"When you golf with your boss, you don't just have to lose, you also have to make it look good!"
That may be your first thought. Most bosses can handle losing, but that doesn't mean there aren't some things to make note of when playing golf with your boss.
Have fun
No one, even your boss wants to go play a round of golf with someone who is so serious about the sport that she can't enjoy the game.
Temper the temper
Bosses do tend to believe that a round of golf with some of the folks from the office will reveal character. Whatever you do, do not lose your temper over a bad shot, slow players ahead, or anything else.
Caution with coaching
If you are a better golfer than your boss - or you hit a lucky shot - your boss may ask you for a tip about the game. If you can avoid coaching the boss without offending her, do it. Chances are she was asking just to take the pressure off herself - not because she wants coaching. If you do offer a tip, don't offer a second. One request for a tip is not your license to coach or critique the boss for the rest of the round.
Observe the rules
Never cheat when playing with the boss. Not one stroke. Even if, the boss can't count to six.
Follow etiquette
Always follow the golf etiquette your grandfather taught you when playing with the boss. Defer to her to decide if any variation from old-school golfing manners will be tolerated.
Don't drink if the boss doesn't
If the boss isn't drinking, don't start. If she's drinking, don't feel pressured to drink and certainly don't drink to excess. Stay sharp so as not to do or say something you'll regret.
Let the boss keep score
You can't get in trouble for marking the wrong score if the boss is marking the scorecard. If she asks you to keep score, be sure to ask her for her score at every hole - don't count her strokes.
Let the boss drive
Unless the boss specifically asks you to drive the cart, let her drive. You'll reinforce her control and make her more comfortable by letting her drive.
Don't look for lost balls
When you hit a ball out of bounds and can't see your ball, don't hold up the group for even a moment looking for the ball. Have plenty of spares when you start the round.
Be sociable
Show an interest in your boss at a personal level. Most bosses have kids and every parent loves to brag a bit. Give your boss a chance to talk about her family.
Respect the course
By demonstrating respect for the course, you show your good character. Your boss will presume you treat company assets the same way you treat the course. Fix all of your divots and ball marks.