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Curated Questions

Celebrating The Power Of Questions

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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.

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

Keep questioning!

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tags: Ken Woodward, Curated Questions, Andrew Caulk, disinformation, misinformation, information warfare, strategic communication, military intelligence, national security, media literacy, critical thinking, propaganda, narrative warfare, attention economy, social media manipulation, war games, Taiwan conflict, American foreign policy, Iran war, military strategy, public affairs, credibility, truth in communication, information strategy, cognitive bias, normalcy bias, media bias, news literacy, questioning assumptions, leadership questions, curiosity, sense-making, strategic inquiry
categories: Community, Leadership, Mental Wellness, Personal Growth, Politics, Strategy, Parenting, Problem Solving
Wednesday 04.15.26
Posted by Kenneth Woodward
 

#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.

Keep questioning!

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tags: Curated Questions, Ken Woodward, Frank Sesno, questioning techniques, active listening skills, interview preparation, curiosity practices, journalism skills, communication strategies, bridge building questions, echo question technique, strategic questioning, audience awareness, Ask More book, deliberate curiosity, question preparation, polarization solutions, conversation skills, media literacy, critical thinking, interpersonal communication, empathy development, AI and questioning, fact checking, creative questioning, professional development, leadership communication, conflict resolution, relationship building, student engagement, public speaking, investigative journalism
categories: Community, Social Impact, Connection, Education, Leadership, Listening, Personal Growth, Journalism
Wednesday 11.19.25
Posted by Kenneth Woodward
 

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