Winston Churchill: A Lesson in Leadership


“Never in the field of human conflict was so much owed by so many to so few,” is one of the most memorable quotes of British wartime prime minister and statesman, Winston Churchill. It referred to the pilots defending the skies above his country during the Battle of Britain in 1940 when Churchill’s government stood isolated and alone against the threat of Nazi tyranny. We might also transfer its meaning, however, to the broader issue of modern leadership.

Many modern companies and organizations owe their flourishing success story to the vision and leadership of a single or small group of people. When a company grows to employ tens of thousands of people as a result of that vision, it seems appropriate to have a similar sentiment of much being owed by many to a few bold individuals with the courage and motivation to take charge and lead to see the job through.

In this blog, we will explore in more depth the lessons that modern business leaders can take from men like Winston Churchill.

It’s first important to understand the country Churchill was leading during the Second World War. After a long career in politics and the military between 1900 and 1929, he entered a period known as his “Wilderness Years,” which would last until his return to Neville Chamberlain’s government as First Lord of the Admiralty in 1939. As early as 1935, with his concerns on Hitler, the rise of Nazism and the rearmament of Germany being dismissed as “warmongering,” Churchill summed up the situation facing Britain, “Germany arming at breakneck speed, England lose in a pacifist dream, France corrupt and torn by dissension, America remote and indifferent.”[1] The Britain of that time was one gripped by apathy, greatly reduced in martial power (apart from its navy), and vehemently averse to war after its experiences in the Great War of 1914-1918.

As Chamberlain pursued his policy of appeasement, Hitler’s power in Europe grew, and eventually, even the arch-appeasers were forced to face reality. On September 3, 1939, the very day Britain declared war on Germany, Churchill returned to government, and by May 1940 after a series of humiliating defeats in Europe led Chamberlain to resign, he was leader of the Conservatives and prime minister. Through that time, from the wilderness back to the government, Churchill demonstrated perhaps his greatest personal and leadership trait: steadfast determination. He was confident in the information he had on Hitler, as well as his instinct on the nature of ambitious dictators, both of which were able to guide his views. Even when faced with continuous and scathing opposition from his peers and the wider establishment in Britain, he never wavered.

As a wartime leader, Churchill faced a mountain of issues. He had to think and act strategically, which means making considerable sacrifices that lead to considerable hardship for the British people and imperial subjects around the world. His inability to divert enough attention to Asia, for instance, led to the fall of many far-eastern colonies, including Singapore and Hong Kong. He also had to communicate persuasively to help convince his own people to continue the war effort even when Nazi bombs rained on British cities night after night with apparently no path to absolute victory open to Britain. Another challenge he faced was what a modern manager might call the task to build a diverse and inclusive team in the form of his war cabinet.

There were a number of critical moments that helped to illustrate Churchill’s own strength in leadership, which ultimately contributed not just to overcome the problems described above, but also to leading his country to final victory in 1945. The first such incident was actually something that happened years earlier in 1915 during the First World War. The Gallipoli Campaign was an unmitigated and deadly disaster that cost the lives of a quarter of a million Allied and Ottoman troops to no real gain. Dean Williams, lecturer at the Harvard Kennedy School wrote for Forbes:

“The failed campaign led to the humiliation of the British. Churchill was dismissed from his cabinet position, excluded from the War Council, and allowed no hand in the further conduct and administration of the war…Gallipoli has become an enduring symbol of the worst kind of military folly and waste.”[2]

This event, then, was critical in spurring Churchill’s prudence. He had to decide decisively, of course, what to pursue and whatnot, but each decision was taken with all the care and planning that was possible before finally being executed. Avoiding wasteful campaigns with no hope of victory or meaningful gains, even if it means short-term sacrifice, was a critical point in his leadership development.

The second major event was at the start of the war when he constructed his wartime cabinet. He first included Lord Halifax, who was a member of Chamberlain’s failed government, as a way of garnering greater support within his own party who had opposed Churchill for so long. He also reached across the house to bring in Labour Party leader Clement Attlee, as well as senior party member Arthur Greenwood. Finally, recognizing the importance of keeping organized labor on his side during wartime, the fifth member of the war cabinet was union leader Ernest Bevin.[3]

The ability to construct a team that includes a majority of members from an opposing domestic political ideology demonstrated pragmatism, magnanimity, and the ability to create unity among groups who were previously the most bitter of opponents. Only a leader of true strength and conviction can do that without any fear or compromise.

The third critical point came at the end of May 1940. The British Expeditionary Force was in full retreat to the evacuation point at Dunkirk, France was on the verge of capitulation, and all seemed to be lost as the Blitzkrieg overcame western Europe like a great tsunami. Even while Lord Halifax pushed for the exploration of a negotiated peace settlement with Hitler, Churchill resolved to fight on.[4] Where was Churchill’s pragmatism in the face of apparent defeat? He could have ended the war with Hitler and spared Britain the years of misery and destruction that were to follow with the Blitz. This event demonstrates Churchill’s ability to see the bigger picture. No peace deal negotiated with Hitler with the then-neutral Mussolini as mediator would have been favorable to Britain. Even in peace, Britain would be humiliated and disgraced.

One more critical event that illustrated Churchill’s leadership was the Battle of Britain, which raged from July to October 1940, and was a critical turning point in the conflict. At the start of the aerial campaign in which the Nazi Luftwaffe sought aerial supremacy over the English Channel to shield their forces for an invasion of the British mainland, the British position seemed hopeless. The nation stood alone against Hitler, the Royal Air Force was outmanned and outgunned, but Churchill’s determination to find innovative ways to use superior flight technology in the form of the RAF Hurricane and Spitfire fighter aircraft models, as well as the home advantage of many pilots being able to be recovered after bailing from their aircraft, saw the country through to victory in October 1940. It was the first significant defeat for the Luftwaffe and the German military, with 1,977 of their committed 2,550 aircraft destroyed in combat and 2,585 invaluable pilots killed with 925 more captured.[5] A furious Hitler turned his attentions instead to Operation Barbarossa, the invasion of the Soviet Union.

The courage and steadfastness to carry on, accumulating tiny victories day by day, translates very well into the modern context. Churchill demonstrated that an effective leader can “keep calm and carry on” as the old Ministry of Defence propaganda posters used to say.

Did these leadership qualities make a real difference during the war? Or, were other events like the Soviet Union and the United States of America’s entry into the conflict on the Allied side the more decisive factors overall? No one could deny the Russian and American contributions to the final victory. The support in goods and materiel provided by the US to Britain, as well as the blood and sacrifice of Soviet soldiers on the eastern front, seemed to be ultimately responsible for the final victory in Europe.

On the other hand, Britain’s continued wartime resolve, Churchill’s famous wartime speeches — especially “We will fight them on the beaches…” — the country’s tangible victories in the Battle of Britain, the Battle of the Atlantic, and the North Africa Campaign (eventually with American help) all serve as a living testament to the value of Churchill’s vision and courage; to his leadership qualities that ensured such victories were able to come about.

At the end of the war, as the British went to the polls in 1945, Churchill was met with a humiliating and to some a shocking electoral defeat. His wartime cabinet colleague and leader of the Labor Party, Clement Attlee, led his party to a landslide victory. Churchill once again entered a kind of “wilderness” period, now excluded from some of the most significant meetings and events at the end of the war with other world leaders such as Truman and Stalin. This defeat shows that sometimes even the greatest success of one’s life can go hand in hand with the greatest failures. Churchill demonstrated his resolve once again by returning to power in 1951, serving 4 more years in what would be a total of 13 years of a Conservative government in Britain.

What lessons can be taken from Churchill’s wartime and government leadership experience? The BBC’s World Affairs Editor, John Simpson, wrote in 2015 about how Churchill was a “great leader” but also a “flawed man.”[6] This is perhaps one of the most valuable lessons that a modern leader can take from the leadership of Churchill. We will summarize this and other leadership qualities below:

First, a modern leader should know the value of being able to strengthen leadership in yourself and others. Churchill’s steadfast and determined character and its positive leadership impact weren’t isolated to just the man himself. It inspired a nation and even the world to stand up and fight against a wave of tyranny and evil. A modern leader needs to first strengthen themselves, but also be able to strengthen others around them.

Second, a modern leader should embrace the front lines and understand all the details about what goes on within their organization so that they can think and act strategically to avoid potential disaster as Churchill did after his painful lesson in Gallipoli. By getting to grips with what’s happening from the very front line of the company to the deepest backroom operations, a CEO can understand the real big picture and plan accordingly.

Third, a modern leader should honor the stakeholders of a company or organization, regardless of their personal feelings or animosities towards them. A CEO might not particularly like other executives in the team, or other stakeholders in the wider structure such as members of the board. But just as Churchill had to embrace his ideological enemies at home to fight a greater enemy abroad, so too does a CEO have to honor all stakeholders and build a “war cabinet” of all the talents.

Fourth, a modern leader needs to be able to convey character and build responsibility within the team under them. Churchill conveyed his character through wartime speeches and public appearances in Britain and at the front. He closely identified himself with both victory and failure in the war. When Britain lost, so did he and he recognized his responsibility to grow from the experience and do better. When the leader has this sense, others gain it too, right down to the common foot soldiers in their hundreds of thousands.

Finally, a modern leader needs to be able to place common interests at the heart of all they do. If Churchill was unable to move past his personal vanity, then his war cabinet would have been stuffed with Conservative cronies and sycophants and not the strategically important individuals that it did contain. If he only focused on the short-term benefits of a ceasefire in 1940, then he would have led his country to a humiliating defeat in the form of a negotiated peace deal with Hitler, instead of having the foresight to carry on and fight for a bigger picture. It was in everyone’s interest that Churchill take these routes, and his leadership qualities led him to choose those correct paths each time.

In conclusion, then, though it has been more than half a century since Churchill’s death in 1965, the lessons of his leadership continue to apply not only to the world of government but also to the world of business and beyond.

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