Happy Hour Etiquette for the Boss

How you handle yourself at the bar says a lot about you as a leader.
Happy Hour sticky note
By going to happy hour, bosses are presented with an opportunity to get to know their employees on a more personal level. (Photo: moomsabuy/Shutterstock.)

Your staff is gearing up to head to their favorite neighborhood watering hole to drink and socialize after a long day at work. They’ve encouraged you to join in on the fun, but the boundaries are blurry. You’re the boss – should you go to happy hour? And if you do, should you pay?

The rules certainly vary depending on office culture – small companies tend to be more social, while traditional offices are more reserved. We consulted with experienced business owners and experts to find best practices for mixing bosses and happy hour.

Make a late entrance

A happy hour gathering is a great opportunity for bosses to get to know their staff on a more personal level, increasing morale and creating a more supportive environment.

“When I take my team to happy hour, I treat them as I would my friends and drop the normal employee­employer boundaries,” said Ryan Lockhart, founding partner of group46, a full­service marketing agency.

However, keep in mind that most employees go to happy hour to get to know each other, not their boss. In fact, a survey from CareerBuilder.com found that just 11 percent of workers use happy hour as a way to bond with the boss. Don’t plan to stay the whole time, and consider arriving fashionably late.

“It would be best for the supervisor to make a slightly late entrance and a rather early exit to give staff members the time they want to truly unwind,” said David Bakke, a business expert and contributor at MoneyCrashers.com.

Pay for drinks while you’re there

Whether you’re formally hosting the happy hour or just attending, you should plan to pay for at least one round of drinks.

“If a boss is not going to pay, then don’t go,” said Precious Anderson, founder of The Anderson Firm, an Atlanta­based legal and business boutique. “There may be a chance that everyone has already pre­paid their own tab if the boss arrives late, but if the bill is outstanding, the boss should expect it to come their way and count it as a firm outing that will hopefully contribute to good times that spill into the office the next day.”

Lockhart agrees that there’s value in picking up the tab.

“I see it as a huge benefit for the overall morale and performance of the team on a day-to-­day basis,” he said.

“I always pay for happy hour when I join my employees, and make it a point to invite everyone within our small company.”

However, bosses don’t need to foot the bill for an extended outing.

“If people continue to drink [after the first two rounds], they should be responsible for paying for their drinks from that point forward,” says Mark Tuchscherer, founder and CEO of web and mobile development firm Geeks Chicago. “The company does not want to promote drinking for hours and hours.”

Leave before it gets rowdy

As the night goes on and the drinks keep flowing, employees tend to be less inhibited than perhaps they should be around their boss. Business owners should leave after a couple of drinks to avoid potentially embarrassing situations.

Happy hour gave Cincinnati­based Bill Fish, president of ReputationManagement.com, an opportunity to build personal relationships with his New York staff when he was in the city on business. But, he kept a professional distance by limiting the time he spent at the bar.

“I made a point to always leave after two hours, maximum. I’d close the tab and go on my way. I didn’t want to create a situation where people were drinking far too much and getting in situations they would regret down the road,” he says. “I did hear stories from time to time about things that went off the rails later in the night, but I was long gone by that time, so it wasn’t a major concern for me.”

Even though happy hour gives employers the opportunity to grow closer with their staff, bosses should strive to be a role model: Indulge, but not too much, treat your team to a round or two, and don’t arrive at the office hung over the next morning.

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