The Decisions That Define Us: Leadership Lessons from General Stanley McChrystal’s "On Character"

The Enduring Foundation: Building Leadership Upon Character

In a world often captivated by the dazzling allure of strategy and the immediate impact of action, we sometimes overlook the bedrock upon which all sustainable leadership is built: character. It is the quiet, consistent force that underpins our decisions, shapes our interactions, and ultimately defines the legacy we leave.

Today, we delve into General Stanley McChrystal’s compelling work, On Character: Choices That Define a Life (just released this month and an instant New York Times bestseller), a book that serves as a potent reminder that who we are is inextricably linked to how we lead.

About the Author: A Life of Leadership in Service

General Stanley McChrystal brings to the subject of character a perspective shaped by decades of consequential leadership. A retired four-star U.S. Army general, he commanded the Joint Special Operations Command and later led all U.S. and coalition forces in Afghanistan—roles that demanded not only strategic brilliance but unwavering ethical clarity.

Beyond his military achievements, McChrystal is known for his thoughtful approach to leadership and his ability to articulate complex ideas with clarity and depth. As a senior fellow at Yale University’s Jackson Institute for Global Affairs and co-founder of the McChrystal Group, a leadership consulting firm, he has translated the lessons of military leadership into actionable frameworks for organizations across all sectors.

What distinguishes McChrystal is not merely his experience, but his depth of reflection. In On Character, he steps away from the metrics of command to examine the essence of moral leadership. With candor and intellectual rigor, he invites readers to rethink what truly defines those who lead—not by rank or résumé, but by the choices they make when no one is watching.

The Fabric of Who We Are: McChrystal's Exploration of Character

On Character is not a traditional memoir, nor is it solely a leadership manual. Instead, it is a profound exploration of the essence of character, viewed through the lives of individuals—some famous, others less so—who embodied particular virtues or vices. McChrystal masterfully weaves together historical accounts, personal reflections, and insightful analysis to illuminate how the seemingly small choices we make each day accumulate to form the tapestry of our character.

The book is structured around various facets of character, examining traits such as honesty, courage, loyalty, and humility, often juxtaposing figures who exemplified these qualities with those who starkly did not. This comparative approach allows readers to not only understand the abstract concepts but also to see their practical implications in the lives of others.

McChrystal does not shy away from the complexities and nuances of character. He acknowledges that individuals are rarely paragons of virtue or embodiments of pure vice. Instead, he presents a more realistic view, highlighting the ongoing internal battles and the constant need for self-awareness and intentionality in shaping our character. He emphasizes that character is not a static entity; it is a dynamic process of becoming, influenced by our choices and our responses to the challenges we face.

One of the powerful aspects of On Character is its accessibility. While McChrystal draws upon a wide range of historical and literary examples, his writing remains grounded and relatable. He avoids jargon and speaks directly to the reader, inviting us to reflect on our own values and the choices we make. The book serves as both an education and an inspiration, prompting us to consider not just what we achieve, but how we achieve it.

Why Character Still Matters More Than Ever

In a world hungry for innovation, disruption, and speed, character can seem like an afterthought. But McChrystal makes a case—an urgent one—that character is not the soft side of leadership; it is the solid core. As institutions wrestle with crises of trust, and as leaders everywhere are scrutinized not only for results but for the way they achieve them, character emerges as the bedrock of enduring influence.

This is not a theoretical argument. McChrystal weaves in gripping historical profiles and contemporary examples—figures like Harriet Tubman, Dwight Eisenhower, and Malala Yousafzai—whose leadership stemmed not from titles or tactics but from deeply-rooted values. Each profile serves as a lens through which readers can examine their own defining choices.

Leadership in Our Current Environment: The Indispensability of Character

In today’s rapidly evolving and often turbulent environment, the principles outlined in On Character are more relevant than ever. We navigate a landscape marked by rapid technological change, increasing social complexity, and a constant barrage of information. In such a world, where trust can be easily eroded and ethical lines can become blurred, the character of our leaders serves as an anchor.

Consider the challenges many organizations and communities currently face: navigating uncertainty, fostering collaboration across diverse teams, and making decisions with incomplete information. In these moments, it is not just strategic acumen or technical expertise that guides us effectively; it is the underlying character of our leadership that inspires confidence and fosters unity. When leaders demonstrate integrity, empathy, and a commitment to doing what is right, even when it is difficult, they create a culture where others are more likely to follow suit.

McChrystal’s exploration of virtues like humility resonates deeply in a world that often celebrates self-promotion. True leadership is not about ego; it is about service. A humble leader is open to learning, willing to admit mistakes, and focused on the collective good rather than personal aggrandizement. This kind of leadership builds stronger teams and more resilient organizations.

Similarly, the discussion of courage extends beyond physical bravery to encompass moral courage—the willingness to stand up for one’s values, even in the face of opposition. In an era where difficult ethical dilemmas are commonplace, leaders who possess this moral fortitude are essential for navigating complex situations with integrity.

Significant Leadership Points from On Character

Several key themes emerge from McChrystal’s work that hold particular significance for all leaders:

• Character is Built, Not Inherited: McChrystal emphasizes that character is not a fixed trait we are born with but rather something we actively cultivate through our choices and habits. This is an empowering message for leaders, suggesting that we have agency in shaping who we become and, consequently, the kind of leader we are.

  
  

• Small Choices Matter: The book underscores the profound impact of seemingly insignificant daily decisions. It is in these moments—how we treat others, whether we are truthful in our communications, the standards we hold ourselves to—that our character is truly revealed and formed. Leaders must be mindful of the cumulative effect of these choices.

  
  

• Character Influences Outcomes: McChrystal illustrates how character directly impacts results. Trust, which is fundamental to effective leadership, is a direct byproduct of a leader’s integrity. Teams led by individuals of strong character are more likely to be cohesive, motivated, and successful in the long run.

  
  

• Self-Awareness is Crucial: Understanding our own strengths and weaknesses, our biases and tendencies, is a critical step in developing strong character. Leaders who are self-aware are better equipped to make sound judgments and to lead with authenticity.

  
  

• The Responsibility of Leadership Extends to Character Development: Leaders have a responsibility not only to model good character but also to foster its development within their teams and organizations. This involves setting clear ethical standards, encouraging open dialogue about values, and holding individuals accountable for their actions.

A Call to Intentionality

On Character is an invitation to introspection and a call to intentionality. It reminds us that leadership is not solely about strategy or execution; it is fundamentally about who we are. By examining the lives of others, both those who soared to great heights through their character and those who faltered due to its absence, McChrystal provides us with valuable lessons for our own journeys.

As leaders, we are constantly under scrutiny. Our actions, both big and small, send signals to those around us. By prioritizing the development of our own character, we not only become more effective in our roles but also inspire those we lead to strive for higher standards.

Inspiring Supporting Insights

“People of character do the right thing even if no one else does, not because they think it will change the world, but because they refuse to be changed by the world.” — Michael Josephson, Founder of the Josephson Institute of Ethics

“In looking for people to hire, you look for three qualities: integrity, intelligence, and energy. And if they don't have the first, the other two will kill you.” — Warren Buffett, CEO of Berkshire Hathaway

“The function of leadership is to produce more leaders, not more followers.” — Ralph Nader, Consumer Advocate and Former Presidential Candidate

"Integrity is doing the right thing, even when no one is watching." — C.S. Lewis, British Writer and Theologian

"The best way to lead is to lead by example." — Dale Carnegie, Author and Lecturer

Thank you for joining me today as we reflected on the enduring importance of character in leadership through the insightful lens of General McChrystal’s On Character.

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