"When you have a trusting environment, it is exactly to hold each other accountable." - Jaimie Reese
"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
Questions Asked
When did you first understand the power of questions?
Do you know how many questions you’ve asked?
How can I help?
Can you prioritize your top 25?
If you ask a lot of questions, are you going to get the answers you want?
How can we both be successful in this exchange?
Out of those 155 questions early in your career, which ones have become your top 25 today?
Can one question answer several others?
How do you decide which questions are the most impactful?
How does timing influence the questions you ask?
What are the most pointed questions you can ask?
Is this question germane to the outcome we’re trying to achieve?
What are other ways to get information outside the question-and-answer period?
How can you build trust with the people you’re questioning?
What happens when you ask too many questions too quickly?
What kinds of questions give you the most useful insight?
Were there any particular questions that became favorites for you—ones that cracked the nut or revealed key insight?
How does the timing of events or contracts shape your questioning?
If schedules slip, what should we ask first?
How can we re-phase instead of remove funding?
What questions help a partner be successful rather than feel threatened?
What happens if we don’t change our schedule or requirement?
Could we deliver capability faster by changing what we ask for?
Which of these requirements are truly the most important?
Do we need X, Y, and Z—or just X and Y?
How risky is that?
Can we meet the requirement differently?
Can we drive risk out of the system?
If you could get one thing in 12 months versus three things in three years, which would you choose?
Do you really need all of these at the same time?
How do questions enable us to explore trade-offs?
How can we work together to make sure money and schedules align?
Who else needs to be in the room for this discussion?
Who are the stakeholders we’re not hearing from?
If you keep asking the same people the same questions, are you going to keep getting the same answers?
Do people fear questions because questions demand change?
How do you create a trusting environment for disruptive questions?
How do you establish ground rules for safe dialogue?
Can we agree on what success looks like before we begin?
How can I help you be successful?
How can we make sure this conversation stays constructive?
What would it take for this to be a win-win?
Who else should know about this decision before it’s final?
How do we get ahead of this issue rather than react to it?
What if we talked to stakeholders now instead of later?
Why not talk to Congress or other oversight groups early?
How do you create a safe space upward—for bosses and senior leaders—not just for peers or teams?
If a leader is introverted or remote, how can I intentionally build connection?
How do I create time to build relationships when the work itself pulls me inward?
How important is time to developing good questions and good answers?
Can we really be thoughtful when we’re constantly rushed?
Will AI truly give us back time—or just drive us toward the middle?
How can we carve out space to think deeply?
What happens if we let speed replace smoothness?
Is fast always better than slow?
Which two can we pick—cost, schedule, or performance?
How does cost–schedule–performance apply outside defense work?
How can we measure performance in human terms?
How do you get the right people in the right place at the right time?
What are the biggest workforce problems to solve first?
How can we balance short-term actions with long-term sustainability?
If we fix this, can we sustain it?
What are we really trying to measure?
How do we know if we’re winning?
How should we measure attrition—and what does “good” attrition look like?
Why are people leaving early?
What data aren’t we looking at?
What would happen elsewhere in the system if we changed this one number?
How do we reduce volume rather than only measure speed?
What are people actually doing each day—and which of those tasks add value?
Who can we centralize or remove work from to free capacity?
What else is driving workload that we haven’t named?
When moving into a new role, how do you decide what to accomplish first?
What is the role of this organization—what outcomes is it truly meant to deliver?
Are we meeting those mission sets?
What should this group be doing a year from now versus today?
Who decides that?
Are we organized correctly for what the command really needs?
Do we have the right expertise for our core mission?
Do people have the tools they need to succeed?
If not, what’s preventing that access or training?
Who would agree that we’re good at this—and who wouldn’t?
How do you know you’re good at it?
If you had to measure it, how would you?
What are the barriers to measuring your work?
Who else should be part of setting those measures?
Are my questions truly my own—or am I borrowing someone else’s bias?
How can I ask questions that build trust instead of suspicion?
How can I hold people accountable while maintaining trust?
What happens when trust erodes?
What does trust mean to me personally?
Can you lead change without trust?
What does accountability look like inside a trusting relationship?
Can I trust the organization as much as it trusts me?
What happens when that balance breaks?
Is this still the right place for me to contribute?
Am I happy?
Is staying aligned with my values or my circumstances?
What would make me happy again?
Is it time to make a change?
When should you choose bravery over stability?
Would I have stayed if 9/11 hadn’t happened?
What do I remember most about that day?
What did leadership look like in that moment?
Can you be high-ranking and still be a poor leader?
What can we learn from bad leadership as well as good?
How do you show people you care in crisis?
What questions were we asking immediately after the attacks?
How do we decide what capabilities our warfighters need most urgently?
What can we do quickly?
How do we keep moving forward when we don’t have all the answers?
What did that event teach us about resilience and teamwork?
Would I still be here without that shared experience?
What events keep us in a mission—and which drive us to leave?
What is your “right-now” question?
What are the big questions you’re wrestling with today?
How do I ask questions for someone else’s care when I’m not an expert?
Can you explain that again in simpler terms?
Yesterday you said one thing; today it’s different—what changed?
Who is making what decision and when?
What are the next steps in her care?
How are you feeling today?
Did you eat?
Have you talked to the doctor about that?
Can we write that question down for the next nurse or physician?
What’s not being asked that should be?
How do we make sure there’s continuity in care across shifts?
What symptoms or small changes might actually matter more than we think?
How can I be present enough to advocate effectively?
How can we create time to care and to question in a busy life?
What has this experience taught me about presence, patience, and questioning?
Where in your organization are you confusing niceness with trust, avoiding the accountability conversations that would actually strengthen relationships?
What expensive problem are you repeatedly solving because you never had time to ask why it keeps happening?
Which of your metrics measure what's easy to count rather than what actually determines success or failure?
When did you last learn more about leadership from someone's failure to lead than from any success story?