Theodore Roosevelt stands as one of the greatest leaders in American history.
Theodore Roosevelt on Leadership distills his leadership lessons, so they can be transferred seamlessly into the 21st century.
TR’s timeless example can be put to work in business, finance, the not-for-profit sector, a government agency or the military.
The 10 leadership lessons that follow are a sampler from Roosevelt’s project of self-creation and service.
10 Theodore Roosevelt Leadership Lessons
1. Leaders Are Created, Not Born. TR’s life and work is an enduring answer to the eternal question: are leaders born—or are leaders made?
Roosevelt believed that leadership is an ongoing project of self-creation. He offered his life as a template for anyone who would seek to re-create themselves into an effective leader.
If I have anything at all resembling genius, it is in the gift for leadership…. To tell the truth, I like to believe that, by what I have accomplished without great gifts, I may be a source of encouragement to Americans.
2. Courage is the Foundational Virtue. Theodore Roosevelt was a warrior. His virtues and shortcomings are best evaluated with an eye toward the world in which he lived. Death was a constant companion. The consequences of the barbarism of the Civil War was very much in evidence in every part of American life.
In this world, courage was paramount. Physical courage was prized. Moral courage, perhaps even more rare, was necessary for enduring service.
Roosevelt overcame a weak physical endowment and corresponding temperament. He aimed for his example to stir others—indeed the nation as a whole–to undertake the same transformation.
There were all kinds of things of which I was afraid at first, ranging from grizzly bears to “mean” horses and gun fighters; but by acting as if I was not afraid I gradually ceased to be afraid.
3. Action, Action, and Still More Action. Theodore Roosevelt had a consistent bias for action. He believed in the initiative. He was never comfortable or effective on defense, responding to a state of affairs set by others.
Whether it was the construction of the Panama Canal, taking on J.P. Morgan, or any number of other memorable challenges, TR took the risks of action, over the greater (if sometimes less evident) risks of inaction or delay.
Whatever I think is right for me to do, I do. I do the things that I believe ought to be done. And when I make up my mind to do a thing, I act.
4. Put Your Team Ahead of Yourself. One of Roosevelt’s formative real-time leadership experiences was leading his regiment in the Spanish-American War.
TR led from the front. He placed himself into undeniable danger, remaining on horseback while facing a rain of steel.
He placed those he was serving before himself. As a result, many of the Rough Riders remained committed to him for the remainder of their lives.
No man has a right to ask or accept any service unless under changed conditions he would feel that he could keep his entire self-respect while rendering.
5. Leaders are Learners. From youth, Roosevelt was a voracious reader: “Reading is a disease with me.”
TR’s curiosity, his ceaseless learning, never abated. The book, the classroom, formal education, these were far from the only venues for learning. They produced many of those he called the “educated ineffectives.”
Roosevelt’s example, combining the life of ideas and the life of action, was central to his project of self-creation as a leader.
As soon as any man has ceased to be able to learn, his usefulness as a teacher is at an end. When he himself can’t learn, he has reached the stage where other people can’t learn from him.
6. Bring History to Life, Create the Future. TR was first among equals, a practicing politician who was also an accomplished historian. He, along with intimates such as Senator Henry Cabot Lodge of Massachusetts, would frequently turn to historical exemplars as they dealt with contemporary problems.
There is nothing cheaper than to sneer at and belittle the great men and great deeds and great thoughts of a bygone time—unless it is to magnify them and ascribe preposterous and impossible virtues to the period.
7. Maintain Open Channels With Adversaries. Many people think in all-or-nothing terms: either you’re for me, or you’re against me. That can be appropriate in some circumstances, but, at least as often, it’s not.
Roosevelt’s focus on results, on outputs, rendered him flexible as to means. He would, he said, “work with the tools at hand.”
TR, as governor of New York, met regularly with his frequent adversary and uneasy ally, the “Easy Boss,” Senator Thomas Collier Platt. This prompted some criticism from critics who feared that such meetings would necessarily compromise Roosevelt or his positions on vital matters.
Roosevelt nonetheless maintained regular meetings and communications with Platt and other nettlesome personages:
If my virtue ever becomes so frail that it will not stand meeting men of whom I thoroughly disapprove, but who are active in official life and whom I must encounter, why I shall go out of politics and become an anchorite. Whether I see these men or do not see them, if I do for them anything improper then I am legitimately subject to criticism; but only a fool will criticize me because I see them.
8. Keep Commitments. Today, commitments are violated willy-nilly as they become inconvenient or undesirable. This has always been even more the case among politicians.
TR was notable in striving to meet commitments. He would meet commitments to his children to play, even if it meant that meetings of state would have to end.
Memorably, he declined numerous entreaties to walk back his commitment, made impulsively on election night in 1904, not to seek re-election in 1908.
In TR’s reckoning, holding to his word was vital to earning and maintaining the trust of those he served:
It is a peculiar gratification tome to have owed my election…above all to Abraham Lincoln’s “plain people’; to the folk who worked hard on the farm, in shop, or on the railroads, or who owned little stores, little businesses which they managed themselves. I would literally, not figuratively, rather cut off my right hand than forfeit by any improper act of mine the trust and regard of these people…. I shall endeavor not to merit their disapproval by any act inconsistent with the ideal they have formed of me.
9. Family First. Roosevelt was a dedicated family man. To a notable extent for a public figure holding great responsibility, he was an attentive father and husband.
There are many kinds of success worth having. It is exceedingly interesting and attractive to be a successful business man, or railroad man, or farmer, or a successful lawyer or doctor; or a writer, or a President, or a ranchman, or the colonel of a fight regiment, or to kill grizzly bears and lions. But for unflagging interest and enjoyment, a household of children, if things go reasonably well, certainly makes all other forms of success and achievement lose their importance by comparison.
10. Be Authentic: Live Your Values. Roosevelt was authentic in the true sense: he was the author of his character. He strove to live his demanding values, the better to serve a nation that could advance by the same values.
Most of all, I believe whatever value my service may have, comes even more from what I am than from what I may do.
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