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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
 

#54 Jill Reilly: The Permission Paradox & Why Questions Matter More Than Approval!

"The most fundamental relationship in any change process is the one that you have with yourself. It's the questions that you ask yourself first and foremost that are the game changers." - Jill Reilly

In this episode of Curated Questions, host Ken Woodward is in conversation with global citizen and author Jill Reilly to explore the power of questioning in navigating life’s complexities.

Jill shares her journey from the Midwest to South Africa, Zimbabwe, and beyond, reflecting on her experiences as an aid worker and the lessons that shaped her understanding of change and personal agency.

They discuss the importance of self-permission, processing grief, and the need to adapt amidst societal and technological upheaval. With insights from her new book The Ten Permissions: Redefining the Rules of Adulting in the 21st Century, Jill emphasizes the transformative potential of asking the right questions to unlock personal growth and resilience.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

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tags: Ken Woodward, Curated Questions, Jill Reilly, permission, questions, approval, self-permission, personal agency, curiosity, life transitions, career change, South Africa, cultural intelligence, adult learning, mindset shift, breaking patterns, family expectations, authentic connection, willpower, being willful, navigate uncertainty, AI age, future of work, personal growth, self-discovery, questioning techniques, life choices, global citizen, aid worker, The 10 Permissions, transformative questions, personal boundaries
categories: Community, Social Impact, Connection, Leadership, Listening, Personal Growth, Change Management, Problem Solving
Wednesday 10.22.25
Posted by Kenneth Woodward
 

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