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It’s hard to imagine a more difficult leadership assignment in the history of the world than what Winston Churchill faced.

There is a reason his most iconic portrait by Yousef Karsh was dubbed—The Roaring Lion—due to his penetrating scowl and fierce resolve.

It can be helpful to draw inspiration from some of history’s greatest leaders and we gain perspective by remembering the sheer magnitude of the challenges they faced.

The Big Idea—Today we will explore the incredible leadership traits that Churchill demonstrated during one of history’s most foreboding times.

The darkest hour

Churchill was appointed Prime Minister on May 10, 1940.

By that time, Hitler had invaded Poland, Norway, Belgium, Luxembourg, the Netherlands, and Denmark—and was preparing to attack France.

Exactly a month after Churchill’s appointment, Germany invaded France and declared war on the United Kingdom.

France surrendered just 12 days later.

Britain refused to agree to Hitler’s terms—and by September—Germany began strategically bombing London for the next 56 out of 57 days.

The situation looked hopeless.

In addition to the external pressures, Churchill was widely criticized by his own government officials for his aggressive stance on rejecting any notion of peace with Germany—members of his own war cabinet threatened to resign.

By the end of World War II, most historians estimate that over 60 million people died—two thirds of them were civilians.

It was also the only time in history when nuclear weapons were used for warfare.

Although Churchill was a controversial figure, he was said to have been selected because he was perhaps the only man said to strike fear into Adolf Hitler.

That quality made him the right leader for the right time.

What research reveals about the most important leadership traits

In the business classic—Good to Great: Why Some Companies Make the Leap and Some Don’t—author Jim Collins and his team of researchers conducted one of the most exhaustive projects on what made great companies last—and the traits that were most common amongst their elite leaders.

Collins analyzed 1,435 companies over a span of 40 years to ensure that he was looking at organizations that truly sustained greatness over the long haul.

He created a ranking system of the leaders and termed the best leaders—Level 5 Leaders.

Every single Level 5 Leader had two indispensable qualities that seemed paradoxical—1) Fierce professional will and 2) Deep humility.

These leaders were fanatically driven, exceedingly ambitious, and produced consistently over the long haul.

They cared more about the good of the organization than personal benefit.

They took responsibility when things went badly, and gave away credit when things went well.

According to Collins, the leaders he studied also set up their successors for even greater success than their own, because their egos were not threatened by having other leaders surpass and outlast them.

Wow—now that is a leadership model to aspire to.

And it paints quite a different picture from many of the self-centered and egotistical leaders we so frequently see.

Churchill had the qualities of a Level 5 Leader.

Turn information into action

Churchill demonstrated fierce determination and humility in the following ways:


It has been said that leaders broker in hope. Churchill gave Britain what his predecessor Neville Chamberlain could not. In the movie—Darkest Hour—Churchill says, “I will give people a hope they do not yet know they have.” Great leaders provide the hope before people even know they have it. This is self-leadership at its best.

Undaunted courage

Churchill’s unflinching position and his unwillingness to negotiate with evil probably saved Great Britain from being conquered by Germany. This quote says it all:

“Success is not final. Failure is not fatal. It is the courage to continue that counts.” –Winston Churchill

Constant communication

According to the American Psychological Association’s Center for Organizational Excellence, great communication is the essential bedrock of healthy workplaces. Churchill would speak to his inner circle, then address Parliament, and take to the radio in the evenings to address the people. He would also apparently ride the subway to ask for input from everyday citizens (his version of management by walking around). Great modeling of top-down and bottom-up communication.

Most military leaders also agree that it is vital to communicate more during times of crisis, and when your team is working remotely.

He sought opposing viewpoints

In a massive global study by Mckinsey and Company in 2015, they found that seeking opposing viewpoints is one of the 4 vital traits of a great leader. Churchill deliberately assembled his war cabinet from people who didn’t see things his way, in an effort to counter his own potential for bias. Now that is inspiring humility. This proved to be quite a challenge for him, but he felt it was essential to have people with differing viewpoints to reach the best decisions.


Churchill wore his heart on his sleeve. He was known for frequent displays of both anger and tears. He obviously cared for his countrymen. His vulnerability made him human.

He played a game of inches when the odds looked bleak

When more than 300,000 troops were stranded and awaiting certain annihilation by German forces at the beaches in Dunkirk, Churchill called for civilians with a boat of any kind to help evacuate troops. More than 338,000 troops were rescued that day.

There is a great lesson for all of us here. Don’t let overwhelming odds prevent you from doing what you can. We are all small boats, but every single boat makes a difference.

Have a great weekend!


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Suggested Resources

  1. The Darkest Hour Movie
  2. Good to Great by Jim Collins
  3. The 4 most important traits of a leader study










Dr. Parker Houston

Parker Houston

Dr. Parker Houston is a licensed clinical psychologist and board-certified in organizational psychology. He is also certified in personal and executive coaching. Parker's personal mission is to share science-based principles of psychology and timeless spiritual practices, to help people improve the way they lead themselves, their families, and their organizations. *Opinions expressed are the author's own.
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