build beneficial workflow systems and avoid perpetuating the problems you’re trying to fix. 

Next, Martin shared numerous technological and workflow issues that he has witnessed throughout his career. Some of these issues include inefficient file storage where hundreds of emails are exchanged, failing to work on the most recent version of a file in collaborative projects, bottlenecked team structures where a plethora of decisions have to be made by a single person, and more. Virgil then asks Martin about how Kentico Cloud is working to streamline the collaborative content-creation process, help brands craft a cohesive message, and improve the journey from ideation to execution. 

After the conversation winds down, Virgil dives into Stupid Buzz, where he talks about a buzzword that gets on his nerves. This week’s buzzword is “omnichannel.” Virgil shares his concerns about the way that people use the term incorrectly and points back to its legitimate meaning, which implies understanding your content on a microscopic and big-picture level as it relates to the various platforms it’s being published on. In short, omnichannel content is far more complex and specific than many people suggest through their inaccurate use of the term. 

LINKS

Learn more about Kentico Cloud

https://www.kentico.com/

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During the discussion, Virgil and Heather ‘get real’ on how the conversation around diversity is changing the digital marketing landscape and share some big (and sometimes funny) screw-ups and successes along the way. In the end, the conversation explores the complex topic, pokes fun at many of our predisposed ideas about how diversity in messaging works (its not just about your person count in images) and gives real world examples on the dos and donts we should all try to follow.

Resources discussed:

• https://www.creativemaven.com/ - Heather's marketing agency
• https://storybrand.com/ - Story Brand
• https://www.microsoft.com/en-us/diversity/ - Microsoft Global Diversity and Inclusion
• https://www.womeninsharepoint.com/ - Women in SharePoint
• https://www.womenintechnology.org/ - Women in Technology
• https://www.womenshistory.org/ - National Women's History Museum

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During the podcast, Virgil and Doug discuss the challenges we all face keeping our digital properties accessible. Add to the mix that we have to train our contributors to use the tools at our disposal in an educated way. According to Burgett, “When content editors use WYSIWYG editors they don’t realize that as the enter content into the editor, code is actually being created in the back end. Knowing this helps content editors to Realize the power they have at their fingertips.” Once consistency among content editors has been achieved, Virgil and Doug discuss bad practices to avoid, look at some of the monitoring tools and techniques you can employ, and explore how to provide your customers with all-inclusive digital experiences.

Resources discussed:

• https://developers.google.com/amp/ - Google’s mobile first development methodology
• https://www.w3.org/TR/wai-aria-practices-1.1/ - Understanding the use of ARIA tags
• https://fae.disability.illinois.edu/anonymous/?Anonymous%20Report=/ - University of Illinois’s Functional Accessibility Evaluator
• https://webaim.org/ - Online accessibility compliance auditor
• https://www.paciellogroup.com/resources/contrastanalyser - Accessibility color contrast tester

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During this enlightening discussion, Virgil and Liam discuss the bigger problem in the way we handle customer data, that is, do we actually know where it goes? According to Liam, "One of the key things to focus on regarding GDPR is to make sure you understand how the data moves around and really how it integrates in other applications and systems that you might utilize it in." Take a customer's email as one example; you can forward it in an email, add it to a CRM, put it in an order tracking system, or add it to your email subscription list. But, can you find all of that customer's data and know how to remove it if you receive a request to do so? Virgil and Liam also discuss the importance of good processes and procedures and some of the realities around the effort it takes to be compliant.

If you care about your customer's private data once you have it, then you might want to give a listen.

Resources discussed:

• https://www.eugdpr.org/ - European Union GDPR regulations
• https://www.marketo.com/ - Online marketing automation system
• https://techcommunity.microsoft.com/t5/Security-Privacy-and-Compliance/Compliance-Manager-Preview-is-now-available/ba-p/124662 - Microsoft’s Compliance Manager
• https://ec.europa.eu/eurostat/cros/ - European Commission official stats site

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To help gain a better perspective on GDPR, Virgil is joined by David Komárek, the Content Management Product Owner at Kentico Software. David led the charge at his organization to make Kentico CMS software to be one of the first fully GDPR-compliant Content Management Software solutions on the market. During the discussion, David will share the complex journey Kentico had to take and what they learned about their own data practices as well as those of their customers. David recommends "First, try to learn as much as you can about GDPR . . . use somebody who is informed in GDPR and who can educate your internal staff . . . then look at the data and what you're doing with it". Virgil and David also discuss how to understand what is important to do in managing your customer’s privacy and give some good real-world advice on how to start your compliance journey.

Resources discussed:

• https://www.kentico.com/product/all-features/marketing/gdpr-and-data-protection - About Kentico’s GDPR readiness
• https://www.kentico.com/product/resources/whitepapers/gdpr-compliance-and-your-cms/gdpr-compliance-and-your-cms.pdf - Whitepaper on being GDPR compliant
• https://www.eugdpr.org/ - European Union GDPR regulations

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Listening to this discussion, you will discover that implementing AI in search is not all that easy (shocker!!) and still requires you to follow good content and search practices. Where AI has many practical applications in search, effort is still needed and fundamentals need to be followed. In the end, AI cannot fix your search if your content still sucks.

There is reason to hope, good AI can be very helpful. According to Ben, "Being able to use some form of natural language processing to extract information out of your written text and turn that back into structure is a great way you can start to improve search."

Throughout this episode, Virgil and Ben will share the challenges you will face while giving you thoughts on how you can get your content and search ready to be able to use AI to its full potential.

Resources discussed:

• https://www.wolframalpha.com/ - one of the first search engines to use AI
• https://www.westpac.com.au/ - example organization using AI in their search

Helpful articles from Funnelback:

• https://www.funnelback.com/blog/artificial-intelligence-why-the-farmer-killed-the-fox
• https://www.funnelback.com/blog/intelligent-question-answering
• https://www.funnelback.com/blog/is-the-future-of-search-proactive

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