How To Play Golf With Your Boss...

  1. ...and Let Him Win Without Him Realizing It
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    ...and Let Him Win Without Him Realizing It

    Few things are as daunting as being invited to play a round of golf with your boss. This is three hours alone with the person who’s responsible for your livelihood and could fire you somewhere around the seventh green. But should you let him win? Duh. Here are eight simple rules that will help you do it efficiently and inconspicuously.
  2. Dress the Part
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    Dress the Part

    One of the best things about golf is that you’re allowed, even encouraged, to dress foolishly. “Your goal should be to make your boss look better than you, yet not be embarrassed by you,” says Gary Rudoren, co-author of Comedy by the Numbers. He suggests going for an uncoordinated Payne Stewart look. “Mismatched plaids say, ‘Hey, I’m a student of golf fashion, but not a slave to it,’” says Rudoren.
  3. Play with Decent Clubs
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    Play with Decent Clubs

    Ratty clubs don’t demonstrate frugality. They demonstrate that you don’t care about golf. “You shouldn’t take your father’s old clubs,” says David Owen, a contributing editor at Golf Digest. It’s actually better to rent clubs from the clubhouse. John Peter Hagen, author of Play Away Please, insists most rentals aren’t rusty, warped rejects. “They’re equal, in almost all cases, to what you will purchase,” he says.
  4. Don't Get Wasted
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    Don't Get Wasted

    Golf may be an excuse for daytime drinking, but don’t take it too far. A cocktail is fine, but remember, boss golf is like polygamy: Only one person gets to overindulge. “Even if you can outdrink the big cheese, that’s rarely a good idea,” says Zane Lamprey, the host of NDNet’s Drinking Made Easy. “Better for him to say, ‘Wow, last night got away from me’ than you.”
  5. Let Your Boss Have His Meltdown
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    Let Your Boss Have His Meltdown

    There’s a very real chance that your boss sucks at golf. If he does, he may throw clubs or unleash a tirade of obscenities. In this case, disappear. “If he’s having a bad day, stay out of the way,” says Owen. To be safe, he says, always remember, “No golfer ever gave a s--t about how any other golfer played.”
  6. Definitely Let Him Cheat
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    Definitely Let Him Cheat

    Pretend you don’t see your boss misinterpreting the score. “You’re not there to be a rules official,” says Dr. Joe Parent, author of Zen Golf. Although Richard O’Neill, an associate professor at the State University of New York Medical University, warns that cheating may suggest a pattern of deceit: “One needs to do an assessment of whether one can tolerate a little white lie.” Either way, “It’s his karma,” says Parent.
  7. Don't be a Moron, Let Him Win!
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    Don't be a Moron, Let Him Win!

    Some people will tell you that your boss will respect you more if you compete as an equal. These people are now working at Denny’s. “Isn’t it better if your boss ends up winning?” says Parent rhetorically. Do not, under any circumstance, win—that’s the ultimate golf faux pax. As a wise man once said, lose in an un­assuming way, and keep your job another day.