The Dude here, playing Miss Manners. Suppose your boss is normally at a different location than you. Very common occurrence. He will come to town regularly, and you may be asked to dinner. Either alone or as part of a group. While you might prefer spending time at home with your family, or poking sharp needles in your eyes, it is always in your best interest to accept the invitation and go.
Trust the Dude on this
So you find yourself out with your boss and some peers, or alone. How do you behave?
Don’t drink too much. A glass or two of wine, or a couple beers is fine. Never drink more than your boss, and moderate the alcohol consumption. Alcohol loosens inhibitions, and people tend to say things that are best left unsaid. I have seen rising stars flameout over a simple party fouls like this. Claim you are on a diet, or that you don’t drink (even if you are pickled 90% of the time). The only exception is if it is your last day (a going away party) or your boss’s going away party.
Don’t hog the conversation. You may think you are witty, and that the two cocktails you ill-advisedly had prior to being seated turned you into a golden tongued pundit, but you aren’t. Unless you are Jay Leno, it is best to participate in the conversation, but not draw to much attention to yourself. Watch the group dynamics. People watching is an important Product Management skill, and this is a perfect time to shut up and listen.
Don’t order the most expensive thing on the menu. I don’t care if your boss orders the Filet and Lobster Thermidor for $85. Keep your entrée choices at about the mid-range. You want to be seen as frugal - but not too frugal, and looking for a good deal. Starters and dessert are usually fine to order. But think back to #1 before looking at the Cognac or Port menu.
Have a couple great restaurants in your home town to recommend. Honestly, your Boss probably doesn’t know enough to book a good place. And the receptionist whom he asks will give bad advice. You should have a handful of “special” places. For events with your Spouse, and when important customers come to town. Speak up and recommend. Or you will go to a bad quasi-chain restaurant.
You rarely climb the ladder by the little graces for dining with the team or boss, but you can completely harpoon your career without trying if you handle it wrong.