Having drinks with the boss is not a situation I've often found myself in, especially since I've been self employed. But here is some interesting advice for that scenario, which could also apply to drinking with a client or someone you want to leave with a good impression:
7 Drink Orders Guaranteed to Impress Your Boss
It’s a cardinal rule of corporate life: if the boss asks you for a drink, you say yes. Period. We don’t care if you’re a teetotaler or it’s your 20th wedding anniversary—you’re accepting that invitation. Over a few rounds of cocktails you’ll learn more about the company than you ever will in a boardroom setting, and you’ll put yourself in his or her good graces for the foreseeable future. Blow off the boss? Don’t be surprised if he or she returns the favor one day.I was a bit surprised that the Martini was on the forbidden list. Isn't that a popular one for businessmen? I think the point is not to come across as a lush or a boozer, and the martini might be a bit strong? But they recommend the Manhattan cocktail, and that can be very potent.
But there are rules for boozing with your corporate leader. No whiskeys neat, and no martinis. And definitely no cruiseliner daiquiris that will (rightfully) make you look like a less-than-serious man. Instead, select drinks that are manly and respectable, but won’t floor you in the process. If you’re not sure what those are, don’t worry. With the help of some top mixologists, we’ve compiled them all right here. And for more great drink recs, try one of these amazing spring cocktails. [...]
This advice also seems to be for men. And perhaps a bit old fashioned. But perhaps that's the best way to behave when drinking with the boss? ;-)
Read the whole thing for the list of drinks, pics, and embedded links.