#99 Wanda Herndon: What Are They Really Asking? | Former Starbucks SVP on the Second Question

" I had to start trying to think beneath the questions: what are they really saying?" - Wanda J. Herndon

Wanda J. Herndon trained as a journalist, then spent forty years on the other side of the notebook. Dow. DuPont. Eleven years as Starbucks SVP of Global Communications while the company grew from 550 stores to more than 11,000.

Her curiosity starts with a middle child in Flint, Michigan, who wore out her siblings asking why. She describes learning, after being misquoted, to ask what a reporter is really asking. She calls listening a discipline she never mastered. And the question that carried her through divorce: what is this moment trying to teach me?

Crisis work as a puzzle solved with who, what, why, when, where, how. Mentoring as a two-way street. Why she always asked Howard Schultz why. Being the CEO of you. Owning Flint rather than letting others define it.

And her right now question: will we survive this chaos, and what can I do to help?

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#98 Ken Woodward: Paid To Say I Don't Know

" 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 design made it startling. Participants could decline any question with no penalty. Guessing wrong cost them money. The AI advice they received was usually wrong. Every incentive pointed toward three simple words, and access to a machine nearly eliminated their willingness to say them.

What got suppressed wasn't accuracy. It was the willingness to be seen not knowing.

In this solo episode, Ken opens with a lie he told a friend in a room where nothing was at stake, then traces the same reflex through a sidewalk in Southeast D.C., five questions he couldn't answer, and a backyard conversation that ran five hours past its twenty-minute plan.

"I don't know" isn't a report on empty shelves. It's a doorway, and it's the only one.

What question are you avoiding because not knowing would cost you something?

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#97 Ken Woodward: The Last Time Was A Tuesday

"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 calendar, the date, the list of names. The last one got past him anyway.

That is the shape of this episode. We do not know which time is the last time, and preparation does not change that. Ken walks through Tim Urban's arithmetic on parents, a return to his hometown that was supposed to be final and wasn't, and an upcoming lunch with his ninety-three-year-old aunt, who is the last door into a generation that has already closed. In Ambiguous Loss, Pauline Boss offers a useful frame: closure is largely a myth, and the real skill is holding something open without needing it to shut.

The question idea underneath it: every unasked question has an expiration date you cannot see. Some are saving for a better moment. Some you can't ask because you don't yet know you will want the answer.

Ken is recording before he flies, without a resolution, because the not knowing is the point.

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#96 Ken Woodward: A Slightly Smaller Life

"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 came away with shallower knowledge, and when researchers propped the door open, placing live source links right beside the summary, almost nobody walked through.

Sixty-eight percent of Google searches now end without a click. With an AI Overview on the page, eighty-three percent.

This episode is about what that costs. Not wrong answers, wrong answers get caught. It's the second question that never gets asked, which leaves no error message and no gap in the record. Just a slightly smaller life that you experience as a completely normal one.

Then: a man on a corner in Northeast D.C. who gave me a name that wasn't his, and what it took to get the real one.

One more thing, I need your help naming something.

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#95 Dr. Lani Watson: Even Socrates Didn't Ask: On the Hidden Power of Questions

" 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." - Dr. Lani Watson

Dr. Lani Watson has spent her career on a question most of us never stop to ask. What is a question, and why does it hold such power?

Known online as The Questions Doctor, Lani is a philosopher and the author of Q: The Hidden Power of Questions in a World That Wants Answers. In this episode, we sit with the idea that questions are a kind of everyday magic. A power we all carry and rarely notice. They change our brains. They change our relationships. They shape the very answers we receive.

We talk about Socrates and the gift of not knowing. We talk about a world racing toward answers, and what we lose when we rush past the question. We talk about who gets to ask, and who does not.

Come sit with the questions a while. There is power in the asking, and it belongs to all of us.

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#94 Ken Woodward: The Station Never Called: The Listener's Question

"Listening is not real until the listener makes a sound back." - Ken Woodward

A sound-powered telephone runs on nothing but the sound of your own voice. No battery. No amplifier. I served on submarines, and I never forgot the joke we played on every new sailor: we sent him hunting the whole ship for batteries that do not exist. The power was in him the entire time. He only had to speak.

This is a solo episode about listening. About the repeat-back, the discipline of saying a message back until it lands correctly. About a 2025 study that found the follow-up question is the clearest sign that real listening is happening. About what Dr. Haru Yamada taught me, that to ask and to listen are one motion.

And it is about one officer I served with, a question I never asked him, and why I let it go unasked. The circuit is always live. Who is the station you have never called?

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#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.

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#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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#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?

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#89 Ken Woodward: The Question We Wait to Be Asked

"The avoided question and the awaited question. Same person. Two sides of one ache." - Ken Woodward

Nearly all of the research on curiosity studies the person asking. A new study out of New York University, led by Dr. Niobe Way and Rachel Taffe, turned the lens around and asked the receiver instead. They gave 641 young people a single written prompt: what is the question you most wish someone would ask you, and why. More than ninety-seven out of every hundred had an answer ready.

In this solo episode, Ken sits in that other chair. He walks the eight kinds of questions people long to receive and the six reasons underneath them, and finds that almost none of them are about information. People want to be seen, to be cared for, to be given permission to say the loving thing they have been holding back.

Drawing on more than thirteen hundred conversations from his two years walking every street in Washington, D.C., Ken offers the lived proof: the woman undone by "good to see you," the friend he carries, the questions strangers had been waiting years for someone to ask.

He closes on two pillars of the same practice. The question you are avoiding, and the question you are awaiting.

A meditation on the plainest question in the language, and what it costs to drive around for years with one sitting unasked in the seat beside us.

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

"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.

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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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#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.

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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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