Churchill’s Personal Traits

The consummate example of leadership in adversity, Winston Churchill demonstrated that success is impacted not just by what you do, but who you are.

Editor’s Note:
While a graduate student in history at Claremont Graduate School in the 1980s, Steven F. Hayward served as editor of a regional business magazine, a job which included numerous discussions with local businesspeople. As Hayward’s interview subjects learned about his academic interest in history and politics, talk would turn to politics. The dearth of political leadership was a common complaint. Just as common was admiration for Winston Churchill, though such admiration was rarely based on more than a basic knowledge that he “stood up to Hitler” and gave powerful speeches. Well equipped by his studies, Hayward seized the opportunity to offer further details of Churchill’s leadership. “I began to see that Churchill’s story offers valuable lessons for executives and entrepreneurs,” he writes. “Many was the time that a businessperson would call back asking again for the details of a Churchill story I had told.”

The result is Churchill on Leadership, a book that should be on the “must-read” list for all current leaders and those who aspire to lead. Hayward masterfully distills the essential leadership patterns from Churchill’s life (drawing from his successes and his failures), supported by a large collection of Churchill’s own words, a concoction of candor, wit, and conviction that makes it downright fun to read.

The following excerpt shows that Churchill’s leadership in the face of adversity transcends politics and foreign policy; indeed, it is quite applicable to our current economic climate. As it was difficult to select the “best” excerpt to include here, we strongly encourage business leaders to read the entire book and add it to their personal libraries as a frequent source of refreshment.

GOOD WORK HABITS, coherent organizational structures, and superior communication skills do not in and of themselves constitute leadership or guarantee success. Leadership is equally a matter of personal character as of executive skill. Military historian Maxwell Schoenfeld reminds us that even though Churchill’s executive reorganization of the war effort after he became prime minister was essential to his success, “The central problem was essentially one of leadership, not of staff.”

Churchill learned this lesson early on from his first political patron, Prime Minister Herbert Asquith. Asquith was one of the most dominant and successful politicians of the period, and he led his Liberal Party to several major political triumphs in the years before World War I. He advanced Churchill’s career more than any other prime minister. After one of Asquith’s political victories, Churchill wrote to him admiringly, “It is not always that a leader’s personal force can be felt amid all that turmoil.” Years later, looking back after Asquith’s death, Churchill wrote: “Mr. Asquith was probably one of the greatest peacetime Prime Ministers we have ever had.” The key term here is “peace-time.” Asquith was not up to the task of wartime leadership. “In war,” Churchill wrote of Asquith several years later in Great Contemporaries, “he had not those qualities of resource and energy, of prevision and assiduous management, which ought to reside in the executive…. [The war] demanded a frenzied energy at the summit; an effort to compel events rather than to adjudicate wisely and deliberately upon them.”

What made possible Churchill’s own “frenzied energy at the summit” was a combination of character traits that transcend mere executive skills.

Courage and Optimism
Churchill’s courage was evident from his earliest days as a young lieutenant in the army. Maurice Hankey, cabinet secretary during World War I, wrote later that “We owed a good deal in those early days to the courage and inspiration of Winston Churchill who, undaunted by difficulties and losses, set an infectious example to those of his colleagues who had given less thought than he, if indeed any thought at all, to war problems…. His stout attitude did something to hearten his colleagues.” After Churchill left the war cabinet for the front line trenches in France, Hankey lamented in his diary: “Since Churchill left the Cabinet and the War Council we have lacked courage more than ever.”

The key to Churchill’s courage was his unbounded optimism. Only an optimist can be courageous, because courage depends on hopefulness that dangers and hazards can be overcome by bold and risky acts. “I am one of those,” he remarked in 1910, “who believe that the world is going to get better and better.” He deprecated negative thinking. In a speech to his officers in the trenches in France in 1916, Churchill exhorted: “Laugh a little, and teach your men to laugh….If you can’t smile, grin. If you can’t grin, keep out of the way till you can.”

“It is a crime to despair,” he wrote after the disaster of the Munich agreement in 1938. “It is the hour, not for despair, but for courage and re-building; and that is the spirit which should rule us in this hour.” In his last major speech as prime minister in 1955, surveying the growing threat nuclear weapons posed to the very survival of civilization, Churchill concluded: “meanwhile, never flinch, never weary, never despair.”

“All will come right” was a favorite phrase. He repeated it often in the darkest days of World War II, and he seldom ended a wartime speech without a ringing note of optimism, usually drawn or adapted from a famous English poet. (He ended one speech with a lyric from Arthur Hugh Clough: “But westward, look, the land is bright!”) After Churchill had been hit by a car and nearly killed in 1931, he summed up his optimism into a credo: “Live dangerously; take things as they come; dread naught, all will be well.” “When you get to the end of your luck,” he wrote in the 1930s, “there is a comfortable feeling that you have got to the bottom.”

Optimism is also the key to the can-do spirit, to the don’t take- no-for-an-answer attitude that is essential to successful executive leadership. Nearly all human organizations are subject to an inertia that results in an it-can’t-be-done attitude. This was always unacceptable to Churchill. “Churchill’s supreme talent,” one of his aides recalled, “was in goading people into giving up their cherished reasons for not doing anything at all.” When apprised of delays in shipbuilding in 1939, for example, Churchill sent a memorandum to one of his senior administrators: “It is no use the contractors saying it cannot be done. I have seen it done when full pressure is applied, and every resource and contrivance utilized.” And Churchill once urged a diplomat in a cable: “Continue to pester, nag and bite. Demand audiences. Don’t take NO for an answer.”

Churchill’s optimism and cheerfulness tend to be obscured by the accounts of his occasional depression, what he called his “black dog.” There is no doubt that the pressures of office and the fearfulness of events often left Churchill profoundly discouraged – especially when he was out of office and powerless to affect events that he understood so clearly. But these occasional collapses of Churchill’s spirit have probably been exaggerated (along with the popular image of his drinking), and in most cases they were short-lived. It is worth noting that Churchill often turned to his favorite hobby – painting – when he was discouraged, but that unlike serious manic depressives or brooding artists who paint dark scenes or write morose poetry, Churchill always painted in bright, vivid colors, a reflection of an underlying optimism and happiness of soul. (Regarding his choice of colors for painting, Churchill wrote: “I rejoice with the brilliant ones, and am genuinely sorry for the poor browns.”)

One aspect of his optimism that was especially important was his legendary sense of humor. But this, too, had a serious underpinning in his mind. “It is my belief,” Churchill said, “that you cannot deal with the most serious things in the world unless you also understand the most amusing.”

Kindness, Magnanimity, and Gratitude
Like any ambitious, demanding person in a position of great responsibility and facing enormous pressures, Churchill could be abrupt and hard on his subordinates. “It is a wonder any of my colleagues are speaking to me,” he once remarked during an especially difficult period early in World War II. But as with the accounts of his occasional depression, accounts of Churchill’s domineering manner or rudeness have been exaggerated, and his kindness and consideration for his subordinates overlooked.

“The idea that he was rude, arrogant, and self-seeking is entirely wrong,” wrote General Ismay, one of his closest aides during the war. Martin Gilbert, who interviewed nearly all Churchill’s secretaries and assistants in the course of research for his massive biography, wrote: “The overriding impression that his secretaries gave me was of a man who worked hard himself, drove them equally hard, but did so with humor and kindness, alert to their personal needs and quick to apologize for any outburst of anger.” The many diaries, memoirs, and other records of experiences with Churchill are replete with observations similar to this account from Lord Normanbrook: “He would at intervals find time to say or write a few words of appreciation which showed a quite exceptional generosity and kindness.”

Churchill also was an exceptionally forgiving person – an aspect of magnanimity. “I do not harbor malice,” he wrote in a letter in 1921. “I always forgive political attacks or illtreatment not directed at private life.” This trait was most on display after World War II began, when Churchill’s position was unassailable on account of his clear and consistent warnings over the previous years. If anyone had a right to say “I told you so” and demand retributions against the position and careers of the officials who had been derelict in their leadership, it was Churchill. But he did no such thing. From a Conservative Party official who had even tried to remove Churchill from Parliament just a few months before the outbreak of war, Churchill most graciously accepted an apology, writing: “I certainly think that Englishmen ought to start fair with one another from the outset in so grievous a struggle and so far as I am concerned the past is dead.”

His largest magnanimity was reserved for Neville Chamberlain, the architect of the disastrous Munich agreement with Hitler that Churchill had so bitterly criticized. Chamberlain worked assiduously to keep Churchill out of office in the months and years before war came, and when waning political support compelled his resignation in May 1940, he was not enthusiastic about Churchill replacing him as prime minister. But once Churchill was in the government, Churchill was extremely loyal and supportive of Chamberlain, and after Churchill became prime minister, he defended Chamberlain against critics. (Churchill had kept Chamberlain in the government as a member of the war cabinet.) John Colville noted in his diary that Churchill “never countenances a word against Chamberlain.” When a group of MPs demanded a parliamentary “inquest” against those responsible for the conduct of policy before the war (meaning chiefly Chamberlain), Churchill spoke out forcefully against the idea. “This,” he said to the House, “would be a foolish and pernicious process….Of this I am quite sure, that if we open a quarrel between the past and the present, we shall find that we have lost the future.” Churchill’s final kindness to Chamberlain was his eulogy in the House of Commons after Chamberlain’s death of cancer in November 1940. Churchill sought to put their past disagreements in the most generous light possible without ignoring them entirely:

It fell to Neville Chamberlain in one of the supreme crises of the world to be contradicted by events, to be disappointed in his hopes, and to be deceived and cheated by a wicked man. But what were these hopes in which he was disappointed? What were these wishes in which he was frustrated? What was that faith that was abused? They were surely among the most noble and benevolent instincts of the human heart – the love of peace, the toil for peace, the strife for peace, the pursuit of peace, even at great peril, and certainly to the utter disdain of popularity of clamor. Whatever else history may or may not say about these terrible, tremendous years, we can be sure that Neville Chamberlain acted with perfect sincerity according to his lights and strove to the utmost of his capacity and authority, which were powerful, to save the world from the awful, devastating struggle in which we are now engaged. This alone will stand him in good stead as far as what is called the verdict of history is concerned.

It was Churchill’s kindness, his sincere interest in people, and magnanimity that enabled him to win people over consistently. The historian George Dangerfield recounts a typical scene in which Churchill’s benign countenance won someone over. “He [a skeptical union worker] and his colleagues had come to think of Mr. Churchill as a modern Nero, with an awful lust for gore; but no – ‘the bloodthirsty one looked as lamblike and as amiable as the gentlest shepherd on earth….If patience and courtesy, if anxious effort and sincerity count for respect, then Winston Churchill is entitled as a man to gratitude.'” Another embattled union leader echoed this theme in a memoir of his first meeting with Churchill: “I had formed an opinion of Winston Churchill as a daring, reckless, swashbuckler individual who was afraid of no one….I expected arrogance, military precision, abruptness. When he appeared, I knew I was wrong. He came in, his fresh face all smiles, and greeted me simply, without a trace of side or trappings. I felt I had found a friend.”

The most remarkable example of Churchill’s magnanimity was his refusal to criticize the British people when they voted him out of office in a landslide just two months after the war ended in 1945. When a colleague spoke to Churchill of the “ingratitude” of the people as the votes were coming in on election night, Churchill replied: “Oh no, I wouldn’t call it that. They have had a very hard time.” In his resignation message, he said “It only remains for me to express to the British people, for whom I have acted in these perilous years, my profound gratitude for the unflinching, unswerving support which they have given me during my task, and for the many expressions of kindness which they have shown toward their servant.” Though Churchill was bitterly disappointed and discouraged, he summoned up his typical good humor when speaking of the blow. When the King offered Churchill a knighthood shortly after the election loss, he declined the honor, saying: “I could not accept the Order of the Garter from my Sovereign when I had received the order of the boot from his people.”

Independent Judgment and Self-Criticism
Because Churchill was an excellent talker and master of argument, it is too often supposed that he was not a good listener and did not take criticism well. He was thought to be stubborn, though it should be recognized that stubbornness is the twin of determination, and therefore requires to be kept in proportion. In fact, an important part of Churchill’s method and success was his independent judgment and self-criticism. “Every night,” he remarked to one of his aides during the war, “I try myself by Court Martial to see if I have done anything effective during the day. I don’t mean just pawing the ground, anyone can go through the motions, but something really effective.”

Although Churchill’s supreme self-confidence always led him to believe he could persuade his colleagues about the course of action he favored, he always sought criticism and advice from his colleagues and subordinates. One of his aides at the Treasury in the 1920s said of Churchill that “He always took criticism very, very meekly. One could say exactly what one liked in the way of criticism….He wanted the full critical value from subordinates.”

After setting out his ideas in memoranda to his staff, it was typical of Churchill to conclude with the request: “By all means confront me with the facts and put the worst complexion on figures.” On his first day back at the Admiralty in 1939, Churchill sent his initial thoughts to the senior staff with the concluding wish: “The First Lord submits these notes to his naval colleagues for consideration, for criticism and correction, and hopes to receive proposals for action in the sense desired.” (Churchill’s emphasis.)

In a speech to the nation early in the war about the government’s war policy, Churchill declared that “We do not shrink from fair criticism….Criticism in the body politic is like pain in the human body. It is not pleasant, but where would the body be without it?” In World War I, he had written that “the object [of parliamentary deliberation] is to find out what is the best thing to do, and counsel and criticism are necessary processes to that end.”

Despite Churchill’s tendency to dominate meetings with his volubility, he always encouraged a complete discussion of issues, and never penalized or fired anyone from openly or vigorously disagreeing with him. “Opportunity was always given for full discussion,” one of his wartime aides wrote. Lord Bridges wrote after the war, “I cannot recollect a single Minister, serving officer or civil servant who was removed from office because he stood up to Churchill and told Churchill that he thought his policy or proposals were wrong.” Moreover, Churchill never overruled the service chiefs of staff, even when he strenuously disagreed with their decisions.

Churchill’s own self-criticism and independence of judgment, combined with his habit of seeking advice and criticism, led him to change his mind from time to time. As noted earlier, he once said – and meant – “I would rather be right than consistent.” The same dominating purpose usually reveals itself in Churchill’s positions; typically he was changing his mind about means rather than ends. But because he changed his mind and even his party affiliation on two occasions, he set out his thoughts at length in an essay titled “Consistency in Politics”:

A Statesman in contact with the moving current of events and anxious to keep the ship of state on an even keel and steer a steady course may lean all his weight now on one side and now on the other. His arguments in each case when contrasted can be shown to be not only very different in character, but contradictory in spirit and opposite in direction: yet his object will throughout have remained the same….We cannot call this inconsistency. In fact it may be claimed to be the truest consistency….A Statesman should always try to do what he believes is best in the long view for his country, and he should not be dissuaded from so acting by having to divorce himself from a great body of doctrine to which he formerly sincerely adhered.

Loyalty to the Team
Throughout his life and after Churchill has suffered from the reputations of being an overly ambitious glory-seeker. It is a charge that he himself would not necessarily dispute. He disliked sharp party partisanship, and his rugged independence led him to switch parties twice, infuriating many of his fellow MPs.

This fierce independence of opinion and loose allegiance to party led many to consider him unreliable and disloyal. While this judgment is reasonably well-founded as it applies to Churchill the independent politician, a closer look will show that during periods when he held a responsible high office, Churchill was extremely loyal and supportive of his colleagues and superiors – he was a genuine team player. Throughout his “Wilderness Years” in the 1930s, even as his party leadership snubbed him and turned a disdainful ear to his advice, he campaigned vigorously on behalf of the Conservative Party during general elections.

Once a policy was arrived at or a political quarrel decisively settled, Churchill would cease his criticism or opposition and get on board. After losing a long and often bitter fight against the India dominion policy in the early 1930s, Churchill told one of his opponents that “you need not expect anything but silence or help from us.” He was fond of quoting the words of Lord Cranborne, who had opposed the Reform Bill of 1867: “It is the duty of every Englishman, and of every English party to accept a political defeat cordially, and to lend their best endeavors to secure the success, or to neutralize the evil, of the principles to which they have been forced to succumb.”

Because of Churchill’s formidable speaking skills, his cabinet colleagues often relied on him to assume the burden of defense against criticism in the House of Commons. This he always did with vigor and usually with success, even when he was not in full agreement with the cabinet policy or when the policy clashed with his own previously expressed opinions on the issue.

Rest, Relaxation, and Change of Pace
Churchill is reported to have said once that “There is no good time for a vacation, so take one anyway.” Churchill was the master of the working vacation. Churchill took many long trips, both in and out of office. He seldom took a trip that was complete leisure, even when he was out of office. “My work and my holidays are the same,” he wrote to George Bernard Shaw. He would always take along trunkloads of work, usually materials for his current book project. During World War II he would spend nearly every weekend at the prime minister’s country retreat, Chequers (the British equivalent of Camp David).

The importance of recreation for Churchill was not so much to find rest from his preoccupations as it was to stimulate his mind through a change of pace. “Human beings do not require rest,” he once remarked to an aide. “What they require is change, or else they become bloody-minded.” He elaborated on this theme in his essay “Painting as a Pastime,” which described how he took up painting in the months immediately after his dismissal from the Admiralty in 1915 – a period of profound stress and disappointment for him. Churchill quickly became as proficient as an artist as he was as a writer, though he was bashful about exhibiting his paintings. (Pablo Picasso is reported to have said of Churchill’s painting: “If that man were a painter by profession he would have no trouble in earning a good living.”) For the rest of his life Churchill derived profound relief through painting, though he only found time to work on one painting during World War II. “If it weren’t for painting,” he remarked in 1955 shortly after resigning from his second premiership at the age of 80, “I couldn’t live; I couldn’t bear the strain of things.”

“Change is the master key,” he wrote. “A man can wear out a particular part of his mind by continually using it and tiring it, just in the same way as he can wear out the elbow of his coat….Change is an essential element in diversion of all kinds.” The remedy – change – is supplied through hobbies. “To be really happy and really safe, one ought to have at least two or three hobbies, and they must be real,” Churchill wrote. Churchill’s other great hobby was bricklaying; he built a large brick wall substantially by himself at Chartwell, his country home.

Churchill’s reliance on changes of pace explains in part his unusual work habits. In addition to the change of pace afforded by travels, the various aspect of his daily routine – dictating in bed in the morning, taking naps and baths, working late after dinner – all ensured that each working day would have several different phases. “For every purpose of business or pleasure, mental or physical,” he wrote in My Early Life, “we ought to break our days and our marches into two.” This was why he held almost unfailingly to his afternoon nap. When an American executive told Churchill that his office routine consisted of the regular 8 to 5:30 day in the office, five days a week, Churchill replied: “My dear man, you don’t mean it. That is the most perfect prescription for a short life that I’ve ever heard.” He went on to advise the executive about the virtues of a regular nap: “Don’t think you will be doing less work because you sleep during the day. That’s a foolish notion held by people who have no imagination. You will be able to accomplish more. You get two days in one – well, at least one and a half, I’m sure. When the war started, I had to sleep during the day because it was the only way I could cope with my responsibilities.”

Calmness under Stress
Churchill was no stranger to the number one problem faced by all executives – stress. Churchill’s colleagues and friends marveled at how calm he was amid the most trying circumstances. In part his ability to deal with stress and trial was a function of his courage and fearlessness. He would, for example, set up his painting easel near the front line trenches in World War I, and paint away as shells were exploding nearby. He would seldom duck when shells exploded, sensibly observing that by the time you hear the report of an exploding shell, it is too late to duck. It was this innate courage that enabled him to gather strength in a crisis. Though all Churchill’s colleagues said that he held up to the stress of the war extremely well, he was not immune to the effects of stress. Churchill suffered two heart attacks during World War II, and nearly died from pneumonia as well.

There is no silver-bullet solution for stress, of course. Churchill’s main method for dealing with stress was never to be in a hurry. Churchill could have invented the slogan, “Never let ’em see you sweat.” Certainly he epitomized this popular axiom. “Winston’s disregard of time,” one of his top aides wrote, “is sublime.” Churchill’s calmness amid commotion and crisis not only imparted confidence to his colleagues and subordinates, but was also the key to his enormous productivity and concentration. One of his secretaries wrote: “I do admire the unhurried way in which he gets through such a colossal amount of work, and yet never seems otherwise than at leisure.”

The lesson of Churchill’s extraordinary calm and aversion to haste is that hastiness dilutes your concentration, disrupts your priorities, and makes it impossible to follow a consistent method of work. Churchill’s calmness and seeming leisure were closely related to his immense powers of concentration, and were in many ways the linchpin of his success.

Personal Contact
Much is made these days of MBWA – Management By Walking Around. Churchill was a relentless practitioner of the idea. He not only valued the face-to-face contact that visiting the scene provided, but it was also a means of gathering unfiltered information firsthand.

Visiting the scene was a practice that dated from Churchill’s earliest days, and was perhaps an extension of his first career as a war correspondent. As under-secretary for the colonies, he undertook a tour of Britain’s African colonies, reporting back directly to the King about what he found. As home secretary, he toured prisons, which few home secretaries had done before him. As First Lord of the Admiralty from 1911 to 1915, he visited more ships and naval facilities than any First Lord before or since. Between 1911 and the outbreak of World War I, Churchill made 26 trips on the Admiralty yacht Enchantress, visiting more than 50 ships as well as numerous harbor and shipyard facilities. His habit of arranging interviews with junior officers and enlisted personnel was not always welcomed by the top brass, but it served Churchill’s purpose of gathering information through nonbureaucratic channels and forming his own view of the details of operations. “He had a yarn with nearly all the lower deck men of the ship’s company,” the Daily Express newspaper wrote of a submarine visit in 1912, “asking why, wherefore, and how everything was done. All the sailors ‘go the bundle’ on him, because he makes no fuss and takes them by surprise. He is here, there, everywhere.” As minister of munitions during World War I, Churchill went to France so often – 13 times over the last year of the war – that he eventually established an office for himself in Paris.

As prime minister he visited munitions and aircraft factories, shipyards, airfields, radar stations, command posts, front-line coastal defenses, and everything in between. In addition, his foreign travels added up to more than 200,000 miles by the end of the war. His travels stand in sharp contrast to those of his predecessors. Herbert Asquith in World War I never visited his French allies or the commanders and troops in France. Neville Chamberlain during the first year of World War II made very few visits to the allies in France, and paid few visits to warmaking facilities on the home front. Churchill’s trips, on the other hand, had the tonic effect of rallying morale wherever he went, as well as providing him a window on the war not available from 10 Downing Street.

Face Bad News Squarely and Candidly
Throughout his career, Churchill always believed that bad news should be faced directly and acknowledged candidly to the public. His father’s famous motto had been “Trust the people.” Churchill would echo this sentiment at many points in his career. In this respect Churchill once again ran against the grain of ordinary political practice, which he once aptly described as “The habit of saying smooth things and uttering pious platitudes and sentiments to gain applause, without relation to the underlying facts.” On the contrary, Churchill advised, “Tell the truth to the British people. They are a tough people, a robust people. They may be a bit offended at the moment, but if you have told them exactly what is going on you have insured yourself against complaints and reproaches which are very unpleasant when they come home on the morrow of some disillusion.” It was a mistake, he often argued, “to shrink from stating the true facts to the public.”

This is an aspect of Churchill’s realism, which was always in equipoise to his idealism and optimism. When faced with mounting criticism about the poor progress of the war in early 1942, Churchill demanded a formal vote of confidence debate in the House of Commons to force the issue. “It is because things have gone badly, and worse is to come,” he said, “that I demand a Vote of Confidence.” Churchill prevailed, by a vote of 464 to 1. Churchill would confront two more confidence motions in the House during the course of the war, each time winning by large margins precisely because of his candor and forcefulness.

He also liked to deliver bad news personally, not only war news to the House of Commons, but to the Allies as well. One of the toughest moments of the war for him was when it became apparent that a second front against the Germans in France could not be opened up in 1943, as had been promised to Marshall Stalin. Churchill decided to go to Moscow to tell Stalin personally: “It was like taking a lump of ice to the North Pole,” Churchill said.

Steven F. Hayward is a fellow at the American Enterprise Institute and senior fellow at the Pacific Research Institute for Public Policy. He received his doctorate in history from the Claremont Graduate School. Read more of his writing at


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