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3 Things Leadership Books Didn’t Teach Me

Because I fell asleep.

When someone writes a book about leadership drawing from their own experience, it’s a red flag for me. As Douglas Adams writes in The Restaurant at the End of the Universe before introducing the incompetent Ruler of the Universe: “It is a well-known fact that those people who most want to rule people are, ipso facto, those least suited to do it.” Besides, if you were to distill the entire cottage industry of leadership books into an ingestible formula, it would be the most powerful sedative known to humanity. It won’t replicate better leaders, but it will cure their insomnia.

But what about the books that keep you awake? Here are some insights I’ve gleaned on leadership from some of my favorite works of literature and fantasy.

1. Childlike resilience

Do you need inspiration for overcoming adversity? Read G. K. Chesterton’s epic poem The Ballad of the White Horse, which British soldiers carried with them in World War I. In this retelling, King Alfred fights to preserve England, and Christianity, from the invasion of Germanic heathens. At the turning point of the war, Chesterton introduces a divine child who persists in rebuilding blocks after they fall down. It’s the childlike wonder and determination for doing something over and over again that Chesterton says in Orthodoxy is most true about God. Chesterton writes: “It may be that He has the eternal appetite of infancy; for we have sinned and grown old, and our Father is younger than we.” Even when the enemies had occupied most of the country, King Alfred reflects God’s childlike wonder and persistence. For leaders to be effective, they must not simply be resilient, but be fueled in the face of failure by a faith that overcomes the darkness with eternal joy.

2. Servant strength

Have you ever had a boss assign a task when it’s clear that they’ve never been in your position? They’ve always been in charge and never considered what they are asking of you? And what if your boss then writes a leadership book? Well, that’s why one of my favorite examples of servant leadership is found in Brandon Sanderson’s fantasy epic The Way of Kings. One of the protagonists, Kaladin, earns the trust of his crew by training them for survival, risking his life to advocate for their care, and treating their wounds after battle. As one of his comrades reminds him, “Strength does not make one capable of rule; it makes one capable of service.” Kaladin rises to a place of leadership in the series not by dominating and concentrating power but through selfless service that yields trust and camaraderie among his team for greater success.

Kaladin’s example reminds me of Ralph Waldo Emerson’s essay “Compensation” when he writes about the necessity of humility for leaders: “Our strength grows out of our weakness. The indignation which arms itself with secret forces does not awaken until we are pricked and stung and sorely assailed. A great man is always willing to be little.” Isn’t that what Paul says about Jesus in the Christ Hymn of Philippians 2, who was exalted precisely through humility and suffering? And how Paul reconciles his own physical weakness with the strength Christ provides (2 Cor 12:9)?

3. Delegation and empowerment

Speaking of the dangers of concentrating power, the wizard Gandalf in The Lord of the Rings empowers others in their roles to accomplish a shared mission. For instance, Gandalf leads the Fellowship of the Ring but values the diverse set of skills each member contributes. Most importantly, Gandalf trusts the hobbit Frodo with carrying the Ring to Mordor. As a wise leader, Gandalf recognizes and nurtures the potential of those often overlooked. He recognizes what Tolkien said about the hobbits in a letter, that they are “free from ambition or greed of wealth” and even though they are made small they possess “the amazing and unexpected heroism of ordinary men ‘at a pinch.’” Like Tolkien, Gandalf is suspicious of the dangers of too much power and leads effectively by sharing tasks and empowering others to succeed.

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