"The biggest reason somebody will avoid answering a question is because they don't trust you with the answer." - Debbie Millman
Debbie Millman has spent 21 years asking questions on Design Matters, the show she started in 2005 before podcasting had rules. In episode 100 of Curated Questions, she takes the receiving chair.
Debbie traces her craft from a survey-style list she asked everyone, work she now calls terrible, to a method she describes as storytelling through questions, where each question carries the context a guest needs to respond to a fully realized moment in their life. She explains why she avoids false wisdom language, multiple-choice framing, and interpretation the guest hasn't offered yet, and makes the case that people withhold answers when they don't trust you with them.
The conversation ranges across branding, her clients, the questions she brings to any redesign, the rebuild of The Rumpus with Roxane Gay, and what AI costs students who skip the difficulty. She closes with the question consuming her at 65: how to live this last third.
This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.
Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions)
Keep questioning!