Leadership Lessons From The Life of Woodrow Wilson


I recently finished John Milton Cooper, Jr's biography of President Woodrow Wilson. Here are five leadership lessons I have learned from the life of the 28th president of the United States.

The Benefit of Biographies

The American historian and social critic, Arthur M. Schlesinger, said "Biographies of American presidents constitute a chronicle of wisdom and folly, nobility and pettiness, courage and cunning, forthrightness and deceit, quarrel and consensus." [1] John Milton Cooper, Jr's 700-page tome on the life of Thomas Woodrow Wilson was everything Schlesinger described.

I could, without exaggeration, write a short book on the lessons I have learned from the life of our twenty-eighth president. Rather than providing a massive list of these insights, I am confining this post to five leadership lessons and incorporating a little of the supporting material from Cooper. The notes section below contains the pages numbers from which the observations and quotes are drawn.

Leadership Lessons

1. Be bold.

Wilson said, "There's nothing that succeeds in life like boldness provided you believe you are on the right side." John Milton Cooper, Jr writes, "Wilson was bold, extremely sure of himself, and often stubborn."

Consider this, two years before he became president he never held political office. He served as President of Princeton and transformed it. He was "a dynamic reformer" as Governor of New Jersey. As President of the United States he led the country into and through World War I. He appointed Louis Brandeis (the first Jewish person) to the Supreme Court. He provided for the first child labor law, and an eight-hour workday.

His biographer wrote, "Boldness and thinking big marked Wilson all his life, and those qualities helped make him the only president who rose to the top in two professions entirely removed from public affairs." As a scholar he was the leading political scientist of his day. As an academic president, he transformed Princeton into a leading university.

Leaders advance the cause because they see what others do not and are willing to move toward that vision. Such work calls for boldness. Where do you need to be more bold?

2. Know yourself and lead from your strengths.

The presidential race of 1912 pitted Woodrow Wilson against incumbent William Howard Taft and ex-President Theodore Roosevelt. Defeating Roosevelt was Wilson's greater challenge in this race. His comments to a friend reveal his sense of self-awareness:

Do not be too confident of the result, I feel that Roosevelt's strength is altogether incalculable. . . . He appeals to . . . [people's] imaginations; I do not. He is a real, vivid person, whom they have seen and shouted themselves hoarse over and voted for, millions strong; I am a vague, conjectural personality made up more of opinions and academic prepossession than of human traits and red corpuscles. We shall see what will happen!"

Wilson knew himself. He was quiet thinker. He had a "single-track mind," meaning his preferred way to work was to think, reflect, plan, and prepare, after which he would deal with a task and stick to his game plan.

A leader must know if he/she is a lively Roosevelt, a reflective Wilson, or someone entirely different. Strong leaders lead from their strengths. What are yours?

3.  Practice the power of the pause.

Wilson worked hard, but he knew how to rest. With rare exeception he never worked on Sunday. He also knew what put fuel back in his tank. Golf relaxed him and he played it often. Baseball was his favorite sport. Living in Washington he was able to follow it. On one of his vacations, "he admitted to devouring detective stories." Cooper notes that "although Wilson never learned to drive, car rides would remain his favorite form of relaxation for the rest of his lfe." (200, 208, 256, 258)

Woodrow Wilson understood what this time did for his body and his mind. His brother-in-law, Stockton Axon, observed that Wilson:

had a "creative, literary type of mind" that would be absorbed "with a tremendous theme, an epic." He therefore wanted his time away from work "simply to relax, not have business follow him." Because he wanted "to let his mind play, to give it a thorough rest, he talks small talk with the members of his family, he recites limericks and makes puns and tells anecdotes.

All work and no play does make one a "dull boy." Leaders need time away to rest and refuel. What puts fuel back in your tank? When was the last time you got away to rest and refresh?

4. Leverage technology for your leadership.

Wilson had his eyes open to the technological changes of the time:

In June 1883, he bought his first typewriter, a Caligraph, which cost the substantial sum of $87, and thereby jumped aboard the technological bandwagon of the time. Typewriters had been on the market for less than a decade and did not yet feature either standard keyboards or common mechanisms for producing capital letters. Nonetheless, the typewriter gave Wilson another means with which to overcome his slowness in reading and writing.

Today, technology is advancing by leaps and bounds. Social media is just one tool of technology which a leader must leverage. Are you regularly stopping to consider ways to harness technology to enhance your leadership?

5. Remember that you are an instrument of God's will.

Cooper noted that Wilson did "think of himself as an instrument of God's will. But according to his beliefs, every person was an instrument of God's will, and even his own defeats and disappointments were manifestations of the purposes of the Almighty.

In 1919, Wilson suffered a massive stroke. His physician, Dr. Grayson, recalled the president's words after losing a significant legislative vote on the League of Nations in 1919:

Grayson later recalled that the president asked him to read to him from the Bible, 2 Corinthians 4:8--"we are troubled on every side, yet not distressed; we are perplexed, but not in despair"--and then said, "If I were not a Christian, I think I should go mad, but my faith in God holds me to the belief that He is in some way working out His own plan through human perversity and mistakes."

Years later in 1923, Wilson said:

Perhaps it was providential that I was stricken down when I was. Had I kept my health I should have carried the League. Events have shown that the world was not ready for it. . . .  His daughter Margaret later recalled him saying with a smile, "Perhaps God knew better than I did after all."

Leaders are instruments in God's hands whether they acknowledge it or not. God "works all things according to the counsel of his will" (Ephesians 1:11). In some respects, it seems Wilson learned this lesson the hard way. But he learned it!

Knowing leadership is an instrument of God's will means that leaders are stewards, given a trust by God. How should that knowledge shape your leadership today?

Learn From Biographies

Leaders can glean so much from reading the lives of great men and women. Click here for details on Cooper's Pulitzer Prize Finalist. It is an outstanding work, full of historical insight . . . and wisdom for those who seek it.

"Hear instruction and be wise."

Proverbs 8:33 ESV


[1] Editor's note to The American Presidents series, Grover Cleveland by Henry F. Graff. New York: Times Books: Henry Hold and Company. 2002. Page xviii.

Lesson 1: Pages 5, 8, 81, 116, 126, 250, 390, 400.

Lesson 2: Pages 162, 181, 201, 211, 225, 227, 237, 255, 293, 374, 383, 389, 442.

Lesson 3: Pages 139, 171, 180, 201, 208, 256, 258, 309, 413, 440, 492, 514, 560-61.

Lesson 4: Page 41.

Lesson 5: Pages 442, 560, 590.