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Surviving a Trip With the Boss
Power Trip · February 22, 2004

Leo Bringer remembers his flight with the know-it-all boss. It was mercifully short.

He and another co-worker were sitting in economy class — three across with their boss in a nearby seat — waiting to take off. "He knew everything you could think of," remembers Bringer, an Elmhurst, Ill., human resources manager. "He was telling us how far it was to the airport from our hotel and what was there to do at our destination."

So when a crew member asked for volunteers to take the next flight, guess who raised their hands at virtually the same time? Bringer and his colleague.

"As we exited the plane, we explained that we could really use the airline vouchers to take a vacation later in the year," he remembers telling the abandoned boss, who apparently was accepting of the situation.

Abbreviating a trip with a bigheaded boss isn't always so easy. A significant amount of business travel today is done in groups: Employees and their supervisors frequently travel together to a sales presentation or conference or to meet a prospective client. How do you make sure you return from your next trip with a job? (And conversely, if you're a supervisor, how do you make sure your star employee doesn't bolt the company after you come home?)

The short answer: with a lot of common sense. And go easy on the alcohol too.

Here are six tips for surviving the next trip with your supervisor (or employee):

View a trip as an opportunity — not an affliction. A trip together is a chance for a supervisor to learn about life in the trenches from an employee. It's also an opportunity for an employee to get the boss's perspective on work. Play your cards right and you could end up with an improved relationship; go into the trip fearing the worst and it could become a self-fulfilling prophecy.

Remember: It's business travel. It's easy to forget that when you're staying at a hotel — especially a resort hotel — and you begin to see your co-workers dressing casually. You might even start thinking you're on ...vacation. Big mistake. Actually, it may be the biggest mistake you can make when traveling with the boss, because it affects your perspective, your productivity, and possibly even your prospects for a promotion.

Just say no. Alcohol and traveling with the boss is generally a bad idea, most agree. Williams remembers the executive who made a pass at her one evening after having too much to drink. "He kept asking me, 'What's your lucky number?' And then he'd dangle his room key in front of me," she says. Ugh. Booze lessens your inhibitions, but it can also ruin a business relationship. Williams turned the exec down — and he didn't show up for the next day's meeting because he was too humiliated.

Know when to say yes, too. At the same time, understand that there will be things you might be asked to do (or might have to ask an employee to do) that you wouldn't at work. For example, it might be appropriate for a supervisor to ask you to wear a suit and tie to dinner one evening (it you might be wise to say yes). However, it might be less appropriate for an employee to ask a supervisor to look after a pet Chihuahua (never mind that a canine doesn't belong on a business trip unless you're a professional dog trainer visiting a dog show).

Remember, it's still your boss. Being out of the office can make you forget the corporate hierarchy. And that, too, can spell trouble. That's what A. Mark Hom discovered when he traveled with his supervisor, a fiercely independent — and at the time, pregnant — supervisor, a few years ago. "As soon as we got off the plane, due to her pregnancy, she had to go use the ladies' room," he recalls. In an effort to help her, he pulled her luggage off the carousel. "Well, when she came out of the ladies' room and saw that I had had the temerity to take her luggage off the revolving track, she was incensed, told me that she was fully capable of doing that herself and told me never to do that again. I never did," says Hom, an Alameda, Calif., attorney.

Don't leave your sense of humor at home. That's the consensus of all the business travelers I spoke with. Whether it's Hom chuckling at his determined boss, Williams laughing at the lecherous executive, or Bringer smirking at the chatty supervisor who has to fly solo, a little wittiness can take you a long way when you're away. That's my own experience, too.

I don't like to end a column on a downbeat. But sometimes, despite your very best efforts, you're still stuck with a boss or employee who is unbearable. Often, the only way to deal with that person is to ride it out. Figuratively speaking, and sometimes, literally.

Patrick Cahill remembers one such business trip, with a manager who had a strange way of driving the company car — he'd keep accelerating the vehicle and then coasting, accelerating and coasting. His head bobbled with each push of the gas pedal.

When Cahill suggested the ride needn't be so turbulent, the manager feigned ignorance. "When I asked why he wasn't using the cruise control, and then I offered to drive, he started to get irritated with me," he says. "I just shut up and bobbled for the rest of the journey."

Christopher Elliott is a travel commentator based in Key Largo, Fla. All e-mailed questions may be edited, condensed or republished at the site's discretion.

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