Personal Insights
Should you be friends with your supervisor?

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Friendly? Sure. But friends? Well, read on. Experts agree it’s essential to have clear boundaries when there’s a power imbalance.

By Beth Greenfield

Millie, a content program about women and money, is licensed from Dotdash Meredith, publisher of Real Simple, InStyle, Investopedia, The Balance and more.

There was a moment back in my 20s when I thought I was friends with my boss. We worked at a fun downtown company, and he’d often invite me and other staffers to go out drinking and carousing. We’d all wind up oversharing. Sure, I reported to him, but he was cool! More like a pal... right?

Imagine my surprise when he pulled me aside one day to deliver a harsh performance rebuke. It was mortifying—but even worse because I had allowed myself to consider us equals, both in the office and out.

Today, I see it as a lesson learned, one that experts say is vital when it comes to being professional.

“Boundaries with your boss are essential,” says executive career coach Julia Korn, founder and CEO of the Authenticity Guide. “Should you be collegial? Yes. Friendly? Yes. But crossing over to ‘friends’—wherein you’re communicating about non-work-related things outside of work, relying on each other emotionally or otherwise engaged in non-professional topics more than work-related topics? That’s a no-no.”

Acquaintance vs. friend vs. friendly

“It’s absolutely appropriate to be friendly with your boss,” says executive coach Dana Theus. “But don’t get ‘friend’ and ‘friendly’ confused.” The difference, she says, is that friends have a mutually supportive relationship, and one person doesn’t necessarily have power over the other.

With a boss relationship, “one does have power, and that’s the agreement you make with a company and boss when you accept that assignment,” Theus adds. “It’s a fundamentally different power relationship than a friendship.”

Of course, it can sometimes be hard to tell the difference because we spend a lot of time with our co-workers. “We tend to develop connections with them,” says Phoebe Gavin, a career and leadership coach. This is good, as it’s a way to build community. The challenge, however, “is that there is an organizing factor for those relationships based on a chain of command and everyone being economically dependent on the employer,” she adds.

How being friends with your boss could backfire

Lisa, a longtime editor, recalls becoming fast friends with a past boss. But things got “confusing” when review time came around, she says: “I always felt like I wasn’t quite getting what I deserved, in terms of money and promotions. I know my boss didn’t want to seem like she was playing favorites—but on some level, I guess I expected her to.”

That’s a common point of friction, says Korn—that is, when the boss needs to make a tough decision related to a pal’s employment. “You may think your friendship with your boss shields you from a layoff or being held back from a big promotion, but it won't,” she adds. “This can often add to the pain and hurt of an already tough situation.”

And sometimes, your friendship with your boss may not play in your favor at all—and actually do the opposite.

Indeed, a study in the Journal of Experimental Social Psychology found that in certain office situations, managers feel compelled to be extra hard on a colleague who is also a friend and to even pass that friend over for advancement so as not to appear biased.

Bosses should err on the side of caution

These dynamics can be as difficult for the supervisor as they are for direct reports.

“It can be really challenging to manage people that you are friends with because you often have to give them bad news,” says Gavin. “You have to tell them to do things they don’t want to do. You have to give them feedback, sometimes negative, on their performance. You have to tell them ‘no.’ And sometimes you have to make decisions about their personal economics, like if they get promotions or raises.”

So while it may be tempting to be friends with the people you manage—“we all want our teams to like us,” Korn says—just remember that it blurs important lines.

Be clear and be yourself

Don’t be so fearful of murky boundaries that you fail to connect with your manager, advises Theus. “You’ve got to get to know people, and if you want your boss to see you as a human being, you have to be a human being,” she says. So, for example, if you’re going to lunch with some co-workers, “go ahead and invite your boss—just don’t confuse it with friendship.”

In general, though, Korn recommends steering clear of alcohol when socializing with the boss, as “impairment and work aren’t a good combination” (see: my 20-something-year-old self) and to “socialize outside of work with caution and consent” (meaning it should always be optional).

With that said, there is one boss Gavin encourages you to become friends with: a former boss. “Those friendships can be really, really powerful,” she says, “both personally and professionally.”

Beth Greenfield is an award-winning journalist, writer and senior editor who specializes in lifestyle, health and wellness.