How To Drink Like A Boss, When You’re Drinking With Your Boss

How To Drink Like A Boss, When You’re Drinking With Your Boss


I spend several evenings each week dining with others, sometimes it’s with clients and other times it’s with the higher-ups. No matter the dining partner, at some point adult beverages will show up.

During the last few decades, I’ve seen a lot of damage caused by alcohol. From a good friend dying due to a DUI to another being fired because he didn’t know when enough was enough. If allowed; alcohol can be an ugly partner.

When drinking in the corporate world, here are a couple of thoughts: First, if drinking’s not your thing don’t cave to the pressure. I once worked with a person that wouldn’t come to the company picnic because alcohol was going to be served, a solid move standing up for his beliefs. Fast-forward 5 years, he gets a promotion and at the quarterly dinner I see him with a snifter of brandy, apparently his beliefs weren’t that deeply rooted. Second, if someone in your dining party doesn’t drink don’t bust their chops.

Banner Elk

So, when drinking with the higher-ups what’s the best way to go about it?

  1. If it’s after work don’t show up in cut-offs and a wife beater, unless you work at the cut-offs and wife beater factory.
  2. Exercise control, more than likely they’ll be picking up the tab; this is not the time to look at an open bar as a challenge.
  3. You have two ears and one mouth, use them proportionally. Don’t gossip or try to pry information out of your boss.
  4. If you drink, order a drink, not some novelty drink in order to get a laugh. Ordering a Sex on the Beach or a Slow Comfortable Screw might make the server chuckle (not really), but it’ll signify to your boss that you’re a total Ass-Hat.
  5. Don’t ramp up your alcohol content. If you start the night drinking beer, continue that path. If the crowd switches to shots of Fireball at 10:00 PM resist the urge. Upgrading or bouncing around with the alcohol content is a sure way to become a babbling idiot, right before you black-out.
  6. Don’t try to keep up. If you’re not used to drinking hours on end, this is not the time to start.
  7. Avoid talking about work unless your boss brings it up first. If peers and alcohol are present, stay away from talking about money.
  8. If your boss orders a Mud Slide and that’s not one of your go-to drinks, don’t follow suit, you’ll look like a brown-noser.
  9. Keep your belly full, even if it’s an appetizer.
  10. Have some cash. Just in case everyone bails and leaves you with the tab, you’ll have a way to cover it. You can sort it out in the morning after everyone realizes you saved the night.


Sin City


If you’re used to ordering an Alabama Slammer and wish to broaden your horizons, he’s some alternatives that might help.

  • Order a craft beer, It’s hard to get in trouble with beer; unless you drink 12 of them with a 9% ABV.
  • Bourbon & Ginger ale, a classic and no need for a top shelf bourbon.
  • Normally the house red wine won’t let you down and won’t throw up a red flag on the expense report.
  • Channel your inner Don Draper and order an Old Fashioned.
  • If you can take it, order a scotch neat.


As with most things in life, it comes down to being accountable and being smart, that’s it.

PSA time – If you feel that alcohol is becoming or has become that ugly partner do yourself and your family a favor and get help. From meetings at Alcoholic Anonymous to websites like One Year No Beer there’s help out there, but you have to take the first step.


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