#93 Ken Woodward: Built to Reach, Not to Catch

"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.

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#90 Ken Woodward: Right Now Questions - Union Market, DC: When Now Becomes Next

"When someone asks us about now, many of us answer with next." - Ken Woodward

We took the mic into Union Market and asked strangers one question. What is your Right Now Question? Their answers, and the quiet trend running underneath them.

On a warm June afternoon in Washington, DC, we stood in Union Market and asked the people passing through a single thing. Not what they do. Not where they are headed. Just this. What is your Right Now Question?

What came back was a market full of strangers, each one carrying something. A job. A move. A book they could not choose. A neighborhood changing faster than anyone can hold. Listen for the trend running underneath the answers, then meet us on the other side for what we noticed.

A few of the Right Now Questions we heard:

Am I going to get this job?
What does peace look like?
Do I stay, or do I go?
Do the new neighbors know what this used to be?
Where will these protests lead us?
What is so hard about being kind?

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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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.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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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.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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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.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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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.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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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.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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

"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.

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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.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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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.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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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.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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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.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#69 Addy Graff: Ask Three Questions — Then Go Play

"Sometimes my parents say ask three questions and then you can play." - Addy Graff

In this delightful episode of Curated Questions, Ken Woodward sits down with a-year-old explorer Addy Graff to discover how curiosity takes root early in life.

A seasoned traveler who has visited roughly 40 countries and every neighborhood in Washington, DC, Addy shares how asking questions helps her learn about people, cultures, and new experiences. From sampling adventurous foods like snails to practicing French in local shops, she demonstrates a fearless approach to discovery.

Addy reflects on lessons from school about thoughtful versus superficial questions and explains why the best ones invite stories rather than one-word answers. Encouraged by her parents to ask meaningful questions at the dinner table, she is already developing the habits of a lifelong learner.

Whether researching travel for the book she is writing or choosing the most interesting path while wandering a new city, Addy reminds us that curiosity is less about age and more about posture. One that keeps the world expansive, welcoming, and full of possibility. Follow along on her adventures through her Dad's Instagram account at https://www.instagram.com/austinkgraff/

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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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.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#62 Haru Yamada: Flashlights, Lanterns, and the Way We Listen

"Not being a hundred percent sure all the time is a weird strength." - Haru Yamada

In this episode of Curated Questions, Ken Woodward is in conversation with Dr. Haru Yamada, a sociolinguist, intercultural communication scholar, and author of Kiku: The Japanese Art of Good Listening, to explore what it really means to listen. Haru traces her early understanding of questions back to age four, when she moved from Tokyo to New York and had to use questions as a tool for language, belonging, and survival.

Together, they unpack how culture shapes communication: English often rewards “flashlight” questioning, the precise, content-driven clarity, while Japanese culture tends to favor a “lantern” approach that illuminates context, relationship, and what isn’t said. Haru also shares the harrowing accident that reshaped her understanding of listening as a health practice, linking felt-heard experiences to relational, mental, and even physical well-being.

In a noisy, multitasking world, this conversation reframes listening as an active, life-giving skill, and a compass for navigating each other with empathy.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#61 Rob Walker: The Art of Noticing: How Asking Better Questions Changes What We See!

"If all you do is pay attention to what everyone else is paying attention to, then by definition you're not likely to innovate anything or create anything very original or different or surprising." - Rob Walker

Writer and cultural observer Rob Walker joins Ken to explore how questions and noticing reshape the way we move through the world. Rob traces his origin story back to discovering journalism at 18—a framework that gave a shy, introverted kid permission to ask questions on behalf of others.

They dig into his book and newsletter The Art of Noticing, talking about everyday noticing assignments, why “what am I missing?” is a powerful self-question, and how small acts of attention can mark time and make life more memorable.

Rob shares the story behind the Significant Objects project and why story—not price tag—creates real value in the objects we keep. From New Orleans as a “conversational city” to his teaching on point of view and manifestos, Rob reflects on questions as both agency and responsibility, in democracies, organizations, and personal life. Be sure to subscribe to Rob's Substack The Art of Noticing newsletter at https://robwalker.substack.com/

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#57 Jaimie Reese: Building Enduring Trust Through the Questions We Ask!

"When you have a trusting environment, it is exactly to hold each other accountable." - Jaimie Reese

What does it take to build trust in one of the world’s largest bureaucracies? Former U.S. Navy Senior Executive (SES) Jaimie Reese joins Ken Woodward to explore how genuine curiosity and courageous questioning can reshape systems, teams, and lives. From the aftermath of 9/11 to boardrooms and the Pentagon, Reese shares hard-won lessons on leadership, timing, and the art of listening when stakes are high.

Through stories that move from crisis to calm, she unpacks why trust isn’t granted by authority but earned through everyday inquiry—how slowing down, asking better questions, and truly hearing the answers can transform any organization. Jaimie traces the invisible threads between humility, communication, and change, revealing what happens when leaders replace certainty with curiosity.

This episode challenges every listener to reimagine leadership as an ongoing dialogue. Because, as Jaimie reminds us, “Leadership is a conversation you have with the future—one question at a time.”

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#55 Ken Woodward: The Locked Door: How Avoided Questions Hold the Key to Transformation!

"Your avoided question isn't just personal development, it's an act of resistance." - Ken Woodward

In this episode of Curated Questions, host Ken Woodward explores the transformative power of confronting the questions we're avoiding. Delving into neuroscience, psychology, and personal reflection, he highlights why these avoided questions create discomfort and how they serve as a gateway to significant change.

Ken introduces tools and methodologies to help listeners identify and tackle these questions, both in their personal lives and within organizations. With practical advice and real-world examples, this episode encourages listeners to pause, reflect, and take actionable steps towards growth.

Ken also underscores the importance of curiosity and its role in overcoming avoidance, ultimately leading to meaningful transformation.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#54 Jill Reilly: The Permission Paradox & Why Questions Matter More Than Approval!

"The most fundamental relationship in any change process is the one that you have with yourself. It's the questions that you ask yourself first and foremost that are the game changers." - Jill Reilly

In this episode of Curated Questions, host Ken Woodward is in conversation with global citizen and author Jill Reilly to explore the power of questioning in navigating life’s complexities.

Jill shares her journey from the Midwest to South Africa, Zimbabwe, and beyond, reflecting on her experiences as an aid worker and the lessons that shaped her understanding of change and personal agency.

They discuss the importance of self-permission, processing grief, and the need to adapt amidst societal and technological upheaval. With insights from her new book The Ten Permissions: Redefining the Rules of Adulting in the 21st Century, Jill emphasizes the transformative potential of asking the right questions to unlock personal growth and resilience.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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#48 Ken Woodward The Curated Questions Origin Story: When It All Began!

" Once you have the question, the hard part begins." - Ken Woodward

In this solo episode, host Ken Woodward delves into the origin and development of the 'Curated Questions' project, which began in 2018. Ken shares his personal journey of curiosity, inspiration from Tim Ferriss' podcast, and the influences that led to the creation of his blog and subsequent podcast.

Highlighting notable milestones and influential interviews, Ken discusses the structure and purpose of the Curated Questions website and its various elements, including famous questions and lists. He also reflects on the profound impact of asking meaningful questions, illustrated with personal anecdotes.

The episode encourages listeners to embrace curiosity and engage with the world through the power of well-chosen questions.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

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