Curated Questions: Conversations Celebrating the Power of Questions! Building Enduring Trust Through the Questions We Ask! | Jaimie Reese #57
"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
00:00 Building Trust and Accountability
01:07 Introduction to Curated Questions
01:51 Meet Jamie Reese
03:05 Jamie's Early Career and Learning the Power of Questions
05:36 The Importance of Prioritizing Questions
06:37 Building Relationships Through Questions
10:17 Navigating Requirements and Funding in the DOD
14:31 Engaging Stakeholders
22:16 The Role of Diverse Voices in Decision Making
28:29 Creating a Safe Space for Questions
36:44 The Importance of Time in Asking Questions
37:36 Reflections on Time Management
39:21 The Importance of Time Management
40:03 AI and the Art of Asking Questions
40:52 Balancing Speed and Quality
43:07 The Cost, Schedule, Performance Triangle
43:26 Applying Business Principles to Human Capital
45:38 Managing a Large Workforce
46:08 Strategic Workforce Development
52:38 Data-Driven Decision Making
55:10 The Role of Questions in Leadership
59:11 Navigating Organizational Change
01:02:42 Finding The Skeletons in The Closets
01:11:14 Building Trust and Accountability
01:12:50 The Value of Trust in the Workplace
01:14:09 Balancing Organizational Trust and Personal Sacrifice
01:15:04 The Decision to Leave the Federal Workforce
01:15:56 The Importance of Trust in Relationships
01:17:11 Facing Unhappiness and Making Changes
01:17:59 Reflecting on Career and Organizational Loyalty
01:19:49 The 9/11 Experience: A Day of Chaos and Leadership
01:21:13 Evacuation and Immediate Aftermath
01:23:07 Returning to Work Post-9/11
01:24:15 Leadership Lessons from Crisis
01:30:44 Navigating Healthcare for a Loved One
01:35:20 The Importance of Being Present in Healthcare
01:38:31 Final Thoughts and Ways to Connect
Resources Mentioned
NAVSEA (Naval Sea Systems Command)
Kevin Kelly – Wired magazine founder, author of The Inevitable
Jaimie Reese on LinkedIn