Fighting With Your Boss

Fighting a boss is only fun in video games.

Fights between a manager and report can be some of the most stressful experiences in life. Sustained conflict can cause years of strain. Here we’ll try to help you navigate these situations, to limit the damage and to maximize the outcome.

Great Managers Don’t Get Into Sustained Conflict

Great managers don’t get into sustained conflicts with their direct reports. If they’re a really great manager, they either avoid the situation, solve the situation, fire the person, or quit.

Great managers wouldn’t be great if they sat around bickering with their direct report for years.

You Probably Won’t Win

Remember, if you’re in a sustained conflict with your boss, they’re not great. And that’s fine - most managers aren’t great and you’ll be continually disappointed if you expect to only have great bosses.

You’re probably not great at your job either, statistically speaking. I say this not to be a buzzkill, but because expecting either person to suddenly be an egoless, high EQ, selfless actor is setting yourself up for disappointment. How you analyze the situation must be practical, focusing on what’s likely instead of what’s fair.

If you find yourself in a sustained conflict with your mortal manager, there’s only three options of what could happen:

• You try to get them fired

• You adapt - leave or learn to live with it

• You try to get them to change

Trying To Get Them Fired

You’re very unlikely to get your manager fired. There’s a lot of reasons for this, and it’s often not fair, but it is what it is. There are a few main ways you can get your manager fired:

• Be really, really good. If you’re good enough to get your manager snuffed, you probably know it. No need to keep reading, enjoy the rest of your day champ.

• Have many other people complain about them. This is still not a very high probability, but sometimes several direct reports telling a manager’s manager they have problems does lead to action.

• Get lucky. Maybe your manager is already on thin ice. There’s no way for you to really know this.

In any case, I wouldn’t count on winning this battle. This sucks and often isn’t fair, but you should really avoid letting perceived unfairness drive you to stick out a job you hate for longer than you should. You have to choose if you want to be righteous or if you want to get on with your life.

You Adapt

Another main option is leaving - quitting, or switching teams - or learning to live with your manager’s faults. Most people can’t learn to live with someone they’ve gotten in major long term fights with.

Practically speaking, if your conflict has lasted over a year, you should almost definitely leave - change teams or quit. In any case - move on with your life. It’s extremely tragic when I see people stay in roles that are damaging to their careers and self worth because they hate their manager. If you can afford to move on, you probably should.

Trying To Get Them To Change

We have to put on our practical, real-world glasses here - most not-great managers are not going to very meaningfully change. Further, managers are even less likely to change in the ways that would meaningfully resolve the conflict you have with them.

Maybe your manager sometimes sends you a Slack after hours. This probably isn’t causing you too much turmoil, but you could probably ask them to stop that.

But the biggest conflicts come from things closer to your manager’s DNA. They’re mean. They’re cold. They don’t listen. These are things that cause people serious distress. They are also things that are really hard to get people to change on, certainly not in a time frame that works for your mental health.

If you’re under a year of conflict, you could try to impact some change and you’re going to have the best luck giving them simple, mechanical things to do.

So, for example, you might ask them for the following:

• Schedule messages for the next day instead of sending late at night

• Give me feedback in 1:1s in a synthesized way vs in real time

• Review a career growth plan that I put together

• CC me on emails for this project

Things you probably will not see big results on:

• Be nicer

• Give me more positive feedback

• Include me in every conversation about a topic no matter how casual

Again, you have to ask yourself if simple mechanical changes are enough for you to be able to sustain the relationship without conflict.

It Might Be You

It’s quite possible that you have more to blame than the manager for the conflict you’re having. Nearly half of all manager/report conflicts are from something you’re doing as a direct report.

The most common thing you could be doing is a bad job. Conflict and debate over how good of a job you are doing is the top source of report-generated conflict. Simply-ok managers will often try to performance manage by annoying you with lots of feedback, sometimes with an attitude attached. That’s not great, but them fixing their feedback style doesn’t fix you not doing a good job.

If you find yourself in this position, consider asking your manager’s manager or a manager’s peer for their take. If your manager and their manager or their peer all agree you’re not doing a great job, you have to accept that this is the organizational POV and accept it and fix it or move on.

Another source of report-generated conflict is reports with unrealistic expectations of their manager. Especially for college hires, expecting your manager to be as authoritative as a college professor, or as caring as a parent, or as friendly as a mentor, can all contribute to unnecessary strife. Remember, while there is some selection criteria for management, most managers are, by definition, average. Managers don’t exist to perfectly manage you any more than you exist to perfectly report to your managers.

On Positive Feedback

Narrowly, a common complaint is that a manager isn’t giving enough positive feedback. When this happens, it almost always one of two things:

• The manager doesn’t think you’re doing a good job

• It’s not the managers style

If you find yourself wanting more positive feedback, you could ask for clarity on your performance. However, asking for just more positive feedback almost never works. Trust me, you don’t want the awkward, forced positivity from someone who isn’t naturally inclined that way. Imagine Bill Belichick giving you a forced “you did a wonderful job with that presentation” comment.

Summary

• If you’re in a sustained conflict with your manager, you’re probably not going to “win”

• Set your expectations realistically and if you want to see change, try to ask for things as mechanical as possible

• If you’re fighting with your manager for over a year - if you can afford to, find something else. Life is just too short.

Share to Twitter , Hacker News , LinkedIn