In this special edition of Conversations On Character, General Stan McChrystal joins McChrystal Group Partner Erin Sutton for a thoughtful discussion on the unique role Chiefs of Staff play in shaping and protecting organizational character. With insights from Jeanette Herbert (National Geographic) and Tito Crespo (Chimes International), the conversation explores how values influence leadership, decision making, and collective culture at the highest levels.
Key themes include:
- The Chief of Staff as a steward of character and culture
- Navigating the “say-do” gap when values are tested
- Building a team culture grounded in honest conversations
- The importance of conviction, integrity, and redemption in leadership
Watch the full conversation below and explore what it means to lead with character—especially when it matters most.
Summary of Discussion
Character and the Chief of Staff: A Leadership Conversation with General Stanley McChrystal
“Character is an organization’s fate. And if that’s true, then Chiefs of Staff are often its stewards.” – General Stanley McChrystal
Why Character Matters—Especially for Chiefs
Drawing from his latest book, On Character: Choices That Define a Life, General McChrystal opened with a clear message: character may be difficult to define, but it is essential to leadership. For Chiefs of Staff—often serving as the connective tissue between executives and the broader organization—character isn’t just a personal trait. It’s a job requirement.
“You lead every minute of every day. Whether you realize it or not, people are watching, and they’re making decisions about whether to follow your example.”
Chiefs are often the first to sense cultural drift, notice ethical blind spots, or be put in a position to either uphold or compromise values. As McChrystal put it, “The Chief is the mooring point.”
The Conviction Behind the Role
Herbert emphasized that character is deeply embedded in the Chief of Staff function: setting behavioral norms, acting as a proxy for leadership, and reinforcing culture through everyday interactions. She encouraged Chiefs to explore their convictions by reflecting on emotional responses and moments of discomfort.
“If you investigate what makes you deeply angry, it often leads you to what you believe in most.”
Tito Crespo shared how his upbringing, military service, and executive experience all contributed to a values-driven leadership style. From Army principles like duty and selfless service to corporate challenges around competition and collaboration, he highlighted the importance of staying grounded in integrity.
When Values Are Tested
A standout theme from the discussion was how Chiefs should respond when a leader’s behavior doesn’t align with their stated values. McChrystal offered this perspective:
“People will forgive you for not being the leader you want to be. But they won’t forgive you for not being the leader you claim to be.”
The panel explored the difficult but necessary responsibility of confronting misalignment. Whether it means providing direct feedback, protecting the team, or making tough personal decisions, integrity must remain non-negotiable.
Creating a Culture of Conversation
Character isn’t built in a vacuum—it’s shaped through dialogue, reflection, and shared experience. The panel urged leaders to create space for meaningful conversations, not just about strategy or performance, but about values.
“What if we got coffee and, instead of talking about the weather, we talked about what honesty really means to us?”
Sutton shared that even casual value-based conversations can ripple outward, shaping team dynamics and reinforcing culture far beyond formal settings.
Redemption, Not Perfection
The conversation closed with a powerful reminder: character is not about being flawless—it’s about how we respond when we fall short.
"Your team is going to stumble. Some will stumble badly. But if we don’t create a culture where redemption is possible, what message are we sending?”
The panel emphasized that leaders—especially Chiefs of Staff—must model resilience, accountability, and a commitment to learning. That’s how cultures rooted in trust are built and sustained.
Let’s Continue the Conversation
This discussion is part of General McChrystal’s ongoing series exploring character in leadership. To access more reflections and resources, including our On Character Discussion Guide and upcoming events, visit mcchrystalgroup.com.
Are you a Chief of Staff looking to take the next step? Join us this fall for McChrystal Group’s Chief of Staff Leadership Retreat, where we’ll continue the conversation with leaders from across industries.
