It's a lose/lose situation. You get his hopes up. He thinks you're cheap. Giving a waiter five dollars on twenty-three dollar tab is normally a good tip. It's more than 20% which is more than average. Giving a waiter five dollars on twenty-three after complimenting his service, however, is the lose/lose situation.
It doesn't matter how busy or slow or what time of day it is. It doesn't matter if your words are genuine or insincere. As soon as you let slip how great you thought the server did, you might as well have included how you don't plan on tipping him to his expectations. Unless you graciously give a ridiculous amount of money to him, he will be disappointed in your ability to tip.
Most servers hate their jobs. Granted, there are a few who enjoy what they do, but on the whole, I would be willing to bet that 90% of the servers in the United States dislike their occupation. When a person clocks in for a shift with this attitude, he is more likely to have a pessimistic view toward the guests. It may not be reflected in the way he carries himself or speaks, but little things throughout the shift will be viewed from a different perspective.
When a person watches a movie and then raves about how good the film was to his friends, he is placing high expectations on that movie. When his friends go see the movie, they expect to love it, but because it was over-hyped, it only leaves them disappointed. The same thing happens when a guest verbally informs his server how pleased he was.
In the service industry, this is known as a verbal tip. A waiter is so rarely recognized for his or her services to the guest. Sure, that recognition comes in the form of gratuity (on what they hope is) on every tab. Very seldom, though, will a guest take the extra step to let the server know they are appreciated. Nine times out of ten, this guest will leave an inadequate tip. As a result of this, a server is immediately turned off by a guest's verbal remarks on the service. If he's been waiting tables longer than a month, he will expect a small amount and will view any fair amount to be insufficient.
There are exceptions to everything and this theory should not be excluded. A good rule of thumb, however, is to just avoid giving any verbal tip. I'm not suggesting ignoring the server, but you're showing your appreciation in a monetary form. There's isn't any reason to give him any reason to be ungrateful for that sum.
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