How to Lead Like Winston Churchill—3 Important Leadership Lessons

Jul 4, 2021 4 min read
How to Lead Like Winston Churchill—3 Important Leadership Lessons

In this guest post, Bruce Harpham shares three important leadership lessons from the life and work of Winston Churchill.

I love to learn from the most successful people in life. It’s one of the best ways to gain new insights and accelerate your learning.

When it comes to leadership, it’s hard to find a better example than Sir Winston Leonard Spencer Churchill. I’ve been fascinated by him ever since I visited the Cabinet War Rooms in London, England some years ago.

Many know Winston Churchill from his exceptional leadership during the Second World War. That is only part of the story. Churchill has much to teach us, whether you are into politics or not.

When you choose to study Churchill, you have a great wealth of resources to use. I draw on Churchill: A Life by Martin Gilbert. It’s a well-crafted book that clocks in around 1,000 pages. Consider this article your introduction to Churchill’s story. I am also indebted to the excellent resources provided by the Churchill Centre.

Lessons From Winston Churchill

I will teach you three important leadership lessons from the life and work of Winston Churchill. Master just one of these leadership lessons, and you will set yourself apart from most people. If you work on all three skills, you may rival Churchill’s achievements.

How to make the most of your opportunities


As a young man in the British Army, Winston Churchill was constantly seeking interesting opportunities. For him, the Second Boer War of 1899-1902 proved an excellent opportunity. Unlike other officers, Churchill did not limit himself to military duties. Churchill made the most of his time during the war. Even at a young age, he understood the public would be interested in reading about the conflict.

During the war and afterwards, Churchill wrote about his experience constantly. He secured an assignment to write about his experiences for the Morning Post at the comfortable pay of £250 per month (equivalent to $40,000 US Dollars in 2013 terms according to Measuring Worth.)

This assignment ignited Churchill’s lifelong passion for writing and publishing. He later went on to write numerous works of history, multiple volumes of memoirs and win the Nobel Prize for Literature.

Publish like Churchill

History shall be kind to me for I intend to write it. – Winston Churchill

Did you know that Winston Churchill published forty-three books in his lifetime? By any standard, that is an incredible accomplishment. It is all the more impressive when you remember that Churchill had substantial responsibilities as a cabinet minister, military officer, diplomat, and leader. That determination to write could not be contained.

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