Stingy Bosses, Ill-Mannered Guests, & In-Flight Traffic Jams

Oct. 6, 2009 — -- Q: My boss takes our team of four out for lunch twice a month at fairly expensive restaurants. The issue is, she never tips—ever. I asked her about it and she's very up-front about never tipping. Another person even backed her up! My other co-worker and I said we shouldn't go to places where tipping is customary if they don't believe in it, but they don't care. Once, we surreptitiously left a tip ourselves, but we can't afford to do that regularly. Help!

A: Is this really someone you want to be working for—never mind having lunch with? The willingness to screw over an innocent waiter who depends on tip income is not a trait you want in your manager. And what would a client think? If I saw someone being that cheap and inconsiderate, it would affect my perception of their company.

There are ways you can try to sidestep this—invite a higher-ranking colleague to join you, in hopes they'll pay (and tip properly); get petty cash to use as a tip; suggest meeting in your office over takeout (which you volunteer to pick up)—but they won't solve the problem. I'd encourage you to talk with your boss again (in private, of course) and try to get her to see reason. When she told you about her no-tipping policy, did you and your polite colleague explicitly say it makes you uncomfortable? I'd make that clear, even though it's difficult to convey criticism to your manager. If she brushes off your concerns, I would honestly start thinking about transferring out of her department or to another company.

Q: On my last cruise, we were assigned to a dinner table with a family who had horrible manners. They blew their noses in napkins and told ethnic jokes about the waiters! It honestly affected our enjoyment of the cruise. What should we have done?

A: If your tablemates' manners are just mildly bad—slurping soup, cutting up their entire steak at one time instead of bite by bite—I'd say deal with it. But if they're truly atrocious (and in my book, telling ethnic jokes qualifies as atrocious), you can ask the maitre d' to reseat you. Just speak to him immediately after dinner on the first night, as it's easier to change tables early in the cruise. (This is also why you should never skip dinner in the main dining room on the first night of your cruise—you might get stuck with the tablemates from hell.)