Hosted by Rachel Gil, this exclusive Cresset conversation featured General Stanley McChrystal, one of the most respected voices in modern leadership and a retired four-star general. In a time marked by geopolitical instability and cultural flux, the discussion centered on the enduring value of character in leadership, the habits that shape resilient individuals and organizations, and the role of personal responsibility in navigating complex environments. Drawing from his latest book, On Character, McChrystal offered a compelling argument: character—not skill, charisma, or even experience—is the ultimate differentiator for effective leadership.
Key Themes
- Character as the True Leadership Metric: McChrystal asserted that character is defined not by intention but by action—what we consistently choose to do, especially under pressure.
- The Character Equation: He introduced a powerful framework—Character = Conviction × Discipline—emphasizing that deeply held beliefs must be paired with the discipline to live by them daily.
- Leadership in Crisis: Drawing on high-stakes moments from his military career, including his resignation amid controversy, McChrystal illustrated how ethical leadership often requires painful but necessary decisions.
- Culture and Informal Leadership: The health of any organization is shaped more by its informal culture than formal policies. Leaders must model values with consistency and authenticity to earn trust and build cohesion.
- Agency and the Power of Choice: McChrystal stressed that character is built, not inherited. In a world filled with distractions and rationalizations, the ability to choose wisely—and repeatedly—is a core leadership competency.
- Generational Impact and Legacy: He encouraged leaders to define the legacy they wish to leave and live accordingly, knowing their influence may outlast their title or tenure.
- Hope for the Future: Despite global uncertainty, McChrystal expressed optimism in the next generation’s potential to lead with integrity, reset cultural norms, and restore faith in institutions.
- The Strategic Value of Character: Whether navigating politics, global business, or personal decisions, McChrystal argued that character is not just a moral compass—it’s a strategic asset that drives sustainable leadership.
Order a complimentary copy of On Character: Choices That Define a Life.
