#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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#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.

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

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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.

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

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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.

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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#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.

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)

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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.

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.

Be sure to check out the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions)

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#65 Mitchell Osmond: Everything Is Hard - Choose Your Hard

"Literally everything in life is hard. The question is, what cost are you willing to pay? And you pay that willingly and happily because you value it." - Mitchell Osmond

In this episode of Curated Questions, Ken Woodward sits down with Mitchell Osmond, founder of Dad Nation Co., and host of the Dad Nation Podcast (Top 5% globally), to explore a hard but liberating truth: everything in life is difficult; the question is which difficulty we choose.

Mitchell shares the moment a single question at a funeral, “Are you living a life worthy of imitation?” forced him to confront his health, marriage, finances, and legacy. From that reckoning emerged a framework for growth rooted in discomfort, integrity, and honest self-inquiry.

Together, Ken and Mitchell examine why confidence is built through keeping promises, how avoiding hard questions quietly shapes our futures, and why legacy is forged at home as much as at work.

The conversation challenges the myth of ease, reframes struggle as a signal of alignment, and invites listeners to define success on their own terms. Ultimately, this episode is a call to stop outsourcing meaning, and to choose the hard that leads to a life worth living.

Mitchell is launching a new group coaching program, the High Performance Husband Accelerator! All the details can be found at https://www.dadnationco.com/accelerator

Mitchell is offering The Connection Code as a gift. 50 questions to spark the fun and get the fire back is available at https://www.dadnationco.com/code

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

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#63 Ken Woodward: The Inquisitive Almanack: 2026

"Direction often emerges not from knowing what you want, but from finally admitting what you don’t." - Ken Woodward

The Inquisitive Almanack: 2026 Edition closes the year with something Curated Questions has never quite done before—an affectionate, slightly irreverent, and deeply thoughtful almanack for the inner life.

Inspired by Benjamin Franklin’s Poor Richard’s Almanack, this episode blends dry wit, invented bureaucracy, and hard-won wisdom to offer forecasts not for the weather, but for the heart, mind, and questions we carry.

You’ll hear interior weather reports, proverbs for the asking class, arbitrary rules of inquiry, lunar phases of curiosity, and predictions for the questions most likely to surface in 2026—across leadership, relationships, parenting, teams, and personal life.

Released intentionally as the final episode of the year, this Almanack isn’t a recap or a resolution guide. It’s a pause. A breath. A lighter place to rest before the calendar turns and begins asking new things of us.

Come curious. Leave rested. And carry one good question forward.

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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#60 Radhika Dutt: From Goals to Puzzles: How Questions Outperform OKRs in Real Teams!

"We vote with our labor for the world we want to create. If you don't reflect on what you're doing, how do you know you're casting the right vote?" - Radhika Dutt

In this episode of Curated Questions, host Ken Woodward engages entrepreneur and author Radhika Dutt in a profound exploration of how questions can transform organizations from goal-driven to puzzle-solving entities. Radhika is the author of "Radical Product Thinking" and shares her journey from MIT to becoming a serial entrepreneur to developing the puzzle-based leadership OHLA framework (Objectives, Hypotheses, Learnings, Adaptations).

The conversation reveals how traditional goal-setting, rooted in 1940s assembly-line thinking, fails in today's complex environment, where creative problem-solving matters more than repetitive execution.

Radhika demonstrates through a live experiment how "puzzles" energize while "goals" burden, explaining that puzzles tap into internal motivation rather than external pressure. She emphasizes the critical importance of reflection, a practice she credits with enabling better decision-making both personally and professionally.

Drawing from her nine languages and global experience, including living in post-apartheid South Africa, Radhika offers insights on creating psychological safety for questions across cultures. The episode culminates with practical guidance on implementing puzzle-based thinking in organizations, showing how asking better questions leads to ownership, engagement, and transformative results.

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

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#59 Ken Woodward: The Insight Pause: When a Single Truth Rewrites Your Story!

"The Insight Pause is sitting in the rubble of your shattered worldview before clearing a single stone." - Ken Woodward

In this solo episode, Ken Woodward introduces The Insight Pause—a five-step framework for navigating the moments that crack open our worldview. Through his own story of confronting the hidden history behind the Indigenous names and artifacts that shaped his childhood landscape, Ken explores how insights arrive fully formed, unsettle our identities, and demand more than quick fixes or defensive reactions.

He walks listeners through the foundational skills that prepare us for these moments, the instant of recognition, the sacred pause that follows, and the slow work of integrating unsettling truths into a new, liberated worldview.

Whether you're rethinking long-held beliefs, noticing contradictions you can’t ignore, or sensing that something in your life no longer fits, this episode offers a practical and compassionate guide for holding discomfort without collapsing into denial or overreaction.

Discover how the Insight Pause can transform the questions you carry—and the person you’re becoming.

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

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#58 Frank Sesno: How Bridge-Building Questions Cross Divides!

"I'm gonna make an appointment with my curiosity." - Frank Sesno

Emmy award-winning journalist Frank Sesno shares how curiosity and strategic questioning shaped his four-decade career covering presidents and world leaders as CNN's Washington Bureau Chief and White House correspondent. From a fourth-grade question about astronauts to interviewing five U.S. presidents, Frank reveals the power of deliberate curiosity and active listening.

Frank breaks down his approach to preparing for high-stakes interviews, explaining how he blocks conversations into thematic acts while remaining flexible. He introduces the "echo question" technique, which is simply repeating a person's emotionally charged word back to them, that transforms surface answers into more profound truths. Frank emphasizes that the best questioners are the best listeners, focusing on what people say and what they don't say.

In "Ask More: The Power of Questions to Open Doors, Uncover Solutions, and Spark Change," Frank discusses why bridge-building questions are critical in our polarized moment. He explores how AI makes human curiosity more valuable and shares his practice of "making an appointment with curiosity" to create time to deliberately formulate meaningful questions.

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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#56 Garrett Wood: Safety, Burnout, and the High-Achievement Mask!

"The closer you become with these people while you're wearing that mask, the more distant you actually feel from the people around you." - Garrett Wood

In this episode of Curated Questions, host Ken Woodward engages in a deep conversation with Garrett Wood, a national board-certified health and wellness coach and certified clinical hypnotherapist. Garrett shares his insights on the hidden tolls of high achievement, addressing issues such as perfectionism, imposter syndrome, and burnout. He explores the power of questions and how they can transform our understanding of identity, worth, and achievement.

The discussion dives into the paradox of wearing masks to gain social acceptance, the first signs of burnout manifesting as cynicism, and the importance of creating authentic connections. Garrett also discusses practical strategies, such as non-sleep deep rest, to enhance performance and creativity, as well as the role of self-compassion in maintaining mental health.

This episode offers valuable perspectives on how to navigate and make sense of the world through the power of questioning.

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

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