"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 (https://substack.com/@curatedquestions?))

Keep questioning!

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/)

" I had to start trying to think beneath the questions: what are they really saying?" - Wanda J. Herndon

Wanda J. Herndon trained as a journalist, then spent forty years on the other side of the notebook. Dow. DuPont. Eleven years as Starbucks SVP of Global Communications while the company grew from 550 stores to more than 11,000. Her latest book is Working Class to Breaking Glass: One Woman's Fight to Belong and to Lead, and is available at your favorite bookshop.

Her curiosity starts with a middle child in Flint, Michigan, who wore out her siblings asking why. She describes learning, after being misquoted, to ask what a reporter is really asking. She calls listening a discipline she never mastered. And the question that carried her through divorce: what is this moment trying to teach me?

Crisis work as a puzzle solved with who, what, why, when, where, how. Mentoring as a two-way street. Why she always asked Howard Schultz why. Being the CEO of you. Owning Flint rather than letting others define it.

And her right now question: will we survive this chaos, and what can I do to help?

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 (https://substack.com/@curatedquestions?))

Keep questioning!

Resources Mentioned

 Orin Smith (https://en.wikipedia.org/wiki/Orin_C._Smith)

Nikki Giovanni (https://www.nikki-giovanni.com/)

Starbucks (https://www.starbucks.com/)

 Audre Lorde (https://alp.org/about/audre)

Flint Michigan (https://en.wikipedia.org/wiki/Flint,_Michigan)

Howard Schultz (https://schultzfamilyfoundation.org/team-member/howard-schultz/)

Onward by Howard Schultz (https://a.co/d/0cG7QyPF)

 Pour Your Heart Into It by Howard Schultz (https://a.co/d/00OhYP7W)

 Alpha Kappa Alpha Sorority, Inc. (https://aka1908.com/)

 Greater Seattle Chapter of The Links, Inc. (https://www.greaterseattlelinks.org/)

Wanda Herndon website (http://wcommgroup.com/)

Wanda Herndon on LinkedIn (https://www.linkedin.com/in/wandajherndon)

Wanda Herndon on Facebook (https://facebook.com/wandajherndon)

Wanda Herndon on Instagram (https://instagram.com/wandajherndon)

Producer Ben Ford (https://www.producerbenford.com/)

" You do not knock on a door that's been painted over. One word scores the paint and reopens it." - Ken Woodward

Researchers paid people to admit when they didn't know something. Given access to AI advice, they almost never did.

The design made it startling. Participants could decline any question with no penalty. Guessing wrong cost them money. The AI advice they received was usually wrong. Every incentive pointed toward three simple words, and access to a machine nearly eliminated their willingness to say them.

What got suppressed wasn't accuracy. It was the willingness to be seen not knowing.

In this solo episode, Ken opens with a lie he told a friend in a room where nothing was at stake, then traces the same reflex through a sidewalk in Southeast D.C., five questions he couldn't answer, and a backyard conversation that ran five hours past its twenty-minute plan.

"I don't know" isn't a report on empty shelves. It's a doorway, and it's the only one.

What question are you avoiding because not knowing would cost you something?

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 (https://substack.com/@curatedquestions?))

Keep questioning!

"Every unasked question has an expiration date." - Ken Woodward

Ken tries to say goodbye to a shipmate before leaving the submarine. The man goes on emergency leave, and the goodbye has already happened without him noticing it. He had the calendar, the date, the list of names. The last one got past him anyway.

That is the shape of this episode. We do not know which time is the last time, and preparation does not change that. Ken walks through Tim Urban's arithmetic on parents, a return to his hometown that was supposed to be final and wasn't, and an upcoming lunch with his ninety-three-year-old aunt, who is the last door into a generation that has already closed. In Ambiguous Loss, Pauline Boss offers a useful frame: closure is largely a myth, and the real skill is holding something open without needing it to shut.

The question idea underneath it: every unasked question has an expiration date you cannot see. Some are saving for a better moment. Some you can't ask because you don't yet know you will want the answer.

Ken is recording before he flies, without a resolution, because the not knowing is the point.

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 (https://substack.com/@curatedquestions?))

Keep questioning!

"There is just a slightly smaller life that you experience as a completely normal one." - Ken Woodward

Seven experiments. Ten thousand people. Half learned a topic from an AI summary, half from ordinary web links. Same facts. The AI group came away with shallower knowledge, and when researchers propped the door open, placing live source links right beside the summary, almost nobody walked through.

Sixty-eight percent of Google searches now end without a click. With an AI Overview on the page, eighty-three percent.

This episode is about what that costs. Not wrong answers, wrong answers get caught. It's the second question that never gets asked, which leaves no error message and no gap in the record. Just a slightly smaller life that you experience as a completely normal one.

Then: a man on a corner in Northeast D.C. who gave me a name that wasn't his, and what it took to get the real one.

One more thing, I need your help naming something.

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 (https://substack.com/@curatedquestions?))

Keep questioning!

" This aporia, this state of confusion and bafflement, is actually a fantastically exciting, liberating, intellectually stimulating place to be because you're really facing something that you don't know that you thought you did." - Lani Watson

Dr. Lani Watson has spent her career on a question most of us never stop to ask. What is a question, and why does it hold such power?

Known online as The Questions Doctor, Lani is a philosopher and the author of Q: The Hidden Power of Questions in a World That Wants Answers. In this episode, we sit with the idea that questions are a kind of everyday magic. A power we all carry and rarely notice. They change our brains. They change our relationships. They shape the very answers we receive.

We talk about Socrates and the gift of not knowing. We talk about a world racing toward answers, and what we lose when we rush past the question. We talk about who gets to ask, and who does not.

Come sit with the questions a while. There is power in the asking, and it belongs to all of us.

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 (https://substack.com/@curatedquestions?))

Keep questioning!

Resources Mentioned

Lani Watson (https://www.philosophyofquestions.com/)

 Q: The Hidden Power of Questions in a World That Wants Answers by Lani Watson (https://www.penguin.co.uk/books/459733/q-by-watson-lani/9781847927842)

Socrates (https://en.wikipedia.org/wiki/Socrates)

Plato (https://en.wikipedia.org/wiki/Plato)

Anne-Laure Lecunff (https://anne-laure.net/)

 Intellectual Virtues Academy (https://www.ivalongbeach.org/)

 Jason Baehr (https://www.linkedin.com/in/jason-baehr-529a8a63 (https://www.linkedin.com/in/jason-baehr-529a8a63/?lipi=urn%3Ali%3Apage%3Ad_flagship3_profile_view_base_contact_details%3B%2FATNQ1n4RtepSeByGUrjfQ%3D%3D))

 Right Question Institute (https://rightquestion.org/)

 Ian Robson (https://www.linkedin.com/in/ian-robson-ab140710 (https://www.linkedin.com/in/ian-robson-ab140710/?lipi=urn%3Ali%3Apage%3Ad_flagship3_profile_view_base_contact_details%3BVIiXJN4qT5ORRBXVxyVvIg%3D%3D))

The Questioning Strengths Assessment (https://gilded-syrniki-638aee.netlify.app/)

Producer Ben Ford (https://www.producerbenford.com/)

Beauty Pill (https://www.beautypill.com/)

"Listening is not real until the listener makes a sound back." - Ken Woodward

A sound-powered telephone runs on nothing but the sound of your own voice. No battery. No amplifier. I served on submarines, and I never forgot the joke we played on every new sailor: we sent him hunting the whole ship for batteries that do not exist. The power was in him the entire time. He only had to speak.

This is a solo episode about listening. About the repeat-back, the discipline of saying a message back until it lands correctly. About a 2025 study that found the follow-up question is the clearest sign that real listening is happening. About what Dr. Haru Yamada taught me, that to ask and to listen are one motion.

And it is about one officer I served with, a question I never asked him, and why I let it go unasked. The circuit is always live. Who is the station you have never called?

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 (https://substack.com/@curatedquestions?))

Keep questioning!

"Nothing in us reports on an absence. No creature ever needed a sense for the path it did not walk." - Ken Woodward

More than sixty percent of Google searches now end without a single click. We type the question, read the summary, and leave. The trip is gone.

Neuroscientist Anne-Laure Le Cunff argues that curiosity needs a gap to switch on, and that learning deepens while the question stays open. The answer closes the window.

But the reaching is not our failure. Wanting the missing piece is old equipment, and it worked well for a very long time, because you used to have to walk over the ridge to find out. What changed is the hit rate. We catch every time now, in three seconds, and the machinery on the other side never gets to run.

This week we look at which gaps are worth keeping open, why resistance is the mechanism rather than the toll, and what ten years of a daily question taught me about the limits of my own idea.

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 (https://substack.com/@curatedquestions?))

Keep questioning!

" Show what you know by the questions you ask." - Robert Doore

Robert Doore carries two names, Robert Doore and Rides at the Door, and a journey most maps don't draw: from Big Red football on the Blackfeet Reservation to becoming the highest-ranking Native American in the NFL since Jim Thorpe.

Now the President and CEO of Chief Mountain Sports and Consulting, he tells Ken he didn't learn the power of questions early on. He learned it at 21, in a Washington, D.C. room full of generals and cabinet officials, when he found the courage to ask a mentor, "How did you get to be so smart?" The answer, be well read, ask lots of questions, became his Jedi training.

The conversation moves through Maslow's summer with the Blackfeet, teaching "Indian 101" to policymakers, representation as a door-opener, and fear as the cousin of failure. Robert's right now question: What does success look like? His answer isn't money. It's impact.

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 (https://substack.com/@curatedquestions?))

Keep questioning!

Resources Mentioned

Robert Doore's website robertdoore.com

 Chief Mountain Sports and Consulting (https://robertdoore.com/)

Blackfeet Nation (https://blackfeetnation.com/)

 Star Wars (https://en.wikipedia.org/wiki/Star_Wars)

Jim Thorpe (https://en.wikipedia.org/wiki/Jim_Thorpe)

 Abraham Maslow (https://en.wikipedia.org/wiki/Abraham_Maslow)

Chief Two Guns White Calf (https://en.wikipedia.org/wiki/John_Two_Guns_White_Calf)

 Elouise Cobell (https://en.wikipedia.org/wiki/Elouise_P._Cobell)

 Erin Brockovich (https://en.wikipedia.org/wiki/Erin_Brockovich)

 Disney's version of Pocahontas and John Smith (https://en.wikipedia.org/wiki/Pocahontas_(1995_film))

An Indigenous Peoples’ History of the United States by Roxanne Dunbar-Ortiz (https://en.wikipedia.org/wiki/An_Indigenous_Peoples'_History_of_the_United_States (https://en.wikipedia.org/wiki/An_Indigenous_Peoples%27_History_of_the_United_States))

 Carlisle Indian School (https://en.wikipedia.org/wiki/Carlisle_Indian_Industrial_School)

General Richard Henry Pratt (https://en.wikipedia.org/wiki/Richard_Henry_Pratt)

 Glenn "Pop" Warner (https://en.wikipedia.org/wiki/Pop_Warner)

 Billy Mills (https://en.wikipedia.org/wiki/Billy_Mills)

 Audrey Lorde (https://en.wikipedia.org/wiki/Audre_Lorde)

 Dances With Wolves (https://en.wikipedia.org/wiki/Dances_With_Wolves)

 Yellowstone TV Series (https://en.wikipedia.org/wiki/Yellowstone_(TV_series))

 National Native American Hall of Fame (https://nativehalloffame.org/)

 John Harrington (https://en.wikipedia.org/wiki/John_Peabody_Harrington)

NCAI Tribal Directory (https://www.ncai.org/tribal-directory)

 Rocky Balboa (https://en.wikipedia.org/wiki/Rocky_Balboa)

Robert Doore on LinkedIn (https://www.linkedin.com/in/robert-doore-business-executive (https://www.linkedin.com/in/robert-doore-business-executive/?lipi=urn%3Ali%3Apage%3Ad_flagship3_profile_view_base_contact_details%3BDT6wVsr4ToOC%2FqC5H48fiA%3D%3D))

Producer Ben Ford (https://www.producerbenford.com/)

Beauty Pill (https://www.beautypill.com/)

"That is what a patriot is. Someone who loves the country enough to trade the myth for the question." - Ken Woodward

We took a single question to two places: the garden of the Heurich House in Washington, DC, and a town-center street in Rockville. What are you asking, right now, about America at two hundred and fifty? We did not coach anyone. We asked, and we listened. What came back was not one mood. It was several, sitting side by side. A civility one immigrant was taught here and watched thin. A fear for the vote. An institution lost and a resolve to become one. The next two hundred and fifty years held in one hand and tonight's parking in the other. A whole country found again in a crowd at a pool.

Underneath all five runs one thread: the fear lives at a distance, and the hope lives within reach. Agency far away arrives as something done to us. Agency close enough to touch arrives as hope. The episode follows that thread back to the founding, to Frederick Douglass, and to what the word patriot is supposed to mean.

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 (https://substack.com/@curatedquestions?))

Keep questioning!