Why Becoming Friends With Your Boss Might Be A Terrible Idea

Being friends with your boss can turn into a nightmare if your relationship gets too close. Here’s how a few people dealt with it.

Why Becoming Friends With Your Boss Might Be A Terrible Idea
Photo: Klaus Vedfelt/Getty Images Photo: Klaus Vedfelt/Getty Images

Michael Carter* knew his friendship with his boss had gotten a little too close when his boss confided that he was cheating on his wife.


Before he worked for this fortysomething oversharer, Carter worked in recruitment for a large, well-known tech company when he realized there weren’t many growth opportunities in his division. At 27, Carter landed a job with much more responsibility at a startup where he was one of six employees. The open office and the size of the staff made it easy for people–even introverts like Carter–to get close quickly. That included Carter’s boss.

“He wanted to be everybody’s friend,” Carter recalls. “He would often just start talking about his kids, his family, Formula One, make a few jokes.” But things started to get awkward when his boss insisted that the whole staff go out for drinks together every couple of weeks.

“Some Fridays after work I just want to go home,” Carter says. “But he wanted to be friends, and he was my boss and signed my paychecks, so I felt obligated to be friends and go for a beer with him, even if sometimes it was exhausting.” Not to mention that it created the kind of tipsy intimacy that would lead to the boss confiding to one of his junior employees that he was having an affair.

Having a friend at work can make us feel happier and more motivated to get stuff done. So being chummy with your manager could have additional benefits. “If you are closely connected to someone at a higher level in the organization, they may be able to promote you, spread your reputation, [or] provide you with access to information that is useful,” said Monique Valcour, a professor of management at EDHEC Business School in France in a previous interview with the Harvard Business Review. But that’s exactly what put Carter in a tough spot: In his mind, his salary was inexorably tied to his relationship with his boss, so he had to maintain a friendship he was less than comfortable with.

While great bosses use emotional intelligence to bring teams together, surface talent, and resolve conflicts, others have trouble setting healthy boundaries.

That’s what happened to Jessica Harris* when she was 22 and working at a large media nonprofit. She and her manager, a 35-year-old man, started working together more closely during a really stressful project. “We vented to each other a lot and commiserated, which brought us closer together,” she says. But, says Harris, “in hindsight it was a really unhealthy relationship.” She recognized it when he asked Harris to accompany him to a strip club to entertain an important client. She went, but acknowledges it was “so inappropriate.”


There was no way to reestablish a professional boundary after that, Harris admits, but she was able to move to another department. “He resented me for it,” she recalls. “We stopped being friendly after that.”

Carter also was able to get out of his job at the startup. Another major software firm contacted him about an open position and made him an offer with a significant salary increase. He told his boss he was planning to leave. “He made me a counteroffer, but while he offered me a lot of money, I wanted my space back, and to not be caught in the middle of his marital affairs.”

So he gave the startup four weeks’ notice. Carter says that during that time, his boss took it personally and insulted him repeatedly. “He fired and rehired me about four times,” Carter recalls. On his last day, the boss apologized and gave him a leaving present. But the whole experience left Carter with the sense that he would not be willing to contact his old boss for any reason in the future. “Being so close to him allowed me to see the personal side of him, and that just struck me as unprofessional,” he says.

What should you do if your boss is trying to turn you into their bestie?

Debra Jack works in communications, and she says a C-suite executive that she used to work with asked her to write the copy for his profiles for dating sites. Jack says she tried to get out of it, but ended up doing it because she felt like she couldn’t say no. She left that job a few months later. “In an ideal situation, you’re a trusted confidant and adviser, with easy rapport and chemistry,” says Jack. Her advice to others feeling like they are being put in an unprofessional relationship is to determine their personal comfort zone. “Some might be comfortable doing everything that’s asked of them, but that’s not for everyone.”

For Jen Holmes, the best way to end an inappropriate request or line of questioning is to unequivocally shut the boss down. “Be very direct and say, ‘I don’t really want to talk about that,’ and change the subject to a more appropriate work topic,” says Holmes. Hopefully, she says, doing that a few times will send a strong message to the boss. “Being direct is the only way to successfully advocate for yourself in most scenarios,” says Holmes. “No one has to try to decode what you mean, and they can’t claim ignorance if you’ve stated a preference for or against something.”


*Names have been changed to protect the privacy of the employees and the managers.

About the author

Lydia Dishman is a reporter writing about the intersection of tech, leadership, and innovation. She is a regular contributor to Fast Company and has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.