"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…