🌀 Winston Churchill – Leadership & Life Lessons In The Spotlight

🌀 Winston Churchill – Leadership & Life Lessons In The Spotlight

🌀 Winston Churchill – Leadership & Life Lessons In The Spotlight

🌀 Winston Churchill – Leadership & Life Lessons In The Spotlight

🌀 Winston Churchill – Leadership & Life Lessons In The Spotlight

Winston Churchill - Leadership & Life Lessons In The Spotlight

Winston Churchill — Leadership & Life Lessons In The Spotlight


As you may know, Winston Churchill was a soldier, writer and statesman who led England and the Allies to victory over Nazi Germany in World War II. Winston Churchill is remembered as a witty man with a dry sense of humor. History also confers upon him a prickly personality, impatient and demanding. Still, when one thinks of a leader, Winston Churchill stands up as one of the most noteworthy in modern history. In this article, I’m going to talk about Winston Churchill’s leadership & life lessons.

What does it take to become a leader as well renowned and well respected as Winston Churchill?

As Britain’s most charismatic Prime Minister who led the nation through victory during the Second World War, Winston Churchill excelled where even history’s best brains would have dismally failed.  His strength and resolve during World War II gave the British people hope in their darkest hours. His courage and sense of purpose were the driving force that ultimately led the Allies to victory.

Though Winston Churchill certainly had his faults, he must be ranked as one of history’s greatest leaders and profiles of courage.

When Western Civilization was threatened by the ominous expansion of totalitarianism, Winston Churchill defended liberty against tyranny, exuded a confidence in victory and provided something freedom-loving people across Europe and the United States desperately needed: hope. Thus, Winston Churchill’s storied, spectacular career holds numerous lessons for 21st century leaders.

Winston Churchill’s stout, formal silhouette is instantly recognizable to most Britons, as are some of the former prime minister’s personality quirks.

He authored 37 books, producing more words than Shakespeare and Dickens combined. Whereas his ability to inspire fighting men and civilians alike was his most pronounced strength, there’s still much more to admire about Winston Churchill’s leadership style. The examples Churchill set should still serve as reminders of what it takes to be a great leader.

We’ll explore the five critical elements that made Winston Churchill a great leader in his own right.

Looking at his life, we can pick out a few important traits that will help you become a better leader. Step back in time with me and let Winston Churchill’s own words teach us some time-tested leadership lessons that are applicable today. Here are five of my favorites.

Lesson #1: Oratory Is Mandatory

Winston Churchill - Leadership & Life Lessons In The Spotlight - Oratory Is Mandatory

A great orator will never be forgotten. It is as a speaker that Churchill achieved his greatest leadership influence. As President Kennedy said, echoing Edward R. Murrow, Winston Churchill “mobilized the English language and sent it into battle.” There are few qualities of Churchill’s that have gone down in history quite as much as his skill as an orator. His speeches have gone down in history as great inspirations to the British people in wartime.

Winston Churchill is rightly remembered as a great speaker and an excellent writer as well.

His speeches during the Second World War are credited with maintaining the national morale. He did not just communicate with his immediate staff and colleagues but with the entire nation. By treating everyone as an important part of the team and keeping them regularly informed about developments, he inspired people to give of their best. Besides, by some estimates, his prolific writings include a staggering 20 million words. For this, Winston Churchill was awarded the Nobel Prize in literature, in 1953.

Not only could Winston Churchill write a masterful speech, he could deliver one with true power and feeling.

He was a superior orator and gave some of the greatest speeches in history. His voice was full of confidence and steadfastness. In Britain’s darkest hours, families huddled around their radio, scared, anxious, and worried about what was happening. Churchill’s voice flooded into their homes, bringing with it the comfort of knowing that the country was in the best of hands.

Communication is a skill. So like any skill, it’s learnable.

Winston Churchill was born with a lisp, but through training and deliberate practice, he was able to suppress it and go on to become one of the most quoted communicators of all time. But communication is more than just public speaking to large audiences. As well as being a visible leader of the masses, Churchill also connected with individuals through interpersonal communication and rapport building. His alluring aura consolidated the Britons. He often visited factories and towns. People who interacted with Churchill felt as though they were capable of achieving anything under his guidance and leadership.

Being a leader is about lighting the way to mutual goals, and it’s dynamic, exciting, and inspiring.

If you want to become a leader, you MUST become a good communicator… and that’s where honing your public speaking skills comes in. Every aspect of leadership encompasses public speaking. People “buy” people. As an inspiring speaker you will learn how to be passionate in the right moments and vulnerable in the right moments. People will be able to relate to you more as a human being. Public speaking can definitely serve you in your career by promoting more alliances, liking and trusting you more as they see you being empathetic.

Lesson #2: Fortune Favors The Brave

Winston Churchill - Leadership & Life Lessons In The Spotlight - Fortune Favors The Brave

If people were asked to describe Winston Churchill in one word, who can doubt that courage would be the anticipated response? In common with many other effective leaders, he exhibited courage in numerous ways. All of his accomplishments can be comprehended as arising from a shared root of courage–advanced through a related trait: audacity.

As a leader, your attitude is a little thing that makes a big difference.

In their darkest hour, when the British people were on the verge of making a deal with Hitler, Winston Churchill inspired them to continue on. Perhaps we can better appreciate his legendary quotes if we understand that Britain’s epic struggle was the context in which many of them were delivered. To the British people, Churchill exhorted, “Never, never, never give up.” Succinctly and truthfully put — Churchill’s attitude was a life saver. Never underestimate the power of a positive attitude. As a leader is will make you or break you.

Great leaders have courage. Courage is not only necessary but essential. 

Churchill oozed courage. The theme of courage ran through his whole career from soldier to politician. He was brave. He was willing to do whatever it took to win. Without courage leaders wouldn’t be able to disrupt the status quo. They wouldn’t have the stomach to do what is needed. You have to have a certain amount of courage and inner strength to lead the British Empire during the Second World War! Courage is often regarded as one of the utmost skills for a leader.

Courage is contagious. A leader needs to be courageous in order to inspire courage in others.

Such leaders build confidence in the team around them by showing how small reversible experiments (risks!) can really be game changers, demonstrating that failure is actually encouraged and how speaking up with conviction can have a 10x positive effect on a difficult situation. This is a skill that can be learnt and one that we have had many a success with installing into executive teams. That way, a courageous leader drives the organization to the next level through bold decision making, problem solving and risk taking.

A critical mass of brave leaders is the foundation of an intentionally courageous culture.

Every time we are brave with our lives, we make the people around us a little braver and our organizations bolder and stronger. Bottom line, it’s those brave souls who are willing to embrace risk, solicit feedback, model accountability and drive change, who will create courageous workplaces in which innovation and creativity are the norms, not the exception. In fact, most failure in leadership is a failure of nerve — a lack of courage. If you want to accomplish the difficult and do the extraordinary, then an essential superpower you can develop in yourself and model for others is to rise strong by growing your courage skills individually and together.

Lesson #3: Vision Isn't an Option

Winston Churchill - Leadership & Life Lessons In The Spotlight - Vision Isn't an Option

Great leaders, like Churchill, have a vision that guides their every move. They know what they stand for. They are crystal clear in what needs to be done.  They have clarity on where the team — or country in Churchill’s case — should be heading. Great leaders aren’t shy when it comes to sharing their vision with others. They paint a vivid picture of what success will look like and more importantly what it will mean.

Despite the pressure and sacrifices being made, Churchill stuck to his vision and frequently conveyed it to his people. By no means was this vision wrong and would he be reneged.

Winston Churchill is quoted as saying that the resolute British troops under his stewardship would strive by hook and by crook to beat the “monstrous tyranny” of the Nazis. Explaining Britain’s unwavering vision, Churchill described ultimate victory as their next destination. He had the courage and perseverance to see it through. And he inspired his people to follow his lead, no matter how hard it was. When you have your team vision and objectives, you must keep galvanizing your team to achieve them. Don’t drop it when times are hard.

A great leader will have visions and is not shy of showing them to his followers. 

Apparently, having a clear goal is as vital as any weapon you would bring to war. It is a powerful tool that can be used in times of chaos and adversity. As for Churchill’s vision, it is “total victory”. He was one of the first advocates of the “V” sign, which he used it to rally for victory. Another commendable trait Winston Churchill had was his ability to think ahead and plan for the future. Churchill saw that coal ships were using oil to help the coal light and he realized that, one day, the coal would be replaced entirely with oil. He even went so far as to establish a committee to prove that coal would be surpassed by oil fuels. He then went on to make sure that reserves of oil were kept in case of war.

Every leader has a vision. If you want to see success as a leader, you need to effectively share your vision and ideas.

The vision is the destination, and your leadership is the driver on the road towards that objective. Many leaders have a tendency to only share the big picture of an idea because it tends to be more inspiring and exciting. However, sharing the details of a vision is just as important as the picture. That said, when talking about your vision, be short and sweet. If you speak for an extended period of time, your vision will get lost. Employees won’t get on board if they don’t understand.

Typically, leaders are in love with their vision. They have a hard time letting anyone touch their vision.

More often than not, their vision is years in the making and a culmination of all their hopes and dreams. It summarizes everything they are and everything they value. They would rather fail than have anyone desecrate a vision that they have come to believe in. At least, this is what a “visionary” often thinks. Conversely, great leaders have learned to give others on their team the hammer and chisel and let them contribute. They encourage their team to take this hammer and chisel and go chip away. They allow their team to have ownership. The price of success, of a vibrant, breathing vision, is partnership. The willingness to share your vision, to give the keys of the kingdom to your team, is one of the most powerful things you can do as a leader.

Lesson #4: Nothing Beats Action

Winston Churchill - Leadership & Life Lessons In The Spotlight - Nothing Beats Action

Winston Churchill was anything but a “self-made man.” He was born to the aristocracy at Blenheim Palace. Nonetheless, as much as anyone could be, he was self-created. This process of self-creation never ended. He was continually evolving in significant ways, not held back by the needs for predictability and consistency that limit so many others. This also enabled him to recover from setbacks that most would have accepted as career-ending.

Without action everything else is meaningless. You can have the best intentions but it’s what you actually do that matters.

Leaders often spend too long deliberating; they obsess about all the possibilities. A leader that is overly cautious can often be rendered useless.  You need to do something in order to move forward. After all if you’re not moving forward you’re actually moving backward. Winston Churchill understood the importance of doing something — and doing it now.  He would put a sticker on orders that read “Action This Day”. Ideas are nothing if not put into execution. Great leaders execute relentlessly and stick to their guns no matter what.

All of a great leader’s characteristics would be meaningless, unless they are put into action.

After France collapsed, he was concerned that they would pass over their battle ships to Germany, coercing him to initiate the attack on the Battle of Oran. This just shows how serious Churchill was to carry on — no surrender! Leaders are successful when they and their teams accomplish their goals. That occurs when everyone is accountable for their job and they hold each other accountable. The leader sets the tone and example. When leaders jump in and start making phone calls, sending out emails, scheduling meetings and reporting about what they have accomplished, that is the example set for the team.

Why is it so hard to take action sometimes? I think the genius behind Nike’s “Just do it” campaign is that it feels empowering and a little reckless to many people to just take action.

The attraction with Nike’s slogan is that most people want to be that kind of person, bold and decisive, but find in reality they are not.  They wait and analyze the questions and issues before them way to long before taking action and by the time they do something, the moment is gone and the impact of the action has dissipated.  They suffer from “paralysis by analysis”. As a leader, people look to you to make decisions every day that impact their work environment and the success of the team.  Decisiveness is one of the qualities an exceptional leader needs to possess.  In leadership, if you take too long to make decisions or avoid making them all together, you will absolutely handicap your effectiveness and limit the success of the team.

Leaders who are indecisive create a power vacuum and if they are not careful, they may find their influence waning over time.

The truth is that teams, like nature, abhor a vacuum. If you are indecisive and do not step up to take action, someone on your team will eventually do it for you.  The result over time will be that team members will stop coming to you for decisions because you take too long and instead, they will ask the “unofficial leader” of your team what to do. Make sure you practice being decisive and taking action. If you struggle in this area, push your comfort zone a little and practice making decisions a bit earlier than you would normally. Get feedback from your team, your boss and co-workers about your effectiveness when it comes to taking action. Find a co-worker or mentor who is skilled and comfortable taking decisive action and learn from their process.

Lesson #5: Failure Is Not Fatal

Winston Churchill - Leadership & Life Lessons In The Spotlight - Failure Is Not Fatal

Winston Churchill’s journey of self-creation and self-assertion was marked by ever-greater examples of determination against all odds, against polite and expert opinion–sometimes in the face of rationality itself. The trials and errors might well have been viewed as constituting a failed career–had not fate summoned him to formal leadership in the struggle against Hitler in 1940.

Failure can strengthen, rather than destroy, your leadership.

Leaders will experience failure–sometimes disastrous, disgraceful failure that seems to unravel their leadership potential. And it is all too easy to respond to failure with rashness and shortsightedness, rather than grace and perseverance. People and life are often more forgiving that we expect, and if we will humbly seek to learn from our failures, they will usually not destroy us. In fact, our failures may even be the mechanism by which we are prepared for greater tasks ahead. You must own your mistakes and accept your shortcomings. Failure prepares you for the greater tasks that lie ahead of us. Great leaders know that failure does not define you — it shapes you!

Success is not final, failure is not fatal: it is the courage to continue that counts.

If you are going to last as a leader you have to let this truth resonate down deep. Every leader experiences failure. Failure is merely an event that happens on the road to success. What matters is not that you failed or even tasted the joy of success, but that you had the courage to continue. It has been said that failures are outcomes we had not planned for and certainly didn’t want. Yet failures are inevitable in our lives because any human endeavor can inevitably have one  of two possible outcomes-success or failure. What is not inevitable is how we chose to respond to failures.

Failures are inevitable but what matters is our determination to continue and our ability to bounce back.

Resilience can be learned and life experiences can teach us to toughen up and renew our efforts. Be determined to learn from your failures, analyze why you were not successful and, in time, you will notice that your personal capacities will grow and enhance. Refuse to retreat into helplessness and self-pity but instead be determined to adapt and move on. It is far more preferable to view failures as opportunities for learning. The only people who never fail are those who never try (Ilka Chase). There are many well-know people who are associated with being outstandingly successful but endured a series of previous failures before their resilience paid off.

Last but not least, failure teaches wisdom.

Success feels good, but failure–as long as you don’t let it get the best of you–brings wisdom and growth. Leaders who have failed have a depth of understanding that can’t be obtained any other way. Until you’re tested, it’s hard to imagine being able to endure struggle. But failure, when it comes, can take you far beyond the limits you imagined for yourself. Every failure is an opportunity to rethink your own limits and realize how much stronger and more capable you are than you ever thought. If you focus on positive thinking, even the harshest defeat is only a stepping-stone.

Wrapping Up

Winston Churchill - Leadership & Life Lessons In The Spotlight Final Thoughts
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 honour and good sense. Never yield to force. Never yield to the apparently overwhelming might of the enemy.Winston Churchill

By being open and direct, becoming a great communicator, and having the courage to lead by example, you can become a legendary leader, just like Winston Churchill. He knew the value of speech, and despite not being a natural orator, he worked on his skills and slowly made his influence felt in every corner of the Allied Forces.

Sure. We live in difficult, yet exciting times. Throughout history, there have always been battles to fight, and today is no exception.

Against this rising tide of evil, the world needs spiritual leaders to rise to the call, with eternal vision and a firm resolve. We must recognize, as Winston Churchill did, that crisis always spells opportunity. “A pessimist sees the difficulty in every opportunity; an optimist sees the opportunity in every difficulty.” Winston never gave up. Whether is was mastering painting, battling his own political party or defending his country, Churchill was not a quitter. He’s an excellent example of a man whom when confronted — confronts right back and never surrenders.

Winston Churchill wasn’t always liked — in fact many people opposed him and tried to thwart his moves.

He wasn’t always right and he was far from perfect as a man. But he was effective. Leadership shows up differently from person to person but the underlying traits that Churchill portrayed show up in the very best leaders. Sir Winston Churchill was a brave, strong and confident leader. He was a great leader. That no one can disagree with.

Now, this does not mean that all men should look for a fight — only that we should care about the fights that MATTER.

I hope this inspires you to do great things in unusual times. I will leave you with this quote from Winston Churchill: “This is no time for ease and comfort. It is time to dare and endure.” Perseverance, an eye on the future, and a willingness to make allies will carry you through the world successfully. Are you up to make a difference? To fight for what you believe in? Share your thoughts in the comments below!

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🌀 Winston Churchill – Leadership & Life Lessons In The Spotlight

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