#92 Robert Doore: Show What You Know By The Questions You Ask

" 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.

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#91 Ken Woodward: The Fear Is Far, The Hope Is Near: America At 250

"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.

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#88 Ken Woodward: Learning to Be Asked

"Ian thought a question was a way to find out who was above him and who was below him. The fire taught him it was a way to find out who was beside him." - Ken Woodward

Ian told me he had gotten better at asking questions, and then said the thing that caught my attention. He used to be afraid to ask. Partially fear of looking nosy. Mostly afraid that asking one question,would open him up to being asked one back. I knew that fear from the inside, so the two of us got on a call to dig in.

This episode follows what we found. The scarcity in the house that raised him, and how a stretched mind cannot afford a question. The old wiring that treats being pushed out of the group as a threat to survival. Why his fear was not timidity but an accurate read of how people actually work. And the small weekly circle, built on one plain question, that changed the physics until the thing he feared was simply no longer true.

With a debt to Brian Fretwell and Finding Good, a nod to Seth Godin and Polly Wiessner, and a question at the end I do not have the answer to.

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#87 Ken Woodward: The Anatomy of a Question

"The question was not broken. It was unfinished." - Ken Woodward

Buried in the introduction of the twentieth century's most famously unread book is the most precise dissection of a question ever written.

In this solo episode, we open Martin Heidegger's Being and Time and recover his anatomy of inquiry: every question has a subject, a source, and an intent, and most questions fail not from bad wording but from missing parts.

We test the anatomy against the streets of Washington, D.C., including a backyard in Marshall Heights where a five-hour-and-forty-five-minute conversation revealed what sixty-one years of an unasked question feels like.

Then the reckoning. The man who drew the map of questioning joined the Nazi Party, deleted his Jewish teacher's name from his own dedication page, and spent forty-three years refusing the one question that came addressed to him.

Knowing the anatomy is not the asking. This episode is about the difference, and the drive home.

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#86 Ken Woodward: The Smallest Act of Authorship

"The smallest act of authorship is a question." - Ken Woodward

Nine months ago, Naomi Campbell of the Right Question Institute said one word that gave me a word I had been searching for: agency. I felt it land in my body before I understood it in my head. I promised my listeners I would come back with an answer. This episode is that answer.

Agency is the authorship of our own lives. Not control, which none of us has. Authorship is something smaller and more stubborn. It is the refusal to be only what the world wrote about us. And the smallest act of authorship, it turns out, is a question. The moment we ask, we stop receiving the world and start writing on it.

I carry two stories from my walk across Washington. A man I call Doc, raised by a mother who would not let him absorb anything without questioning it first. A woman I call Pearl, who answered the worst day of her life by building a neighborhood for the children coming up behind her.

Agency is inherent. It can be suppressed, but never removed. The whole question is whether we pick up the pen.

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#85 Larry Robertson: What Will You Soon Realize You Already Know?

" The more you play around with it, and the more you see the power in a question, the more you realize that it actually is the cure for the uncertainty that ails many of us." - Larry Robertson

Larry Robertson has spent three decades advising leaders on growth, innovation, and strategy. He is also a US Fulbright Scholar, a columnist, and the author of four award-winning books. His newest, Great Question: The Art of the Ask and Getting More of What You Really Want, draws on more than 140 interviews spanning neuroscience, psychology, business, and the arts.

Larry believes we are not a storytelling species. We are a questioning species. He arrived at that conviction book by book, pattern by pattern, over two decades of research.

In this conversation, we explore the power of questions as a form of agency. We examine intellectual humility and what happens when you stop performing certainty. We discuss leadership, polarization, and the Braver Angels framework. We also unpack Larry's five-element Art of the Ask.

Questions are not a technique. They are a behavior. They are something you already know how to do. This conversation is a reminder to start practicing again.

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

"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.

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

"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.

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

"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.

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

"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.

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

"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.

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

"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.

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#76 Ken Woodward: The Questions You're Living Inside: How to Stop Answering Questions You Never Chose

"The harm was architectural. It was not a matter of intention. It was a matter of never checking the blueprint before I opened my mouth." - Ken Woodward

The Questions You're Living Inside: How to Stop Answering Questions You Never Chose is the premise of this week's solo episode.

Every question builds a room. Most of us never notice the construction.

In this solo episode, Ken Woodward explores what he calls the architecture of questions, the load-bearing assumptions embedded in every question we ask, answer, or inherit. Using a morning commute observation about a flatbed truck carrying prefabricated wall panels, Ken unpacks why the questions shaping our lives were often built by someone else, for someone else's benefit.

Through two anchor stories, a painful misheard exchange during his 2,085-mile walk through Washington D.C., and an emotional moment from his conversation with Naomi Campbell of the Right Question Institute, Ken traces the difference between a question's skeleton and its resonance.

The invitation is not demolition. It is something prior to answering.

Read the blueprint first.

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#75 Phil Liebman: It's Not The Answers — It's Having the Questions

"It's not having the answers I teach people — it's having the questions. And that just upsets the entire architecture of safe thinking." - Phil Liebman

Phil Liebman spent years being mentored by one of the most relentless questioners he'd ever encountered. It changed everything about how he leads and coaches. In this conversation, Phil unpacks the difference between knowing mode and learning mode, why most of us were systematically educated out of curiosity, and what it actually takes to form a powerful question.

He introduces his cycle of curiosity and certainty, a four-quadrant framework that explains why three-quarters of the best thinking happens before any action is taken.

Phil shares hard-won lessons from decades of executive coaching, traces his intellectual foundation back to mentor Dr. Lee Thayer, and makes the case that leadership is a performing art, not a management science.

The episode closes with a personal health scare that became an unexpected masterclass in what curiosity can do when fear shows up uninvited.

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#74 Eila Park Robertson: How Questions Can Save A Fractured Democracy

"Lean into courage and see what happens." - Eila Park Robertson

Former ABC News journalist, award‑winning filmmaker, and crisis communications strategist Eila Park Robertson joins Curated Questions to explore what happens “when listening saves democracy.”

Drawing from a childhood navigating violence, immigration, and loneliness, Eila shares how asking genuine questions became her superpower for building trust with people who would never normally talk to the media. She explains why Western culture has forgotten how to listen, how that loss feeds polarization, and what it really takes to build bridges across political and ideological divides, starting with presence, curiosity, and courage.

Eila and Ken dive into introverts as secret leaders of the room, why outrage‑only politics is burning us out, and how personal relationships can transform deeply held beliefs. They also explore climate storytelling, South Korea’s fight against authoritarianism, and practical ways to resist despair and rebuild community in an age of fractured attention.

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#73 Ken Woodward: Mortar & Pestle: The Fragrance Of An Intentional Life

"There's a difference between avoidance and stewardship of our own attention." - Ken Woodward

When life grinds us down, something essential is revealed. In this solo episode, Ken Woodward explores why questions are the fundamental technology humans use to make sense of a world that has broken wide open.

Drawing from a personal essay about growing up in rural Arizona and the disorienting experience of having a lifelong worldview bubble pop, Ken examines the overwhelming flood of inputs modern life delivers and why not every question in that flood is yours to carry.

He contrasts two kinds of wisdom, the certainty-hardened and the question-exhausted, and makes the case that the most meaningful conversations happen with people who have crossed a difficult threshold and been changed by it. The grinding of life, like a mortar and pestle, doesn't destroy us. It reveals us.

The fragrance was always there, waiting.

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#70 Dr. John A. King: Refined, Not Defined: Discipline of Relentless Resilience

"They’re literally allowing their past to define them, not refine them. And refinement is an active process, and you have to be prepared to do the work if you’re gonna grow." - Dr. John A. King

In this powerful and unflinching conversation, Ken Woodward is in conversation with Dr. John A. King, author, speaker, and PTSD recovery expert, whose life journey moves from profound trauma to purposeful advocacy. A survivor of childhood sexual abuse and trafficking, John transformed personal devastation into a mission to help others move from surviving to thriving through his foundation and mental wellness work.

King reflects on how questions have guided his healing, challenging the tendency to live “from the outside in” and instead pursuing happiness through intentional inner work, and living "inside out." He shares the discipline behind lasting change, emphasizing the incremental progress of 1% shifts that compound over time, and the daily choice to let hardship refine rather than define us.

Together, they explore resilience, identity, and the courage to rewrite one’s story. This episode is a candid reminder that recovery is not instantaneous but forged through persistence, self-honesty, and the relentless decision to keep moving forward.

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#68 Ken Woodward: Hope Is A Muscle

"I don’t want hope as a primary strategy for living well." - Ken Woodward

In this solo episode of Curated Questions, Ken Woodward explores hope not as a feeling or slogan, but as a muscle, something built, weakened, and strengthened through use.

Prompted by Alex Honnold’s free-solo climb and his own season of uncertainty, Ken reflects on the collapse of trust in institutions and the fragility of inherited forms of hope. Drawing on psychological and neuroscientific research, he reframes hope as a cognitive skill set rooted in agency and pathways, the belief that we can act and imagine multiple routes forward, even without certainty.

Ken examines how rumination, paralysis, and outsourced responsibility erode hope, and how well-chosen questions can interrupt despair and reengage possibility. Moving from individual to collective hope, he invites listeners to consider where their own “hope muscles” have atrophied and what small, concrete actions might rebuild them.

This episode is not a lesson on hope, but a vulnerable, out-loud search for it, grounded in questions, courage, and shared responsibility.

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#66 Ken Woodward: What Happens When A Question Is Asked?

"Questions are not neutral; they're interventions." - Ken Woodward

What actually happens inside us when a question is asked?

In this solo episode of Curated Questions, Ken Woodward explores the neurological, emotional, and psychological impact of being asked a question.

Moving beyond techniques or tactics, Ken examines how questions hijack attention, trigger chemical responses in the brain, open unresolved mental loops, and sometimes activate fear or defensiveness.

Drawing from neuroscience and a powerful encounter during his Washington, D.C. walking project, he reflects on a question that has remained open for years: What real difference are you making?

This episode reveals why some questions feel like relief before they’re answered, why others linger long after they’re asked, and how certain questions don’t just reveal who we are, but actively shape who we become.

Questions, Ken argues, are not neutral requests for information. They are interventions. And understanding their power changes how we ask, how we answer, and how we live with them.

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