How To Survive 18 Holes With Your Boss

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Your boss just asked you to join him in his weekly golf round. The good news is that nobody gets fired on the golf course. I mean, when would the appropriate time for the firing occur? The 18th? If the fired beat the firer, wouldn’t that make it painfully awkward? If you crush a guy by 10 strokes and then tell him not only did he lose his ball on the last hole, but he also lost his job, doesn’t that seems a bit excessive? Anyway, I digress. The bad news is that you will have to be on your literal and figurative game the entire time so as to not make the previous scenario a reality. Your boss is most likely trying to get to know you better, and if you want to cruise down that company fairway, then listen up.

Muted Dress

You know that saying “Dress for the job you want, not the one you have?” Fuck that. If you come to the course wearing a John Daly-esque outfit thinking you’ll impress your boss, it’s going to be rough. The best course of action is imitation. Dress as similarly to your boss as you possibly can. Come in pants and a polo. If he’s wearing shorts, tell him you were wary of the weather and have shorts as a backup. Under zero circumstances may you wear a flat bill. Only Ricky Fowler pulls that off and most people hate him anyway.

Come Prepared

I don’t know what your golf game is like, but if you lose a ball and have to ask him for one, that’s embarrassing as hell. Head to Walmart and grab a 12-pack of balls, plenty of tees, and throw a new golf glove in that cart. Definitely have a divot fixer and a ball marker. Those simple things will show that you respect the course and the game. This may even indicate that whether it’s a round of golf or a budget meeting in disguise, you have your shit together.


Mulligans, gimmies, lost balls, and so on can be tricky because you haven’t played with your boss before. You don’t know what kind of game he plays. Again, imitation is your best wager. If he takes two off the first tee, feel free to do the same. If he putts out a two-footer, you better tap in all your putts for the rest of the day. Nothing will make you feel more like a jackass than bending the rules and getting the sideways glare that says, “Really, man?” There is one exception you may flirt with, which is hitting back one of his long putts, closely followed by a confident, “That’s close enough for me, sir.”

Round Rage

If you play golf with me, you’ll quickly find out that long irons aren’t just for far approaches but that they also double as a fairway javelin. If that’s your style, too, then you have 18 holes to keep it together. I don’t care if he’s the John McEnroe of his club, you need to keep your cool. I’m not outlawing any swearing, but if you’re more liberal with your F-bombs than “The Wolf of Wall Street” script, you’ll probably raise some eyebrows. Your boss will be more inclined to invite you back out if you don’t embarrass him in front of the people he sees every week.


Have I mentioned that I think you need to imitate his behavior? Join him in the clubhouse and when he buys a few beers, follow suit. DO NOT bring you own booze to the course. He doesn’t want to throw back some Black Velvet three holes in. This isn’t “see how tanked you can get by the turn.” I would start on the light side in the clubhouse and have a cash reservoir when the beverage cart comes around. This opens you up to being able to buy him a few on the course. If the round goes well, he may even return the favor at the end.

All in all, just have a respectful evening with your boss. If you have the game to crush him, hold back a bit, but definitely don’t let him win. He’ll know it, you’ll know it, and it will be mutually humiliating. Well, unless you really hate your boss. Then grip it and rip it. Job security is overrated anyway.

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Striving for that perfect Dad body one vending machine candy bar at a time.

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