Winston Churchill and the 12 Ineffable Qualities of Leadership: Bob Plamondon for Inside Policy

The greatest man of the 20th century has plenty to teach today’s politicians, writes Bob Plamondon.

By Bob Plamondon, April 23, 2021

Whatever you think about ideology, policy and politics, few would debate that very little gets done without leadership. A good case in point is Louis St-Laurent, who was the cover feature of a recent issue of Inside Policy for lessons on how to get things done in Canada – and for good reason. Weak party leaders rarely get much of an opportunity to have an impact because they do not win at the ballot box.  Those who win yet struggle to inspire leave little in the way of a legacy.

Having written about every Conservative leader from Macdonald to Harper as well as two Liberal Prime Ministers, I am fascinated by the differences that make some successful and others less so.  While I continue to explore the historical record on Canadian political leadership, rarely does a day go by when I am not drawn to Winston S. Churchill.  While there is no shortage of written material on the greatest man of the 20th century, I have attempted to highlight what I consider to be twelve qualities that contributed to his success and consequently the admiration of freedom-loving people around the world. Aspiring politicians, take note.

  1.    Purpose

While he could have coasted on his pedigree, Churchill was infused with purpose and a sense of destiny.  He had little interest in accumulating wealth and initially set his sights on the preservation of the British Empire. That was eclipsed by a more fateful and consequential ambition: “We are fighting to save the whole world from the pestilence of Nazi tyranny and in defence of all that is most sacred to man.”

Despite having been knocked down and shunned for more than a decade, Churchill led from the backbenches in the House of Commons to identify and condemn Hitler and his Nazi regime. When all seemed lost and the call came in 1940 to lead Churchill wrote, “I felt as if I were walking with destiny, and that all my past life had been better preparation for this hour and this trial.”

To those who sought appeasement or a negotiated settlement with Hitler, Churchill reminded the British people that there were worse things than war: “Slavery is worse than war. Dishonour is worse than war.”

He was determined to make his mark on history.  “The longer you can look back,” he said, “the farther you can look forward. The wider the span … the greater is the sense of duty in individual men and women, each contributing their brief life’s work to the preservation and progress of the land in which they live.”

  1. Courage 

While he did not advocate recklessness in others, he saw bravery as an essential ingredient to life.  “Courage,” he wrote, “is rightly esteemed the first of human qualities because … it is the quality which guarantees the others.”

To a fault, Churchill sought to place himself in the line of fire.  He wrote, “Nothing in life is so exhilarating as to be shot at without result.” It ached him as Prime Minister not to be at the front lines.  He was inspiring and irrational in equal measure.

While in Canada he told Parliament that Great Britain had not “journeyed across the centuries, across the oceans, across the mountains, across the prairies, because we were made of sugar candy.” Nations which went down fighting endured, Churchill observed, “but those which tamely surrendered were finished.”

  1. Passion

For a country with a stiff upper lip, Churchill was easily moved to tears. To those around him, he quipped, “I blub an awful lot, and you know you have to get used to it.”  He said the qualities of being subdued and reserved were ones in which he was least endowed.

Tears poured down Churchill’s cheeks in the House of Commons when the atrocities inflicted on the Jews in Europe were brought to light. A British general observed Churchill sobbed from the moment he set foot in France following D-Day and when he marched with Charles de Gaulle upon the liberation of Paris. Churchill’s emotions enhanced his authenticity and connection with the British people.  And he cried equally from pleasure and from sadness.

  1. Learn from mistakes

Churchill once said, “I am always ready to learn, although I do not always like being taught.”

His wife, Clementine, thought he would die of grief in the aftermath of the military calamity in the Dardanelles in the First World War when Churchill was First Lord of the Admiralty.  As Chancellor of the Exchequer, he followed the near-unanimous advice of the experts and returned Great Britain to the Gold Standard to disastrous effects.

But these errors, among many others, prepared him for leadership and decision-making in the Second World War.  “I should have made nothing,” he told his wife, “if I had not made mistakes.”

To Churchill, someone who couldn’t take a knockdown wasn’t worth a damn.  His failures made him wise but did not deter him from bold action.  When confronted in the House of Commons about whether he had learned his lessons from the past he disarmingly responded, “I am sure the mistakes of that time will not be repeated.  We shall probably make another set of mistakes.”

  1.  Humour  

To Churchill, humour inspired confidence and lightened spirits. When the Nazis were taking over Europe Churchill said Hitler’s appeasers were akin to those who fed a crocodile hoping it would eat them last. After Hitler’s invasion of Czechoslovakia, Churchill observed it had “Opened the eyes of the blind, made the deaf hear, and even in some cases the dumb spoke.”

When he was criticized for the courteous even subservient wording of his declaration of war against the Japanese, Churchill noted, “Some people did not like this ceremonial style. But after all, when you have to kill a man it costs nothing to be polite.”

Pointed exaggeration was another technique that could induce a smile. “There are two people who sink U boats in this war,” he said to a member of the Admiralty. “You sink them in the Atlantic and I sink them in the House of Commons. The trouble is that you are sinking them at exactly half the rate I am.”

While on the opposition benches, he began a speech with a story from his childhood.  He recalled visiting the circus that featured an exhibition of “freaks and monstrosities.” What he most wanted to see, but was prevented by his parents because of its revulsion, was the “boneless wonder.”  Pointing to a minister sitting on the Treasury bench opposite, Churchill said after a wait of 50 years he finally saw the “boneless wonder.”

  1. Trust the people

It seems ironic that a man with a steel resolve would have as his political motto “trust the people.” He saw himself as a servant of the state and said he would be ashamed to be considered its master.

It was his faith in the toughness and wisdom of the British people that enabled Churchill to deliver grim news. By speaking honestly and respectfully he also insured himself against reproaches when hard times followed.

Trusting the people did not mean he tilted like a weathervane. He said that politicians who were not prepared to do unpopular things in times of clamour were not fit to be ministers. Churchill listened carefully to the hearts of the people but did what he thought was best for the British nation for the long-term.

By siding with the people, Churchill was often seen as a traitor by the aristocracy. Concerning the House of Lords (our equivalent to our unelected Senate), Churchill said the people would never allow themselves to be dictated to and domineered over “by a miserable minority of titled persons, who represent nobody, who are responsible to nobody, and who only scurry up to London to vote in their party interest, in their class interests, and in their own interests.”

  1. Country over party

Most people today view Churchill as a conservative icon, but he was not strongly attached to party or ideology.  Over his political career, he changed parties twice. To those who thought him disloyal Churchill humorously observed, “Anyone can rat, but it takes a certain ingenuity to re-rat.”

He broke with the Conservative Party over its opposition to free trade. “High protective tariffs,” he argued, “are to the poor and the poorest of the poor a cursed engine of robbery and oppression.”

He was compassionate and argued that there should be a minimum standard of living for all people.  He saw virtue in regulation and the taxation of luxury goods. He once teased the Americans during the prohibition era: “We realise $100 million pounds sterling a year from our liquor taxes which I understand you give to your bootleggers.”

In both the Liberal and Conservative parties, he was wary of extreme factions. “There are fools at one end and crackpots at the other but the great body in the middle is sound and wise.”

Churchill, however, did find socialists to be a confused lot.  There were some, he said, who regarded private enterprise as a tiger to be shot and others as a cow they can milk. “Only a handful see it for what it really is – the strong and willing horse that pulls the whole cart along.”

He also worried about the tendency of government bureaucracies to grow “like a horde of injurious locusts” and where money is taken from some and given to others, “with the greater part will be spilled on the way.”

Churchill saw members of Parliament as owing their primary duty to constituents and not party.  “What is the use of sending Members to the House of Commons … who merely endeavour to give satisfaction to the Government Whips by cheering loudly every Ministerial platitude?” He urged constituencies not to return tame, docile, subservient MPs who were incapable of independent judgment.

While he revelled in the asperity of political discourse, Churchill built relationships with his political opponents and others through The Other Club, an entity he co-founded that comprised 12 Liberals, 12 Conservatives, and 12 outsiders. He attended over 300 convivial dinners of the club where the common good was sought.

  1. Let grievances die

When given power and responsibility Churchill cared little about what someone had said about him in the past.   “Forget old quarrels” was a Churchill motto, which he followed when appointing a cabinet comprised of representatives of three major parties and the factions within them.

Churchill did not believe in vengeance against domestic political opponents but rather “a judicious and thrifty disposal of bile.” Hatred, he admonished, plays the same part in government as acids in chemistry.

The harsh economic and financial provisions of the Versailles Treaty imposed on Germany after the First World War were to Churchill, “Malignant and silly to an extent that made them obviously futile.” He did not hesitate to overpower an enemy in battle, but his aim was to make it easy for the enemy to accept defeat. And after the battles were won, he was not punitive but urged that shiploads of food be sent to Germany.

  1. Don’t get mired in detail

While prodigious in his knowledge and capacity to process data, he demanded that his briefing material be provided on one or two sheets of paper.  He thought no issue was so complex that its essentials could not be boiled down to its essence. Those who could not accomplish this task, he thought, were either lazy or incompetent. He noted that the Treasury Department defended itself from scrutiny by producing volumes of material in such length that it had no chance of being read. While unmatched in eloquence, he was irritated by those who used obscure language when communicating with the public in the hopes they would be thought of as clever.

  1. Challenge groupthink

Churchill said his biggest mistakes came from following conventional thinking and the advice of experts rather than respecting his instincts. Often the experts were correct but not always.

He also worried about the temptation of subordinates to tell him what they thought he most wanted to hear. Churchill’s preference was to hear the brutal facts, as unpleasant as they might be.

He doubted the wisdom of those who attempted to explain the politics of foreign lands, noting that “very few understand the politics of their own country – and none the politics of the other countries.”

Unlike Hitler, who almost never visited a bombsite, Churchill went regularly to the East End of London during the blitz to witness the damage and boost morale. “I see the damage done by the enemy attacks, but I also see side-by-side with the devastation and amid the ruins quiet, confident, bright, and smiling eyes, I see the spirit of an unconquerable people.”

Groupthink almost prevented Churchill from becoming prime minister.  Canadian Prime Minister Mackenzie King was not alone when he said Churchill was a danger to Great Britain and the Commonwealth.

  1. Ditch the sanctimony

At a time when Jews were treated with prejudice across much of Europe, Churchill came to their defence.  “What is the sense of being against a man,” he said, “simply because of his own birth? How can any man help how he is born?”

Churchill was not one to moralize.  After visiting the American newspaper baron William Randolph Hearst at two of his residences he remarked, “Two magnificent establishments, two charming wives.” Of course, it was one wife and one mistress.  When his son Randolph was fighting in North Africa in 1941 his wife was having an affair with the American envoy to Europe.  Churchill appreciated the diplomatic benefits of such an arrangement far more so than did his son.

He was no fan of temperance even when in the company of abstinent Muslim leaders. “My religion,” said Churchill, “prescribed as an absolute sacred ritual smoking cigars and drinking alcohol before, after, and if need be during, all meals and the intervals between them.”

  1. Find a hobby

Churchill took regular naps, not to slack off but because he said it allowed him to get in two normal days of work in a 24-hour period.  But he understood that work and nothing else over long periods would be incapacitating.  While Churchill dabbled as a bricklayer, he was an avid and accomplished painter.  “If it weren’t for painting,” he wrote, “I could not live; I could not bear the strain of things.”  It was his therapy and over his life, he produced 540 canvases. He also found the cinema helped to take his mind away from the stress of saving the world from Nazi tyranny.

Bob Plamondon has written five best-selling books, including The Shawinigan Fox: How Jean Chrétien Defied the Elites and Reshaped Canada.  He sits on the Board of Directors of the Ottawa Chapter of the Sir Winston Churchill Society.