Food & Drink

How to Get Drinks With Your Boss, Like a Boss

What took you so long
Anthony Humphreys/Thrillist

Drinks with your boss can be one of the most enjoyable aspects of bothering to have a job. But while this is ideally a casual outing, there’s still protocol involved, which is why we anonymously polled bosses from across America for 16 tips on how to ace these professionally advantageous, high-proof sessions.

Does my boss have an agenda? Is this some sort of test?
Probably not. His goal is most likely nothing more than getting to know you better socially in order to make your office relationship more productive, and to reaffirm that your “soft skills” are solid enough to bring you to client meetings.

Are you sure? It feels like there’s an agenda.
Bosses almost always ask employees out in groups. If he asked you out by yourself, you’re either getting promoted, talked to about your underperformance (or someone else’s), or fired. But assuming some coworkers will be joining you, again, there’s likely no ulterior motive here.

So I can just act like I normally do in bars?
Not exactly. “An attorney once told me that you can’t win the lawsuit in your deposition, but you can lose it in one,” says one of our experts. “That’s how I feel about drinks with the boss: you won’t get promoted because you have a high tolerance or know a ton of jokes, but you can screw things up by being a jackass -- and as much as I’d like to believe that wouldn't affect how I treat you at work, I'm human.”

Talking with the boss
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What’s the worst thing I could start a conversation about?
The unanimous response: work. If your boss brings it up, go with the flow, but otherwise avoid the subject like the plague -- which is admittedly a lot to ask because plagues are by definition very hard to avoid.

Anything else to steer clear of?
The usual -- relationships and other topics that fall under “oversharing”. Politics and religion (unless your boss wants to strengthen the team by fomenting discourse, in which case he’ll hopefully play moderator or things could get ugly). Sparking a convo about your boss’s past accomplishments is actually fine, as long as you don’t look like you’re groveling before his majesty.

Bringing up salary is a terrible idea, right?
Absolutely right, but you’d be surprised how many people use this casual setting to pop the paycheck question, or the even more annoying “Where do you see my future at the company?”. At best your boss will hear you out but offer no substantive answer, so instead of finding out what the worst is, call Miss Cleo.

Talking up a colleague
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Can I talk smack about coworkers?
Best to avoid it. Smack talking is America’s national pastime, so it’s not like your boss expects you to be above this when he’s not around. But by doing it in front of him, you risk ripping on someone he privately feels is a solid -- or better -- employee.

Scotch Neat
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So this isn’t a test, but still, my first drink order seems pretty crucial.
Yeah, he’s definitely taking mental notes, but all he wants to see is that you can order with confidence. “If a person working for me can’t order a drink without having a nervous breakdown, then that person is not going to be working for me much longer.”

Any advice for what to order, beyond “not the Pina Colada”?
Go basic -- gin & tonic, Scotch neat, etc. “Anything overly complicated looks like you’re trying to make a point.”

If I have what he’s having, is that going to be awkward?
It depends on how specific his order is. “If it’s a beer, no big deal. If it’s a Grey Goose Up With A Twist, that might be weird.”

Ordering A Drink
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Should I be worried about price?
Unless your drink’s double the cost of what he’s ordering you’re all good. If you’re handed the menu in a wine situation, “don’t blow the budget on Petrus or Chateau de Rothschild unless you just banked some serious coin for the firm”.

I have no idea what those wines are. Is that a problem?
No one’s going to look down on you if, like most people, you don’t know jack about wine -- just ask for help from a colleague or the wine steward, or pass the wine list to someone else. Definitely don’t err on the side of pricey: “No one is impressed by an expensive wine that tastes bad, but they do remember the idiot who ordered it.”

Should I try to keep up with my boss if he’s a total stallion?
Unless you want your next morning to involve sprinting out of the conference room of one of the world’s largest oilfield services companies because you thought it wise to match drinks with a seasoned superior whose nickname involves potatoes, probably not.


Haggar Slacks
Anthony Humphreys/Thrillist

I can’t believe I’m asking this, but… what should I wear?
Our friends at Haggar suggest the original business-casual, slacks. They created them back in 1938 to answer a man's wardrobe needs during his “slack time”, but today’s offices are informal enough that you can wear them to work and whatever imbibing follows.

Since slacks from the 1930s would make you look like you still weren’t convinced that airplanes existed, they’ve updated their archived classics into every-day/all-day styles appropriate for guys who don’t say things like “that fella’s the elephant's eyebrows!”. (Note: some slacks are too awesome for Mon-Thu to handle.)

Checking the phone
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I have to check my cell phone, right? I mean, I can’t not check my cell phone.
If possible, check it while your boss is in the bathroom, or while you’re in the bathroom; otherwise, just check every 15 or 20 minutes. If it’s personal, ignore it. If it’s work, but not pressing, ignore it. If it’s a sudden emergency, handle it, everyone will understand. If it’s an ongoing emergency… why aren’t you still at the office?

If non-work friends randomly show up, how long can I say hey to them before it’s rude?
10-15 minutes max. “That should be enough time to exchange quick hellos, hit paws, and move on.”

The Check
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Do I even make the pretense of reaching for the check?
This is going to get expensed. You know it, he knows it, even the waiter knows it. Still, something along the lines of “Can I help with this -- we didn’t really talk about work much” shows that you don’t take situations for granted. And that you managed to have drinks with your boss without talking about work.

Special thanks to Sweetwater Social. If your boss likes foosball, shuffleboard, and rich mahogany, this is the place for those drinks.