"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!

"Some questions need eye contact. Some questions need silence. Some questions need the telltale crack in our own voice that tells you, you've finally said something true." - Ken Woodward

We live in a moment when almost any question can be answered instantly, eloquently, and for free. That is a remarkable thing. It is also worth examining carefully.

In this episode, Ken Woodward draws a distinction between two kinds of questions: tool questions, which AI handles brilliantly, and threshold questions, which require something the machine cannot provide. Time. Risk. The sound of your own voice saying something true for the first time.

This is not an episode about the dangers of AI. It is an episode about the quiet cost of convenience, what we give up when we trade a live, risky question for a fast, polished answer. And what it looks like to protect the capacity for wonder in an age that makes outsourcing almost everything feel like efficiency.

Three practices. A few guardrails. And one question to carry with you when you close the machine.

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!

#100 Debbie Millman: Earning Trust & Storytelling Through Questions

#81 Ken Woodward: What the Machine Can't Hold