my boss is a terrible restaurant guest (2024)

A reader writes:

I’ve worked for my C-Suite boss for almost five years. We are in a line of work where we attend a lot of lunches and dinners at nice restaurants, most often as guests of vendors and clients. While I generally enjoy the fine dining opportunities, I find my boss to be an insufferable restaurant patron.

My boss considers herself a “foodie” so she is often the one who suggests a restaurant for these meals; she prefers to go to places she has not been before when someone else is paying. She rarely deems a restaurant good enough to go back to more than once!

Like clockwork, at the beginning of every meal she peruses the drink menu, announces that nothing sounds good, and asks the bartender to make her something off-menu (usually with lots of instructions and ingredients). Without fail, she does not like that custom drink and sends it back in a way that implies that the server didn’t take all of her instructions or the bartender is bad at his job.

She often complains loudly that a dish is missing “something” or another vague criticism, and if she’s loud enough for the server to overhear and inquire, she asks for the dish to be removed from the bill. If the server isn’t paying as much attention as she would like, she comments to the table about how the tip should be lowered (particularly cringy when we are not the ones paying).

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Instead of ordering dessert, she will start her meal over and order a co*cktail and appetizer while everyone else drinks espresso, a move that usually confuses our dining companions and also can throw off the servers, not to mention it extends the meal another 30 minutes or longer just when we were close to wrapping things up.

Admittedly, I may be more sensitive to her particularities because I waited tables in a high end restaurant to support myself through high school and college. That experience has trained me to be a much more gracious, patient diner and to be a lot more forgiving when things aren’t perfect.

However, I find it so embarrassing to eat with her that I’ve been turning down invitations (and missing some important networking opportunities). While I know her poor manners are a reflection on her and not me, I have noticed that our hosts are more frequently asking for me to pick a restaurant I think she’d find “acceptable” or suggesting that we “skip the meal this time.” So I get the feeling others have picked up on this as well. Should I say something to her?

Your boss is an ass!

Her behavior would be boorish in any circ*mstances, but particularly in a business context (where there’s generally an assumption you’ll overlook small issues because the food isn’t the point of why you’re there) and particularly when someone else is paying (because her behavior conveys that the host’s choices have displeased her). But even if this weren’t a business context and/or she were the one paying, her behavior would be rude — and mortifying to any decent person she was with.

As for what to do … what’s your relationship with your boss like and how does she take feedback generally? Would she be open to something like, “I think Lucinda and Jeff were embarrassed that you seemed so unhappy with the food and service” or “I think it made them uncomfortable when you kept sending the drinks back”? Or even a more direct, “Contacts have been suggesting we skip dining recently, and I think they’ve noticed you’re often unhappy with the food and service” or “When you criticize the restaurant, people we’re eating with get uncomfortable — it’s landing like you’re criticizing their hospitality”?

If you think she’d be willing to hear that — and, importantly, if she’s generally a reasonable person when she’s not dining out — you could give that a try. But I’m skeptical that she’ll be open to hearing it; people who behave this way are usually eager to tell you why they’re justified, and you’ll probably be inviting a rant about bad service.

Most likely, you’re better off reminding yourself that your boss’s behavior really doesn’t reflect on you. You’re not the one sending back drinks or berating the server, and people aren’t going think you endorse her actions; they’re aware of the power dynamics in play (and it sounds like they’re subject to them a bit themselves too). If you really want to underscore that, you could mention how much you enjoyed your meal or how delicious your appetizer is — but even if you don’t, it’s likely to be clear that you don’t stand with your boss on this stuff. You could also make a point of warmly thanking the server, or even going out of your way to find them as you head to the bathroom and thanking them for their patience or saying that the rest of you are enjoying the food. The subtext will be clear.