How to Get Along with Your Boss

You don't have to be best friends, but a great working relationship will make both your lives a lot easier.

Remember when people used to say "boss" when people were describing something that was really cool? Like, "Those shoulder pads are really boss, man." "Look at that perm. That perm is so boss." It's what made me want to become a boss. And I'd look so good in a perm and shoulder pads. But now "boss" is just slang for "jerk in charge." -The Office

When I was 21 years old, I was hired to teach English at a prestigious private school. I was young, energetic, and really green. Nine years later I still teach at the same school, and while I’d like to think I’m still young and energetic, I’m no longer green. What I learned is that like any career, teaching is a field where you learn not only how to navigate the task at hand, but how to navigate the relationships with your colleagues. And in nine years of teaching, I've had nine different bosses (some of them at the same time). That’s a lot of navigating.

Make no mistake, your relationship with your boss can make or break the quality of your daily work life. But here's the thing: the relationship doesn't rest solely on his or her shoulders. You’re the other half. So in that spirit, here are a few ways to maintain a healthy, thriving relationship with the person in charge.


Choose Your Battles

Sometimes the squeaky wheel gets the grease, but sometimes the squeaky wheel gets removed from the machine because it squeaks too much and is a pain in the ass.

Like a marriage, your relationship with your boss requires that you choose your battles carefully. I have a tendency to get hung up on the principle of things. Usually, I don’t care about the decision itself; I care about its implications and what (or who) my boss was considering when she made it. At any given time, there are at least five or six decisions above my pay grade with which I could take issue, but I have to consider which battles are worth fighting.

First, I have to make sure that my vision is in line with the vision of my organization. I’m a teacher, which means I should want what I think is best for kids, even if it sometimes inconveniences me. If I think a decision made over my head negatively impacts my students, that’s a battle worth fighting. If it’s only about me, that’s a battle I’ve already lost.

Remember that when your boss is making decisions, they’re not solely considering you – they’re (hopefully) considering the mission of the organization.

Be Solution-Oriented

  A few years back, one of my supervisors was rolling out a new initiative. It was his concept, his baby. And some of us weren’t exactly euphoric about it. During a small-group meeting, we were asked to give our feedback about the initiative, so naturally, I used this opportunity to voice my total disdain; I think I even threw the word “asinine” in there. The next day I found myself in my supervisor’s office. And he wasn’t happy.

I told him that he can’t ask for feedback if he doesn’t want honest answers, and he agreed. He said he wasn’t unhappy with my negative feedback; he was unhappy that I was being problem-oriented. He said, “If you don’t like what I’m doing, I need you to tell me, but I need you to come to me with ideas for improvements; otherwise, you’re just bitching.”

He had a point, and it was a professional conversation that forced me to grow up a little bit. The lesson: bosses deal with employees’ complaints all day long. So be the employee who has solutions instead of only complaints – otherwise, yeah, you’re just bitching.  


Stop Seeking Approval

  A few close friends still like to tease me about how frequently I would pop into the boss' office my first few months of teaching. I thought that if the principal liked me, it meant I was doing a good job, so I was always looking for my next affirmation. The problem was, those affirmations seldom came.

I didn’t have a bad boss, I just had a busy one. It only took a few of my “pop-ins” for me to realize that my face-to-face time with my boss wasn’t helping my case. He finally sat me down and said, “If you’re not hearing from me, that’s a good thing. It means I know you’re doing your job and doing it well. Now go do your job.”

The unfortunate truth is that most bosses will not give you the affirmation that you need or deserve. But remember, you don’t work hard so that someone will say “good job.” You work hard because you have dignity, and you believe in what you’re doing. At the end of the day, if you can’t say that the company got its money’s worth out of you, that’s not your boss’ fault – it’s yours.


Have Some Empathy

  Your boss has a life outside of the workplace. Their life comes with the same stressors as yours, and believe me, there are days when they would be happy to switch places with you. My current boss has three kids (who each play a different sport) and a husband who, like her, has a high-stress job. She works harder than any boss I’ve had in the nine years I’ve been teaching, and there are days when I know she’s going to forget to respond to my email, or she’ll tell me the wrong time for a meeting. And around the time I start to get frustrated with her, I remember that this is a woman who gets absolutely no breaks but believes in what she’s doing and is trying her damnedest to do it right. 

Your boss will make mistakes. They will make decisions you don’t like. They won’t always give you the recognition you feel you deserve. But remember that your boss probably also has a boss of their own, and feels the same pressures you do on a daily basis. It doesn’t make you a chump to give them a break; it makes you respectable employee.

You’re an adult, which (hopefully) means you’re thinking more about your career than simply your next job. But if you and the boss on the next rung of your career ladder can’t stand each other, your days won’t be a great deal of fun – even if whatever work you're doing is interesting, high-paying, and rewarding to boot. The relationship between you and your boss shouldn’t keep you up at night, but it is one that deserves at least some attention. Get to work.

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