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Curated Questions

Celebrating The Power Of Questions

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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.

Keep questioning!

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tags: Curated Questions, Ken Woodward, Jaimie Reese, leadership, trust, inquiry, curiosity, communication, transformation, Navy leadership, executive coaching, organizational change, decision-making, emotional intelligence, psychological safety, professional growth, leadership podcast, reflective leadership, authentic communication, integrity, crisis management, culture building, mentorship, resilience, innovation, purpose, change management, listening, leadership development, personal growth
categories: Leadership, Listening, Mental Wellness, Personal Growth, Change Management, Grief
Wednesday 11.12.25
Posted by Kenneth Woodward
 

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