Winston Churchill is one of the most celebrated leaders of the 20th Century and perhaps the savior of democracy as we know it. Someone I would love to have met, I got to know Winston through articles, his speeches, and reading “The Last Lion: Defender of the Realm.“

Inspirational even through words, Winston would have made a ferocious entrepreneur. His triumphs and tribulations through WWII are eerily similar to the struggles a founder and CEO goes through to build a successful company. I believe there is a lot to be learned from Winston on how to be a better leader.

Give people something to believe in
Everyone always talks about how an entrepreneur needs a vision, as if they are as easy to create as writing your name. Creating a clear and concise vision is incredibly hard. But even more difficult is getting people to believe in that vision against all odds.

Even in Winston’s case, if he had run around saying “we’re going to defeat Germany,” doesn’t mean people would have believed him. At the time Germany’s army was superior in nearly every facet and as they rolled up European country after European country, their momentum appeared to be unstoppable. Britain could have just waited like a sitting duck, for the enemy to crush them. But they didn’t.

“You ask what is our aim? I answer in one word: It is victory, victory at all costs, victory in spite of all terror, victory, however long and hard the road may be, for without victory there is no survival. Let that be realized; no survival for the British Empire and all it has stood for, no survival for the urge and impulse of the ages, that mankind will move forward towards its goal. ~ Winston Churchill (May, 1940, Speech at the House of Commons)

Instead, Winston gave them something to believe in, even larger than the salvation of Britain. They were fighting for the world’s democracy.

“And now it has come to us to to stand in the break, and face the worst that the tyrant can do. Bearing ourselves humbly before God, but conscious that we serve an unfolding purpose, we are ready to defend our native land against the invasion by which it is threatened. We are fighting by ourselves alone; but we are not fighting for ourselves alone.” ~ Winston Churchill (July 14, 1940 , BBC radio speech)

What I found most intriguing about Churchill’s leadership style was how vulnerable he allowed himself to be. Never afraid to show a tear in front of his people, he used a mixture of emotion, grit, and near poetry to inspire his country. He wasn’t considered strategic, or a great military mind, or even well liked before the events of WWII. But when it was his turn to inspire his people he rose to the occasion. The loyalty the people showed him goes to show that inspiration is even more important than strategy.

Don’t give up
They called him the bulldog. Many often felt he was a direct representation of the British common man, he was tenacious. His round body, occasional snarl, and top hat uniform only added to the image of a dog who wouldn’t back down from a fight. Even during the Battle of Britton, when Germany was on the brink of destroying the entire country, he willed his people to never give up. With bombs falling he preferred being above ground to see what was happening than to be hiding in the bunker.

“Never give in. Never give in. Never, never,never, never – in nothing, great or small, large or petty – never give in, except to convictions of honor and good sense. Never yield to force. Never yield tot he apparently overwhelming might of the enemy.” ~ Winston Churchill addressing the boys of Harrow

No different than a successful entrepreneur, Churchill never quit. Granted a company going under is very different from thousands of people dying, but what he constantly showed was that no matter what occurred, he wasn’t going to take no for an answer. He always pushed through, to the point of sending FDR a hand written letter nearly every week for two years asking for the Americans to help in the war. Some would call that obnoxious, others would call that relentless.

Unwavering confidence
There are a lot of times during WWII when privately, even Churchill struggled to see how Britain could survive Germany. Especially in 1940 and 1941, before the Americans or the Soviets joined the war, Britain was fighting by themselves. With their finances hurling towards bankruptcy and their people starving, he found it in himself to show complete confidence to his country.

“He gave his countrymen exactly what he promised them: blood, toil, sweat, tears, and one more thing – untold courage.” ~ Time Magazine

To everyone, including Churchill, it was clear that Germany was superior, but by his speeches you never would have known it. It reminds me of smaller brands picking a fight with larger brands, who theoretically should be crushed with one fell swoop. Churchill constantly reminded Hitler of his fate.

“He Hitler may carry havoc in the Balkan States; he may tear great provinces out of Russia, he may march to the Aspian; he may march to the gates of Indai. All this will avail him nothing. It may spread his curse more widely throughout Europe and Asia, but it will not avert his doom.” ~Winston Churchill

One of Churchill’s traits, which I believe all entrepreneurs need, is the ability to find the positive out of a negative. Apparently Churchill’s mood was volatile, especially in private, where he could express the intense emotions of anger, stress, sadness, and frustration he was feeling. But at the same time he would take the bad news and then move on to the positive, discussing what his country could do with the resources it now had.

Being Winston Churchill, just like being a CEO, was at the end of the day an incredibly lonely job.

The journey is long

“Long dark months of trials and tribulations lie before us. Not only great danger, but many more misfortunes, many shortcomings, many mistakes, many disappointments will surely be our lot. Death and sorrow will be the companions of our journey; hardship our garment; constancy and valor our only shield.” ~Winston Churchill (October, 1940 , Speech to the House of Commons)

Building a great company is a multi-year journey. There are very few Instagram like successes, instead most companies can take several years to hit their stride. Which means taking care of yourself so you don’t get burned out and actually enjoying the ride, is critical if you want to arrive at the end in one piece.

Churchill wasn’t known for taking care of himself. His daily diet of cigars, alcohol, and minimal sleep were a recipe for disaster. Known for the work rate of a young man, Churchill would out work, out read, and out worry all of his staff. Early in the war it wasn’t a problem, but as the war waged on without an ending in sight, his body began to deteriorate. Eventually suffering a heart attack and experience several periods of utter exhaustion.

Being a war time leader or a CEO requires you to be on 24 hours a day, 7 days a week. Your physical strength, emotional sanity, and mental freshnesses are needed to be at the top of your game, at all times.

Be thoughtful with your words

“Never in the field of human conflict was so much owed by so many to so few” ~ Winston Churchill (Referring to the RAF in the Battle of Britain during a Speech to the House of Commons)

If anyone has heard of Churchill, they have heard of his legendary speeches. Never one to miss an opportunity, he demonstrated just how important it is to be thoughtful about what you say. A type of influence that most CEO’s don’t realize, Churchill understood just how powerful his words were. Often writing his speeches not just for the people of Britain, but for the entire population of the world.

“It fell to me to express it, and if I found the right words you must remember that I have always earned my living by my pen and by my tongue. It was a nation and a race dwelling all round the glow that had the lion heart. I had the luck to be called upon to give the roar.” ~ Winston Churchill

It is easy to take for granted, opportunities to address your company. Thinking it’s just another company meeting or just another email, is definitely a mistake. Each time you get the chance to address the company you should think hard about what you want to say and what words you want to use. You don’t need to be as verbose as Churchill, but words are a powerful way to paint the picture you want painted.

In a culture that communicates in 140 character phrases, be thoughtful with what you have to say.

Personal touch matters
In Churchill’s mind there was no substitute for a personal visit. Through a rough exterior, his ability to charm was legendary, something he didn’t jus reserve for world leaders. Many of his visits were to the common man in Britain, in particular visiting cities after bombing raids or battle fields after victory. Not always welcomed by his generals he made it his mission to be seen as much as he was heard.

“As soon as it delivered him to a scene of destruction, out he’d climb to take off on foot. He might poke at the end of a bomb craters with his walking stick, or scramble up a pile of rubble to get a better view of the damage…He always sought out the people.” ~ The Last Lion: Defender of the Realm

The loyalty he experienced with the people of Britain was in large part due to his personal visits. Never too important for the everyday family, he would tour around London after bombing raids, visiting the shelters, and talking to people on the street. Asking how they were doing and what he could do to help. He had a way of keeping people upbeat.

As an entrepreneur, being on the ground is critical. Spending time with everyone across the company, even if they aren’t your direct report, gives you a sense of how people are feeling, what their frustrations are, and how connected or disconnected the whole organization is. Visiting customers, partners, and your investors provides insights that you just can’t capture through email, twitter, Skype, or any other virtual communication tool.

Leverage Wins
Leverage taught Churchill some of his hardest lessons. Generally considered a trusting guy, he wore his emotions on his sleeve, sometimes to a fault. He cared about what people thought and although he could be tough with his opinion he would often give in to partners so they would be happy. This was most evident with the Americans and Russians, two countries he desperately needed to help win the war.

After two years of fighting alone, Britain brought the least strength to the table in their partnership with the US and Russia. Both FDR and Stalin knew this, which means they took advantage of Churchill every chance they could. No different than how Britain took advantage of the countries it had colonized in the past. Churchill was learning a tough lesson about how leverage wins.

Being leveraged is a painful lesson many entrepreneurs learn along the way with investors, partners, competitors, acquiring companies, etc.

Everyone makes mistakes
No matter how many companies you build, everyone makes mistakes. It gets easier over time to avoid the simple mistakes, but the ever changing circumstances constantly create new challenges. At Contour I made a ton of mistakes, something I was constantly aware of as I tried to learn from them as fast as possible.

It was shocking to read just how many military mistakes Churchill made. He was thrust into the Prime Minister position, with complete war power, with minimal experience. Since Napoleon, the world had never seen a military force as dominating as the Germans and to make matters worse, the technology being used in WWII was completely overhauled from WWI, making the strategies used to win the first world war nearly irrelevant. No different then when the market or technology platform shifts under your feet.

“He simply did not grasp that fleet actions of that sort were now a thing of the past. Although he could never bring himself to entirely give up the old, when the facts demanded, he embraced the new, in the case of sending task forces to the Indian Ocean, almost literally overnight.” ~The Last Lion: Defender of the Realm

As fast as Churchill learned from his mistakes, the cost was irrevocable. Losing thousands of men and hundreds of war craft in single battles, he was paying a heavy price to gain the knowledge and instincts he would need to be a great war leader.

People want consistency
Most entrepreneurs have a unique ability to see an opportunity few around them even understand. Often guided by gut instinct, their leadership by sense has a hard time scaling when you get to dozens, hundreds, or even worse, thousands of people. Moving such a large force takes a unique type of communication and planning process, something Churchill wasn’t great at. His belief in using a fluid planning process (i.e. attack opportunistically) didn’t go over well with many of his own generals let alone the US military leaders who were used to rigid plans.

“He was not at all a theoretical strategist who considered the best thing to do and then made quite certain nothing detracted from it, and that the proper forces were concentrated in the proper place.” ~ Sir Edward Ian Jacob

One of the hardest parts for a CEO is to balance planning with gut instincts. Churchill’s instincts about Stalin were right, but they were ignored by FDR. While watching the Japanese struggle to improvise, was the opposite of what Churchill wanted in his military. A fear shared by most CEO’s the inability to pivot to opportunities just realized is a paralyzing feeling. But at the same time people need consistency and a plan they can hold on to.

Consistency is really hard, especially if you personally feed off the energy of new ideas. Your “brainstorming” can be taken as a new plan and a new direction, which not only drives your team nuts but ultimately lowers their confidence in your leadership.

Not Everyone Will Agree With You
Realizing that your title doesn’t mean you’re always right can be a humbling lesson to learn. Especially as you begin to lead you want everyone to agree with you. But the best leaders realize this isn’t going to happen. Even Churchill struggled with this, wanting everyone to like him and agree with his strategies.

“The P.M. is starting off in his usual style!!…I don’t think I can stand much more of it…His method is entirely opportunistic, gathering one flower here, another there! My God how tired I am of working for him.” ~ Alan Francis Brooke 

It was interesting to read about Churchill’s struggles. His inspirational words worked with everyone he met, but how he managed his team did not. Often not listening to their advice, he would go with what he wanted to do until everyone had bought into his plan. His relentless style wore people down to the point where key relationships of his would explode in frustration.

As a leader you have to make some really hard decisions. But at the same time you have to enable your capable team to make most of those decisions for you. A trust that can take a long time to build and that can be destroyed instantly if you don’t listen.

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If you want to learn more I highly recommend the “History of the English Speaking People” a four part series about the history of Britain from Winston’s perspective and “The Last Lion: Defender of the Realm,” the final volume of three, which covers WWII in grave detail.

Image Credit: Imperial War Museum once and twice, Unknown Author, United Kingdom Government via WikiCommons