#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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#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)

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#67 Matthew Pridgen: When Cognitive Dissonance Breaks Open

"You can only live with so much cognitive dissonance in your life." - Matthew Pridgen

Matthew Pridgen joins Ken Woodward for a raw, wide-ranging conversation about how questions can crack open denial and move us toward truth, repentance, and reconciliation.

Matthew shares his dramatic journey from addiction and a near-fatal suicide attempt to a decades-long pursuit of faith, justice, and historical honesty. His pivotal moment was when an eight-year-old girl asked, “Why did you take my church down?” after a tent revival in Charleston’s historically Black East Side, which became the question that launched his racial awakening.

Together, they explore how American “mythology” hides the realities of slavery, Jim Crow, and modern dog whistles, and how the Black church has sustained a prophetic witness against oppression.

The episode highlights the personal cost of cognitive dissonance, the freedom of living without lies, and a central challenge for today: are Christians willing to abandon Christian nationalism and follow Jesus’ actual teachings?

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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#40 Ken Woodward: Reviving Franklin's Junto: How Questions Built America

In this episode of Curated Questions, host Ken Woodward uncovers a forgotten antidote to our fractured discourse: Benjamin Franklin's Junto. In 1727 Philadelphia, a 21-year-old printer gathered tradesmen—the 'leather apron crowd'—for Friday night discussions that would revolutionize American civic life. This wasn't just a social club; it was a systematic experiment in collective wisdom that led to the creation of America's first volunteer fire company, lending library, public hospital, and the University of Pennsylvania.

Ken explores Franklin's 24 carefully crafted questions that transformed ordinary workers into civic leaders, revealing how debates conducted 'without fondness for dispute, or desire of victory' built both personal character and community institutions. Through themes of personal development, community awareness, civic engagement, and mutual support, the Junto proved that structured curiosity could turn individual ambition into collective flourishing.

Drawing from Franklin's original rules, including banning words like 'certainly' and fining members who spoke too definitively, Ken explains how the Junto combined three elements that modern groups often keep separate: personal growth, civic action, and genuine friendship. The episode includes a vulnerable reflection on intellectual loneliness and ends with a direct challenge: Start this Friday. Find three curious people. Ask one of Franklin's questions. See what happens.

#24 Ken Woodward: Impactful Questions: Are You Better Off...

This episode dives into the significant political question posed by Ronald Reagan during the closing moments of his 1980 presidential debate with Jimmy Carter: 'Are you better off than you were four years ago?'

Ken Woodward explores the context of the 1980 political climate, marked by economic difficulties, high inflation, unemployment, and international issues such as the Iran hostage crisis and concerns about U.S. global standing and nuclear threats. Reagan's question, which became iconic in U.S. political discourse, was noted for its simplicity, personal relevance, emotional resonance, and strategic timing. The question invited voters to reflect on their circumstances rather than abstract policies, ultimately contributing to Reagan's landslide victory.

The episode details six crucial lessons for crafting influential questions, emphasizing audience perspective, engagement, simplicity, timing, self-reflection, and a call to action. Listeners are encouraged to consider how such questions have shaped their decisions and to apply these insights in personal and professional contexts.