Traveling With Your Boss? Here’s How Not to Make a Fool of Yourself

Illustration by Erik Mace/Yahoo

There’s a business trip on the calendar, and you’re traveling with your boss. While it might seem like common sense, there are some very simple dos and don’ts of to remember when you’re traveling with your superior. If you want to keep your job, we suggest you read on and take notes.

Don’t pack like you’re going on vacation

Appropriately dressed woman on work trip. (Photo: Thinkstock)

Translation: Leave the Herve Leger dresses, short shorts, and sheer blouses at home. Regardless of where your work trip takes you—New York City, Jamaica or Miami— this is not the time to show some skin, bare your cleavage or prove just how toned SoulCycle has made your legs. The rule is simple: If you wouldn’t wear it to work, don’t wear it on a work trip. Office-appropriate dress codes still apply. Should your job take you somewhere warm (who among us has been able to avoid the Las Vegas Convention Center), make sure to pack light fabrics that breathe as opposed to slinky ones that make others breathe heavy—it’s an important differentiation.

Related: The Bizcation: The Ultimate Way to Enjoy Business Travel

Just say no to the in-flight service-slash-mini bar-slash-lobby bar

Tiny liquor bottles on ice (Photo: Thinkstock)

We get it, the jingle of tiny bottles on the flight attendant’s cart as it passes by you on a long plane trip is tempting. Or the way the miniature versions of your favorite liquor are arranged so beautifully in your room’s mini bar. Or how that beautiful, deep mahogany lobby bar seems to be calling your name, asking you to sit down and stay a while. Just. Say. No.

Getting drunk or even buzzed can lead to awkward moments when spending off-duty hours with your boss. This is not the time to get sloppy and explain to him/her that you really do deserve that promotion/raise/corner office. That’s not to say you can’t have a drink with dinner—being a straightedge isn’t necessarily good either—but know your limit and stay South of it. Like Deep South of it.

Keep the conversation topics bland and water-cooler appropriate.

Keep conversation work friendly (Photo: Thinkstock)

I’m sorry you’re getting divorced, but just because we boarded a plane together doesn’t mean I want to hear about it. This is not the time to bare your soul to your boss. If you wouldn’t casually say it while small talking in the office hallway then don’t say it now. It may feel like personal time given that you are out of the office—perhaps spending a lot of time together in the airport or hotel—but that doesn’t mean confessing all your private affairs is a good idea. Your boss likely does not want to hear about your ne’er-do-well brother, complicated finances, weird rash, nasty divorce, or last Tinder date. Not only does it cross into some uncomfortable gray area, it could perhaps work against you later should they be one of the loose-lipped variety. Keep your personal business just that—personal.

Stop calling/texting your significant other

Keep texts to your girlfriend/boyfriend/husband/wife to a minimum (Photo: ThinkStock)

You’re on a work trip and miss your girlfriend/boyfriend/husband/wife. That does not give you permission to spend half the trip on your phone, texting flirty messages, endless emojis, and selfie after selfie of you in front of the [fill in recognizable landmark here]. Check in with him/her from the privacy of your own hotel room at the beginning of the day and again at the end if necessary. Constant communication—especially during a meeting or lecture—is unprofessional, not to mention annoying for those around you. Your relationship should be able to withstand a few days apart. Remember, absence is supposed to make the heart grow fonder, not make you go over your data plan.

This is a work trip, not a dating app

Stop flirting with the waiter/concierge/guy at bar or—gasp—coworker. (Photo: Thickstock)

Sure, you’re away from home and meeting new people you may or may not find attractive. Or perhaps you never noticed just how cute your coworker is (and he/she is funny! Who knew?), but still, out-and-out flirting is a bad idea that can get you into trouble and send a message about you that you don’t want communicated. Keep things rated G to avoid a bad rating from your higher-ups.

Related: Hotels Are Courting a New Generation of Business Travelers

Go on a social media diet

A work trip is not the time for revealing selfies. (Photo: Thickstock)

So you’re keeping it together during your meetings/work meals but the second you leave your boss’ sight, you post a selfie on Instagram.

Photo: You in front of the mirror in your hotel room. Caption: “Look at my new dress! Too risqué for a business dinner?”

Photo: You with a bored look on your face. Caption: “Ugh, work trips are such a drag!”

Your boss may or may not follow you, but if you have a non-private account he or she likely looks at your posts from time to time. Remember that before hitting “share.” Do yourself a favor and use the few days away to take a break from social media. Your future, older, wiser and super-successful self will thank you.

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