Becoming friends with your coworkers is all but inevitable: You spend eight hours together, five days a week—adding to about 90,000 hours over the course of your lifetime. You share lunches, work project, lines for the bathroom, and stories about your cat. (If that’s not enough to bond people together, I’m not sure what is.)
And if there’s one thing all your friends have in common—be they work wives or college besties—it’s that they’re total boss ladies. But what happens when someone you’re dying to befriend is your actual boss?
Being friends with your boss can be a complicated maneuver. How do you make sure personal life stuff doesn’t spill over into your 9-to-5? Will other colleagues think you’re getting preferential treatment? What if you have a disagreement?
“It’s tricky waters,” concedes Kathy Caprino, career coach and founder of Ellia Communications. “You have to build strong boundaries so that the friendship doesn’t impact how you do your work in a situation where the power between you is not equal.”
How, exactly, do you do that? Keep reading for an expert-approved strategy to bond with your boss, extra-curricularly.
Test the waters
Wendy Toth, the director of content for LuckyVitamin and creator of the blog Power Suiting, says that when it comes to deciding how close to get with a manager, she likes to make the first move. “I lead with what I’m comfortable sharing, and let them respond with what makes them comfortable,” she says. “It usually starts with talking about work, then pop culture, then moves into the realm of hobbies and eventually stories about family.”
According to Toth, hot-button topics like romance and politics are advanced-level and should only be broached after your friendship has firm footing. And one subject that should be avoided at all costs: office politics.
Agree on boundaries
Let’s say you’ve settled into a comfortable rapport and can easily chat about your shared love of The Good Place (Kristen Bell is the best!), your fave yoga studios, and your kids’ latest antics. It’s time to set some smart, effective workplace boundaries.
Amanda Augustine, career advice expert for TopResume, says, “While it’s nearly impossible to never discuss work, it might be necessary to lay a few ground rules and agree on the topics that are off-limits, such as compensation, performance reviews, and company gossip.”
These boundaries not only keep your new friendship healthy, they can help prevent resentment from bubbling up in the ranks.
These boundaries not only keep your new friendship healthy, they can help prevent resentment from bubbling up in the ranks. According to Lynn Taylor, workplace expert and author of Tame Your Terrible Office Tyrant, if you and your boss get a rep for continuing that compensation convo over cocktails, “your coworkers may cry foul and claim a hostile work environment exists because your boss is favoring you over them.”
Augustine recommends avoiding this worst case scenario by being transparent about your friendship and proving to your team that no one is receiving preferential treatment. “Actions speak louder than words. Remain professional in the office and save your friendship for when you’re off the clock,” she says.
Keep yourself in check
“If you want this friendship to work,” Caprino says, “you have to be emotionally healthy and able to regulate your own thoughts and behaviors to make sure that anything challenging in the friendship will not bleed over into how you do your work—or how you perceive your boss and her management capability.” So if she flakes on your weekend plans, it doesn’t give you permission blow off your 10 a.m. meeting—or tell your coworkers she’s unreliable.
“Be very mindful and aware of your thoughts and feelings about this person,” Caprino adds. “If your anger, resentment, or hurt feelings affect your functioning and thinking at work, get some outside, neutral, help from a friend, coach, or accountability buddy.” Navigate through the storm affectively though, and the reward could be big: Research shows working with friends could help you both succeed.
To gauge the health of your friendships—in and out of work—ask yourself these questions. And here are more tips for making new friends as an adult.
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