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.”