Curated Questions: Conversations Celebrating the Power of Questions!
Curated Questions: Conversations Celebrating the Power of Questions!
Ken Woodward
Building Enduring Trust Through the Questions We Ask! | Jaimie Reese #57
1 hour 45 minutes Posted Nov 13, 2025 at 5:00 am.
Building Trust and Accountability
Introduction to Curated Questions
Meet Jamie Reese
Jamie's Early Career and Learning the Power of Questions
The Importance of Prioritizing Questions
Building Relationships Through Questions
Navigating Requirements and Funding in the DOD
Engaging Stakeholders
The Role of Diverse Voices in Decision Making
Creating a Safe Space for Questions
The Importance of Time in Asking Questions
Reflections on Time Management
The Importance of Time Management
AI and the Art of Asking Questions
Balancing Speed and Quality
The Cost, Schedule, Performance Triangle
Applying Business Principles to Human Capital
Managing a Large Workforce
Strategic Workforce Development
Data-Driven Decision Making
The Role of Questions in Leadership
Navigating Organizational Change
Finding The Skeletons in The Closets
Building Trust and Accountability
The Value of Trust in the Workplace
Balancing Organizational Trust and Personal Sacrifice
The Decision to Leave the Federal Workforce
The Importance of Trust in Relationships
Facing Unhappiness and Making Changes
Reflecting on Career and Organizational Loyalty
The 9/11 Experience: A Day of Chaos and Leadership
Evacuation and Immediate Aftermath
Returning to Work Post-9/11
Leadership Lessons from Crisis
Navigating Healthcare for a Loved One
The Importance of Being Present in Healthcare
Final Thoughts and Ways to Connect
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Show notes
"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!
Episode Notes
Resources Mentioned
The Pentagon
DASN
OSD
NAVSEA (Naval Sea Systems Command)
Kevin Kelly – Wired magazine founder, author of The Inevitable
Ferris Bueller’s Day Off
ReeseReimagined.com
Jaimie Reese on LinkedIn
Producer Ben Ford
Beauty Pill