"When you have a trusting environment, it is exactly to hold each other accountable." - Jaimie ReeseWhat 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 Notes00:00 Building Trust and Accountability01:07 Introduction to Curated Questions01:51 Meet Jamie Reese03:05 Jamie's Early Career and Learning the Power of Questions05:36 The Importance of Prioritizing Questions06:37 Building Relationships Through Questions10:17 Navigating Requirements and Funding in the DOD14:31 Engaging Stakeholders22:16 The Role of Diverse Voices in Decision Making28:29 Creating a Safe Space for Questions36:44 The Importance of Time in Asking Questions37:36 Reflections on Time Management39:21 The Importance of Time Management40:03 AI and the Art of Asking Questions40:52 Balancing Speed and Quality43:07 The Cost, Schedule, Performance Triangle43:26 Applying Business Principles to Human Capital45:38 Managing a Large Workforce46:08 Strategic Workforce Development52:38 Data-Driven Decision Making55:10 The Role of Questions in Leadership59:11 Navigating Organizational Change01:02:42 Finding The Skeletons in The Closets01:11:14 Building Trust and Accountability01:12:50 The Value of Trust in the Workplace01:14:09 Balancing Organizational Trust and Personal Sacrifice01:15:04 The Decision to Leave the Federal Workforce01:15:56 The Importance of Trust in Relationships01:17:11 Facing Unhappiness and Making Changes01:17:59 Reflecting on Career and Organizational Loyalty01:19:49 The 9/11 Experience: A Day of Chaos and Leadership01:21:13 Evacuation and Immediate Aftermath01:23:07 Returning to Work Post-9/1101:24:15 Leadership Lessons from Crisis01:30:44 Navigating Healthcare for a Loved One01:35:20 The Importance of Being Present in Healthcare01:38:31 Final Thoughts and Ways to ConnectResources MentionedThe PentagonDASNOSDNAVSEA (Naval Sea Systems Command)Kevin Kelly – Wired magazine founder, author of The InevitableFerris Bueller’s Day OffReeseReimagined.comJaimie Reese on LinkedInProducer Ben FordBeauty Pill