#100 Debbie Millman: Earning Trust & Storytelling Through Questions

"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!

#64 Ken Woodward: What Questions Are You Carrying Forward? Reflections on 2025

"What are the questions you will be carrying into the year, such that it will be a celebration of your becoming?" - Ken Woodward

This year-end Curated Questions episode is a reflective curation of the questions that shaped several conversations throughout 2025. Rather than offering a rapid recap of every episode, Ken highlights a handful of moments that reveal how intentional questioning can clarify purpose, interrupt unhelpful patterns, and guide meaningful becoming.

Across stories from entrepreneurs, scientists, artists, and personal reflection, the episode explores questions that ask us to define the change we seek to make, consider who we are becoming, and choose where to place our attention. Along the way, listeners are reminded that good questions often emerge only after many imperfect ones, that perspective shapes dignity and connection, and that small mental reframes can act as powerful resets.

As the year closes, the episode becomes an invitation: to name the questions that mattered most in 2025, to carry one forward with intention into 2026, and to trust that a better world is built by those willing to keep questioning.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Ensure to subscribe to the Curated Questions Dispatch weekly newsletter on Substack.

Keep questioning!

#63 Ken Woodward: The Inquisitive Almanack: 2026

"Direction often emerges not from knowing what you want, but from finally admitting what you don’t." - Ken Woodward

The Inquisitive Almanack: 2026 Edition closes the year with something Curated Questions has never quite done before—an affectionate, slightly irreverent, and deeply thoughtful almanack for the inner life.

Inspired by Benjamin Franklin’s Poor Richard’s Almanack, this episode blends dry wit, invented bureaucracy, and hard-won wisdom to offer forecasts not for the weather, but for the heart, mind, and questions we carry.

You’ll hear interior weather reports, proverbs for the asking class, arbitrary rules of inquiry, lunar phases of curiosity, and predictions for the questions most likely to surface in 2026—across leadership, relationships, parenting, teams, and personal life.

Released intentionally as the final episode of the year, this Almanack isn’t a recap or a resolution guide. It’s a pause. A breath. A lighter place to rest before the calendar turns and begins asking new things of us.

Come curious. Leave rested. And carry one good question forward.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!