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In restaurants, apartment buildings and seemingly every stop on the way in between the two, the etiquette of tipping is an increasingly elaborate, fraught social dance. This is especially true in NYC, and in their latest issue, New York Magazine waded into the debate: should we keep the current tipping culture as is, or switch over to a system where servers net higher salaries, and "service" charges are automatically added to the bill?
The feature mostly focuses on bartenders and waitstaff, but they interviewed a local doorman, too, who notes, "I know who doesn’t tip at the holidays. We distribute the cards on the door of each unit on December 12, and through New Year’s I total what we got and what apartment gave me more." (Just like when you're going out to eat, don't expect it to go unnoticed if you cheap out on the gratuity.)
In the world of restaurants, (generally low-paid) back-of-the-house workers like kitchen staff have been lobbying for service charges that would be spread more evenly among employees—as opposed to individual servers collecting tips from customers—and in apartment buildings, there's actually a similar option: the tipping pool.
In this system, residents put however much money they want into the pot, which is then distributed by management to staff throughout the building. This can be better for the employees you don't happen to see every day, like the guy who handles the building's garbage, and is also a convenient (maybe too convenient) way for the building's cheapskates to save face. Not surprisingly, big tippers would rather have the doorman know who the source of the extra cash is, and even doormen we've interviewed have mixed feelings about the tipping pool system.
Admittedly, there are lower stakes to changing the system in apartment buildings, where employees are already paid a full baseline salary with benefits (and are often unionized), as opposed to restaurant workers, who are frequently paid well below minimum wage with the expectation that they'll make it up in tips. However you tip at the holidays, remember: your doorman will always prefer cash.