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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.

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.

“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.”

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.”

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