Three Generals Who Changed How I Think About Leadership

What Eisenhower, Gavin, and Powell can still teach us about leadership.

America was born because a revolutionary army learned how to adapt and eventually become a conventional army.

George Washington understood something that has remained true through 250 years of American history: military strength depends on far more than weapons or battlefield skill. Armies are institutions made of people. They require judgment, trust, discipline, and leaders capable of holding those things together under extraordinary pressure.

I have spent much of my adult life around that institution—as an Army officer, teaching at West Point, a paratrooper deployed to Iraq with the 82nd Airborne Division, a member of Congress serving on the House Armed Services Committee, and eventually Under Secretary and Acting Secretary of the Army at the Pentagon. Along the way, I studied great commanders and served alongside leaders who shaped my own understanding of what leadership demands.

Three generals, in particular, have stayed with me: Dwight Eisenhower, James Gavin, and Colin Powell.

They came from different generations and faced very different wars. What connects them is something more useful than a list of victories. Each understood a different dimension of leadership that remains relevant far beyond the military.

Dwight Eisenhower: The General Nobody Expected

By late 1943, the Allies were preparing one of the most complicated military operations in history: crossing the English Channel, landing an enormous army in Nazi-occupied France, and beginning the liberation of Western Europe.

There were more obvious choices than Dwight Eisenhower. George Marshall, the Army Chief of Staff and one of the architects of America’s war effort, was widely considered a leading candidate.

Eisenhower was an unusual choice in one obvious respect. He had never commanded troops in combat before World War II. Only a few years earlier, he had been a relatively obscure Army staff officer whose strengths were planning, organization, judgment, and an unusual ability to work with powerful people.

By 1943, he had successfully commanded Allied operations in North Africa and the Mediterranean. Still, his résumé looked unconventional beside some of the celebrated battlefield commanders around him.

Yet FDR chose Eisenhower to lead Operation Overlord, the Allied invasion of Normandy better known as D-Day.

The reason becomes clearer when you look at the people he had to manage. George Patton was brilliant but occasionally uncontrollable. British officer Bernard Montgomery was talented, but unbearable. Charles de Gaulle had his own conception of France’s interests. Winston Churchill had his own conception of practically everything. Somebody had to keep all of them moving in roughly the same direction. Eisenhower did.

He listened, negotiated, absorbed disagreement, and understood when an ego could be indulged, when it had to be contained, and when the mission required him simply to make the call.

That mattered on D-Day. When bad weather threatened the invasion in June 1944, the final decision to launch belonged to Eisenhower. He gave the order. Before knowing whether the invasion would succeed, he also wrote a statement accepting responsibility if it failed. The blame, he decided, would be his.

Then came another test of leadership. On April 12, 1945, Eisenhower toured Ohrdruf, a Nazi concentration camp and subcamp of Buchenwald liberated by American forces. What he saw left him physically sick: corpses, starvation, and evidence of systematic murder.

But Eisenhower was already thinking about what would happen after the war. He worried that one day people might dismiss the evidence of Nazi atrocities as propaganda. So he pushed for journalists (Hitler shut down the press when he came into power), members of Congress, and other witnesses to visit the camps themselves and document what they saw. He wanted photographs, film, testimony, and firsthand accounts that would make the truth impossible to erase. He was thinking beyond the battle, beyond the war, and beyond his own lifetime.

James “Jumping Jim” Gavin: The Visionary

James Gavin has always felt a little closer to home.

Decades before I deployed to Iraq with the 82nd Airborne Division, Mount Carmel, Pennsylvania native ‘Jumpin Jim’ Gavin helped turn that division into one of the most formidable fighting forces in the U.S. Army. What makes him remarkable is how early he understood that warfare was changing. Airborne warfare was still a radical idea when Gavin volunteered for the Army’s fledgling parachute forces in 1941. Armies had spent centuries moving soldiers across land and sea. Aircraft suddenly created another possibility: troops could maneuver through the sky, appear behind enemy lines, seize key terrain and transform the geometry of a battlefield. West Point graduate Gavin threw himself into figuring out how. He became one of the officers shaping America’s emerging airborne doctrine as the Army developed its first field manuals for parachute and air-landing troops.

Gavin fought in Sicily and Normandy, jumped into the Netherlands during Operation Market Garden, and later commanded the 82nd Airborne Division during the Battle of the Bulge. He became known as the “Jumping General” because he did something unusual for a senior commander: he jumped into combat with his paratroopers, always the first one out of the aircraft (and the last one in the chow line making sure his paratroopers ate first), ultimately making four combat jumps during the war.

As a young officer, he also helped develop the doctrine that made airborne forces usable, helping turn an experimental concept into battlefield capability. His rise was extraordinary: in just four years, he went from captain to a two-star major general - the youngest WWII division commander at age 37. That combination is what makes Gavin so compelling. He imagined a new way of fighting, helped write the book for it, and then put his own life behind the idea.

And he kept looking ahead. After World War II, as the Army’s first chief of research and development, Gavin became an early advocate for using helicopters to move troops rapidly around the battlefield—years before air mobility became central to the Vietnam War.

Gavin understood a danger that confronts every successful military: victory can make an institution overly attached to the methods that just worked. History keeps moving.

That lesson feels especially important now. Drones, artificial intelligence, autonomous systems, directed energy, cyberwarfare, and increasingly sophisticated electronic warfare are changing the battlefield again. The Army that wins the next major conflict will almost certainly need capabilities, organizations, and doctrines that look different from those that won the last one.

Gavin’s example is a reminder that adaptation cannot begin after the shooting starts. You have to build the future while everyone else is still comfortable with the present. He was instrumental in the desegregation of the US Army and went on to become the US Ambassador to France during the Kennedy Administration. He was the author of five books and will always be beloved by American paratroopers - especially every August 16th - National Airborne Day.

Colin Powell: Defining the Mission

Colin Powell’s rise was extraordinary. The son of Jamaican immigrants, he entered an Army still living with the legacy of segregation, at a time when Black officers faced major barriers to advancement. He served two tours in Vietnam, including with the 101st Airborne Division, rose through the senior ranks, became a White House Fellow, the President’s national security adviser, and ultimately became the first Black Chairman of the Joint Chiefs of Staff.

By then, Powell had become something unusual in American public life: a general whose credibility extended well beyond the military. Presidents trusted him and the public knew his name.

When I arrived at the Pentagon as Under Secretary of the Army in 2016, Powell had been retired from uniform for more than two decades. His influence was still everywhere, particularly in the way a generation of military leaders thought about the use of American power. He took me under his wing and I spent time with him at his home at McLean, Virginia. We talked often about our beloved Army, the wars in Iraq and Afghanistan, and national public service opportunities.

His experience in Vietnam helped shape what became known as the Powell Doctrine. Powell came away convinced that American troops should never be sent into war unless the country clearly knew what it wanted them to accomplish and was prepared to give them what they needed to do it. The doctrine reduced that conviction to a series of deliberately simple questions: What American interest is at stake? What are we trying to accomplish? Do we have enough force to do it? Does the public support the mission? And how will we know when it is over?

The 1991 Gulf War showed the approach in practice. Saddam Hussein had invaded Kuwait, and the mission was clear: force his army out. Powell helped ensure that the United States went in with enough troops and international support to do exactly that. Once Kuwait was liberated, the mission was over. That clarity was central to Powell’s view of leadership.

He also believed bad news had to travel upward. Leaders cannot fix problems their subordinates are afraid to bring them.

Powell’s own career eventually demonstrated how consequential that principle could be. As Secretary of State, he presented the case for Iraqi weapons of mass destruction to the United Nations in 2003. Much of the intelligence behind that presentation proved wrong, and Powell later called the episode a “blot” on his record.

It complicates his legacy, but it also makes the lesson more important. Powell spent his career insisting that America should never send troops into harm’s way without a clear purpose, a realistic plan, and a shared understanding of what success would mean.

Wisdom is Learning from Others’ Mistakes

When you learn from great military or civilian leaders, you truly learn from their mistakes along the way. There’s a reason why great leaders like Warren Buffett deliberately reads five to six hours every day - in his case, five newspapers, biographies and financial reports - he calls it compound learning. Knowledge is power and by reading and sharing the stories of these three great American generals - especially during America’s 250th birthday - I hope you two can learn from them too.