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Leading Up: How to Manage a Toxic Boss

As published by The Green Notebook by Andrew Milburn

Every year across all services, a number of commanding officers are relieved of their duties due to a “loss of trust and confidence” — that singularly cryptic and unhelpful phrase. 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. The more senior an officer gets in rank, and the closer he comes to the nexus between policy and strategy, the weightier that responsibility becomes.

Many, maybe most, of us who have served in uniform have found ourselves working for a poor leader.  And yet, our professional education offers little guidance to deal with the burden of toxic leadership by mitigating its effect upon subordinates and organization.

While at the Marine Officer Basic School in the early 90s, my fellow lieutenants and I learned valuable lessons about how to lead subordinates. As for handling those placed above us, however, we would have to rely on our own painful experience, collecting lessons that became apparent only in retrospect.

Learning to lead up, just like learning to lead down, requires emotional intelligence. It takes the ability to read people, understand their motivations and play to them accordingly, for the sake of the organization. However, even those who possess this degree of empathy will struggle in the face of stubborn misanthropy.

All commanders, regardless of rank, need leadership, a guiding hand as they shoulder a level of responsibility that often brings with it a profound sense of isolation. Many are reluctant to seek such guidance from above for fear of appearing uncertain. Others are simply unaware of their failings or lack confidence in their own ability. While good leaders value subordinate feedback and solicit it without devolving their own responsibility for final decisions, those who are less secure tend to see such behavior as pandering to subordinates, a symptom of weakness.

In the hierarchical structure of the military, the burden of responsibility for leading the commander in the right direction falls on the shoulders of the next senior man in that unit. In an organization that places so much emphasis on command, it takes both character and talent to play an effective role as second fiddle. The job of deputy, executive officer, or second-in-command, whatever the title, requires someone with the ability to read his boss, give him advice even when he is loath to take it, cover his blind spots, execute his intent, and free him from all the necessary but tiresome chores that might otherwise distract him from doing those things that only he – as the commander – can do. Even working for the best commander in the world, it’s a demanding assignment. And if the commander happens to be a tin-pot tyrant, the role of deputy becomes all the more difficult, and necessary. Fortunately, he’s not alone in this responsibility, but has a potential ally in the unit’s senior enlisted advisor. Together they must shield the organization from the impact of an unruly commander. And, in extremis, petition his relief.

But what of cases where a leader’s behavior falls short of being illegal or immoral? Are subordinates ever justified in resorting to this last option with commanding officers who are simply poor leaders? I used to think not, but have – in the course of my career – come to change my mind. To explain why, I need to briefly mention my own experiences, and a classic work of fiction, all of which combined to shape my views.

As a captain, I was a company commander in one unfortunate battalion where the commanding officer, executive officer, and sergeant major were referred to by the other officers as “the triumvirate of evil,” a term which paints a pretty clear picture of the effect that these three had on the unit. In this case, the next in line, was unprepared, or perhaps lacked the moral courage, to try to mitigate the triumvirate’s worst excesses.

The commander in question was by no means incompetent but made the life of his officers miserable, frequently berating them in public, and constantly threatening to relieve them of their duties.

The company commanders, whose responsibility it was to fill this leadership void by embarking on a course of action to curb its detrimental effect, instead sought solace in mutual complaint while remaining ostensibly loyal. Battalion morale hit rock bottom, and despite draconian threats, disciplinary infractions soared. The battalion commander went on to attain flag rank.  How, you might ask?  One explanation is that a platoon’s worth of subordinate officers who served under him failed to check their bosses’ worst excesses, wield influence over his behavior, and exercise the moral courage required to report his conduct to competent authorities.

His successor, equally eccentric, was obsessed with minutiae, given to fits of public rage and confused by tactical operations. As his operations officer, I vacillated between sympathy for someone I felt was out of his depth and outrage at his behavior, but was nonplussed in my approaches to change him. Now, granted the wisdom of intervening years, I can understand why I failed. I made no attempt to understand him or his motivations which should be, as I will explain, the first step in dealing with any boss, good or bad.

Instead, I re-read a book that I had first picked up years before while an under-graduate: The Caine Mutiny. Herman Wouk’ classic novel is a skillfully woven narrative about conflicts of loyalty and the pressures of command set in the Pacific during the Second World War. Captain Queeq, the captain of the fictional USS Caine, is an officer whose increasingly eccentric behavior makes the lives of the crew miserable until, during a typhoon, he makes decisions that his subordinates believe will cause the ship to founder. As the ship careens, helpless at the mercy of the storm, the ship’s XO, Lt Maryk, relieves Queeg and assumes command. During Maryk’s subsequent court martial, the prosecuting lawyer picks apart the defense’s contention that Queeg’ relief was justified on the grounds of his insanity, laying bare the XO’s complaints as being no more than a series of petty grievances at having to serve a hard taskmaster. In the end, Maryk is acquitted but only after his defense lawyer, Lt Greenwald pushes Queeg into staging a tantrum in court thus turning the jury against him – a last ditch tactic that leaves Greenwald ashamed.

The message of The Caine Mutiny is that, though the institution may sometimes make mistakes by selecting the wrong person for command, it cannot be left to subordinates to decide how to redress those mistakes. To do so, this argument runs, would undermine the time-honored traditions upon which the institution is founded.  In the words of the protagonist, Lieutenant Willie Keith: “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.”

This was the moral that I was looking for. I made the book required reading for the officers of the battalion – a message that was not lost on them. It seemed to quell the rumblings of discontent, but probably only in my presence. Again, the battalion’s morale suffered, but the battalion commander was promoted at the end of his tour, and went on to acquire a star before his behavior caught up with him.

Now, with the experience of intervening years, I find Wouk’s conclusion unsatisfying. It  conflates loyalty to the individual with loyalty to the institution and offers no middle ground between blind fealty and mutiny. To serve an incompetent commander as though he “were the wisest and the best” makes key subordinates accomplice to the kind of leadership that achieves short term results but at the expense of the unit’s longer term competence, morale and cohesion.

That battalion commander wasn’t my last experience of a difficult boss, but it was the last time that I took such a passive approach. From that point on, I made an attempt to mitigate those aspects of my boss’s behavior that I considered unacceptable and to adjust my own behavior accordingly. I was, after all, simply learning a different style of leadership to the one that I was accustomed to but with the same intent: to glean from others the actions and behavior that would best serve the organization.

From these experiences, I assembled a rough guide for those who find themselves in the position of deputy to a boss whose actions are having an adverse effect on the organization. I like to think of these steps as an escalation of force. There should be no room in today’s military for a commander who is resistant to change, but it is a subordinate’s responsibility to do everything he can first to bring about that change before going over his commander’s head. There are five steps in this process, though – as in my escalation of force analogy – it may not be necessary to go beyond the second step.

Step One: Understand your boss.

You cannot hope to influence someone you cannot understand. This precept holds good in dealing with all commanders, good or bad, but for the sake of discussion, we will focus here on problematic ones. I am normally reluctant to resort to stereotypes, but for the sake of simplicity, will categorize various types of bad bosses according to their primary motivations (or fears). In my experience, it’s seldom been the case that a dysfunctional commander’s personality fits neatly into one of these categories, but rather that his behavior tends to conform with one more than another. There are five such categories:

  • The Careerist: As the name suggests, the Careerist is focused primarily on getting to the next rung in the ladder. He focuses with meticulous attention on any aspect of the unit’s functions that are likely to draw the attention of higher headquarters, but spends little effort in developing his subordinates for greater responsibility. The Careerist usually has a successful tour in command, but leaves the unit no better than it was before his arrival.


  • The Genius: This type of commander believes that he is the smartest person in any room. This is not necessarily an unrealistic belief since these individuals are usually highly intelligent, but somewhere along their path to command they have allowed this quality to assume disproportionate significance. As a consequence, they have little time for the ideas of others. The Genius takes delight in tripping subordinates up by remembering things that they do not, and loves to ask questions that only he can answer. His overbearing style tends to stultify initiative, and his conviction that only he has the answers can lead him to treat those beneath him dismissively.


  • The Nitpicker: This type of commander prides himself on his attention to detail, to the point of obsession. This trait has previously stood him in good stead in the various staff jobs that he has held throughout his career, but now prevents him from grasping the big picture and causes him to avoid delegation. He loves inspections and powerpoint briefs, forums that allow him to exercise his strengths but abhors the messy uncertainty of problem framing.


  • The Fear-Biter: This type of commander is uncomfortable with the isolation of command and gives vent to this insecurity by lashing out at subordinates. The Fear-Biter is terrified of appearing not in control of his unit, which leads him to struggle with delegation and otherwise exhibit a prevailing lack of trust. He avoids making decisions, through endless prevarication — repeatedly asking for more information and weighing and re-weighing possible consequences. The Fear-Biter often resorts to group punishment in response to disciplinary infractions, and leaves in his wake a legacy of scorched earth and resentment.


  • The Incompetent: The Incompetent may be fine handling the day to day functions of a unit, but struggles in any situation requiring an in-depth knowledge of his profession. He is often someone who has managed to get to where he is because of his skill in some area unrelated to his current duties.

I don’t pretend that this list is exhaustive. I could, perhaps, have added the Workaholic, the Tantrum-Thrower, and the Narcissist, but decided that these categories exemplify traits that are commonly found across the other five outlined above. All of these categories have one singular trait in common: an inability to employ indirect leadership – a critical skill for any commander above company level.

Step Two: Find Common Ground

Just as with any aspect of leadership, there is no formula for this step. The general rule here is to understand why he is the way he is, and to use that understanding to guide him in the right direction.

This means taking the time and effort to study the areas that a commander considers most important then gradually, and in an unostentatious manner, convincing him that he might not be the only one with worthwhile ideas.

It might involve a concerted effort between the executive officer and senior enlisted advisor to persuade the commander that his current area of focus properly belongs in the hands of more junior personnel, while helping him understand the more substantive issues of command.

Or it might involve showing the commander how actions that benefit the organization will also enable him to get ahead and — conversely —  how actions harmful to the unit, or its members, will reflect badly on him.

By taking an incremental approach best suited for a commander’s particular personality and concerns, subordinates can gain his trust and ease his grip on the reins.

If followed with determination, step two usually proves successful. In my experience, difficult commanders are seldom irredeemable — no service makes a habit of promoting dullards to senior rank, and even poorly disguised incompetence is often a question of experience rather than aptitude. It does, however, require deft handling for subordinates to shape their boss without embarrassing him by exposing his shortcomings, or by making him feel as though he’s being schooled.

In some cases, however, a commander may prove unable or unwilling to learn, which brings us to the really difficult part of this discussion: what to do in cases with a truly recalcitrant boss.

Step Three:  Intervention

This is the most difficult step, but equally necessary before a subordinate can, in good conscience, pull the trigger on a poor leader. Intervention in this case means making a last-ditch attempt to explain to him the effect of his actions on the organization. It requires the ability to deliver an unequivocal message directly without allowing it to sound like a threat. And it takes a significant amount of moral courage.

Intervention may involve just the deputy commander, or a small group of individuals whose opinion the commander is most likely to respect. Because it is so important to get this right, this step should be discussed in depth and rehearsed by those involved.

In most cases involving poor command climate, the message is delivered anonymously by survey – a method which is comparatively easy for a poor leader to shrug off until it’s too late. Perhaps because this step is so difficult, it is often omitted altogether, and I can, from personal experience, think of only two cases of subordinates staging a direct intervention. In both cases, it worked.

Step Four: Appeal to higher

This step involves answering two questions: First, whether the commander is truly bad enough to warrant going over his head, and if the answer to the first question is yes, how best to do so.

Answering the first question requires thinking beyond current circumstances, to the potential impact on other, larger organizations and on the institution itself, if the commander in question is allowed to advance. At the same time, subordinates must understand that the decision to report a commander’s actions to higher authority may blow back on them, if the allegations are perceived to be unfounded. Although there is no formula for making such a momentous decision, the general rule must be this: If a commander, by his actions, has had a sustained negative effect on the unit’s moral, competence or cohesion, without redeeming purpose, then he is no longer fit to command. This is a question of judgment certainly, but that’s why the holding of a commission in the United States military carries such weight.

In answering the second question, that of “how,” there are a couple of useful rules of thumb. The first is that whenever possible this message should be delivered in person, directly.  As a battalion commander, I can remember being greeted by a delegation of lieutenants with a message about an errant company commander, and by listening to them I was able to get a good feel that their concerns were not exaggerated. The second rule is that, although it may seem bizarre to document the behavior of a superior officer, being able to produce such a record will help inform the higher commander’s decision. Before making such a decision he may also consider it wise to convene an investigation, unless time constraints prohibit such action, or the officer’s alleged conduct has been so egregious as to require his immediate suspension.  Either way, having documentation will be extremely useful.

Step Five: Get the word out

This step applies not to the subordinates who initiated a commander’s relief, but to the higher commander who made the decision to do so. The “never complain, never explain” mindset has no place in any profession that proclaims a bias for self-improvement. The ritualistic cliches of officialdom only shroud these incidents in opacity, and lead to uninformed speculation.

When an officer fails while in command, those following in his footsteps should have the opportunity to learn from his mistakes. Transparency quells rumors and provides an open forum for discussion, while showing that those in authority have nothing to hide. The circumstances behind each notable case of relief should be disseminated throughout the profession, and compiled as case studies in formal schools.

If professional military education were to focus as much on leading up as on leading down, it would limit in duration and scope the damage caused by the Captain Queeg’s of this world.  Empowered by this guidance, subordinates would have a clear path to mitigate and redress the pernicious influence of such leaders. And service leadership would less often have to resort to that hollow phrase, “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 the best-selling combat memoir When the Tempest Gathers: From Mogadishu to the fight against ISIS, a Marine Special Operations Commander at war.