What Churchill can teach you about leading in crisis

I cannot recall any period when its stresses and the onset of so many problems all at once or in rapid succession bore more directly on me and my colleagues than the first half of 1941.
— Winston Churchill, The Grand Alliance

1941 was a kaleidoscope of challenges for Winston Churchill and the people of Great Britain. Hitler continued his menacing assaults by land, sea, and air. Mussolini and Italy were a constant threat. The land of the Rising Sun was charting it’s battle plans against the West. North Africa was a war front. Greece and Turkey were on very shaky ground. The United States, while lending aid, had still not entered the war.

These were difficult days. Churchill notes:

An effort here meant a risk there.
— Winston Churchill, 1941 (The Grand Alliance)

Leadership is effort and risk. Difficulties are common. Sustaining setbacks, persisting through problems, finding solutions, building and supporting alliances, and charting a course through the fog of a crisis are a part of the leadership task. Paul’s words are apropos:

Therefore when we could bear it no longer, we were willing to be left behind at Athens alone, and we sent Timothy, our brother and God’s coworker in the gospel of Christ, to establish and exhort you in your faith, that no one be moved by these afflictions. For you yourselves know that we are destined for this.
— 1 Thessalonians 3:1-4 ESV

If we are destined for problems, how do we navigate them especially those bigger problems we tag with the label, “Crisis”?

This summer I am making my way through The Grand Alliance, volume three of Churchill’s six-volume masterpiece, The Second World War. This chronicle begins in 1941, which arrived with a whirlwind of adversity for the Prime Minister. Observing Churchill navigate these days is a front-row seat to crisis management at its finest. Here are thirteen lessons from Churchill’s expert crisis leadership.

When leading in a crisis . . .

1. Embrace the challenge.

Leaders embrace difficulties. As Churchill noted, “It is so much easier to stop than to do.” Inertia increases with problems, but not for leaders. Churchill writes:

Our physical resources were harshly limited. The attitude of a dozen powers, friendly, opportunist, or potentially hostile, was unknowable. At home we must face the war against the U-boats, the invasion threat, and the continued Blitz; we had to conduct the group of campaigns in the Middle East; and, thirdly, to try to make a front against Germany in the Balkans. And we had to do all this for a long time alone. (italics mine)

“Alone.” The word lands with a thud of impending finality. Churchill doesn’t complain.

In the film, A League Of Their Own, manager Jimmy Dugan (played by Tom Hanks) confronts right-fielder Evelyn Gardner (played by Bitty Schram) after a poor play. She begins to cry and Dugan delivers the classic line: “Are you crying? . . . There’s no crying! There’s no crying in baseball!”

Churchill does not cry or complain. He gets to work.

Question to ponder: What leadership challenge are you ignoring or complaining about that you must embrace?

2. Pursue strong allies.

Churchill maintained a steady correspondence with Franklin Roosevelt. The “Former Naval Person” (as he described himself in letters to FDR) knew Great Britain would fight alone, but the British would be hard-pressed to win alone. The U.K. needed the U.S..

Churchill worked hard to develop “intimate contacts” with the President. A letter dated 1 January 1941 includes these words, which were heartfelt and wisely timed to build the relationship:

At this moment, when the New Year opens in storm, I feel it my duty on behalf of the British Government, and indeed of the whole British Empire, to tell you, Mr. President, how lively is our sense of gratitude and admiration for the memorable declaration which you made to the American people . . . . with this trumpet call we will march forward heartened and fortified.

Question to ponder: Who are the “strong allies” you need in your moment of crisis?

3. Clarify immediate objectives.

When adversity attacks from every corner, heads swivel and focus blurs. Wanting to do “the right thing” some wait to do anything. Not Churchill. On January 6, 1941 Churchill wrote to General Ismay, for the Chiefs of Staff Committee:

The speedy destruction of the Italian armed forces in Northeast Africa must be our prime major overseas objective in the opening months of 1941.

Churchill never wavered from this objective. Hitler was poised to move toward Greece and Turkey in his efforts to pursue world supremacy — and Churchill knew it — but he also knew he had to secure Northeast Africa before releasing troops for aid in the north. He clarified his immediate objective.

Question to ponder: Of the many things you should do in this crisis, what is the one thing you must immediately do?

4. Press for speedy action.

Churchill was deliberate, not rash. Many mistake the latter for the former. Rash is a weed disguised as a daisy. Rash will multiply problems and diffuse energy. Deliberateness expects “action toward objective.” This was the Churchillian way.

In late January, 1941, Churchill received word from General Wavell that British forces committed to a campaign in Kenya were dragging their feet. Wavell notified the war council that General Cunningham decided to delay plans to take Kenya, a mistake in Churchill’s mind as it effectively sidelined 70,000 troops and wasted precious time.

The Prime Minister pressed Wavell to get moving. It took some doing, but Wavell and Cunningham pressed the war machine into action and the efforts proved effective. Churchill wrote,

Under the strong pressure from home Wavell eventually decided to make the effort . . . . how right we were at home to press them to speedy action.

The popular aphorism, “He who hesitates is lost” (most likely an adaptation of a line from Joseph Addison's 1712 play Cato), enjoys favor because it expresses a general truism: Tough times call for immediate and bold action — not rash action — but deliberate and determined steps toward a common objective.

Question to ponder: Is there any place where you have grown slack in your pursuit of immediate objectives?

5. Stay informed.

Reading these volumes I stand amazed at the breadth and depth of Churchill’s knowledge. His command of history, geography, and military campaigns past and present is awe-inspiring. How did he do it?

One of Churchill’s secrets is his demand for and dependence upon the “one-page” summary. Writing to Secretary of State for Air and Chief of the Air Staff on December 2, 1940, the Prime Minister says:

I should be glad if your Intelligence Branch would let me have a paper (not more than two or three sheets) upon this vital matter (German Air Strength for 1941). . . . While I want the report to be short, I want to be cognizant of the data and reasoning processes on which it has been built up.

Churchill required these — and he read them, devoting tremendous amounts of time in order to keep abreast of military happenings. About this work Churchill adds,

This was, of course, a heavy addition to my work. I had, however, been accustomed to read all the top-level daily telegrams and special reports since I became Prime Minister.

Too often I have been guilty of requiring reports and failing to read them. Not Churchill. He stayed informed, often via the “one page.”

Question to ponder: What essential information do you need to keep abreast of your crisis? Demand it in a one-page.

6. Keep watchful after short-term gains.

Anthony Eden, who had a long and storied service to the U.K including Prime Minister (1955-1957), was serving as Foreign Secretary in 1941. In a letter to Churchill dated 6 January, 1941 he congratulates the Prime Minister upon the victory at Bardia, then offers this wise caution:

The object of this minute, however, is to call attention to a less satisfactory sector of the international horizon, the Balkans. . . . It is essential that our victories in North Africa should not result in any decrease of watchfulness (italics mine) on the part of the Turks and Yugoslavs, and we are doing what we can in the political sphere to ensure this.

Victories are taxing. A win brings a sigh of relief, but often with it a dropping of the guard. Such was the case of Elijah in 1 Kings 18-19. Elijah dropped his guard and lost a battle he should have won.

Both Paul and Peter encourage watchfulness on the part of those who would live well for Christ (1 Peter 5:8; Ephesians 6:10-20). Paul’s words are appropriate for leaders and followers everywhere:

Keep alert with all perseverance.
— Ephesians 6:18 ESV

Question to ponder: Scan the horizon of your current crisis. Has a short-term victory caused you to lose sight of a potential threat? What internal threats (organizationally) or external threats (politically, culturally, socially, spiritually) exist? What must you do to be ready?

7. Identify, Unleash, and Celebrate trusted “Seconds.”

Churchill was brilliant, strong, resolute, and tended toward egotism, but he was not a soloist. He identified, unleashed, supported, and celebrated outstanding leaders around him:

Re Harry Hopkins, trusted advisor to FDR who visited Churchill: “Thus I met Harry Hopkins, that extraordinary man, who played, and was to play, a sometimes decisive part in the whole movement of the war.”

Re General Dobbie, deemed too old by some, but appointed by General Ironside as Governor and Commander-in-Chief of Malta: “In General Dobbie Malta found a governor of outstanding character who inspired all ranks and classes, military and civil, with his own determination. He was a soldier who in fighting leadership and religious zeal recalled memories of General Gordon, and, looking farther back, of the Ironsides and Covenanters of the past.”

Re Lord Beaverbrook, the brilliant Minister of Supply who observed and calculated better than most): Beaverbrook was bold, insightful, and demanding. He saw contingencies and exercised oversight. Churchill said of him: “In all these Beaverbrook was a potent impulse.”

Re Field-Marshall Dill, former Chief of the Imperial General Staff: No British officer we sent across the Atlantic during the war ever acquired American esteem and confidence in equal degree. His personality, discretion and tact gained him almost at once the confident of the President. At the same time he established a true comradeship and private friendship with General Marshall.

Questions to ponder: What are you carrying that you need to give away? Who do you need to publicly celebrate for their efforts in your common cause?

8. Do the quiet work of leadership.

Many hear “leadership” and think Washington crossing the Delaware, King marching on Selma, or Oprah coaxing millions through the medium of television. That’s the public side of leadership: Standing in the front, building teams, getting strategic, offering direction, and rallying the troops, but there is a quiet side to leadership that is equally the leader’s job: quietly pondering, patiently enduring, and silently wrestling. We see this in Churchill. Late in 1941, Churchill traveled through u-boat infested seas to the U.S. aboard the battleship, Duke of York.

Reflecting on that voyage he writes:

I recalled Napoleon’s remark about the value of being able to focus objects in the mind for a long period of time without being tired . . . . As usual I tried to do this by setting forth my thought in typescript by dictation. . . . I produced three papers on the future course of the war . . . . Each paper took four or five hours, spread over two or three days. As I had the whole picture in my mind it all came forth easily.

In other places Churchill writes of the leader’s quiet work:

  • “Many long hours did we spend revolving this grave issue.”

  • “I spent a good part of Christmas Day preparing my speech” [to the Congress of the United States].

  • “The days passed, counted in hours. Quite soon I realized that immediately after Christmas I must address the Congress of the United States, and a few days later the Canadian Parliament in Ottawa. These great occasions imposed heavy demands on my life and strength, and were additional to all the daily consultations and mass of current business. In fact, I do not know how I got through it all.”

What was the outcome of all this quiet work? It set the stage for greater cooperation between the U.S. and Great Britain and moved both nations toward ultimate victory in World War II.

Questions to ponder: What issue do you need to think through in order to resolve? What thoughts do you need to put down on paper? What ideas do you need to pass on to others for consideration?

9. Keep your sense of humor.

Churchill is known for his quick wit and funny bone. While he could be biting and sarcastic, his humor served him well in early 1941. Advances in radar enabled the British to fool German planes, thus lessening the damage of their deadly bombing runs. At one point U.K. scientists managed to fool the Germans into bombing an empty field thereby saving the Rolls-Royce factory from destruction. Though Germany claimed the factory, Churchill knew better. He writes:

The German communique claimed the destruction of the Rolls-Royce Works at Derby, which they never got near. Two hundred and thirty high-explosive bombs and a large number of incendiaries were, however, unloaded in the open country. The total causalities there were two chickens.

Two chicken! This is the same man who advised his officers in World War I:

Laugh a little & teach your men to laugh - great good hum'r under fire - war is a game that is played with a smile. If you can't smile, grin. If you can't grin, keep out of the way till you can.

Crisis are serious times, but a little well-timed humor eases tension, provides joy for the heart and serves as “good medicine” for soul and morale. See Proverbs 17:22.

Question to ponder: Is your current crisis robbing your joy? How can appropriate humor lighten the load for you and your team?

10. Take time for fun.

“Fun” sounds out of place in a crisis, but Churchill enjoyed it. He was spending the weekend at Ditchley in May 1941, enjoying a little respite by watching a Marx Brothers comedy when he received word of a heavy air raid on London.

I went out twice to inquire about the air raid, and heard it was bad. The merry film clacked on, and I was glad of the diversion.

At that point in the evening, there was nothing he could do. Recognizing his limitations, Churchill took the time for levity. Leaders learn to live with and in tension: Levity and loss, delight and danger, victory and defeat — and keep a level head through it all.

One way Churchill regularly filled his tank was through painting. See my resource Churchill’s Paintbrush for help in identifying the fuel that helps you lead with joy, stamina, and peace.

Question to ponder: What momentary respite would provide relief, encourage your soul, and put a little fuel in your tank?

11. Don’t let the idealist turn you sideways.

The night Churchill was watching the Marx brothers via the clacking projector, his friend the Duke of Hamilton interrupted the levity for the second time. Hamilton reported, “Hess has arrived in Scotland.”

Rudolf Hess, Deputy Fuehrer and intimate member of Hitler’s inner circle, had parachuted alone near the Duke’s estate in Scotland. This must have seemed as crazy at the time as it does in retrospect. “Piloting his own plane and dressed as a flight lieutenant of the Luftwaffe, he had flown from Augsburg and baled out.”

Why would Hess do that?

Hess, somewhat unstable of mind and grandiose in his thinking, thought he could convince the King to oust Churchill, side with Hitler, and form a pact with Germany. Jr. R. Rees, who wrote The Case of Rudolf Hess, notes Hess was operating out of “an increasing idealistic urge.”

Idealism and idealists have their place, but not in a crisis. In a crisis leaders ignore the clamor of idealism and turn their backs on the idealist. Churchill refused to allow the flurry of idealist excitement to distract him. He wrote:

I never attached any serious importance to this escapade. I knew it had no relation to the march of events.
— Winston Churchill

Question to ponder: Are you allowing a lone but vocal idealist to distract you from the hard work and brutal facts of this crisis?

12. Lift the spirits of your people.

I have said much about the leader in the midst of the crisis, but little about how the leader relates to people in the crisis. The Prime Minister was careful to have boots on the ground and his heart focused on his people during WWII, especially the dark days of the London bombing. His first-hand account enabled him to see through the crisis to the people damaged by it. He writes:

The ordeal had been severe, but the spirit of the citizens was invincible. . . . .I go about the country whenever I can escape for a few hours or for a day from my duty at headquarters, and 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, beaming with a consciousness of being associated with a cause for higher and wider than any human or personal issue. I see the spirit of an unconquerable people.

Churchill saw the resilient spirit of the British people. He commended it, championed it, and in that process helped make it stronger.

Question to ponder: When are you or will you take time to be with the people in this crisis?

13. Pause to Worship.

On Christmas day, 1941, the two leaders of the free world, President Franklin Roosevelt and Prime Minister Winston Churchill attended church together. Churchill writes:

I found peace in the simple service and enjoyed singing the well-known hymns, and one, “O little town of Bethlehem,” I had never heard before. Certainly there was much to fortify the faith of all who believe in the moral governance of the universe.

What are we to make of that brief paragraph in a volume that spans 900 pages? Probably not much. But Churchill and Roosevelt paused for worship. They gave the Holy the assent that a defiant Nebuchanezzar refused.

Crisis and worship are not mutually exclusive. In fact, worship is essential in crisis. David shows us this. On the run from Saul, beat down physically and emotionally, and at his wits end, he “strengthened himself in the Lord” (1 Samuel 30:6).

There are few things like worship to put one’s problems in perspective.

Wise leaders pause to worship. They pause before the Word of God. They pray. They turn their eyes toward heaven to find the strength they need to lead through the crisis they find on earth. In some small way Churchill and Roosevelt demonstrate that. It is the pause that brings power.

Question to ponder: Are you taking time to seek God, worship God, pray to God in this crisis? What specific challenge do you need to bring to Him?

Why Your Leadership Matters

Great Britain, 1941

As the New Year dawned, Great Britain stood defiant. Churchill’s theme for The Grand Alliance is:

How the British fought on with Hardship their Garment until Soviet Russia and the United States were drawn into the Great Conflict.

All nods to their tenacious fight, Hardship was an unpleasant garment to wear. Knowing this, Roosevelt wrote an encouraging note to Churchill on January 20, 1941, which included these words from Longfellow:

“Sail on, O ship of State!
Sail on, O Union, strong and great!
Humanity with all its fears,
With all the hopes of future years,
Is hanging breathless on thy fate!”

Leadership matters. We are still sailing on, finding comfort under the long shadow of Churchill’s great leadership. Most don’t know it. Fewer care. But his time stewarded well made a difference. May God grant you wisdom to steward well your days that the ship you pilot can sail on with all the hopes of future years.


All quotes, unless otherwise noted are found in The Grand Alliance, Volume 3 of The Second World War by Winston S. Churchill. Boston: Houghton Mifflin Company. 1950.

  1. “I cannot recall any period . . .” from page 3.

  2. “An effort here meant a risk there.” Page 3.

  3. “It is so much easier to stop than to do.” Page 101.

  4. “Our physical resources were harshly limited . . . “ from pages 3-4.

  5. “No crying in baseball . . .” from the film, “A League Of Their Own.”

  6. “At this moment, when the New Year opens in storm . . .” from page 22.

  7. “The speedy destruction of the Italian armed forces . . .” from page 5.

  8. “Under the strong pressure from home . . .” from page 84. “

  9. “I should be glad if your Intelligence Branch would let me have a paper . . .” from page 39.

  10. “This was, of course, a heavy addition to my work . . .” from page 69.

  11. “The object of this minute, however, is to call attention to a less satisfactory sector . . . .” This communication from Foreign Minister Mr. Eden to the Prime Minister, dated 6 January 1941 can be found on page 14.

  12. Re Harry Hopkins . . . from page 23.

  13. Re General Dobbie . . . from page 61.

  14. Re Lord Beaverbrook, the brilliant Minister of Supply . . . from page 688.

  15. Re Field-Marshall Dill, former Chief of the Imperial General Staff . . . from page 688.

  16. “I recalled Napoleon’s remark about the value of being able to focus objects . . .” from page 645.

  17. “Many long hours did we spend revolving this grave issue.” Page 643.

  18. “I spent a good part of Christmas Day preparing my speech.” Page 671.

  19. “The days passed, counted in hours. . .” from page 663.

  20. “The German communique claimed the destruction of the Rolls-Royce Works at Derby . . .“ from page 46.

  21. “Laugh a little & teach your men to laugh . . . .” See Steven F. Hayward. Churchill On Leadership. 1997. Page 115.

  22. “I went out twice to inquire about the air raid . . .” from page 48.

  23. “Hess has arrived in Scotland. . . “ from page 48.

  24. “Piloting his own plane and dressed as a flight lieutenant . . .” from page 49.

  25. Hess was operating out “an increasing idealistic urge.” from The Case of Rudolf Hess, edited by J.R. Rees, p. 2, quoted by Churchill on page 53.

  26. “I never attached any serious importance to this escapade. . . “ from page 49.

  27. “The ordeal had been severe, but the spirit of the citizens was invincible . . .” from pages 44-45.

  28. “I found peace in the simple service . . .” from page 670.

  29. “How the British fought on with Hardship their Garment . . .” from page ix.

  30. “Sail on, O ship of State! . . .” from Henry Wadsworth Longfellow, included in FDR’s letter to WSC on January 20, 1941. You will find this on pages 26-27.