Episode
#191 - Throwback: UX Lessons from a Decade Researching AI with Jess Holbrook of Microsoft
- Podcast
- Awkward Silences
- Published
- Jun 9, 2026
- Duration seconds
- 2969
- Processing state
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Summary
This week we're revisiting one of Awkward Silences' most memorable episodes. Much of the conversation around AI in UX involves how it will shape and change researchers' work. This episodes's guest, Jess Holbrook, who leads UX research for Microsoft AI, thinks a lot about how this technology can be improved with design and UX best practices. Jess has spent over a decade working on the UX of AI at companies like Meta and Google. He's also helped develop foundational principles for the ethical use of LLMs. Jess joined Erin and Ben to reframe the AI conversation, focusing on how UXRs can and should adapt, what working on these systems has taught him about the UX discipline, and his philosophy for building teams that are ready to take on the innovative challenges of tomorrow. Jess's recommendations: Matt Webb , Maggie Appleton , and the Pessimists Archive Newsletter . Highlights 07:15 Human-Centered AI Evolution 17:53 Evolving AI Forecast Strategies 24:04 Diverse AI Team Building 33:27 Navigating Responsible AI Challenges 37:01 Qualitative Analysis with AI Tools 40:15 Optimism and Concerns About AI About Jess Senior Director of Research specializing in human-centered AI. Early stage investor in AI, AI hardware ecosystems, climate, and anything that seems like the world would be better with it in it. Currently leading UX research for Microsoft AI. Previously led the Generative AI team and supported all UX functions for the Responsible AI and data transparency teams at Meta. I also served on the Board of Forging Youth Resilience, a nonprofit that empowers young people to build physical and mental strength for life by providing access to a national network of community-based fitness programs and mentorship. Resources The AI in UX Research Report 20+ Tools for Every Research Ph…