Curated Questions: Conversations Celebrating the Power of Questions!

Ken Woodward
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Curated Questions: Conversations Celebrating the Power of Questions Hosted by Ken Woodward, Curated Questions is a thought-provoking podcast that celebrates the art and science of asking profound questions. This podcast is for curious minds who understand that the right question can unlock new perspectives and drive personal growth. What to Expect Insightful Conversations: Experts from diverse fields share their journey in mastering the craft of inquiry, revealing how it has transformed their lives and careers. Practical Techniques: Gain valuable skills to improve your questioning abilities, applicable in both personal and professional settings. Thought-Provoking Topics: Explore how questions shape leadership, personal transformation, and societal discourse. Why Listen? In an age of abundant information, Curated Questions reminds us that true wisdom lies in asking better questions. This podcast will help you: 1. Enhance critical thinking 2. Improve communication 3. Gain new perspectives on complex issues 4. Develop a nuanced understanding of the world Join Ken Woodward and his guests as they explore the transformative power of thoughtful inquiry. Curated Questions is more than just a podcast – it's an invitation to embrace curiosity, challenge assumptions, and unlock your full potential through the art of asking better questions. Subscribe now and embark on a journey to master the craft of inquiry, one question at a time. Website: CuratedQuestions.com IG/Threads/YouTube: @CuratedQuestions

  1. The Long Tail: What Your Decisions Drag Behind Them | Ken Woodward #84

    4D AGO

    The Long Tail: What Your Decisions Drag Behind Them | Ken Woodward #84

    "The invitation is not to be right. It is to be willing." - Ken Woodward The small decisions we make without examination carry consequences we never see coming. Ken calls this the long tail. It does not stay inside us. It speaks, votes, stays silent when silence enables harm, and over time shapes the people and institutions around us in ways no single decision can account for. Drawing on Roald Dahl's collapse, a question posed by author Jason Pargin about what we would actually do in someone else's position, and a personal story from a church lobby that still lands hard years later, this episode explores the difference between a foundation and a position. A foundation is what you would sacrifice almost everything to protect. A position is a conclusion you have built on top of lived experience that you have likely never examined. The invitation is not to abandon what you stand on. It is to know what you are standing on. And to have the courage to look when something challenges it. 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 Roald Dahl  John Lithgow Giant  James and the Giant Peach Charlie and the Chocolate Factory Jason Pargin Producer Ben Ford Beauty Pill

    21 min
  2. What You Know Changes What You Can Ask | Ken Woodward #83

    MAY 14

    What You Know Changes What You Can Ask | Ken Woodward #83

    "A good answer can close a loop. A good question opens one." - Ken Woodward What if the quality of your questions has less to do with how curious you are and more to do with how much you know? A recent study from the Technion in Israel tracked 68 students over a semester of Introduction to Psychology. Researchers measured not just what students learned, but how their question-asking changed. The findings are worth sitting with. Domain-specific questions got sharper, more original, more complex. General questions did not improve. In some cases, they declined. Knowledge doesn't flatten curiosity. It sharpens it. This episode traces that finding through 32 years of Navy acquisition, through 1,300 conversations on a 2,085-mile walk through Washington DC, and through a conversation with Seth Godin about tension, rubber bands, and the question that only becomes possible after the preparation is done. The argument is simple. You don't become a better questioner by wanting to ask better questions. You become one by learning more about what you're walking into. 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 Raz, T. & Kenett, Y.N. (2026). Knowledge reshapes inquiry by changing question asking ability and impacting academic assessment. *npj Science of Learning*, 11, 19. https://doi.org/10.1038/s41539-026-00402-0 Seth Godin Ryan Holiday Producer Ben Ford Beauty Pill

    22 min
  3. Who Told You That Was Good? | Ken Woodward #82

    MAY 7

    Who Told You That Was Good? | Ken Woodward #82

    "My tree was planted in a metal bucket." - Ken Woodward Some mornings, the ordinary holds the weight of everything. A walk to the garage. An attempt to correct a gait. A drift back to comfort. Ken opens this solo episode with that image and asks why returning to comfort is the default setting of an adult life. Drawing on the work of Nigerian-born British photographer and activist Misan Harriman, Ken investigates the mourning that accompanies genuine personal growth. The mourning for the world you thought you believed in. The mourning for the person you were sure was good enough. Ken traces his own reckoning through the identities that once added up to a clean equation. Each one a nutrient in the soil he was given. Each one another layer of metal on the bucket his tree was planted in. Growing. Just with no room to expand. This episode is about noticing the bucket. Cracking it open. And dragging your roots toward soil that can actually hold them. 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 Misan Harriman Harriman Instagram Post Heraclitus Producer Ben

    19 min
  4. What the Machine Can't Hold | Ken Woodward #81

    APR 30

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

    "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 (https://substack.com/@curatedquestions?)) Keep questioning! Resources Mentioned Claire Brown The Art Engager Podcast Cole Arthur Riley Producer Ben Ford Beauty Pill

    22 min
  5. Still Asking: Ten Lessons From A Decade With Questions | Ken Woodward #80

    APR 23

    Still Asking: Ten Lessons From A Decade With Questions | Ken Woodward #80

    "Claiming your agency to question is a renegade step into your full humanity." - Ken Woodward April 12, 2016, marked the first public demonstration of Kenneth Woodward's obsession with questions. A decade, 80 episodes, and 140,000 downloads later, he returns to the shoreline to share what a decade of study, conversation, and lived experience has washed up at his feet. From a daily inquiry blog that cost him sleep, to 1,300 conversations across 2,085 miles of Washington D.C. streets, to podcast conversations with some of the world's deepest thinkers, questions have been the through line. In this milestone solo episode, Kenneth offers ten honest observations about questions, how they create space, signal desire for change, exercise agency, and reveal what we most need to face. Not conclusions from a master, but mile markers from a fellow pilgrim still very much on the road. The practice continues. So does the asking. 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!

    33 min
  6. Who Benefits From Me Believing This? | Andrew Caulk #79

    APR 16

    Who Benefits From Me Believing This? | Andrew Caulk #79

    "It is easier simply to tell the truth, even if you've made a mistake, because what it does is build credibility over time." - Andrew Caulk What happens when the questions leaders most need to ask are the ones they're most afraid to voice? Andrew Caulk spent two decades in the Air Force as an information strategist, and he's seen how institutions, military, political, and personal, manage their narratives by avoiding the hardest inquiries. In this conversation, Andrew and Ken explore how misinformation and disinformation actually work, why truth is more strategically sustainable than deception, and how the attention economy is quietly rewiring our ability to think slowly. Andrew shares what senior leaders refused to ask aloud in military war games, what the casualty projections for a Taiwan conflict actually look like, and why American will to fight may be the most underexamined variable in geopolitical strategy. The conversation also turns to children, curiosity, and how the questions we allow, or suppress, in our homes shape the next generation's capacity to navigate a noisy world. 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  Cognitive Strategy Group  Right to Forget Law Helio Fred Garcia Inside The  Manosphere documentary  Battlefield Three  Ad Fontis Media Bias Chart  Trust Me, I'm Lying by Ryan Holiday Anchorman 2  Bloomberg Wall Street Journal Associated Press (AP) Reuters The Economist  SCOTUSblog  Freakonomics Ground News  Planet Word Museum  cognitive strategy group.com  Being Human Church  Dr. Kori Schake Jim Mattis Andrew Caulk on LinkedIn Producer Ben Ford Beauty Pill

    1h 57m
  7. The Question Asked in the Wrong Room | Ken Woodward #78

    APR 9

    The Question Asked in the Wrong Room | Ken Woodward #78

    "Those scripts are not wisdom. They are load-bearing walls for other people's power." - Ken Woodward Every room has a question nobody asks. Sometimes that's a failure of courage. Sometimes it's something else entirely, a hierarchy so explicit it pre-sorts who is permitted to speak before anyone opens their mouth. In this episode, Ken reflects on a $100M federal acquisition program derailed by a senior stakeholder who wielded disruption as a weapon. The question that could have changed the outcome existed. It just never reached the person who needed to hear it. Drawing on that experience, a chance conversation with a Vietnamese businessman named Kien, and the current civic moment, Ken explores why we swallow necessary questions, and what it costs us when we do. He offers a ladder of micro-courage for asking harder questions at every level of power, from the private to the public square. One braver question. That's the practice. That's where it starts. Fellow pilgrims, this one's for the rooms we've all been in. 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!

    22 min
  8. The Questions We Didn't Ask Our Grandmothers | Jenny Chan #77

    APR 2

    The Questions We Didn't Ask Our Grandmothers | Jenny Chan #77

    "The most powerful questions aren't really the ones that demand an answer, but really demand a presence." - Jenny Chan Jenny Chan founded Pacific Atrocities Education after her grandmother's death surfaced a box of wartime relics of military yen, rice rationing coupons, and decades of unexplained anger toward Japanese culture. That inheritance of unasked questions launched Jenny into the hidden history of the Pacific Asian War: comfort women, Unit 731's biological experimentation program, and the postwar immunity deals that let war criminals become CEOs and prime ministers. Jenny's research method centers on presence before inquiry. Sitting with survivors long enough to earn the right to ask hard questions. She sees historical memory not as a burden but as an essential context for understanding today's geopolitical decisions. Her work with survivors, students, and Japanese citizens seeking truth suggests that healing begins when forgotten stories are finally allowed to be told. 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!

    1h 10m
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Curated Questions: Conversations Celebrating the Power of Questions Hosted by Ken Woodward, Curated Questions is a thought-provoking podcast that celebrates the art and science of asking profound questions. This podcast is for curious minds who understand that the right question can unlock new perspectives and drive personal growth. What to Expect Insightful Conversations: Experts from diverse fields share their journey in mastering the craft of inquiry, revealing how it has transformed their lives and careers. Practical Techniques: Gain valuable skills to improve your questioning abilities, applicable in both personal and professional settings. Thought-Provoking Topics: Explore how questions shape leadership, personal transformation, and societal discourse. Why Listen? In an age of abundant information, Curated Questions reminds us that true wisdom lies in asking better questions. This podcast will help you: 1. Enhance critical thinking 2. Improve communication 3. Gain new perspectives on complex issues 4. Develop a nuanced understanding of the world Join Ken Woodward and his guests as they explore the transformative power of thoughtful inquiry. Curated Questions is more than just a podcast – it's an invitation to embrace curiosity, challenge assumptions, and unlock your full potential through the art of asking better questions. Subscribe now and embark on a journey to master the craft of inquiry, one question at a time. Website: CuratedQuestions.com IG/Threads/YouTube: @CuratedQuestions

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