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The idiot’s guide to entertaining the boss

By Sheila Norman-Culp | ASAP – 04/29/2007 – 12:00am

Spending time with your boss outside of work? Make sure you don’t look like an idiot.

Big news: The boss is coming to town, you have an important outing ahead. Will it be high times on the company dime, or a series of potential disasters just waiting to blindside you?

Hmm, maybe both. 

Some work issues never go out of season; Malcolm St. Clair directed the movie “Entertaining the Boss” — in 1922 — and managed to get his universal point across even without sound. But you sure don’t want to hear the dead silence that follows when you trample social expectations with your cluelessness. 

If you are going to run through a minefield, you might as well know what explosives look like. Here’s a primer to help you dodge the worst faux pas. The charming-the-boss part I’ll leave up to you.


Rule No. 1: Your bosses are not your friends. They can be friendly, they can be a riot, you could WANT to be their friend — but everything you are doing and saying outside the office will be judged. Even if they insist they are not doing it, they are judging you subconsciously. 

This doesn’t mean you have to be a stiff party-pooper or a paranoid toady. It does mean you edit out your repertoire of sexist, racist and homophobic jokes, and limit your liquor. You also need to find out enough about them and others at the event that you don’t mock a profession or passion dear to their hearts. 

Sue Fox, author of “Business Etiquette for Dummies,” says the biggest mistake people make is trying too hard to impress. 

“Just be yourself and friendly,” she advised in an e-mail interview. “Do not ask too personal a question and never engage in a debate on a particular issue.”


Understanding the reason for the outing is the single most important thing that guides your behavior. A day at the country club could be anything from a relaxed annual party to a winner-takes-all rivalry between departments, a welcoming gesture to a new customer or a key sales pitch with your company’s biggest client. 

Are you going to kill yourself on the links to beat the marketing department? You bet. Are you going to embarrass a business guest by whipping a tennis ball at their head? Let’s hope not. 

No matter who is winning, Fox warns that you should never “get overly excited or behave in an inappropriate manner” such as yelling or swearing. 

Especially when the outing involves some athletic ability — golf, tennis, sailing, skiing, climbing — you need to find out the general level of skill expected and adjust your competitive nature accordingly. If you think you might panic when faced with a cliff and rappelling equipment, beg off. The point is to have fun, not to embarrass yourself.


Eating at our desk at work, snacking in front of the television at home, grabbing a bagel on the run because we’re late; many of us have no clue as to how bad our table manners have become. 

Like many colleges, Florida State University publishes an “Etiquette Survival Guide” to help students navigate their transitions to the business world. It suggests you let the boss take the lead — for example, don’t order three courses when he or she orders one. Pick items in the middle of the menu price-wise and stay away from hard-to-eat meals — Sloppy Joes, anyone? — that could leave big stains running down the front of your shirt. 

FSU’s best advice (one widely ignored in this 24/7 world)? Don’t talk with your mouth full. You might be so eager to tell your story or make your point you don’t realize you are doing this, but see-food is best left to middle school.


Don’t get drunk with your boss. Yes, this is stating the obvious, but it’s amazing how often the obvious must be stated. 

Some etiquette experts suggest not drinking at all at business events — but that could go over fairly badly with, say, a roomful of car salesmen. 

If you don’t drink, don’t. If your boss is drinking and you would like to, go ahead with moderation. If your boss is not drinking, take the hint. 

Whatever you do, don’t end up dancing on the bar during your first month at work.

Actually talking with your boss — for several hours, mind you — is a challenge you need to gear up for. 

Are there any important topics you need to touch on? Are there any burning problems your boss is going to ask about? What common, light topics can you discuss so as to avoid those long, awkward pauses? 

An industry awards banquet is no place to lay out all of your work woes — in fact, no one wants to be at any event with someone who whines for hours. But if you spend a full day or evening with your boss and don’t acknowledge a looming iceberg, he or she is going to feel blindsided. Briefly touch on the subject and promise a full accounting back at the office. 

If there are key accomplishments to note, mention them but move on. Braggarts are tedious. 

“Keep it simple and fun,” Fox says. “Be positive, stick to informative and current events.” 

Those current events do NOT include your recent divorce, custody battle, dating woes, money troubles, drug habits; you get the idea.

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