When I graduated from college, I imagined my future relationships with bosses to be pretty straightforward. I thought I’d come to work, do my job, and make sure that my manager liked me enough to continue giving me a paycheck. At least, that was the impression I got from all the bad TV shows I watched growing up.

Then something caught me completely off-guard: I got hired by people I really, really respected. And yes, that’s awesome—but working for people I genuinely admired came with some unique challenges that I wasn’t prepared for at first.

If you’re lucky enough to find yourself in the same situation, here’s how you can cope:


1. You Feel the Need to Hide Your Freak Flag

It’s natural to look at a boss you really respect and think, “She’s really going to hate me if she knows that I spend my free time at comic book stores.” And so it’s really common for people in this scenario to leave any evidence of whatever weird thing they’re interested in at home. While you might not mind if a supervisor you’re not so thrilled about knows that you still collect baseball cards, I can totally relate to not wanting your super-cool boss to find out that you’re even remotely weird.


How You Can Deal With This

OK, I’ll admit it would be jarring for everyone you work with to see you suddenly walk in with your entire collection of stuffed animals. But don’t be afraid to reveal what you’re like outside of work. If your manager’s really as amazing as you think she is, she’ll probably appreciate getting to know you a little more on this level, even if she truly can’t understand why you like listening to boy bands at your desk.


2. You’re Not Even Remotely Eloquent Around Him or Her

You probably did a lot of reading on how to impress this person when you were still in the interview process, and clearly you were eloquent enough to score the job. However, I can relate to anyone who feels that even simple conversations with your supervisor in the kitchen can seem overly daunting.

“I’ll start by asking about that project we’re working on,” you say to yourself, only to find yourself rambling on and on about how you didn’t leave your apartment for the entire weekend. When you respect your boss, it’s only natural to want to sound smart all the time.


How You Can Deal With This

Relax. This usually happens when people put their bosses on a pedestal. And I’ve done it my fair share of times. As amazing as this person is, I’m confident that he simply wants to be treated like a normal person. So if you bump into him in the kitchen, don’t be afraid to simply ask how his day is going and take it from there, even if that turns into a mundane conversation that has nothing at all to do with work.


3. Your Impostor Syndrome Just Won’t Quit

This one caught me off guard when I took my current job. Even after I received an offer, I was convinced the company meant to email a different candidate. I really thought my current boss was great, and therefore could not have actually wanted to work with little old me. And even after a few months went by, I believed I was nothing more than an impostor who would be found out soon enough.

How You Can Deal With This

The lesson I learned here was simple: If your impostor syndrome won’t quit, tell your boss. There’s no other way for her to know that you’re feeling inadequate. And when she finds out, two things will happen: She’ll reassure you that you would not have been hired if you couldn’t hack it, and she’ll encourage you to keep her in the loop if you continue to feel this way. After all, her top-notch management style is probably one of the reasons you respect her so much, right?



Working for someone you really admire is a good problem to have. That doesn’t mean you should be embarrassed if you fall victim to any of these side effects. The good news is that the solutions to all of them are straightforward and less intimidating than you might be making them out to be. All you’ll need to do is take the leap, inhale deeply, and in all honesty—celebrate the fact that this is currently one of the bigger interpersonal challenges you face every day.


Photo of cool boss courtesy of Shutterstock.