Should I Stop My Boss From Drinking Too Much?

Last Updated Nov 24, 2009 4:53 PM EST

Dear Stanley,

My boss is a good guy, but sometimes he drinks too much and makes a horse's ass out of himself. With the holiday season coming up, there are going to a lot of parties. I like him and don't want to see him torpedo himself in front of HIS bosses. Is there anything I can do?

Signed,

Caring Subordinate

Dear Potentially Doomed Employee,

You are a heroic soul. I salute you. It was nice knowing you. May the road rise up to meet you where you go!

But seriously, you are about to embark on a perilous journey, one that may well be worth taking but still may end in your totally unjustified demise. Do you think that any person likes to be told they drink too much? I assure you they do not. The people who like it the least are the people who drink too much. In fact, if you had a PowerPoint chart on the subject, it would look like this:


Still, I can tell that you like your boss and want to protect him from himself. You must recognize the history of people who tried to protect people in authority from themselves. It isn't good. You know how many people told Caesar not to go to the Senate on the Ides of March? A lot. Did he listen? No. What happened to him? You know the story. Still, you can't blame the loyal ones from trying, and you can try, too -- if you do so very, very carefully and are prepared for failure.

Sit down with your boss at some point soon. Don't make it a formal thing. Just when you're having coffee or something. Make a random observation, like, "Wow, it's holiday time already. All those parties and stuff. Hardly seems like a year ago. I'm still getting over them!" You will have some kind of mutal chuckle. You may then continue with something like, "I'm always afraid I'm going to disgrace myself at those things. Last year I definitely came close to the edge. It's always that last glass of scotch that I don't need." Now you're talking about the subject. See how much he wants to participate. He may clam up at this point -- and you'd better take note. If he truly doesn't want to talk about it, you may be out of luck. But there's a fair chance that he'll regale you with a story of fellow miscreancy. Push the conversation along a little. Get him comfortable. Back off. Advance. Back off. Advance. You may be able to get onto the ground more than once. Then, suspend operations for a while, and come back for another round later. After the matter has been chewed over for a while, you might find it possible to say, "Bob, this year I'm going to stop you before you put the tie around your head and howl at the moon, if that's okay." It's difficult to see anybody getting too irate about a loyal person who wants the best for them. Of course, there are certain cases on the record of just that. So again, watch your step. I'm sure there were quite a few generals who told Napoleon not to invade Russia. Many were executed.