From Captain Queeg to Winston Churchill: Lessons in Leading Up


Every year the military services relieve a number of commanding officers due to a “loss of trust and confidence.” I can’t help thinking that at least some of these officers might have been saved if their subordinates had learned the responsibility to lead up, as effectively as they have learned to lead down.

Most people who have served in uniform have worked for a poor leader. Yet, while we train extensively on how to lead those below us, nothing in our formal professional education prepares us to lead an errant boss in the right direction. Instead, we are left to learn from painful experience. Very occasionally, when a commander’s actions are illegal or immoral, subordinates are clearly justified in hastening their boss’s relief. Short of illegal or immoral behavior, are subordinates ever justified in advocating the relief of a boss who is simply a poor leader? I used to think not, but now I think it may sometimes be appropriate. Before taking such a step, the second-in-command has a responsibility to try to lead the boss in the right direction — to “lead up.”



Leading up isn’t simply manipulation. It requires the ability to understand a leader’s motivations and their strengths while mitigating their faults, for the sake of the organization. And it takes wise judgment and moral courage to do the right thing when these efforts have failed.

Two Approaches to Bad Bosses

As a company commander I worked for a terrible battalion commander. It seemed I had no option but to wait him out. Instead I re-read The Caine Mutiny, Herman Wouk’s classic novel about conflicts of loyalty and the pressures of command, set in the Pacific during World War II. Lt. Cmdr. Queeg, captain of the USS Caine, is an officer whose incompetence and erratic behavior makes the crew miserable. During a typhoon, he makes decisions that his subordinates believe will endanger the ship, and his XO, Lt. Maryk, relieves him and assumes command. During Maryk’s subsequent court martial, the prosecution picks apart the defense’s argument that Queeg was insane, characterizing the crew’s complaints instead as petty grievances sparked by serving a hard taskmaster. Maryk is acquitted only after his lawyer, Lt. Greenwald, pushes Queeg into a tantrum, turning the jury against him. As the officers of the Caine celebrate their courtroom victory, Greenwald upbraids them, arguing that Queeg might have succeeded if they had supported him better, compensating for his flaws rather than nursing their grievances. In the end, the protagonist, Lieutenant Willie Keith, is left to ponder: “The idea is, once you get an incompetent ass of a skipper … there’s nothing to do but serve him as though he were the wisest and the best, cover his mistakes, keep the ship going and bear up.”

The message I took from The Caine Mutiny is that, though the institution may sometimes make mistakes selecting commanders, it is not for subordinates to redress them. To do so would undermine the time-honored traditions of the service. This was the moral that I was looking for. I made the book required reading for my lieutenants, and the message was not lost on them. The rumblings of discontent were silent for a time (probably only in my presence). The battalion’s morale suffered, but the battalion commander succeeded and retired as a general officer.

With the benefit of experience, I find Wouk’s conclusion unsatisfying. It seems to conflate loyalty to the individual with loyalty to the institution, offering no middle ground between blind fealty and mutiny. To serve an incompetent commander as though he “were the wisest and the best” makes subordinates complicit in the type of leadership that achieves short term results at the expense of long term competence and morale. Simple compliance in the face of poor leadership sends the message that this type of behavior is acceptable, even commendable, undermining our military ethos and harming the institution we serve. And as poor leaders continue to climb the ladder, an ever-larger population falls subject to their baleful influence if it is left unchecked.

That battalion commander was by no means my last difficult boss, but that was the last time that I took so passive an approach. From that point, I set out to learn a different style of leadership that was focused on eliciting from those above me actions and behavior that best serve the organization, just as I do from those who work for me. In this journey, I was guided partly by my readings about one of the greatest leaders of the twentieth century, Winston Churchill.

Churchill was notoriously difficult to work for and required firm leadership from below. General Sir Alan Brooke, the Chief of the Imperial General Staff, who became Churchill’s right-hand man for much of the war, wrote:

Winston had ten ideas every day, only one of which was good, and he did not know which it was. … Without him England was lost for a certainty, with him England has been on the verge of disaster time and again. Never have I admired and disliked a man simultaneously to the same extent.

This sentiment will surely resonate with anyone who has worked for a difficult boss.

The relationship between Brooke and Churchill was extraordinary in terms of the stature of the leader and import of the decisions. But the way Brooke handled this relationship was surprisingly prosaic, and imparts useful lessons for anyone struggling with the challenges of leading up.

A Guide to Leading Up

Based on my own experience, and illuminated by the experience of Brooke and Churchill, I offer a guide to leading up. I believe it is more pragmatic and effective than Wouk’s injunction to follow a bad commander as you would a good one. I think of this guide as being similar to an escalation of force continuum: there are five steps in the process, but it may not be necessary to go beyond step two.

Step One: Understand Your Boss

The first step in influencing a boss is understanding them. This holds in dealing with all commanders, good or bad, but we will focus on the bad ones. Sometimes simply understanding what makes a bad leader difficult will point out a path to mitigation.

No one sets out to be a toxic leader, and few are aware when they become one. The same traits that propel a leader into a position of responsibility — drive, competitiveness and ambition — may be impacted by the burden and loneliness of command and create a combustible mix that can make anyone difficult to deal with at times. It is this understanding that causes the Caine Mutiny’s Lt. Greenwald to berate the officers of the Caine: They made no attempt to understand Queeg before vilifying him.

It doesn’t require a psychologist to figure out what makes a leader tick, but it does take patience, empathy and leadership. It is a two-way street — leaders should recognize the value of subordinate feedback and solicit it without devolving their own responsibility for final decisions, but that is not always the case. Alan Brooke was, in the words of historian David Fraser, “the greatest Chief of the Imperial General Staff ever produced by the British Army.” But even he struggled with the challenges of leading the mercurial Churchill. It was only after six months as his right-hand man that Brooke could write:

I had discovered the perils of his impetuous nature. I was by now familiar with his method of suddenly arriving at some decision as it were by intuition, without any kind of logical examination of the problem. I had, after many failures, discovered the best way of approaching him…… and I had found that he was listening more and more to any advice I gave him.

Realizing that he had become the only person to whom Churchill appeared willing to listen, Brooke turned down command of the Eighth Army, a coveted assignment. In so doing, he rendered his country an extraordinary service. Historian John Keegan attributes Brooke with preventing Churchill’s often impulsive decisions from endangering the nation, time and again.

Churchill was not immune to the loneliness of his responsibilities. He was, by his own account, dogged by depression (the Black Dog he called it), and given to bouts of tears and bursts of anger. It’s impossible to quantify the effect that a companion as steady and consistent as Brooke had upon these moods, but it must have helped. Brooke was so often by Churchill’s side that historians were driven to comment on those rare occasions when he was not.

Although carrying the fate of a nation at war is extreme, command at any level is lonely. Bursts of anger may be a reaction to the isolation that accompanies command, causing occasional feelings of insecurity in all but the most self-confident. It can also be an outlet for emotion, which is not necessarily bad; in fact, awareness of this emotion can be constructive. Sometimes this insecurity is compounded by feelings of incompetence. In my experience, these commanders are seldom irredeemable — the military doesn’t routinely promote dullards to senior rank, and competence is often a question of experience more than aptitude. Understanding this, a good deputy will build the boss’s confidence by implementing a plan to bring him up to speed without exposing his shortfalls, while assuring him that his subordinates want him to succeed. The ability to project confidence and to build confidence in others is a key component of leadership.

Step Two: Find Common Ground

A deputy who has learned to understand his boss will be in a position to find common ground: to direct the boss’s motivations or fears towards decisions that benefit the organization. While understanding is about mitigation, common ground is about influence.

Brooke and his staff were frequently frustrated and alarmed by Churchill’s pursuit of what Brooke called “side-shows.” These were schemes, some of them fantastic, to seize a foothold in occupied Europe without launching a cross-channel invasion. But Brooke understood that Churchill, like many of his generals, was haunted by memories of the First World War. His greatest fear was that the Allied armies would get bogged down in a costly stalemate in France, so he looked for other locations where opposition seemed less likely. Understanding this, Brooke reinforced Churchill’s resistance to an American proposal to launch the invasion early, while firmly reining in some of his boss’s more outlandish suggestions, explaining that they would likely end in slaughter, a prospect which he knew filled his boss with dread.

Churchill was a genius; very few leaders are. But many are highly intelligent, and some allow this to assume disproportionate significance. As a consequence, they have little time for the ideas of others, which requires humility, and their conviction that only they have the answers can lead them to be impatient. This perspective may also drive a leader to focus on matters beneath the purview of his current position — in other words, to micromanage. The leader may be pursuing a talent for detail that previously placed him in good stead, but which now causes him to struggle with delegation. A deputy who understands the reason for this behavior is better equipped to find common ground to steer his boss back to more substantive issues.

Churchill had a proclivity to immerse himself in the details of operations which led him at times to lose sight of strategic priorities. During the early stages of the North African campaign, the only place at that time where the British Army was engaged in combat with the German Army, Churchill’s constant meddling with operational and even tactical decisions drove Brooke to distraction.

Although Brooke could never completely dissuade Churchill from embarking on flights of fascination with military detail, he understood what lay behind them, and used this understanding to draw his boss back to the big picture. Churchill was by background a soldier, and still thought of himself as such. He had written a history of the First World War and relished discussions of campaigns and battles, topics that were within his comfort zone. Brooke appealed to this common ground in persuading him that Montgomery, whose ascetic personality could not have been further from Churchill’s, was a soldier’s soldier and the right man to take command in North Africa. Having made that decision, Brooke convinced him to trust his own judgment and leave Montgomery to run the campaign, while Churchill turned his mind to more strategic matters: the German U-boat threat and the bombing of German cities.

In rare cases, a leader may prove unable or unwilling to learn from subordinates, which brings us to the really difficult part of this discussion: what to do with a truly unmanageable boss.

Step Three: Intervention

Although difficult, intervention is a necessary step before a subordinate can, in good conscience, pull the trigger on a poor leader. This is a last-ditch attempt to explain to him or her the effect of their actions on the organization. It may involve just the deputy commander, or a small group of individuals whose opinion the commander is most likely to respect. Assembling too large a group is likely to reinforce a commander’s defensive tendencies and be counterproductive.

Because this step is so difficult, it is often omitted; too often a commander is relieved without realizing (or, sometimes, caring) that his subordinates have turned against him.

Perhaps the closest that Brooke came to staging an intervention was in June 1940 when Churchill seemed determined to send more troops to France even as the British expeditionary force was being rescued from the beaches. Only Brooke’s stubborn insistence made it possible to overcome this rash impulse that might well have led to defeat. It can’t have been lost on Churchill that in the face of Brooke’s vehement opposition, and mumblings in the cabinet about his own suitability for office, his position was precarious. Importantly, Brooke was prepared to stand up to his boss when it mattered. Brooke’s words are good advice for any deputy: “The first time I tell him that I agree with him when I don’t will be the time to get rid of me, for then I can be no more use to him.

Step Four: Appeal to Higher Authority

This step involves answering two questions: first, how to determine when a commander is truly bad enough to warrant going over his head; second, how to bring this to the attention of higher headquarters. There is no simple answer to the first. In making this decision it is important to consider the impact on the current organization, and the potential impact on the institution if the commander is allowed to advance. Although there is no formula for making such a decision, the general rule is: If a commander’s actions have a sustained negative effect on the unit’s morale, competence or cohesion without redeeming purpose, then he is no longer fit to command. This is a question of judgment, but such judgment is part of an officer’s job even if it is often unseen and unrewarded.

In answering the second question, there are a couple of useful rules of thumb. The first is that this message should be delivered in person if at all possible. The second rule is to document the behavior. Although it may seem bizarre to document the behavior of a senior officer, such a record will help inform the higher commander’s decision. Absent exigent circumstances, the higher commander will likely convene an investigation, in which case documentation will be essential.

Appealing to higher authority is not easy, and it carries risk to the deputy’s career. There is a poignant episode in The Caine Mutiny when Maryk and a fellow officer plan to report Queeg’s behavior to Admiral Nimitz himself. They get as far as the passageway outside the Admiral’s stateroom before changing their minds, overawed by the prospect of what they about to do. Queeg’s erratic and dangerous behavior continues until the fateful dénouement.

Step Five: Get the Word Out

This step applies to the higher commander who decides to relieve a subordinate commander. The “never complain, never explain” mindset has no place in any profession. When an officer fails while in command, those following in his footsteps deserve the opportunity to learn from his mistakes. The stock phrase “loss of trust and confidence” obscures the circumstances of each relief, leading to uninformed speculation. Transparency quells rumors, promotes informed discussion, and reinforces that the institution has nothing to hide. If the steps outlined above are commonly followed, those in the profession will understand that the decision to fire a commander was taken only as a last resort.

Instead of Brooke and Churchill, I could have used examples, good and bad, from my own career to illustrate the value of these steps. The steps are, in my experience, universally relevant in dealing with any below-average boss. But they are not commonly understood. Leading up is quite different from the leadership that is taught in service schools, yet it is a critical skill to the military profession. If Wouk had imbued his fictional XO Maryk with the ability to influence Queeg’s behavior, there might have been no mutiny aboard the USS Caine. If Churchill had not had a deputy as capable as Brooke, the conduct of the war, maybe even its outcome, would have been different. And if leading up were included in the professional education of all prospective leaders, there might be fewer instances incurring a loss of trust and confidence.



Andrew Milburn retired in March 2019 as the chief of staff at Special Operations Command-Central. Over a 31-year career he commanded Marine and special operations forces in combat at every rank. He is the author of When the Tempest Gathers: From Mogadishu to the Fight against ISIS, a Marine Special Operations Commander at War.

Image: U.K. Government