What Servant Leadership Looks Like: Seven Lessons from Theodore Roosevelt

bookFor the last few weeks I have been listening to the audiobook by John Knokey, Theodore Roosevelt and the Making of American LeadershipThis has probably been one of the most enjoyable and fascinating biographies I’ve ever read. Knokey traces the development of Theodore Roosevelt’s leadership from his developmental years at Harvard to his two terms as president of the United States.

Most of his time—or at least, the most memorable time—is spent with Roosevelt as a frontiersman in the Dakotas and a military colonel on the way to Cuba. In these anecdote-filled chapters, the reader is given a firsthand introduction to how Roosevelt became a leader and how his leadership forged the spirit of America for the next century.

For anyone interested in American history or presidential leadership this book is excellent. In fact there are many lessons about leadership in the book and countless stories to illustrate them. To summarize, I will distill seven lessons from Roosevelt’s larger-than-life leadership, and make a few applications to Christian leadership in particular.

Seven Lessons on Leadership from the Life and Legacy of Theodore Roosevelt

1. A Servant Leader

This title, “servant leader,” is often thrown around, especially in Christian circles, but truly Roosevelt exemplified the best of this style of leadership. He did not lead from behind but from the front. As a ranchman and a military leader, he won the confidence of his men by suffering with them and calling them to follow him—never to go before him or without him. While upsetting many with his brash personality, those who followed him were enamored with him because of the way he sacrificed himself for them.

As Jesus put it in Mark 10, Roosevelt embodied the kind of leadership that did not boast in position, but aimed to use his position for the good of others. Indeed, like our Lord he always sought to serve others, not to be served. And thus, he modeled a Christ-like, servant leadership.

2. A Personal Leader

Roosevelt never led from a distance, but constantly drew near to the men he led. Through this personal approach, he learned their names, habits, and needs. More importantly, he loved being with them. And thus as he listened and learned their stories, his men grew to trust him. Even more, when acclaim came to him, he gladly shared his glory with them. For him, it was inconceivable to use the men he lead to enhance his reputation. Rather he esteemed them, and his men loved him for it. 

In this way, Roosevelt models the kind of shepherd leadership Peter speaks of when he says that an elder should be among his sheep. Truly, there is great temptation for those in leadership to lead remotely. And yet, Roosevelt counter-example shows how powerful intimate, personal, even loving leadership can and should be.

3. A Fearless Leader

Whether it was in the boxing ring, on the frontier chasing a grizzly, or in thick of battle Roosevelt leaned into action. Early on in his life, his energy and self-confidence led him to make many mistakes. But over time, he learned to temper his words and his emotions. Still, such self-control never stilled his fearlessness.

Even more, his fearlessness was not just his willingness to stand in the face of danger. He was equally willing to admit his mistakes and learn from them. Indeed, “he attacked each day within enthusiasm unknown to mankind”—Yes, I think Jim Harbaugh and his father are cut from the same cloth—and this led to many failures. But overall, like Proverbs 24:16 says (“For the righteous falls seven times and rises again, but the wicked stumble in times of calamity”), Roosevelt modeled a kind of perseverance that resulted in a lifetime of good works.

4. A Diverse Leader

Roosevelt’s diversity can be seen in two ways. First, he enjoyed many different roles of leadership. From his youthful entrance into politics in the New York legislature, to traveling west to lead a cattle ranch, to his terms as New York City police chief, colonel, and vice president, he gained incredible experience. These diverse experiences enabled him to be one of the most prepared presidents our country has ever seen, and this at only 42 years of age.

Second, Roosevelt was able to build relationships with people from all backgrounds. His Roughriders were drawn from all quarters of life, and, as Knokey highlights, his own wide-ranging interests are what made it possible for him to unite such a diverse corp. In fact, the result of unified diversity was a strength that could not be produced by a uniform team of operators.

In short, Roosevelt shows the strength and beauty of what happens when diversity is unified for a common purpose by a common man. In this way, his leadership reflects something of the glory of Jesus Christ, the one who laid down his life to save men and women from every race, nation, tongue, and tribe (see Revelation 7). 

5. A Guileless Leader

While Roosevelt always wanted to be president, he never succumbed to the temptation of political maneuvering. It’s not that he lacked ambition; it’s that unlike so many he did not manipulate people or circumstances to elevate himself. Rather, he always acted on what he thought was right, even gaining enemies by exposing and opposing error.

Following in the footsteps of his father, Roosevelt always pursued what was good and he pursued it with reckless abandon it. Multiple times he would refuse action or opportunity that would improve his standing among men. In short, he was driven by his convictions instead of people pleasing, which again marks qualities necessary for any Christian leader: “For am I now seeking the approval of man, or of God? Or am I trying to please man? If I were still trying to please man, I would not be a servant of Christ” (Galatians 1:10)

6. A Thoughtful Leader 

For all of his activity, Roosevelt was a perpetual reader. For instance, as he chased two criminals down a frozen river in the Dakotas, he brought with him Anna Karenina by Dostoevsky. Many days he would read two books, and in his lifetime, he would write over 30 books and 150,000 letters. In short, Roosevelt’s creative leadership was surely fueled by these moments of silence and solitude, and the wealth of knowledge acquired through years of reading.

It’s a reminder that enduring leadership that unifies diversity, solves difficult problems, and creates many effective strategies for good requires the cultivation of the mind. In this way, reading is not just beneficial for leadership, it is requisite. Conversely, the failure to read, think, pray, and ponder is a recipe for leadership (if not moral) disaster. In our digitally distracted age, Roosevelt’s commitment to reading reminds us again that one of the greatest evidences of manliness today is the cultivation of the mind and the willingness to conquer appetites of (digital) distraction in service to those who we lead.

7. A Developing Leader

Finally, it is worth noting, as Knokey does, how Roosevelt grew as a leader. Often the adage is affirmed that leaders are born, not made. Roosevelt, one of America’s finest leaders, countermands that claim. He was not born a leader, but a sickly child who had to literally and figuratively fight his way into adulthood. He made many mistakes and many enemies along the way, and yet he learned in every operation of life how to be a better leader.

The lessons listed above are highlights of his later life, lessons he learned from years of experience. In this way, his life reminds us that leadership is a skill that can be learned, improved, and grown—especially through suffering—as diligent leaders seek to improve their leadership by admitting their weaknesses and improving their efforts. In the church, Romans 12 and Ephesians 4 teaches that God gives leaders to the church, but those leaders must grow in their leadership. And thus seeing how others have grown as a leader can be greatly encouraging.

Developing a Moral Imagination of Christian Leadership 

Somewhere between faith and love, Christ and his commands, stands the need for Christian leaders to develop a moral imagination of what servant leadership looks like. That is we need more than just principles to guide us, we need a vision of what leadership looks like. Certainly, Scripture is the starting place for this kind of moral imagination. But thankfully, history and biography provides many examples of servant-hearted leaders—men and women—who reflect Christ’s servant-nature.

Indeed, this is what we find when we consider the life of Theodore Roosevelt. In so many ways, Roosevelt’s leadership reflects much of his Christian heritage. His father, also named Theodore, was a founding member of the YMCA and regularly went to care for newspaper boys in the city. As a vocational philanthropist, Roosevelt Sr. spent his life caring for those in need and rubbing shoulders with those unlike himself.

Roosevelt Jr. acquired many of the same practices by watching and admiring his father. When his father died, he thought he could never live up to his reputation, because his father was such a good man. But in time, he proved to be a faithful son. Following in his father’s footsteps, Roosevelt sought the good of others, and thus became in his way a factory of good works, to borrow a description used of William Wilberforce. And its in his selflessness and good natured service, that we see something of a shadow of Christ.

I’m not making any judgments on Roosevelt faith. I’m only recognizing that what we see in Roosevelt’s leadership is that of self-sacrificing, servant leadership that becomes those who claim the name of Christ. In this way, Knokey’s book is worth reading for anyone in leadership and certainly for those who are in Christian leadership.

I have not included the anecdotes to fill out these seven lessons on leadership. Because I could not do justice to Knokey’s colorful book. Instead, I would urge anyone who cares about leadership to pick up Theodore Roosevelt and the Making of American Leadership and read it. After all, if Theodore Roosevelt had the time to read two books a day, as he conquered the world, we can make time to listen or read Knokey’s book and learn a great deal.

Soli Deo Gloria, ds