Being the boss—the one who leads, who everyone looks up to—can be super rewarding. But sometimes, you just want to let your hair down and have a good gossip session over your morning coffee (or happy hour drinks) with the rest of the crew. What’s a boss to do?

There are loads of perks to being at the top of the ladder, but one of the drawbacks is the murky waters of office friendships. Of course, there are no laws that state you can’t buddy-up with your team—but there are a few guidelines you should consider before becoming besties with one of your colleagues.

Read on for a few pointers for making friends in the office—as a manager.


Tip #1: For Most People, Keep it Casual

There’s no question it can be lonely at the top, and making friends in the office when you’re the boss can be a nice consolation. But, don’t let that lull you into believing you don’t still have a job to do.

I learned this the hard way when I first became a manager, years ago. I was young and eager to please my new staff, while still earning my management stripes. I had a great team, and friendships were easily formed among all of us.

It was great for the first few months, but then I had to start, well, managing them. That’s when things got sticky.

Suddenly, I was no longer their friend or drinking buddy; I was management. Enforcing policies, discussing performance, and conducting annual reviews became painful and awkward for all involved. All because I got too involved.

After that, I made a point to keep my friendships with most of my staff casual. The occasional non-work event was fine, but I tried to limit them to short, fun chats. Did I miss out on some of the fun—and good friendships? Probably, but it made life much, much easier when the time came to be their manager.


Tip #2: Make it a Long Engagement

Of course, if you’re lucky, there may come a time when you’ll want to break the first rule, and take your relationship with an employee to the next level. You’ve already spent enough time with this person on a casual level, so when you think you’re ready to go for the friendship, remember, there’s no need to rush—in fact, make sure it’s a long engagement.

Several years ago, I hired someone, and he seemed like a great guy. We got along really well, and he was doing a fantastic job. After testing the waters with a few casual after-work events with my team, we still got along really well, and I saw the makings of a friendship unfolding. So I invited him out for happy hour one evening after work, and our friendship began. Sounds nice, right?

Well, if I had waited just a bit longer to see how things unfolded in the office, I wouldn’t have bellied up to the bar with him at all. Not long after we became friends, his performance began to slide, and I was put in the awkward position of having to confront him about his poor performance. Our friendship quickly fell apart, and life at work was uncomfortable for both of us.

Since then, I have applied a waiting period of sorts before I break my rule and promote one of my team members to friend status. Again, it’s fine to keep it friendly at the office, but keep the non-work socializing to a minimum until you’ve really had a chance to get to know people in a work setting.


Tip #3: Prepare for Disaster

OK, so maybe “disaster” is a bit severe, but if you’re planning on being pals with a colleague, it’s wise to imagine every worst-case scenario before you really cement a friendship.

For example, I was friends with one of my staffers, who happened to be my second in command, several years back. Before we really became friends, I tried to imagine all the ways things could get awkward—for either of us—if something went wrong with our friendship, or at work. In fact, we actually discussed this openly before hanging out socially outside the office. What if I had to confront her about a performance issue? What if I said something rude after a few too many beers at happy hour? We ran through all the ways things could go wrong, and how we thought we’d handle each.

After imagining each scenario, we were not only ready to handle whatever disasters may come our way, but realized we also worked really well together. We’re still friends today, and I can’t recall a single “disaster” we had to face in our friendship—inside the office or out.



If you’re lucky, you’ll end up working with some pretty awesome people—maybe you even hired some of them. If that’s the case, it makes perfect sense that you’d consider a friendship with a few of them at some point. Friendships should be fun, so just be sure to lay down some boundaries for the office before you start choreographing that secret handshake. Then, stick to these guidelines, and you’ll ensure those friendships are rewarding for both of you—without making work too awkward.


Photo of co-workers talking courtesy of Shutterstock.