10 Winston Churchill Leadership Lessons

WSC, Personifying British Defiance (Karsh, 1941)

One layer [of Churchill’s character and personality] was certainly seventeenth century. The eighteenth century in him is obvious. There was the nineteenth century, and a large slice, of course, of the twentieth century; and another, curious layer which may possibly have been the twenty-first.  –Clement Attlee

The 50th anniversary of the death of Sir Winston Churchill is a compelling occasion for reflection.

In a textbook case of projection, a preening popinjay, a BBC news personality called Paxman recently dismissed Churchill as a “ruthless egotist, a chancer, and a charlatan.”

Paxman and many others have speculated that Churchill could not be elected today.

These and other observations imply that Churchill’s leadership example is of limited value in our time. His life and work may provide anecdotes and entertainment, but little elucidation about things that matter.

This is surely wrong.

Winston Churchill’s storied, spectacular career holds numerous lessons for 21st century leaders.

10 Churchill Leadership Lessons for 21st Century Leaders

Among the lessons of Churchill’s leadership:

1. Leaders Are Self-Created. 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. He transcended numerous limitations–from an unprepossessing physical endowment to a distracting speech impediment–transforming himself into the heroic mold conjured in his romantic imagination.

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.

[Churchill] was, to a marked extent, forcing himself to go against his own inner nature: a man who was neither naturally strong, nor naturally particularly courageous, but who made himself both in spite of his temperamental and physical endowment. The more one examines Winston Churchill as a person, the more one is forced to the conclusion that his aggressiveness, his courage, and his dominance were not rooted in his inheritance, but were the product of deliberate decision and iron will.  –Anthony Storr

2. Courage is the First Virtue. If people were asked to describe 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. His career intertwined service as a soldier, a writer, and a politician. The disparate strands were braided tightly in his ultimate contribution, as warlord of the British Empire in the Second World War. His courage continued through his final premiership, in the 1950s, when he sought to broker improved relations between the United States and Soviet Union.

All of his accomplishments can be comprehended as arising from a shared root of courage–advanced through a related trait: audacity.

Courage is rightly esteemed the first of human qualities because it is the quality that guarantees all others. –Churchill

Jenny Jerome Churchill, with sons Jack and Winston

3. Vision Can be Transmitted Faithfully through a Romantic Lens. From youth, Churchill experienced the world as a cavalcade of heroes and heroines, of pageantry and ritual, of bright colors and vivid renderings. Some of this doubtless arose from the great loneliness he experienced, feeling neglected if not abandoned by a beautiful, vivacious mother and a mercurial, doomed father.

My mother made the same brilliant impression upon my childhood’s eye. She shone for me like the Evening Star. I loved her dearly — but at a distance. My nurse was my confidante. Mrs. Everest it was who looked after me and tended all my wants. It was to her I poured out my many troubles, both now and in my schooldays.  –Churchill

His romantic inclinations are also seen in his description of his marriage to the formidable Clementine Hozier Churchill.

[My marriage] was much the most fortunate and joyous event which happened to me in the whole of my life, for what can be more glorious than to be united in one’s walk through life with a being incapable of an ignoble thought?  –Churchill

Clementine and Winston

Churchill’s romantic conceptions also framed his statecraft.

Mr. Churchill sees history—and life—as a great Renaissance pageant: when he thinks of France or Italy, Germany or the Low Countries, Russia, India, Africa, the Arab lands, he sees vivid historical images— something between Victorian illustrations in a book of history and the great procession painted by Benozzo Gozzoli in the Riccardi Palace. His eye is never that of the neatly classifying sociologist, the careful psychological analyst, the plodding antiquary, the patient historical scholar. His poetry has not that anatomical vision which sees the naked bone beneath the flesh, skulls and skeletons and the omnipresence of decay and death beneath the flow of life. The units out of which his world is constructed are simpler and larger than life, the patterns vivid and repetitive like those of an epic poet, or at times like those of a dramatist who sees persons and situations as timeless symbols and embodiments of eternal, shining principles. The whole is a series of symmetrically formed and somewhat stylized compositions, either suffused with bright light or cast in darkest shadow, like a legend by Carpaccio, with scarcely any nuance, painted in primary colors with no half tones, nothing intangible, nothing impalpable, nothing half spoken or hinted or whispered: the voice does not alter in pitch or timbre.  –Sir Isaiah Berlin

4. Insight is Superior to Intellect. Winston Churchill stands as an irrefutable monument to the power of Albert Einstein’s dictum:

The intuitive mind is a sacred gift and the rational mind is a faithful servant. We have created a society that honors the servant and has forgotten the gift.

Churchill was not university educated. He was nonetheless highly learned, largely self-directed. As a result, his thought processes were not limited by convention. His boundless curiosity and capacity for fascination were not wrested into compliance and conventionality by pedants.

He was notably gifted with insight. His variety of worldly experiences expanded it. His temperament, fortified with the assurance of an aristocrat who reached adulthood during the apogee of the British Empire, impelled him to express his often unexpected points of view.

Judgment is a fine thing: but it is not all that uncommon. Deep insight is much rarer. Churchill had flashes of that kind of insight, dug up form his own nature, independent of influences, owing nothing to anyone outside himself. Sometimes it is a better guide than judgment: in the ultimate crisis when he came to power, there were times when judgment itself could, though it did not need to, become a source of weakness.

When Hitler came to power Churchill did not use judgment but one of his deep insights. This was absolute danger, there was no easy way round. That was what we needed. It was a unique occasion in our history. It had to be grasped by a nationalist leader. Plenty of people on the left could see the danger: but they did not know how the country had to be seized and unified.  –C.P. Snow

Inevitably, the same qualities and independence of thought in the face of received opinion lured Churchill into dubious enterprises and understandings. Notable examples include his obdurate, dead-end stance against dominion status for India, and his misguided defense of King Edward VIII amid the crisis prompted by his relationship with Wallis Simpson. Such unreliable judgments reinforced his political isolation in the 1930s. Tragically, they surely undercut the credibility of his early warnings against the gathering storm in Nazi Germany.

When Winston’s right, he’s right. When he’s wrong, well, my God. –Birkenhead

Churchill with David Lloyd George

5. Apply History to Illuminate the Present and Future.  Like Theodore Roosevelt (whom he resembled in many ways), Churchill was obsessed with history. He frequently turned to historical events and characters as if they were at his side. In fact, one might well say that they were at his side, coursing through the currents of his preternaturally active mind and imagination. Even as the emerging destiny of Churchill’s political project–protecting the survival of the British Empire–stirred his forebodings, his immersion in history enabled him to see far into the future. It made him relentlessly adaptive and innovative–qualities not generally associated with a fundamentally conservative vision.

History, for Churchill, was not a subject like geography or mathematics. It was a part of his temperament, as much a part of his being as his social class and, indeed, closely allied to it.  –J.H. Plumb

Mr. Churchill’s dominant category, the single, central, organizing principle of the moral and intellectual universe, is an historical imagination so strong, so comprehensive, as to encase the whole of the present and the whole of the future in a framework of a rich and multicolored past. Such an approach is dominated by a desire–and a capacity–to find fixed moral and intellectual bearings to give shape and character, color and direction and coherence, to the stream of events.  –Sir Isaiah Berlin

Everyone can recognize history when it happens. Everyone can recognize history after it has happened; but it is only the wise person who knows at the moment what is vital and permanent, what is lasting and memorable. –Churchill

History will be kind for me, for I intend to write it.  –Churchill [attributed]

6. Master the Written Word. Churchill’s early encounters with formal education were in large part unsatisfactory. Nonetheless, it soon emerged that he had gifts of memorization and writing–when his interest and passion were engaged.

His project of self-education included exposure to great English writers. Echoes of Macaulay and Gibbon ring throughout his highly crafted books, essays, and speeches.

Churchill’s recognizable writing style at once reflected his thinking, refined it–and, at times, may have hijacked it toward unexpected destinations.

Writing a book is an adventure. To begin with it is a toy and an amusement. Then it becomes a mistress, then it becomes a master, then it becomes a tyrant. The last phase is that just as you are about to be reconciled to your servitude, you kill the monster and fling him to the public.  –Churchill

If you cannot read all your books, at any rate handle, or as it were, fondle them–peer into them, let them fall open where they will, read from the first sentence that arrests the eye, set them back on the shelves with your own hands, arrange them on your own plan so that if you do not know what is in them, you at least know where they are. Let them be your friends; let them at any rate be your acquaintances. If they cannot enter the circle of your life, do not deny them at least a nod of recognition.  –Churchill

7. Master the Spoken Word. It is as a speaker that Churchill achieved his greatest leadership influence. As President Kennedy said, Churchill “mobilized the English language and sent it into battle.”

Churchill acknowledged that he was not an orator. He meant that he was not a speaker, such as David Lloyd George, who could connect deeply with a live audience, receiving and responding to their rising emotions. One wonders if this was a lingering result of his hard-earned triumph over a distracting lisp and the concomitant self-consciousness it inevitably engendered.

By contrast, Churchill prepared extensively, speaking to his audiences with methodically crafted ideas and writing. Many of his legendary witticisms turn out, on inspection, to have been premeditated rather than impromptu. The value was created largely in the interplay of Churchill’s evolving thoughts and words as he drafted the speech, rather than in the interplay of his relationship with an audience during presentation.

He customarily dictated his writing. He referred to this as living “from mouth to hand.”

It was my ambition, all my life, to be a master of the spoken word. That was my only ambition.  –Churchill

Of all the talents bestowed upon men, none is so precious as the gift of oratory. He who enjoys it wields a power more durable than that of a great king. He is an independent force in the world. Abandoned by his party, betrayed by his friends, stripped of his offices, whoever can command this power is still formidable.  –Churchill

Mr. Churchill’s carefully composed attitudes as he sits at the corner of the gangway and makes beautiful inflections with his hands when talking to his neighbor tell of the dramatic artist who has nearly ruined a statesman.  –Harry Boardman

Not only was the content of his speeches wise and right but the were prepared with that infinite capacity for taking pains which is said to be genius. So was his appearance; his attitudes and gestures, his use of all the artifices to get his way, from wooing and cajolery, through powerful advocacy, to bluff bullying–all were carefully adjusted to the need. To call this acting is quite inadequate. What we are speaking of is transformation, a growth and permanent change of personality.  –Dean Acheson

8. Summon Unconquerable Grit in Oneself–as a Prelude to Inspiring Others.  One might be think of resilience as a notable aspect of Churchill’s life and work,  though one imagines that he might incline toward a simple, clear, onomatopoetic descriptor such as grit.

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.

If you’re going through hell, keep going.  –Churchill

Success is not final, failure is not fatal; it is the courage to continue that counts.  –Churchill

Continuous effort—not strength or intelligence—is the key to unlocking our potential.  –Churchill

Never, never, give up.  –Churchill

[T]he House should prepare itself for hard and heavy tidings. I have only to add that nothing which may happen in this battle can in any way relieve us of our duty to defend the world cause to which we have vowed ourselves; nor should it destroy our confidence in our power to make our way, as on former occasions in our history, through disaster and through grief to the ultimate defeat of our enemies. Even though large tracts of Europe and many old and famous States have fallen or may fall into the grip of the Gestapo and all the odious apparatus of Nazi rule, we shall not flag or fail. We shall go on to the end. We shall fight in France, we shall fight on the seas and oceans, we shall fight with growing confidence and growing strength in the air, we shall defend our island, whatever the cost may be. We shall fight on the beaches, we shall fight on the landing grounds, we shall fight in the fields and in the streets, we shall fight in the hills; we shall never surrender, and if, which I do not for a moment believe, this island or a large part of it were subjugated and starving, then our Empire beyond the seas, armed and guarded by the British Fleet, would carry on the struggle, until, in God’s good time, the New World, with all its power and might, steps forth to the rescue and the liberation of the old.  –Churchill

William Orpen’s Portrait (1916)

9. Embrace Exuberance. Churchill battled depressive episodes throughout his life. According to Anthony Storr and others, this was an impetus for his ceaseless activity. Idleness was to be avoided at all costs. So, too, it may lay behind other personality traits, such as his predilection for stimulating company–even as it rendered him vulnerable to mountebanks in his midst.

He embraced exuberance as a fuel for his enthusiasm, which could then be transmitted to others.

In the struggle against Hitler, Churchill was able to combine the bracing realism of the pessimist with the indomitable optimism required to rouse the dispirited, demoralized people he served. His was not the easy optimism of one who had never known failure or misfortune. Rather, it was the hard-earned optimism of one who had proven that he could take a devastating punch–and, against all odds, pull himself off the mat.

A change is as good as a rest.  –Churchill

Solitary trees, if they grow at all, grow strong; and a boy deprived of his father’s care often develops, if he escapes the perils of youth, an independence and vigor of thought which may restore in after life the heavy loss of early days.   –Churchill

You and I think of Winston as self-indulgent; he has never denied himself anything, but when a mere boy he deliberately set out to change his nature, to be tough and full of rude spirits.

It has not been easy for him….Winston has always been a ‘despairer.’ Orpen, who painted him before the Dardanelles, used to speak of the misery in his face. He called him the man of misery….Winston has always been wretched unless he was occupied.  –Brendan Bracken

Bottlescape, by WSC

10. Live and Lead as an Artist. Churchill epitomizes the leader as performance artist. He strode the world stage with others who were consciously artistic in their approach, including Franklin Roosevelt, de Gaulle, and Hitler.

According to some, his writing may have been, in part, an artistic response to his tendency to depression. Whatever the wellsprings, the results were spectacular. Late in life, he was awarded the Nobel Prize for Literature.

In mid-life, he took up painting.

I cannot pretend to feel impartial about the colors. I rejoice with the brilliant ones, and am genuinely sorry for the poor browns. When I go to heaven I mean to spend a considerable portion of my first million years in painting, and so to get to the bottom of the subject. But then I shall require a still gayer palette than I get here below. I expect orange and vermilion will be the darkest, dullest colors upon it, and beyond them there will be a whole range of wonderful new colors which will delight the celestial eye.  –Churchill

Churchill Uniquely Passed the Ultimate Leadership Test

There is an ultimate test of leadership: would events have turned out differently but for their service?

Churchill is one of the rare leaders of history who undoubtedly passes this demanding test. The history of England, the history of Europe—indeed, the history of the world would have turned out differently but for his individual contribution of service in 1940-41.

That is not to say he was always right. He could be disastrously wrong and wrong-headed.

That is not to say he was uniformly successful. By any serious reckoning–including his own–he was not. The means required to save Britain and defeat the Axis powers ensured that many of the arrangements of Churchill’s world would be swiftly swept away. Contrary to some of the condescending revisionists of recent years, the gravity and contradiction of these circumstances were not lost on Churchill himself.

WSC, Momentarily Out of Character (Karsh, 1941)

The Inquest of History

Geoffrey Best, one of Churchill’s most effective recent biographers, concludes:

By the time Churchill died, Britain was fast turning into a land in which such a man as he was could never again find room to flourish, with a popular culture increasingly inimical to his values and likely therefore not to notice or properly appreciate his achievements….In the years 1940 and 1941 he was indeed the savior of the nation. His achievements, taken all in all, justify his title to be known as the greatest Englishman of his age. I am persuaded that, in this later time, we are diminished if, admitting Churchill’s failings and failures, we can no longer appreciate his virtues and victories.

The notable Cambridge scholar, Sir Geoffrey Elton, put it succinctly:

There are times when I incline to judge all historians by their opinion of Winston Churchill–whether they can see that no matter how much better the details, often damaging, of man and career become known, he still remains, quite simply, a great man.

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