How to Drink with Co-Workers When You’re the Boss

Opinions differ on how to spend time with co-workers away from work and how much time you should be spending with co-workers. You could hear everything from, “Don’t ever spend time with people with whom you work” to “It’s fine to have your best friend working for you.” We’re here to tackle what to do with the office happy hour, because when you’re the boss, it isn’t just a free drink on the company’s dime anymore.
Happy hours can be a way for corporate America to show they’re “fun,” and they “care about their employees.” Some places even push around the beer cart on Friday afternoons.
I’ve learned that people who know each other better and like each other more do better work. Liking your co-workers is a key part of being an engaged employee and being an engaged employee pays dividends for the company.
That’s what the company gets, but for the employees — that is most people — happy hour is a way to blow off some steam, gab with to our coworkers, and find new connections with our colleagues. For the boss, they’re a way to help your employees get to know you in a new context. 
There’s one general rule for an office happy hour: don’t get so drunk you say something impolitic. As a boss, your rules are a little different (for you the rule is don’t get drunk at all).

1.      Be one of the first to leave

You don’t have to be the first to leave, but you should not hang around too long. It’s great to show your face and be part of the team (that’s kind of the point), but you also need to give your employees a sponsored space to complain about you. Kind of.
There’s that balance to be found between being friends with your employees and being friendly. Both are good, depending on what works for you and for your company’s culture, but staying too long at the happy hour pushes you into the category of trying too hard. Even when you really like your team, its smart for there to be a slight boundary between you and your co-workers especially when the booze is flowing. This rule makes it easier.
(Basically, you just don’t want to close down the party. So, when that one guy tries to get everyone to do shots you know you have stayed too long.)

2.     Pay the Tab.

Easy as pie, right? If it’s a work sponsored happy hour, work should pay. If you’re on a budget, just tell everyone you’ll cover the first round. Even one free drink does wonders for morale.
You might be wondering, “But, hey! How can I pay if I have to leave early?” My rule was always, I’ll pay while I am there, you’re on your own when I’m gone.
But if you’re going to pay for the team’s drinks once you’re gone, fear not, you have multiple options and so my answer is, “You’re the boss, this is a problem you can solve.”

3.     Talk to the People No One Else is Talking To

There will almost always be one person who is off to themselves or doesn’t feel like part of the team, and this — my dear, out-of-touch superior — is prime team building time. It’s the boss’s job to make everyone a part of the group.
Find out something new about them, and introduce them to someone you think they’ll get along with or benefit from knowing or someone who will at least talk to them. It will make someone’s day if you start playing professional connector, because there’s no confidence boost quite like an introduction from the boss.

And while it may seem a bit silly to have rules about having drinks, you have to remember that being a good boss takes a little bit of thought. There are a lot of folks out there who say, “Just be yourself” or “Just be authentic.” The people who report to you need you to be their boss more than you need to be yourself, so act like the boss even when you are having drinks with them.

Other than that, remember to have a nice time. You’re out of the office, so loosen your tie! People are going to be a little nervous around you, that’s the way this whole “boss” thing works. Try to put them at ease. It’s like riding a horse, they’ll sense if you’re nervous and bolt, so just relax.