There are specific dos and don’ts for drinking with your boss. But according to Percy Rodriguez, the beverage director at SECOND and the Laurent Tourondel group, the most important thing is to order with confidence. “The drink is a nod to who you are, what you like, the mood you're in,” he says. “It's an opportunity for your boss to learn a little bit about you, so take advantage of the facetime.”
But if your go-to says something about your personality that you don’t want your boss to know, you might need an alternative order. If that’s the case, you can’t go wrong with these bartender-approved recommendations.
You have to keep your wits about you when drinking with your boss, so keep it simple and classic. “A dry vermouth with Q Club Soda and a nice twist of lemon is fantastic, as is a good sherry with Q Indian Tonic,” says Joanna Carpenter, bar director of Town Stages. “If I'm drinking with the boss, I want to keep it light and still show them that I've got excellent taste.”
Both the Champagne Cocktail and the Negroni will let you have a couple and make sure you don’t “say anything you might regret later,” says Joel Mesa, beverage manager at Pisco y Nazca. “The Champagne Cocktail will go to your bloodstream immediately, while the Negroni will have a 20 minute delay attached. It really depends on the nature of both your relationship with your boss and the setting.”
You can’t lose with something iconic. “The drink [Old Fashioned] shows a classic sense of sophistication and opens the door to a discussion of whiskey preferences,” says Samuel Ortiz, bartender at Public Belt bar and lounge at Hilton New Orleans Riverside.
“I would suggest a Vieux Carre cocktail, especially if your boss is a Manhattan lover,” says Rachel Kling, bartender at the Quill at The Jefferson. “A classic cocktail native to New Orleans, it is the more complex and less-popularized cousin of its Northern counterpart. It utilizes a split cognac/rye base, which lends a beautiful spice structure and silky mouthfeel to the drink. If you can find it, Angel’s Envy makes a delicious rum cask-finished rye that mixes perfectly in a great Vieux Carre.”
“It's a scene that I see play over and over again at the bar—a customer walks up and orders an Old Fashioned or a simple whiskey on the rocks while out for a drink with their boss,” says Katsuaki Asai, lead mixologist of AZABU Miami Beach. “Sure, it's a safe and solid bet, but I don't necessarily think it's the best choice if you're trying to impress your boss with your cocktail cred.”
Instead, order an exotic whiskey or an untraditional blend. “It will serve as a conversation starter and allow you to flex some insight,” Asai says. “For example, if a customer orders a Suntory Hibiki Japanese Harmony Whisky at AZABU, I know they're ordering based on the blend's tasting notes like vanilla, mild smoke, dark chocolate and spice.”
“While I think we’re past the Madmen fad of discussing business over an Old Fashioned, if you want to mix it up a little while still nodding to tradition, get a Tequila Old Fashioned,” says Nico Szymanski, head bartender at Mr. Purple at Hotel Indigo Lower East Side. “Anejo tequilas have flavor profiles that work well in traditional whiskey cocktails, and the Old Fashioned is a great drink to make this substitute with. My go-to base spirit is Casamigos Anejo.”
But you don’t need to get complicated with it. “Ask the bartender if they have large whiskey cubes,” Szymanski says. “Handing your boss a healthy pour of well-aged tequila over a single oversized cube is sure to raise an eyebrow. And most importantly, it looks cool.”
Something Stirred and Boozy
“The best drink to impress a boss is something stirred and boozy, of course!” says Nima Kasmaii, assistant beverage director at KYU. Something like a strong, stirred rum cocktail “will definitely show you mean business.”
Whatever Matches the Mood
“I say order a top-shelf classic on the rocks if your boss always wears a suit,” says Dustin Durrenberger, the beverage director at Doc B’s Fresh Kitchen. “If your boss is more easy-going, get something a little more adventurous like a funky cocktail.” A cocktail on tap, he adds, is always a great choice.
In addition to the type of person your boss is, keep in mind the situation and how long you’re drinking, notes Chris Resnick, lead bartender at Minnow Bar. “If you’re in it for the long haul, you might want to stick with beer or some low-ABV cocktails like a Bamboo,” he says. “If you’re out to impress, I would stick to a classic but maybe not an overdone one. Every macho guy in a suit will order the Old Fashioned. Maybe go with a Gimlet or Gibson. Or go full tilt and get a Paloma. The key is not to order too obscure as to avoid looking foolish asking for things not every bar has access to.”
“Take the venue into consideration,” says Colin Silva, head bartender at SĒR Steak + Spirits atop Hilton Anatole. “Don't order a Manhattan at a pool hall and avoid the usual domestic suspects at craft beer locations. My answer to all of this is simply bourbon. The bourbon of choice is not as important as the preference of consumption. Be precise without being cumbersome. Bourbon with two rocks, water on the side. By not asking for a splash of water included, you gain control of your drink; you get to show your assertion without calling unwanted attention to yourself. Almost without fail, your boss will ask why you order so precisely. Now, you have a platform to explain your order (and mindset) to a savvy business operator.”
If all else fails, go for the bubbles. “Depending on your bosses’ budget/expense account, bubbles are never a bad move,” Kling says. “Champagne is always number one, but Cava, sparkling wine from Spain, is a great wallet-conscious alternative.”
If You’re Totally Unsure, Play It Safe
Depending on your job, drinking at the bar doesn’t mean you need to order something with alcohol. "If I want to impress my boss, I order myself an iced tea, as I am working tomorrow," says Ian Morrison, beverage director at Left Bank.