#191 - Throwback: UX Lessons from a Decade Researching AI with Jess Holbrook of Microsoft

#191 - Throwback: UX Lessons from a Decade Researching AI with Jess Holbrook of Microsoft

Author: User Interviews June 9, 2026 Duration: 49:29

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


Awkward Silences is a conversation about the human side of building things. Hosts Erin May and Carol Guest, both VPs at User Interviews, don't just talk about theory-they get into the messy, real-world practice of talking to users and making sense of what they say. Each episode pulls back the curtain on the craft of user research, featuring candid chats with the practitioners who do this work every day. You'll hear stories about navigating tricky interviews, the weight of interpreting qualitative data, and how genuine understanding directly shapes better products and smarter business decisions. This isn't a dry lecture; it's a geeky, relatable dive into the questions and quiet moments that define UX research. The Awkward Silences podcast lives in the intersection of technology and business, focusing on the people and processes that connect them. Listen for practical insights, empathetic strategies, and the occasional shared laugh about the inevitable fumbles that come with trying to understand anyone. It’s for anyone who believes that building effectively starts with listening well.
Author: Language: English Episodes: 50

Awkward Silences
Podcast Episodes
#156 - Change Management with Graham Gardner of U.S. Bank [not-audio_url] [/not-audio_url]

Duration: 35:44
Change is an important and inevitable part of developing as a user experience professional. But what does change look like when it happens at the organizational level? That is the focus of this episode, featuring Graham…
#155 - Exploratory Design Research with Will Notini of IDEO [not-audio_url] [/not-audio_url]

Duration: 40:17
The consulting firm IDEO helped pioneer "design thinking" as a way to create products that better solve customer wants and needs, creating fans. Over 30 years later, the interplay between design and research has never be…
#154 - Building the UX Team of Tomorrow with Brad Orego of Webflow [not-audio_url] [/not-audio_url]

Duration: 45:05
The craft of UX research is at an all-time high. How research leaders structure, staff, and scale their teams is more important than ever. Erin and Carol are joined by Brad Orego, Head of Research at Webflow, to talk all…
#153 - Security-Minded UX with Caroline Morchio of Dashlane [not-audio_url] [/not-audio_url]

Duration: 33:55
In our Season 3 finale, Erin and Carol are joined by Caroline Morchio, Head of UX at Dashlane, a credential management platform. Their conversation explores UX research best practices at a security-minded organization li…