• Woody

Leadership Lessons from Winston Churchill

Day 391


On December, 13, 1931, the story of one of history's most impressive leaders almost came to an end before it ever began.

In the middle of the night, on Fifth Avenue, in New York City, Mario Constasino slammed on his brakes in vain before colliding with a pedestrian attempting to cross the street.

Winston Churchill, by his own account, out of habit, looked the wrong way while crossing the street in search of the home of an old friend. Churchill was in New York City attending to speaking engagements in an effort to recoup his losses from the stock market crash of 1929. His death, arguably, would have changed the course of history, likely, for the worse.

Instead, one of the most accomplished leaders in the Modern Era lived to fight another day, rather, another 33 years.

Churchill's own account of this story is both harrowing and beautiful (My New York Misadventure). His patented resilience and dogged determination is clear.

If Sam Walker had chosen political leaders for the subject of his book, The Captain Class, Churchill would have most certainly been among them. In fairness, Churchill's charisma is referenced in the book, but not in support of Walker's argument. While charisma was not an essential part of Walker's criteria, Churchill seems to embody all of the qualities that Walker uncovers.

After the accident, Churchill went on to lead Great Britain through World War II as the Allied forces defeated Hitler's Nazi Germany.

In May of 1940, he was elected Prime Minister of Great Britain, mere months after the war began. A month later, on June 4, 1940, after a successful rescue mission, Churchill delivered his "We Shall Fight Them on the Beaches" speech, one of his most famous orations.

Within the words of this inspirational address to the British people, Churchill said, "I have, myself, full confidence that if all do their duty, and if the best arrangements are made, as they are being made, we shall prove ourselves once again able to defend our Island home, to ride out the storm of war, and to outlive the menace of tyranny, if necessary for years, if necessary alone."

Churchill's speech consisted of more than 3500 words that day, but the last portion, from which the previous quote is extracted, stands out above the rest. And while it doesn't tell the whole story, it paints a vivid picture of the leadership for which he is endeared.

Failure was not an option. "...we shall not flag or fail. We shall go on till the end..." Churchill knew that the people needed something to believe in. He gave them a vision. They needed a leader who was confident and determined to see it through to the end; to serve the collective purpose. And even thought he was willing to do it alone, "...if necessary..." he knew that his people couldn't do it without aide, but that they needed to believe that they could "...carry on the struggle, until, in God's good time, the New World, with all it's power and might, steps forth to the rescue and liberation of the old."

After the speech, Churchill is rumored to have said to a colleague, "And we'll fight them with the butt ends of broken beer bottles because that's bloody all we've got."

Winston Churchill died, on January 24, 1965, a little more than 33 years after that fateful night in New York City, leaving behind a legacy that any aspiring leader would do well to consider. His unwavering confidence in the face of uncertainty, his preparation, his dogged determination to succeed, his devotion to serving his people and the collective purpose, and his humility to know that help was essential to success, accompanied by his willingness to carry on even if that help never arrived, are all qualities that epitomize leadership.

And that's just part of the story.

"Providing a mental picture of a preferred future, mobilizing others toward a common goal, influencing them in a productive, vision-driven direction, Churchill was the perfect example of the conviction and character of a leader."


Churchill: Leader and Statesman

Launching A Leadership Revolution, Chris Brady & Orrin Woodward (no relation)

Fight Them on the Beaches

We Shall Fight Them on the Beaches

My New York Misadventure

10 Surprising Stories About Winston Churchill



60 views0 comments

Recent Posts

See All