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Discussing Stupid: A byte-sized podcast on stupid UXAuthor: High Monkey
Discussing Stupid returns to the airwaves to transform digital facepalms into teachable momentsall in the time it takes to enjoy your coffee break! Sponsored by High Monkey, this podcast dives into stupid practices across websites and Microsoft collaboration tools, among other digital realms. Our "byte-sized" bi-weekly episodes are packed with expert insights and a healthy dose of humor. Discussions focus on five key areas: Business Process & Collaboration, UX/IA, Inclusive Design, Content & Search, and Performance & SEO. Join us and lets start making the digital world a bit less stupid, one episode at a time. Visit our website at https://www.discussingstupid.com Language: en Genres: Business, Marketing, Technology Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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S3E7 - Intentional AI: Why AI can make your content personalization worse
Episode 7
Tuesday, 13 January, 2026
In Episode 7 of the Intentional AI series, Cole and Virgil focus on content personalization and why it is one of the most overpromised areas of AI. While personalization is often positioned as simple and automated, doing it well requires far more clarity and intent than most tools suggest.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:What content personalization actually meansRole based versus behavioral personalizationWhy personalization adoption remains lowThe balance between relevance and creepinessHow AI supports personalization without replacing strategyA role based email comparison of Perplexity, Copilot, and ClaudeA downloadable Episode Companion Guide is available below with tool comparisons and practical takeaways.DS-S3-E7-CompanionDoc.pdfPreviously in the Intentional AI series:Episode 1: Intentional AI and the Content LifecycleEpisode 2: Using AI for Research and AnalysisEpisode 3: AI and Content CreationEpisode 4: Content Management and AIEpisode 5: How much can you trust AI for accessibility?Episode 6: You’re asking AI to solve the wrong problems for SEO, GEO, and AEONew episodes every other Tuesday.For more conversations about AI and digital strategy, visit
