Leadership Lessons at Gettysburg: Why They Still Matter Today

By Dennis Haley

Download

Download the Whitepaper

Sign Up to Receive
Monthly Leadership Articles

In July of 1863, the small town of Gettysburg, Pennsylvania, became the stage for the largest and bloodiest battle ever fought on American soil. Over three days, decisions made under pressure by commanders and citizen—soldiers alike would alter the course of the Civil War and, with it, the nation's future. Leaders on both sides made choices—some bold, some flawed—that still offer timeless lessons for today's executives.

More than 160 years later, leaders continue to walk those same fields—not simply to study history, but to gain perspective on their own leadership journey and the kind of leader they aspire to be. The enduring lessons of Gettysburg reach far beyond tactics or military maneuvers. They speak to the timeless challenges of leadership: making decisions with incomplete information, inspiring teams in the face of exhaustion, listening to trusted counsel, and staying true to principles even when the stakes are high.

Decisiveness Amid Uncertainty

On July 1, Union cavalry officer John Buford faced a defining choice. Outnumbered and without direct orders, he saw Confederate troops advancing and decided to hold the high ground until reinforcements arrived. That single act of decisiveness shaped the outcome of the battle.

Modern leaders face similar uncertainty in shifting markets and disruptive environments. Buford's example shows that hesitation can be as costly as the wrong move—true leadership requires the courage to decide, even without perfect clarity.

Creativity Under Pressure

At Little Round Top, Colonel Joshua Lawrence Chamberlain confronted crisis when his regiment ran out of ammunition. With no conventional options left, he ordered a bayonet charge that stunned the Confederates and secured the Union flank.

Chamberlain's bold choice illustrates the power of creativity in desperate moments. For today's leaders, the lesson is clear: when standard solutions fail, innovation and imagination can turn the tide.

His story is a testament to creative problem-solving. When conventional answers fail, leaders must be willing to imagine alternatives. In today's organizations, that might mean rethinking business models, empowering teams to innovate, or embracing unconventional solutions in the face of disruption.

Listening to Trusted Counsel

Not all leadership lessons at Gettysburg were victories. On July 3, General Robert E. Lee ordered Pickett's Charge despite strong objections from his most trusted subordinate, General James Longstreet. The result was devastating for Confederate forces.

The failure underscores the importance of listening. Leaders must create space for dissent and recognize when confidence risks becoming overconfident. Ignoring trusted counsel can turn bold visions into costly missteps.

Character and Trust

Underlying all these stories is the central element of leadership: character. Soldiers followed Buford, Chamberlain, and Longstreet not simply because of rank, but because of trust. They believed in their leaders' integrity, courage, and commitment to the mission.

In the modern workplace, trust is still the currency of leadership. Teams thrive when leaders communicate clearly, set consistent expectations, and demonstrate values through action. Without trust, even the most brilliant strategy falters.

Leadership at Gettysburg was forged in the crucible of conflict, but its principles remain deeply relevant in our own turbulent age. Whether guiding a company through change, leading a team through uncertainty, or shaping culture in a complex organization, the timeless truths of Gettysburg still point the way.

We return to these fields not to glorify war, but to learn what it means to lead. In doing so, we are reminded that leadership is as much about character and conviction as it is about strategy and success. The lessons endure not because they are frozen in time, but because they echo across generations, each facing its own battles, moments of crisis, and defining choices. Gettysburg shows us that leadership is not about titles or tactics, but about vision, trust, and the courage to act.

Originally Published September 2025