When we think of great leaders, they are impactful in their time and leave a legacy that lasts for generations. They shape the present while setting the course for the future. Some of the most influential leaders in history have occupied the Oval Office. U.S. presidents, much like CEOs and other high-level executives, face high-pressure moments involving crisis management, tough decisions, negotiations, public scrutiny, and the challenge of rallying a team toward a bold vision.
Leading a company is one thing—leading a nation and making decisions that create ripples for generations is another. In honor of Presidents’ Day, here are five impactful U.S. presidents and the leadership lessons they offer today’s CEOs and executives navigating the complexities of modern business.
George Washington: True Leadership Requires Restraint
As the first U.S. president and the only one unanimously elected twice, George Washington exemplified leadership through restraint, amongst other things. Despite his immense power, he chose not to overstep boundaries. Two defining moments highlight this: the resignation of his military commission after the Revolutionary War, ensuring the military remained under civilian control. Later, he voluntarily stepped down after two terms, setting a precedent that eventually led to the 22nd Amendment and peaceful leadership transitions.
In Washington: A Life by Ron Chernow, it is noted that Washington saw the presidency as a duty, not a prize. The lesson for business leaders is clear— leadership is not merely seeking power for its own sake. The more influence one holds, the greater the responsibility to wield it wisely. Great leaders establish principles that serve the collective good rather than hoarding authority.
Andrew Jackson: Boldness Defines Leadership
Few presidents are as polarizing as Andrew Jackson. Both revered and criticized, he was a disruptor whose decisive leadership left a permanent mark on the nation. One defining moment was his dismantling the Second Bank of the U.S. despite opposition. He believed it disproportionately benefited a select few rather than the broader American public, a stance detailed in Jon Meacham’s American Lion: Andrew Jackson in the White House.
For CEOs, the takeaway is that bold, even unpopular, decisions are often necessary for long-term success and evolution. Leaders who drive industries forward must be willing to challenge the status quo and take calculated risks. Decisiveness in the face of criticism separates great leaders from good ones.
Theodore Roosevelt: Great Leaders Are Always Expanding Their Capacity
No president embodied a well-rounded, adventurous life and spirit like Theodore Roosevelt, as perfectly encapsulated by his statement: “Far better it is to dare mighty things, to win glorious triumphs, even though checkered by failure, than to take rank with those poor spirits who neither enjoy much nor suffer much, because they live in the gray twilight that knows neither victory nor defeat.” Roosevelt was a transformational president, scholar, war hero, conservationist, and prolific writer of 35 books.
He was the only American president awarded the Medal of Honor and the first to receive the Nobel Peace Prize. His “strenuous life” philosophy exemplifies that a leader must be well-rounded and constantly evolving, which was meticulously shared in detail through Edmund Morris’s trilogy of books on Roosevelt. The best CEOs are not one-dimensional—they embrace continuous learning. Expanding skills in fitness, writing, and numerous other arenas can improve your decision-making, leadership abilities, and the lens through which you see the world. A leader’s well-rounded, renaissance nature inspires their team to pursue personal and professional growth, ultimately benefiting the organization.
John F. Kennedy: Leaders Inspire Action Through Selling The Dream
Maya Angelou once said, “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.” John F. Kennedy exemplified this truth. Charismatic and aspirational, he had a unique ability to rally people around a bold vision. His famous 1962 speech at Rice University—“We choose to go to the moon in this decade and do the other things, not because they are easy, but because they are hard”—ignited national ambition by tapping into both logic and emotion.
For business leaders, a vivid and aspirational vision aligns their teams, attracts top talent, builds loyalty, and fuels greater innovation. However, charisma alone isn’t enough. Leaders must translate vision into an actionable strategy. Emotion combined with logic creates an unstoppable workforce.
Abraham Lincoln: Strong Leaders Build Teams That Challenge Them
Abraham Lincoln endured personal setbacks and tragedies, but one of his most notable leadership qualities was his ability to turn political foes into allies. In Team of Rivals: The Political Genius of Abraham Lincoln, historian Doris Kearns Goodwin details how Lincoln brought together a divided cabinet and leveraged diverse viewpoints to strengthen his leadership.
For CEOs, the challenge is often finding advisors and surrounding influences who provide honest feedback rather than just telling them what they want to hear. Whether making key business decisions or taking care of your personal well-being, great leaders surround themselves with strong, capable individuals who challenge their ideas, push them to grow, and hold them accountable. Healthy debates lead to better decision-making, innovation, and personal and organizational growth. A secure leader removes their ego and welcomes differing perspectives.
CEOs and Presidents Face Similar Leadership Challenges
CEOs, like presidents, are often perceived as impenetrable figures devoid of flaws. However, many presidents—like countless CEOs—have faced depression, health struggles, and personal crises while leading their organizations forward. Leadership comes with controversy, difficult decisions, and opposition. Not everyone will support your choices, but that is the nature of leadership. By studying the lessons of past presidents, today’s CEOs can navigate challenges with greater wisdom, courage, resilience, and vision.