How to Drink With Your Coworkers

Back in the “Mad Men” era drinking at work was no big deal. (Ed. note: Let’s bring back office bar carts!) You drank to celebrate. You drank to dull failure. You drank because you were bored. And it was okay.

Fast forward to today: While in-office imbibing isn’t completely taboo — some tech companies enjoy kegs right in their kitchens (ours included) — drinking with coworkers, your boss or direct reports is still murky territory. Especially when you swap cubicles for a bar.

The overarching guidelines are fairly obvious: Don’t have too much and don’t embarrass yourself. (Fortunately, these often go hand in hand.) But there’s more to navigating these situations than mere volume. Master the art of after-work cocktails with this simple guide.

The Art of Happy Hour

The Art of Happy Hour

Back in the “Mad Men” era drinking at work was no big deal. (Ed. note: Let’s bring back office bar carts!) You drank to celebrate. You drank to dull failure. You drank because you were bored. And it was okay.

Fast forward to today: While in-office imbibing isn’t completely taboo — some tech companies enjoy kegs right in their kitchens (ours included) — drinking with coworkers, your boss or direct reports is still murky territory. Especially when you swap cubicles for a bar.

The overarching guidelines are fairly obvious: Don’t have too much and don’t embarrass yourself. (Fortunately, these often go hand in hand.) But there’s more to navigating these situations than mere volume. Master the art of after-work cocktails with this simple guide.

Do Encourage Yourself to Be Social

Do Encourage Yourself to Be Social

Before I began working from home full-time, I spent years hustling in an office. There were a number of happy hours I could have attended, but I was typically too burned out — and, to be honest, sick of being around work people — that I often declined.

This was a mistake. While I was at home in my sweatpants with my takeout and HGTV (being super cool, obviously), my colleagues were bonding over beers. Once you pass on a succession of these outings, you fall way behind in forming personal relationships. For me, this led to feeling a bit like an outsider. So sack up and go out for drinks, even when you don’t feel like it.

Don’t Order Your Favorite Cocktail

Don’t Order Your Favorite Cocktail

I’m a sucker for dirty martinis, in that I love the taste so much that I do actually suck them down. As you can imagine, this practice could result in me dancing on a table, crying in a corner, puking or a combination thereof. (Just a guess.)

Instead of ordering a chilled glass of olive juice, which I’m sure I would find equally yummy, I choose a mixed drink I don’t particularly love (like a gin and tonic) when I’m in a situation in which I don’t want to overindulge. This way I sip, not gulp.

Nailing down how much alcohol, food and sugar you can balance is not an exact science. Sometimes it’s one glass of wine. Sometimes it’s three. Not ordering what I love is my go-to solution.

Do Resist the Urge to Gossip

Do Resist the Urge to Gossip

Drinking together can create a false sense of camaraderie. After some social lubrication, you may feel like tonight is the perfect time to tell your coworkers what you really think of your boss. Or you may get the urge to continue down the office gossip rabbit hole when someone else makes a mai tai–induced comment about how incompetent so-and-so can be.

In the moment, this conversation feels intimate and exciting. But the next morning when you try to retrace what you said about whom, you’ll probably regret it. Yes, you probably bonded — and it feels liberating to share with someone who gets it — but it might not feel great at 9 in the morning when you arrive sober at your desks.

Don’t Talk About Work All Night

Don’t Talk About Work All Night

Recommending that you use happy hour to really engage with your colleagues on a deeper, personal level and refrain from any shop talk is completely unrealistic advice. Your jobs are one thing you for sure have in common.

So use work as the gateway to other topics. As a journalist, I could easily segue conversation into colleagues’ personal lives since they usually have a special focus that translated into a passion. Your tech support whiz likely has some strong opinions on the new iPhone, if you ask her (it’s a start).

If you’re the boss, get your reports one-on-one to learn about their hobbies, hometowns, and other details you may not know. Most likely, they’ll be happy you care — and not think you’re random for jumping right in.

Don’t Do Shots … Unless the Occasion Calls for It

Don’t Do Shots … Unless the Occasion Calls for It

Many people who give advice on drinking with coworkers warn against binge drinking and shot taking, of course. For the most part, I agree. A night spent shooting Jose Cuervo rarely ends well, unless you look forward to midnight pizza.

But you know what? Sometimes shots are a good idea. Or at least they sound like a good idea in the moment. Maybe your team secured a really important account and your normally buttoned-up CEO has his tie tied around his head while ordering you all a round of Fireballs at your favorite dive bar. Go for it.

Do Set a Time to Leave

Do Set a Time to Leave

As a general rule for work events, you don’t want to be the first — or last — to leave. Take off too early and you’re the party pooper; stay too long and you’re the wild child. It’s best to excuse yourself somewhere in between so you maintain a healthy amount of face time.

One way to make sure you don’t overstay your welcome is to make plans with friends or your significant other later that evening. Say your work happy hour starts at six: Set a dinner reservation for 8 pm. That way you can have a drink, hang out and then excuse yourself. This is especially helpful if you’re not tight with your coworkers or don’t drink and want an exit plan.

Don’t Assume the Company Is Paying

Don’t Assume the Company Is Paying

Unless happy hour is an official company-sponsored event (and there was an email or announcement designating it as such), your boss probably won’t be slapping down the corporate credit card. And you certainly don’t want her to get unexpectedly stuck with the tab at the end of the night.

When the first round of drinks is ordered, listen in and see if a boss or manager gives a directive to the bartender about who’s taking care of the drinks. If there’s none, assume you’re paying your way and ask for your own check when you put your order in. (You don’t want to get stuck with the group’s tab, either.) Better yet, pay as you go so you’re already closed out.

Don’t Drink and Drive

Don’t Drink and Drive

This one is a huge duh. But while the DMV mandates a legal limit, its parameters are difficult to detect unless you have a police-grade Breathalyzer. You may think you’re fine when you’re not.

Grab a cab or or call an Uber. Doing so not only keeps you safe, it also sets a good example for your coworkers — especially your direct reports. And be sure to keep an eye on others. If someone is too toasted to drive, offer a ride or split a cab. It may feel awkward in the moment to take away Patricia from Accounting’s keys, but you’ll both be glad you did.

Do Suggest Nonalcoholic Outings

Do Suggest Nonalcoholic Outings

Happy hour is an easy go-to because alcohol encourages everyone to relax and be more open on a chemical level. Also, it’s happy hour. There’s something for everyone.

Except for those who don’t drink. For the sake of variety — and not ostracizing the teetotalers in your office — plan some team bonding away from the bar. Group exercise classes or team sports can provide fun settings for people to get to know each other — and let off some steam.

Plus, there are far fewer “rules” to think about at these alcohol-free events: Basically, just show up, have fun and don’t be an over-competitive jerk.

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