Building Enduring Trust Through the Questions We Ask! | Jaimie Reese #57

Curated Questions: Conversations Celebrating the Power of Questions!

"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

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