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What to do when your boss is a bad tipper

Miller writes an advice column on navigating the modern workplace. Each week she will answer one or two questions from readers.

Reader: My boss is a bad tipper. When we eat out for business, he always tips less than 15 percent (sometimes a good deal less). He's not trying to make a statement about poor service. And it's not a matter of him trying to be a good steward of our company's funds, as our business-meal policy does not limit gratuity. He's generally a very frugal guy, and I'm not sure he even knows what an appropriate tip is. I find this rather embarrassing, but I don't know what I can do. I wouldn't mind slipping the wait staff some extra money if I could do it discreetly. I don't feel comfortable saying anything to him because I'm sure he'd take it personally.

Karla: If he were a cheap date, or a sweet, thrifty relative treating you, you could just slip your server a few extra bucks on your way to the restroom. But when your boss is getting reimbursed, it hardly seems fair for you to compensate for his cluelessness out of your own pocket.

You could try steering the boss to one of the few restaurants that have replaced tips with European-style service charges - but he might chafe at being denied control over the gratuity.

I don't generally endorse staged discussions for grown-ups, but they can be a useful way to educate someone who outranks you without causing loss of face. Start a conversation about dining out, and sow the seeds for a lively debate:

"So, I know Washington Post critic Tom Sietsema says 18 to 20 percent is now the norm for tips in sit-down restaurants, but does anyone know if you're supposed to tip on the pretax or post-tax total?"

You can keep the discussion going with questions such as, "Should you tip the same rate for a high-priced bottle of wine as for a bottle of Chateau Cheap-eau?" or, "Do you add a tip for takeout?" And here's an amuse-bouche to chew on: Under federal law, a restaurant can pay a server as little as $2.13 per hour if tips from customers are sufficient to bring the pay rate up to minimum wage. While it's true that the server will receive at least minimum wage no matter what, I can't think of many professions other than panhandling in which one's daily take-home depends so heavily on the whims of strangers.

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Tom's answers:

(1) Pretax tipping is fine, but "really, what's a few extra dollars?"

(2) Although sommeliers Tom has polled can't seem to reach consensus, generally, the primo vino requires expertise to store and decant properly and thus merits a larger tip. [And really, do you skimp on gratuity when you order a Kobe beef filet instead of the flank steak? If you want to tip less, order accordingly.]

(3) Tip a few bucks on takeout from somewhere other than a fast-food counter, to account for the extra effort of packaging your meal for travel.

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