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How to travel with your boss: 7 tips

One of these days, you will have to travel somewhere with your boss. Will the trip be a career maker, or will you come home to clean out your desk?
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Travel on business often enough and it’s bound to happen: You have to travel somewhere with your boss — or his boss or their bosses. Any of these people can affect your career, for the better or for the worse. There is no question that it can be a time of added stress, but it can also be an opportunity to improve your position in the company.

You are probably all too aware of the added stress, so let’s concentrate on the opportunity angle. According to Lee Silber, author of “Career Management for the Creative Person,” there are two things to do when traveling with your boss: Have an objective, and be prepared.

The stated purpose of your trip may be to resolve a manufacturing problem, sign up a new client or gather information about a competitor. The unstated purpose should be this: Advance your career. The particular objective is up to you. For instance, you may want to show your boss that you are a first-rate presenter, or an expert in a particular field, or a person with a wider range of management skills than your boss normally sees in the workplace.

Preparation is key, and for that you need to know two things: what your boss is like, and what the trip can do to show you off to advantage. Here are some pointers:

Flesh out your itinerary. You are likely to be given a basic itinerary that includes your travel dates and times and the location of your hotels. Take it upon yourself to fill in the blanks. For instance, you might note that you intend to meet for breakfast at 7 a.m. to review a presentation. Or you might list the telephone numbers of the clients you plan to visit. Or you might throw in a reminder that a company you will be visiting just posted record profits.

Once you’ve added some meat to your company’s standard itinerary, send a copy to your boss a week or so in advance of your trip. The idea here is to add information to your itinerary that your boss will find useful and that shows efficiency and initiative on your part. This exercise will also help you determine where opportunities lie for you to demonstrate the skills that will help you meet your career objective for the trip.

Learn about your boss. Sure, you may know the company line on your boss: his duties, his responsibilities, what is written about him in the media. But do you know his hobbies, his charities, his workday routine? By learning about the personal side of your boss, you can engage him in conversation that he finds interesting. Likewise, by knowing your boss’s habits and lifestyle, you are less likely to stumble. You won’t, for example, take your vegetarian boss to an all-you-can-eat rib joint.

Learn about the destination. With just a little bit of research, you can become a near-expert on the fastest way to get to and from appointments, the best restaurants for your boss’s favorite dishes, and a couple of cool, off-hours diversions that can impress your boss with your ingenuity. If you are clever, you might even be able to finagle an upgrade somewhere along the way.

Be extra prepared. There’s a chance your travel plans will go awry -- a very good chance. Though you can’t prepare for everything that can go wrong, you can have contingency plans for the more likely difficulties. For instance, know the name of a nearby hotel in case yours has been overbooked. Carry an extra battery for your cell phone, laptop or camera (or your boss’s). Bring along hard copies of PowerPoint presentations. Then, when something does go wrong, you’ll look like a star.

To this list of “do's,” I would also add three “don’ts.”

Don’t complain. Whining about a bad situation is what people do when they aren’t working to resolve the problems that can get them out of it. Complaining reflects a lack of creativity and a focus on all the wrong things.

Don’t lose your temper. Emotions cloud rationality and make for an uncomfortable atmosphere. And what boss wants to supervise a person who can’t control his emotions?

Don’t venture into sensitive subjects. Stay away from topics that might be flammable. Politics, religion, sex and personal hygiene, for instance, can all be career-ending conversation starters.

With some forethought and a little effort, you can turn the next trip with your boss into a career advancement opportunity. Plan ahead and execute carefully. As Silber says, “It will provide the confidence that comes from being prepared.” And confidence, we all know, is half the battle when it comes to impressing the boss.

Terry Riley, based in Santa Cruz, Calif., is a corporate psychologist specializing in the management of travel behavior. Terry is the author of "Travel Can Be Murder" and "The Complete Travel Diet." He also edits , a satirical news report. or .