"The biggest reason somebody will avoid answering a question is because they don't trust you with the answer." - Debbie Millman
"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.
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Episode Notes
00:00 Welcome to Curated Questions
02:19 A Thank You Before Starting
04:37 Debbie Millman Origin Story
04:54 Design Matters Legacy
05:35 The Rumpus Relaunch
06:08 Power of Questions
06:30 Curiosity and Role Models
07:39 Creativity as Inquiry
08:16 Research Before Interviews
10:00 Storytelling Through Context
11:09 From Bad to Better
12:24 Questions as a Skill
13:02 Rephrase the Question
13:50 Narrative Question Craft
15:10 Avoiding False Wisdom
16:00 Trust and Meaning Making
16:54 Staying Curious Without Judgment
18:11 When Interviews Get Canceled
20:03 Questions in Design Work
23:20 Design Politics and Stakeholders
26:50 Teaching Branding in the AI Era
33:11 Curiosity Practices
33:29 Reading Diet Staples
33:59 Choosing What to Read
34:27 No Reflection Method
34:55 Skipping Videos Mostly
35:25 New Yorker Reading Ritual
36:02 Why Reading Wins
36:15 Transcripts Over Audio
37:22 Streisand Audiobook Story
37:42 Research With Highlights
38:15 Great Question Askers
39:05 Roxane Gay Influence
39:52 Maria Popova Connection
40:18 Figuring and Traversal
41:31 New York City Roots
43:48 NYC vs LA Serendipity
44:51 LA as Recharge Season
45:44 COVID Shift to LA
46:52 Rebuilding The Rumpus
50:53 Lazy Questions and Wrap
54:33 Debbie's Right Now Question
Resources Mentioned
Debbie Millman (https://www.debbiemillman.com)
Design Matters (https://www.designmattersmedia.com)
Sterling Brands (https://www.sterlingbrands.com)
AIGA (https://www.aiga.org)
SVA Masters in Branding (https://branding.sva.edu)
Roxane Gay (https://audacity.substack.com)
The Rumpus (https://therumpus.net)
Lambda Legal (https://lambdalegal.org)
NASA (https://www.nasa.gov)
U.S. Department of Justice (https://www.justice.gov)
Paula Scher (https://www.pentagram.com/about/paula-scher)
Dr. Dan Formosa (https://sva.edu/faculty/dan-formosa)
Kevin Kelly (https://kk.org)
"If You're Over 40, You're Ready to Use A.I." — Debbie Millman, NYT (https://www.nytimes.com/2026/07/27/opinion/teaching-kabbalah-ai.html)
The New Yorker (https://www.newyorker.com)
Kottke.org (https://kottke.org)
Craig Mod (https://craigmod.com)
The Marginalian (https://www.themarginalian.org)
The New York Times (https://www.nytimes.com)
The Washington Post (https://www.washingtonpost.com)
Los Angeles Times (https://www.latimes.com)
Maria Popova (https://www.themarginalian.org)
Jason Kottke (https://kottke.org/about)
TED Talks (https://www.ted.com/talks)
Tim Ferriss (https://tim.blog)
Dax Shepard, Armchair Expert (https://armchairexpertpod.com)
Krista Tippett, On Being (https://onbeing.org)
NPR (https://www.npr.org)
Glennon Doyle (https://glennondoyle.com)
Andrew Caulk (https://www.curatedquestions.com/podcast)
Barbra Streisand (https://www.barbrastreisand.com)
Terry Gross, Fresh Air (https://www.npr.org/programs/fresh-air)
Sam Fragoso, Talk Easy (https://talkeasypod.com)
Adam Grant (https://www.adamgrant.net)
Brené Brown (https://brenebrown.com)
Frances Frei and Anne Morriss, Fixable (https://www.ted.com/podcasts/fixable)
Figuring, by Maria Popova (https://www.themarginalian.org/figuring)
Natascha McElhone (https://www.audible.com/pd/Figuring-Audiobook/198484475X)
Traversal, by Maria Popova (https://us.macmillan.com/books/9780374616410/traversal)
Arcosanti (https://www.arcosanti.org)
Santiago Carrasquilla (http://www.santiagocarrasquilla.com)
Art Camp (https://madeatartcamp.com)
Ruth Ann Harnisch / The Harnisch Foundation (https://thehf.org)
Sukey Novogratz (https://justsit.com)
Producer Ben Ford (https://www.producerbenford.com/)
Beauty Pill (https://www.beautypill.com/)