#164 - UX Lessons from a Decade Researching AI with Jess Holbrook of Microsoft
Awkward Silences9 Huhti 2025

#164 - UX Lessons from a Decade Researching AI with Jess Holbrook of Microsoft

Much of the conversation around AI in UX involves how it will shape and change researchers' work. Today's guest, Jess Holbrook, who leads UX research for Microsoft AI, has been thinking 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 joins 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

Jaksot(191)

#185 -  How to Use AI Without Losing Your Research Soul with Nikki Anderson of Drop in Research

#185 - How to Use AI Without Losing Your Research Soul with Nikki Anderson of Drop in Research

Ben Wiedmaier sits down with user research consultant Nikki Anderson to explore how researchers can stay relevant when budgets are tight and stakeholders are stressed. Nikki runs Drop in Research wher...

17 Maalis 52min

#184 - Use Context For More Influence with Kristen DeLap of Econify

#184 - Use Context For More Influence with Kristen DeLap of Econify

Ben talks with Kristen DeLap, fractional COO at Econify, to explore how UX'ers can build influence without formal authority. Kristen brings a unique perspective, having evolved from interior design to...

3 Maalis 39min

#183 - The Best Ways to Use AI in UX Research with Laura Klein of NN/g

#183 - The Best Ways to Use AI in UX Research with Laura Klein of NN/g

Erin and Ben chat with Laura Klein, Principal Experience Specialist at Nielsen Norman Group, about the practical realities of AI in user research. Laura teaches a class on AI for researchers and bring...

17 Helmi 48min

#182 - The Future of Research (In a Moment of Change)

#182 - The Future of Research (In a Moment of Change)

Ben sits down with Basel Fakhoury, CEO and Co-founder of User Interviews, and Baran Erkel, Chief Strategy Officer at UserTesting, for a conversation about the research industry's evolution. With AI re...

3 Helmi 40min

#181 - Why We Need Design Now More Than Ever with Karl Randay of 383

#181 - Why We Need Design Now More Than Ever with Karl Randay of 383

Ben Wiedmaier sits with Karl Randay, Experience Director at 383, to explore how designers can stay relevant in an increasingly automated world. Karl shares insights from working with major brands like...

20 Tammi 51min

#180 - What to Fix in '26 with Maria Rosala of NN/g & John Whalen of Brilliant Experience

#180 - What to Fix in '26 with Maria Rosala of NN/g & John Whalen of Brilliant Experience

Ben is joined by Maria Rosala from Nielsen Norman Group and John Whalen from Brilliant Experience to wrap up 2025 and make some predictions for 2026. Maria and John share practical insights on everyth...

6 Tammi 55min

#179 - The Future of Research Operations with Kate Towsey LIVE

#179 - The Future of Research Operations with Kate Towsey LIVE

Erin May sits down with Kate Towsey, founder of Cha Cha Club and author of Research That Scales, for Research Ops Appreciation Week. Kate shares insights from producing an audio documentary series on ...

22 Joulu 202555min

#178 - How to Measure What Matters with Lyndsi Lee of Turnitin

#178 - How to Measure What Matters with Lyndsi Lee of Turnitin

Ben talks with Lyndsi Lee, UX Manager at Turnitin, about moving beyond traditional metrics like NPS and CSAT to measure user experiences more effectively. The conversation centers on outcome-based ass...

9 Joulu 202547min

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