#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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Keep questioning!

#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.

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

Keep questioning!

#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.

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

Keep questioning!

#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.

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

Keep questioning!