
#191 - Throwback: UX Lessons from a Decade Researching AI with Jess Holbrook of Microsoft
From Awkward Silences by User Interviews
June 9, 2026 · 49 min · Episode 204
About this episode
Jess Holbrook discusses the intersection of UX and AI, sharing insights from his extensive experience in the field.
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…
People in this episode
Hosts: Erin, Ben
Guest: Jess Holbrook
Topics covered
- UX research
- AI technology
- human-centered design
- ethical AI
- team building
- qualitative analysis
Keywords
- UX
- AI
- research
- human-centered design
- ethical use
- qualitative analysis
- team building
Mentioned in this episode
Organizations: Microsoft, Meta, Google, Pessimists Archive Newsletter
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