How To Avoid The Embarrassing Etiquette Dilemmas Of Traveling With Your Boss

Being invited on a business trip with your boss is a great opportunity: You get one-on-one time with a higher-up, the chance to learn from her, and to prove your mettle on the road. But that road can be full of pot-holes, too. Business travel includes all kinds of etiquette quandaries that never come up in the office. Should you eat every meal with your travel companion? What if she drinks too much? How do you avoid awkwardness if you’re sharing a hotel room? I asked several experts for their input on traveling with your boss.

The most important rule to keep in mind is this: “You are never off duty” says Frances Cole Jones, author of The Wow Factor: 33 Things You Must (and Must Not) Do to Guarantee Your Edge in Today’s Business World. “Just because your boss has loosened his tie or had her third margarita does not mean he or she is your friend.” Repeat this mantra to yourself over the course of the trip.

Should you have every meal together? Let your boss lead the way, but don’t feel obligated to stick to her like glue. Jones says that splitting up for breakfast, at the very least, can give everyone “a chance to collect themselves for the day.” If you want to politely carve out some personal time, you can say that you have to return some calls or write some emails.

When it comes to after-dinner drinks, be cautious. “Maybe one drink, but loose lips sink ships,” Patricia Rossi, a business etiquette expert in Tampa, told me. “In this economy, we’re all trying to hang onto our jobs, so we need to have very ounce of wits about us.” Jones says a drink or two is fine, “but don’t keep up drink for drink, and definitely don’t pull ahead.” And this isn’t the time to indulge your taste for obscure high-maintenance cocktails. (An Algerian Typist, anyone?) “Keep it simple,” Jones says. “Beer, wine, or a blank-and-tonic.”

If your boss overindulges and something embarrassing happens, be discreet. “Don’t speak about what you saw when you get back to the office,” Jones advises.

What if you’re sharing a room with your boss? First of all, I’m sorry. But there are ways to minimize the awkwardness of sharing close quarters with the woman in the corner office. Be tidy, to start with. “You’re already sharing a space, you don’t want to make it look like a tornado hit near your bags,” Diandra Lamas, a 23-year-old who has traveled several times with her boss, tells me. “Don’t take a hot shower for 45 minutes,” Rossi says. “Be respectful and tidy.” And don’t let it all hang out: “Bring a bathrobe in addition to super-chaste pajamas,” Jones says.

You can casually discuss ahead of time if you’re an early riser or a night owl. Either way, frame in a polite way, Rossi says: Say, “I’m a night owl, and I have this little book-light to read with; do you mind?” or “I’ll be getting up early for coffee, can I get you anything?”

As for the one other room-sharing question you know you’re worrying about? “If you have to do something lengthier than number one, try to use the hotel lobby,” Rossi says delicately. “Try not to stink up the joint.”

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