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How to Lead Your Organization Like Winston Churchill

Mitchell + McClure
The Startup
Published in
3 min readMay 6, 2020

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“I have nothing to offer but blood, toil, tears and sweat.”

This refrain from Winston Churchill continued to echo throughout his appointment to the House of Commons in the heat of leading Great Britain during World War II.

In fact, this was among the first things he communicated to his Cabinet when he became Prime Minister in 1940. He was transparent in admitting that he inherited a war that he wasn’t positive he could win.

He couldn’t promise victory, but he could promise his resolve.

Maybe as a leader that’s the only thing you can promise right now. I’m here to tell you THAT’S OK.

If you’re reluctant to compare yourself to potential the most prolific war-time leaders, remember that he was considered by many a bumbling idiot and a drunk.

So even if you drink yourself to sleep (cheers), you can still apply these 4 Key Principles to war-time leadership.

And yes, your business is at war right now.

Speed of Decision Making

In a time of war, decisions are everywhere and are begging to be made. Being too slow to respond could cost you the war so you must find a way to make swift and informed decisions.

Just hours after Churchill’s appointment, Hitler’s army began its Western Offensive with the invasions of the Netherlands, Belgium and Luxembourg.

He immediately switched out ineffective leadership with those more capable to surround himself with proven individuals he could trust. He was especially known for promoting talented cross-party leaders even if they vehemently disagreed with him.

A key to Churchill’s early success was his speed of decision making.

In our world we use the OODA Loop. It stands for Observe -> Orient -> Decide -> Act, and then repeats back on itself as many times as it takes to get the job done. This is a tool designed by the US Air Force to filter and act on changing information rapidly.

War-time decision-making is among the hardest. And what makes it so is that the facts are always changing.

Speed is your friend (as it was Churchill’s). Act on what you know. Observe, Orient, Decide, Act.

Power of Pareto’s Principle

The second thing the Ol’ Bulldog had was power.

The Pareto Principle (in this case) is recognizing that your punches need to count because resources are limited. Applying the 80/20 principle is where you find power.

Powerful decisions are the ones that have the greatest impact. We often get distracted by minor decisions and activities. But there’s always a few powerful decisions that change the course of the war.

Churchill did this by rapidly gaining air superiority to prevent imminent invasion, even at the expense of his tank fleet. He knew that if he couldn’t win the war in the air, that the war on the ground didn’t matter.

So in your company, what’s the 20% of the war that matters most? How could you direct an unusual amount of resources to that battle?

Constant Communication

Churchill was no stranger to war as his experience as a wartime journalist pre-dated his role as Prime Minister.

He understood the impact of inspiring and frequent communication.

Churchill wrote every morning to his key people so that all parties were working together on the most up to date information. They were all solving the same problems with the same set of facts.

It was as much a vehicle of facts as it was a vehicle for his vigor and confidence. He shared deliberate speeches to provoke confidence in Great Britain.

And this just isn’t stuff of politics; it’s imperative for the success (and continuation) of your organization. Harvard research indicates that companies that communicate effectively had a 47% higher return in shareholder value over a five-year period.

And one of the keys to effective communication was discipline.

Communication early, often, and with discipline.

Unbreakable Courage

The other key to effective communication was courage. This was perhaps Churchill’s greatest value to Britain. It wasn’t just that he had it; he was a symbol of it.

People felt as if he was the spine of the country.

If he wasn’t broken then neither were they.

They would bend but they weren’t going to break.

They could lean on his resolve to find that same resolve within themselves.

So … when your people lack courage, will they find it in you?

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Mitchell + McClure
The Startup

Executive Coaches | Co-Founders of Mitchell McClure | EOS® Implementers | GiANT Consultant | Certified Virtual Coach®