3 Leadership Lessons from Winston Churchill

Churchill can show us that good leaders are forged by how they overcome failure, resolve to press on, and treat their team.

A good leader can change your life. Being a good leader can change the life of those around you. Unless you’re Jesus, perfect leaders don’t exist. But good leaders are forged in the fires of suffering, tragedy, and failure. Jesus, as a perfect leader, even opened himself up to suffering. His leadership seemed to have ended with his execution, but came to light at the resurrection.

Good leadership is often directly related to how we face challenges. Here are three things you can learn about leadership and trial from the life of Sir Winston Churchill before he led where it mattered most: in the dark days of World War II.

Leaders mess up because people mess up, so embrace failure as a risk of leadership.

Churchill is known for his dramatic pronouncement to his fellow countrymen in 1940 in the face of Nazi Germany — “we shall fight on the beaches…we shall never surrender.” Wind the clock back over 20 years to World War I, and you’d find Churchill leading in another crucial time in England’s history — the Naval office during World War I. Winston’s ingenuity and desire to make a name for himself in World War I got the better of him. He proposed and fought for a naval strategy which he hoped would break the back of Germany. He proposed to send thousands upon thousands of British soldiers around the battlefield of Europe, through the Mediterranean Sea, and land behind the Central Powers, forcing them to surrender. His strategy was a disaster. 15,000 men lost their lives in the maneuver, which shamed and humiliated Churchill out of his position as Vice Lord of the Admiralty. (Side Note: next time you encounter failure as a leader, consider that Churchill’s failure cost human lives on a staggering scale.)

Good leaders, even great ones, eventually fail in some form or another. An initiative falls flat, a strategy collapses, a relationship blows up, you fill in the blank. If you think you’re leading, and you have a perfect track record, chances are you’re not leading at all, or just haven’t been leading long enough. Instead, embrace failure as the risk of leadership. Leaders afraid to fail will never be able to lead.

Leaders have resolve, so find your principles and die on them.

Churchill’s response to the disaster of his strategy was to apply for field service in the British army on the front lines of World War I. He went from the upper stratosphere of government to the gritty trenches of chaotic warfare. There, he found he had what it took to lead men in battle. It was a small task compared to his role in government, yet for Churchill it proved his mettle and made him resolve to press on. William Manchester, in his Churchill biography “The Last Lion”, titled Winston’s years between World War I and his glory of World War II as “The Last Lion: Alone”. His strategic failure and success in combat got him a seat in the British parliament, where for a decade, he warned against Nazi aggression. Most ignored him, some hated him.

Great leaders are not marked by failure so long as they resolve to get back up and press on. Churchill’s resolve led him to discover where his strengths existed. Many leaders fail not because they’re bad leaders, but because their environment is not suited to their abilities and strengths. You may even find that resolve will lead you, like Churchill, back to where you began. Good leaders will always resolve to learn something about themselves in their failures, so no experience is ever wasted. Resolve in a leader will help you to get back up, find your principles, and take on new challenges.

Leaders respect those they lead, so treat your team well.

It’s important to see historical figures for who they are: human beings with flaws. We can learn just as much from Churchill’s flaws as we can his weaknesses. In his “The Last Lion” series on Churchill, Manchester records a fairly common assertion about Churchill: he treated his staff poorly. Once, when his butler shot back at him asking him to justify the way he was speaking, Churchill replied that he would not apologize, because “he was a great man.”

Good leaders prioritize not just getting things done, but how they get things done. This means that leaders must have people skills, and not just people skills but visionary people skills. It means using tasks to accomplish people, not the other way around. Compliant followers will only get things done. At the end of the day, a great leader will understand the value of treating those around him or her with respect and dignity.

There you have it. Leaders fail, have resolve, and show respect. It’s simple, but incredibly hard. Go be like Winston…and don’t go be like Winston.

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