Winston Churchill’s timely advice: Delegation tips for agencies

Written by: Karl Sakas

Want to spend less time running your agency? Once you build a great team, you need to delegate better—and Winston Churchill has some delegation tips for you.

Churchill is known as an inspirational leader—but visionary leadership is easier when you delegate the details, so you can focus on the big picture. As an agency leader, delegation helps you shift from “working IN” to “working ON” the business.

We can learn from how Churchill delegated during tough times, as you lead your agency today. These delegation lessons (and all of the quotes) come from Erik Larson’s excellent WWII biography, The Splendid and the Vile: A Saga of Churchill, Family, and Defiance During the Blitz. Churchill wasn’t a role model in every way—some of the tips come from those around him, and some of his lessons are what not to do—but he’s especially relevant today.

In an uncertain world, it’s tempting to try to do everything yourself. You must step up to lead—yet delegation advice is all the more important now. Let’s explore 7 delegation tips I drew from the bestselling book, as they apply to you and your agency.

#1: Choose the right people.

Accept that you don’t need all the answers yourself:

“[T]o the dismay of fire inspectors who later deemed it a ‘grave fire risk,’ he ordered [a home cinema] installed at Chequers. [Max] Beaverbrook arranged it, and made sure Churchill received the latest movies and newsreels. ‘Max knows how to do these things,’ Churchill said. ‘I do not.’

Add the right advisors:

‘There were no doubt greater scientists,’ Churchill acknowledged. ‘But he had two qualifications of vital consequence to me.’ First was the fact that Lindemann ‘was my friend and trusted confidante of twenty years,’ Churchill wrote. The Prof’s second qualification was his ability to distill arcane science into simple, easy-to-grasp concepts—to ‘decipher the signals from the experts on the far horizons and explain to me in lucid, homely terms what the issues were.’ Once thus armed, Churchill could turn on his ‘power-relay’—the authority of office—and transform concepts into action.”

Have the right deputies:

“The job of private secretary was a prestigious one. Colville joined four other newly assigned men who together composed Churchill’s ‘Private Office’ and served almost as his deputies, while a cadre of other secretaries and typists managed his dictation and routine clerical tasks.”

Choose the right intermediaries:

“Nearly every morning one visitor in particular came to Churchill’s bedroom, Major General Hastings Ismay, newly appointed military chief of staff, known lovingly, and universally, as ‘Pug’ for his likeness to that breed of dog. It was Ismay’s job to serve as an intermediary between Churchill and the chiefs of the three military services, helping them to understand him, and him to understand them. Ismay did so with tact, and a diplomat’s grace. Immediately he became one of the central members of what Churchill called his ‘Secret Circle.'”

Recognize that the right people might make some enemies:

[Churchill] understood that Beaverbrook could be difficult—would be difficult—and anticipated that he would spark conflict [as head of the Ministry of Aircraft Production]. But it did not matter. … Beaverbrook embraced his new task with relish. … As Pug Ismay saw it, Beaverbrook had more in common with a highwayman than an executive. ‘In the pursuit of anything which he wanted—whether materials, machine tools, or labor—he never hesitated, so rival departments alleged, to indulge in barefaced robbery.'”

And choose people who’ve got your back:

“Churchill, describing one incident in which the victim received a particularly vivid rebuke [from his wife], quipped, ‘Clemmie dropped on him like a jaguar out of a tree.’

#2: Be clear about your expectations.

Know your mission… and tell your team:

“After a few moments, Churchill made a half turn toward his son. ‘I think I see my way through,’ he said. He turned back to the mirror. Randolph understood that his father was talking about the war. … ‘Well, I’m all for it,’ Randolph said, ‘but I don’t see how you can do it.’ Churchill dried his face. ‘I shall drag the United States in.’

Convey urgency, as appropriate:

“[During the Dunkirk] evacuation, Churchill began adding red adhesive labels exhorting ‘ACTION THIS DAY’ to any minute or directive requiring an immediate response. These labels, wrote secretary Martin, ‘were treated with respect: it was known that such demands from the summit could not be ignored.'”

Prioritize clear communication:

“‘No detail was too small to draw his attention, even the phrasing and grammar that ministers used when writing their reports. … Churchill was particularly insistent that ministers compose memoranda with brevity and limit their length to one page or less. ‘It is slothful not to compress your thoughts,’ he said.

Take decisive action:

“In his first twenty-four hours in office, Churchill revealed himself to be a very different kind of prime minister. … He now had full control of the war, and full responsibility. He moved quickly to build his government, making seven key appointments by noon the next day.

Seek input… but once you decide, make it clear that it’s no longer a topic for discussion:

“All precautionary plans that contemplated the evacuation of Egypt or the scuttling of the Suez Canal were to be withdrawn from circulation immediately and locked away, with access closely controlled. ‘No whisper of such plans is to be allowed,’ he wrote. ‘No surrenders by officers and men will be considered tolerable unless at least 50 percent casualties are sustained by the Unit or force in question.’ Any general or staff officer who found himself facing imminent capture by the enemy was to shoot it out with his pistol.

#3: Build the right structure… and monitor progress.

Insist on good data…

“Most galling was that his own Air Ministry appeared to be unable to account for 3,500 airplanes out of 8,500 frontline and reserve aircraft believed ready, or nearly ready, for service. ‘Surely there is in the Air Ministry an account kept of what happens to every [aircraft],’ Churchill complained in a subsequent minute. ‘These are very expensive articles.’ … ‘A discrepancy of 3,500 in 8,500 is glaring.'”

… but don’t create too much structure and process:

“Together the two roles gave Lindemann license to explore any scientific, technical, or economic matter that might influence the progress of the war, a compelling mandate but one certain to ignite jealousy within the ministerial fiefdoms of Whitehall. What further complicated things was Lindemann himself, whose main achievement … ‘was to unite against him any body of men with whom he came in contact.'”

Encourage creative solutions:

“Beaverbrook saw grave warning in the September 7 attack. Upon his return to London, he convened an emergency meeting of his top men, his council, and ordered a tectonic change in the structure of the nation’s aircraft industry. Henceforth, large centralized manufacturing centers would be broken up and dispersed to nodes spread throughout the country. … Beaverbrook also grew concerned about how his newly built aircraft were stored before being transferred to combat squadrons. Up until this point, new aircraft had been housed in large storage buildings, typically at RAF airfields, but now Beaverbrook ordered that these aircraft be scattered throughout the countryside, tucked into garages and barns… [T]o Beaverbrook the logic of dispersion was overpowering, no matter the degree of opposition. ‘It secured him premises for the duration,’ Farrer wrote, ‘and enemies for life.””

And be judicious about committees and meetings:

“Beaverbrook joined with reluctance. He loathed committees—of any kind, at any level. A sign in his office shouted, ‘COMMITTEES TAKE THE PUNCH OUT OF WAR.’ Meetings were the last thing he needed.

#4: Assign things to the right people.

Be strategic about personnel assignments:

“With Churchill’s courtship of Roosevelt in so sensitive a phase, choosing an ambassador to replace Lord Lothian became a critical matter. His craftier instincts told him that Lothian’s death might in fact offer him an opportunity to strengthen his hold on his own government. … What Churchill clearly knew from their long friendship was that Beaverbrook had a knack for, and delighted in, making people do what he wanted them to do. … ‘There was nothing Beaverbrook liked better in politics than moving men about from one office to another or in speculating how to do it.’

Switch appropriately between details and the big picture:

“One of the most distinctive aspects of Churchill’s approach to leadership was his ability to switch tracks in an instant and focus earnestly on things that any other prime minister would have found trivial. Depending on one’s perspective, this was either an endearing trait or a bedevilment. To Churchill, everything mattered. … Headed, appropriately enough, by the succinct title ‘BREVITY,’ the minute began: ‘To do our work, we all have to read a mass of papers. Nearly all of them are far too long. This wastes time, while energy has to be spent in looking for the essential points.’ … Often, he observed, a full report could be dispensed with entirely, in favor of an aide-mémoire ‘consisting of headings only, which can be expanded orally if needed.’ … The resulting prose, he wrote, ‘may at first seem rough as compared with the flat surface of officialese jargon. But the saving of time will be great, while the discipline of setting out the real points concisely will prove an aid to clear thinking.’

Watch out for gaps:

“[C]hurchill ordered all his ministers to coordinate their vacations for the upcoming Easter holiday to ensure that key offices were manned and that the ministers themselves were readily available by telephone. ‘I am told,’ Churchill wrote, ‘that Easter is a very good time for invasion.’ Over the Easter weekend, the moon would be full.”

Look for high ROI “multiplier effect” assignments:

“After a few minutes, Churchill broke the silence, saying, ‘Never in the field of human conflict has so much been owed by so many to so few.’

#5: Don’t let problems fester.

Don’t over-delegate:

“”[Churchill’s wife Clementine reported] that she believed the problem with the worst [bomb] shelters was that responsibility for them was apportioned among too many agencies with overlapping authority, and as a result, nothing was done. … ‘Division of authority is what is preventing improvement.’ Her investigations had an effect. Churchill, aware that how the public felt about shelters would influence how they viewed his government, made shelter reform a priority for the coming year.

“See and be seen”—don’t hide in your office or your inbox:

“[American envoy W. Averell] Harriman joined Churchill for dinner at 10 Downing Street, in its armored basement dining room, and almost immediately gained a close-up appreciation for two things he so far had only heard about: what it was like to experience a major air raid and the sheer courage of the prime minister.”

Create “early warning” systems so you have don’t have to be everywhere at once:

“That afternoon [the RAF] discovered that Germany had activated its beam transmitters, indicating that a raid was likely to occur that night. … At five-fifteen P.M., an officer in the filter room placed a call to the headquarters of the London fire service. ‘Good afternoon, sir,’ the officer told the fire service’s deputy chief. ‘The beam is on London.’ … Two minutes later, the deputy chief asked the Home Office to authorize the massing in London of one thousand fire trucks.

Stop hiring incompetent family members or others you feel you can’t fire:

“[Churchill’s son, Randolph] was loud, lacked tact, drank too much, spent beyond his income … and gambled with startling ineptitude.”

#6: Recognize your team’s efforts.

Acknowledge your team’s sacrifices, whether real or imagined:

Lord Beaverbrook was tired. … [After producing nearly twice his aircraft quota, Beaverbrook wrote Churchill] to remind him of his own success. He also took the opportunity to express a degree of self-pity as to how much struggle these gains had required, closing his note with a lyric from an American folk spiritual: ‘Nobody knows the trouble I’ve seen.’ By way of reply, Churchill the next day returned Beaverbrook’s note with a two-word rejoinder jotted at the bottom: ‘I do.’

Show the team the impact of their work:

“Like Churchill, [Beaverbrook] recognized the power of symbols. He sent RAF pilots to factories, to establish a direct connection between the work of building airplanes and the men who flew them. He insisted that these be actual fighting pilots, with wings on their uniforms, not merely RAF officials paroled briefly from their desks. He also ordered that the husks of downed German planes be displayed around the country…  This ‘circus,’ as he called it, was always well received, but especially so in the most heavily mauled locales.”

Help your team find meaning in their work, especially about the not-so-fun parts:

“Diarist Phyllis Warner found that she and fellow Londoners were surprised by their own resilience. ‘Finding we can take it is a great relief to most of us,’ she wrote on September 22. ‘I think that each one of us was secretly afraid that he wouldn’t be able to, that he would rush shrieking to shelter, that his nerve would give, that he would in some way collapse, so that this has been a pleasant surprise.‘”

#7: Take care of your team.

When you ask for sacrifices by the team, be sure you’re pitching in, too:

“On Christmas morning Churchill had breakfast in bed, with [his cat] Nelson lounging on the bedclothes, as he worked through the papers in his regular black box and in his yellow box of secrets, dictating replies and comments to a typist. ‘The Prime Minister has made a great point of working as usual over the holiday,’ wrote John Martin, the private secretary on duty at Chequers that weekend, ‘and yesterday morning was like almost any other here, with the usual letters and telephone calls and of course many Christmas greeting messages thrown in.'”

Show that you care:

“Given the nature of his mission, [American envoy W. Averell Harriman] was more aware than most people of the intricacies of Britain’s food shortages and rationing rules, and bought a bag of tangerines to give to Churchill’s wife. … ‘I was surprised to see how grateful Mrs. Churchill was,’ he wrote, later. ‘Her unfeigned delight brought home to me the restrictions of the dreary British wartime diet.’

Take care of those around you:

“[Lindemann’s] enemies made him out to be a statistical incubus who lived a life stripped clean of warmth and compassion. In fact, he often did kind things for employees and strangers, preferring to keep his role in such deeds secret. … He expressed broader concerns as well. Despite his standoffishness and his love of fine things—his big cars, his chocolates, his Merton coats—the Prof often demonstrated a caring for the common man’s experience of the war. Such was the case that summer when he wrote to Churchill to oppose a proposal by the Ministry of Food to reduce the ration of tea to a mere two ounces a week. … As long as there was tea, there was England. But now the war and the strict rationing that came with it threatened to shake even this most prosaic of pillars. The Prof saw danger.”

Delegation Advice at Your Agency via Winston Churchill

Leadership and delegation are hard—but worth it. To recap my delegation takeaways from Winston Churchill in The Splendid and the Vile:

  1. Choose the right people. Team composition is vital.
  2. Be clear about your expectations. Your team can’t read your mind.
  3. Build the right structure… and monitor progress. Even high performers need guidance.
  4. Assign things to the right people. Let people play to their strengths.
  5. Don’t let problems fester. Things will only get worse.
  6. Recognize your team’s efforts. Saying “thank you” is free.
  7. Take care of your team. Put your team first, and they’ll take care of you.

For more on the topic, see my delegation advice—including why delegation is harder than it sounds—and my framework on reducing your day-to-day involvement in running your agency. It takes time… so why not start today?

Question: What do you take away from Churchill’s delegation tips, as you lead your agency?

Book Cover: "Work Less, Earn More" by Karl Sakas

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