#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
#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…
#147 - UX Research in Healthcare with Nadyne Richmond [not-audio_url] [/not-audio_url]

Duration: 47:19
Erin and Carol explore the complexities of healthcare research with Nadyne Richmond, a healthcare design advisor with a background in big tech who pivoted to healthcare research a decade ago to tackle the pressing issues…