The Dos And Don’ts Of Hanging Out With Your Boss

The dos and don’ts of hanging out with your boss

should you be friends with your boss?

Today we live in a world where it’s okay to be friends with your boss. We don’t live in the Mad Men world, where you need to tiptoe around the office or think twice about sharing personal stories with supervisors. You can talk about your weekend vacation or your best friend’s wedding or even a bad Tinder date. However, there are some things you should take into consideration before opening the line of friendship with your boss.

1. DON’T force any friendships.

Let a relationship with your boss happen organically. Don’t friend them on Facebook, let them friend you as the superior. Many people say not to interact with your boss or coworkers on social media, but we think by denying or avoiding their request, you’re saying, “I have something to hide,” when in reality (and hopefully) you don’t. If you don’t want your boss to see a picture or a status from the weekend, you probably shouldn’t be posting it anyway.

2. DON’T gossip.

There’s nothing more harmful than gossiping or talking poorly about the people you work with. Sometimes it happens, but make sure you vent to people that you don’t work with. And never gossip with your boss. This isn’t The Office.

3. DON’T brownnose.

It’s okay to befriend your boss, but make sure it doesn’t look like you’re exploiting it to get perks at work. The friendship should be unrelated to your time at the office, and you don’t want it to affect you negatively.

4. DO be inclusive.

Just because you and your boss work together, doesn’t mean that’s what you have to talk about when you’re outside of the office. None of your other friends will care about the new product feature that your company just launched, so don’t bore them with the details.

5. DO be careful with what you share.

While being your boss’s friend is acceptable, think twice about the information you share. This should be a rule of thumb with all relationships. Be careful about sharing a personal problem, or something that might affect your performance.

6. DO create a positive relationship.

In terms of your relationship, boss should always come before a friend in the workplace. It’s a great situation to get along with your boss that well, and you don’t want to do anything to compromise that.

What do you think? Is hanging out with your boss outside of work ok?

By: Jenna M. Uszenski 

Meredith Lepore

Meredith is the former editor in chief of the women's career site, The Grindstone. Her work has appeared in Marie Claire @ Work, The Jane Dough, DailyWorth,, Business Insider and Learnvest. She earned her Masters in Magazine, Newspaper and Online journalism from the Newhouse School at Syracuse University. Meredith resides in New York full time and enjoys reading, jogging, SoulCycle and playing with her small dog, Otis.