Curated Questions: Conversations Celebrating the Power of Questions!
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Latest episodes
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What Would You Do If You Were Me? | Ken Woodward #106
October 22, 2026 · 19 min"I sat there with them and realized I had no story to trade. Not a faded one. None." - Ken Woodward With the election less than two weeks away, I caught myself asking how those knuckleheads could vote that way. Underneath it: I would never…
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The Question After the Aha! | Ken Woodward #105
October 15, 2026 · 18 min"A statement claims to be finished, and that claim is exactly what time comes back to audit. A question never claimed to be finished." - Ken Woodward Some ideas arrive like lightning. Others crawl. In 2016, one of my slowest ideas began…
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Still Sharp: Lulu Miller on the Questions We Stop Asking | Lulu Miller #104
October 8, 2026 · 1 hr 3 min" Real curiosity, untethered, unsoftened, it's a pretty intense tool. And I think the kids haven't blunted the weapon by politeness or by fear of looking dumb or by the belief that there are certain things we should know. It's still…
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The People Who Leave Get the Last Word: Revisiting a Question Ten Years Later | Ken Woodward #103
October 1, 2026 · 12 min"What do former members say about the organization?" - Ken Woodward Ten years ago today, I asked a question on my daily practice, IOTD365: what do former members say about an organization? I wrote it after my daughter gave up on an…
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The Questions That Make You Nod: How Agreement Hides Assumptions | Ken Woodward #102
September 24, 2026 · 28 min"Disagreement makes the map visible. Agreement lets it pass for the terrain." - Ken Woodward "Thank you for your service" arrives with a script already written. A World War II veteran taught Ken Woodward a better reply: "You were worth…
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When Certainty Drifts | Ken Woodward #101
September 17, 2026 · 29 min" I ate of that apple. It tasted like safety." - Ken Woodward Once a submarine goes under, nobody aboard knows exactly where they are. The boat runs on an estimate that drifts, and being off course feels exactly like being on course. The…
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Debbie Millman: Earning Trust & Storytelling Through Questions | Debbie Millman #100
September 10, 2026 · 58 min"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…
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What Are They Really Asking? | Former Starbucks SVP Wanda J. Herndon on the Second Question #99
September 3, 2026 · 1 hr 11 min" I had to start trying to think beneath the questions: what are they really saying?" - Wanda Herndon Wanda J. Herndon trained as a journalist, then spent forty years on the other side of the notebook. Dow. DuPont. Eleven years as…
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Paid To Say I Don't Know | Ken Woodward #98
August 27, 2026 · 29 min" 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…
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The Last Time Was A Tuesday | Ken Woodward #97
August 20, 2026 · 28 min"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…
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A Slightly Smaller Life | Ken Woodward #96
August 13, 2026 · 33 min"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…
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Even Socrates Didn't Ask: On the Hidden Power of Questions | Lani Watson #95
August 6, 2026 · 1 hr 30 min" 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…

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