#168 - Summer Throwback: Amy Chess on Asking Better Questions

#168 - Summer Throwback: Amy Chess on Asking Better Questions

Author: User Interviews June 12, 2025 Duration: 40:00

Welcome to Summer Throwbacks, where we revisit some of Awkward Silences' most memorable episodes.

This week features Amy Chess (then at Amazon) unpacking arguably the most important research skill: asking questions. She shares what makes a "good" question, how questions should connect to insights and impact, and how you can improve your question-creation ability.

Research Question 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: 100

Awkward Silences
Podcast Episodes
#161 - Learn More Faster About Customers with Michael Margolis of GV [not-audio_url] [/not-audio_url]

Duration: 51:09
This episode is all about learning from customers...early and often. Our guest, Michael Margolis, UX Research Partner at GV (formerly Google Ventures), has made a career of helping teams do this successfully. He joins to…
#157 - The Future of Design Collaboration with Andrew Hogan of Figma [not-audio_url] [/not-audio_url]

Duration: 41:09
Few companies are most closely associated with UX design right now than Figma, which not only helps designers get their work done, but serves as a bridge for others to get more involved in the process. Erin and Carol are…
#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…