#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
#144 - The Craft of Sample Sizes with Lauren Stern of WHOOP [not-audio_url] [/not-audio_url]

Duration: 46:46
In this episode, Carol and Erin dive into all things research sample sizes with Lauren Stern. No matter your experience with user research, you'll need to recruit folks, making this an evergreen topic. Lauren has coached…
#142 - Quantifying Research Impact with Ruby Pryor of Rex [not-audio_url] [/not-audio_url]

Duration: 47:44
In this episode Carol and Erin are joined by Ruby Pryor, founder of Rex, a consulting firm specializing in UX research and strategic design. They explore the world of measuring the impact of UX research. with Pryor intro…
#141 - The Chaos Theory of Event Networking with Bryan Dosono of eBay [not-audio_url] [/not-audio_url]

Duration: 41:10
In this episode of Awkward Silences, Carol and Erin dive into the world of conference networking and planning with Bryan Dosono, a staff UX research lead at eBay known for his extensive experience curating and organizing…
#138 - Designers as Change Agents with Maria Giudice [not-audio_url] [/not-audio_url]

Duration: 43:26
“I realized that design is about helping people make sense of the world. And I looked at the world differently then… treating everything like a design problem that's solvable [...] [Design leaders today] don't use the po…
#136 - Designing Generative AI at Notion with Linus Lee [not-audio_url] [/not-audio_url]

Duration: 45:29
AI is a big part of Notion's strategy for the future of knowledge work, and they're exploring ways to use AI to make people's lives easier.Linus Lee, a Research Engineer at Notion, spends his time researching and learnin…