How to Travel With Your Boss Without Making a Fool of Yourself

Anxiety Airlines Boarding Pass
From: Your City
To: A Place You Don’t Know
Seat: 10A*
Departs: 8 a.m.**
Arrives: 10:20 a.m.***

*Right next to your boss, 10B, so be cool.

**Your boss planned to meet you there, right? Or were you supposed to arrange transportation for her? Or were you supposed to meet at the office and go to the airport together?

***OMG, were you supposed to be in charge of the rental car?

While J.R.R. Tolkien wrote that “not all those who wander are lost,” those wandering through the airport in search of their boss are legitimately lost. Don’t veer off route before your business trip even begins. Here’s how to ensure a smooth trip and make the most of the one-on-one time with your manager:

Prepare. Think beyond the phone-keys-wallet mantra, and add to it: laptop or tablet, phone and computer chargers, business cards, presentation materials, tickets and anything else that would slow you down should you forget it. (Here are the 14 items you should always pack for a business trip.) After all, it’s one thing to be making a pit stop for underwear when you’re with your friends or family — it’s another thing to do so with your boss in tow.

Your travel preparation should go beyond thorough packing. How are you getting to the airport? Will be there Wi-Fi on the plane? What are the addresses of the hotel and meeting locations? Save yourself a carry-on’s worth of stress and potential embarrassment by figuring out these details in advance, suggests Dan Ruch, seasoned business traveler and CEO of Rocketrip, a company that helps organizations save money by encouraging employees to spend less while traveling for work.

Also talk to your boss to decide which one of you will take charge of various aspects of the trip, like reservations for hotels, rental cars and dinner, he says. “Taking the initiative to plan ahead sets a very good precedent for the trip overall,” he adds. “It shows that you’re organized and proactive.”

Keep it professional. “You’re not on a trip with your buddies — you’re on a trip with your boss,” Ruch says. “It’s important to keep that in mind [and] demonstrate professionalism always.” Specifically:

What you wear: Yes, you want to feel comfy for the flight or drive. No, that doesn’t mean throwing on sweatpants and a T-shirt. Remember the “business” part of business trip when choosing your wardrobe, Ruch says, and “always dress professionally.”

What you drink: “It’s always better to be safe than sorry, especially when alcohol is involved,” says Ruch, who advises a two-drink maximum. “Even if your boss decides to get loaded, it’s your responsibility to stay in control.”

What you say: Given the long hours and one-on-one time, the trip might start to feel equal parts personal and professional. “There will be a natural tendency to overshare,” Ruch says. “Don’t.” Drama between team members back at the office, rumors about why so-and-so quit, the details of your divorce, your opinion of President Obama — all off-limits. “You will always come out ahead and be respected as being professional if you decline to share information that you think is inappropriate to share,” Ruch says.

What you do: This is work, not play, so keep the games, social media and personal activities to a minimum, Ruch says. A 2011 New York Times article quoting Bruce Tulgan, author of “It’s Okay to Be the Boss,” suggests taking cues from your manager while traveling with him or her. “If the boss starts working on his laptop on the plane … the junior employee sitting next to him may want to analyze spreadsheets rather than play an online game,” the article states.

Take advantage of the quality time with your boss. Revel in this one-on-one trip. “As important as it is to be professional and have a clear understanding of what’s appropriate and what’s not, it’s also a really special time,” Ruch says. “You have a captive audience.” He says his best employees have taken business trips with him as opportunities to ask for feedback on their performance. You could also use this time to give input on business strategies or brainstorm ideas for the team.

Of course, you don’t want to push business talk if your boss isn’t up for it, so read the situation. (“If your boss puts on noise-cancelling headphones and starts watching a movie, then it’s time for you to back off,” Ruch says.) Better yet, give him or her an out by saying something like: “I’ve been thinking about X. Would now be a good time to talk about it, or would you prefer to talk about it back at the office?”

Chances are, Ruch says, your manager will be impressed that you brought up the topic and be game to discuss it. And that talk will pay off.

“Have a casual conversation about things that are professionally important to you and that you know will be important to him or her,” Ruch says. “You’ll get a lot of brownie points for that and cultivate a great relationship.”

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How to Travel With Your Boss Without Making a Fool of Yourself originally appeared on usnews.com

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