How To Travel With Your Boss

Traveling with your boss doesn't have to be stressful.
by Updated January 29, 2009

Mention the idea of traveling with their boss to most people, and panic immediately sets in.  I'm sure you immediately imagine just how damaging a bad trip might be to your career, so there's no need for me to go on about it!  What most people forget, though, is that traveling with your boss gives you a great opportunity to make a positive impression.  If you do it right, your prospects in the company can be greatly improved.

There are two major things to remember when traveling with your boss - have a goal, and be prepared.  Firstly, what's the goal of the trip?  Perhaps it's to sign up a new client, solve a problem or gather information.  Underlying that, though, should be the goal to - advance your career.  You need to work out how to put the two together.  If you're going to be giving a presentation, then make sure you have everything ready, you've practiced enough to do a great job, and show how comfortable and confident you are in that situation.  A business trip can be a great chance to show your boss the skills you possess that perhaps don't always get highlighted at work.

Preparation for the trip in general is also important.  Show your boss your level of commitment by adding to the basics.  If your basic itinerary only includes flight and hotel details, maybe type out a sheet with scheduled client meetings, or review meetings over breakfast with your boss.  Add a couple of notes to help your boss be prepared too, such as an outline of who you'll be meeting and what their role is.  Send the enhanced itinerary to your boss a week ahead of the trip.  Remember, the aim of all this is to help your boss be prepared, but make sure you demonstrate your initiative and efficiency at the same time.

Ask around and find out what you can find out about your boss outside of work.  Does he like golf?  Maybe you can fit a round of golf into the trip itinerary.  What's his favorite food?  Well, guess what sort of restaurant you need to book.  If he has any hobbies, learn a little bit about them.  Don't make the mistake of trying to learn everything and then showing off, but learn enough for you to be able to hold an intelligent conversation with your boss on the subject. 

Spend some time researching your destination.  With the help of the Internet, you can find out the tricks of getting around quickly, what restaurants serve your boss's favorite dishes, and any other local attractions that your boss might find of interest.  All of this information can help you if things go wrong with the travel arrangements.  If you turn up at your hotel only to find they've lost your booking and can't fit you in, that's okay - you can tell your boss about the great hotel just two blocks away which is actually closer to your client's office.

Remember, too, the more mundane things - spare batteries for everything, and hard copies of any PowerPoint presentations.  Have a contingency plan for everything you can think of.

Travel can be stressful, and chances are you're already going to be nervous about traveling with the boss, but this is not the time to lose control.  Keep your temper down at all costs, and don't complain or whine if things go wrong.  Use it as an opportunity to demonstrate your resourcefulness and calm response to pressure.  It's important, too, to avoid talking about sensitive subjects, particularly if you've both had a couple of drinks.  Avoid politics, sex, religion and personal hygiene at all costs.  It might seem funny or important at the time, but chances are there's a black tick against your name afterwards.

Traveling with your boss can be a great opportunity, but you can't just head off and hope it works out that way.  Do your homework, make sure you're prepared, and do everything you can to help things go smoothly.  Your boss will appreciate it, and your future career prospects will definitely improve.



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