Your relationship with your boss is just like any other relationship: what you actually do doesn’t matter as much as how it’s perceived. But it’s hard to remember this when you’re taking instructions and trying to deliver on goals. Based on the power structure, you’re not calling the shots in the relationship, so shouldn’t you get the benefit of the doubt? If you’re doing the work, shouldn’t that be enough to keep your boss happy?

That line of thinking may be fairer than what turns out to be true. Most leaders want their subordinates to deliver, certainly, but they vary a lot in terms of their expectations for style, tone, and actions taken. How the relationship feels can end up carrying as much weight as the quality of results achieved. In fact, leaders’ perceptions of the relationship and personal style often color the way they evaluate the quality of the results you’ve attained.

Sometimes It’s About You

It’s not only your boss who might have quirks. It’s also possible that your team members wonder why you have so many requirements or peculiarities. In general, though, it’s usually easier to behave in a way that the boss finds satisfactory if you adhere to three basic principles:

  • A significant part of your job is to help your boss look good — and even feel as comfortable as possible
  • Understanding your boss — having empathy and compassion for them — will make it easier to tolerate even eccentric requirements without getting caught up in them
  • Demonstrating that you are committed to “playing on your boss’s team” will help your boss be calmer and more open when dealing with you

Of course, you still have to be smart and competent about how you approach your job responsibilities.

Not-So-Impossible Bosses

Here are some examples I’ve seen of leaders who are prickly and peculiar — and ways that dedicated, savvy employees responded to make a go of the relationship even when it wasn’t easy.

The boss who wants to see you sweat. This boss didn’t want to find out about problems after her subordinate had already addressed them and everything was in good shape. She trusted herself much more than anyone else. She feared that things would go awry if she wasn’t personally supervising — making sure that her every possible requirement would be met and that her subordinates were learning what she considered “hard lessons.” With this kind of boss, don’t express optimism, say you’ve got it under control, or reassure them that things will work out. Instead, acknowledge all the possible problems and ask for guidance.

The boss who wants you to be their audience. Some people actually want company while they’re working, or for you to observe their skillfulness and praise them so they can feel good about what they’re doing. Often these types are intelligent but insecure. If possible, bring some of your work with you when you meet with them, and suggest things like, “I’m just going to check these numbers while you’re drafting that email.” Then, when they read the email to you, mention all the things you think are smart and why they’re going to work out as planned.

The boss who doesn’t care about anything that doesn’t directly support their financial goals. Don’t even try to make a case to this boss without showing how it ties to his ability to meet or exceed his targets. If you absolutely must address an issue that doesn’t have direct, positive impact on their numbers, point out the lack of connection yourself, but ask for their trust in you — and show that you have a strong track record of supporting their goals in the past.

The boss who wants the team to operate in harmony. For some leaders, having the team get along is almost as important as it is to generate achievements. When there’s conflict, show how you’re trying to bring people together, and present your requests in terms of how they will benefit others as well as yourself.

The boss who is risk averse. Be open about the risks you’ve identified so that your boss doesn’t start “finding” risks you haven’t addressed. Explain in concrete terms how you’ve taken the risks into account and how you plan to mitigate them. Stress that you’ll be vigilant about them. Ask if they’ve had experience with any risks you haven’t seen yet.

Learn to Adapt

In all these examples, it’s most effective not to fight the boss’s tendencies, but to recognize them and act in support of them. If you can successfully show that you’re fully on the boss’s team, you may actually earn the chance to do your own thing because you’ll have built up so much trust.