In my experience as a corporate flight attendant, I have had the good fortune of being a "fly on the wall," which gives me a chance to observe -- in close proximity -- employees traveling with their boss. And usually it's the CEO of the company. It's fascinating to see what happens when employees make blunders that may seem insignificant at the time; but in reality those missteps may potentially hurt their standing or even stunt their advancement in the company.
The first thing you should never do -- so I guess that makes it 10 things -- is never forget that your boss is watching and evaluating you at all times.
If you were chosen to go along on a business trip, it's because you're supposed to be part of the solution -- never part of the problem. And your boss wants to be sure that he or she can count on you to represent him/her appropriately when you're not being watched. Therefore:
1. Remember at all times that this is your boss. Don't get so comfortable in the conversation that you start sharing your problems or inappropriate details of your personal life. Be personable of course, but never air your dirty laundry.
2. Be early. Whether it's meeting at the airport, meeting at a restaurant, or meeting in the hotel lobby, don't be late -- 10 minutes early couldn't hurt. And don't arrive looking stressed and/or disorganized. Have your documents handy and in one place. Have your luggage organized. Don't look as if you rushed out the door at the last minute. If you look a mess, you will likely be considered a mess.
3. Never be rude to staff -- any staff, ever! Whether it's an airline employee, a hotel porter, or a waiter in a restaurant. If you're rude to these people, how will your boss know that you won't be rude to a customer or someone who you didn't realize is a client? Case in point, one evening on an executive-filled flight from Teterboro to Los Angeles, there was a fresh new face among the regulars. I hadn't seen this woman before, but I knew she had stars in her eyes and was doing her best to impress her superiors with her keen knowledge and witty repartee. Problem was, she was rude and dismissive to all the "staff," the pilots, her driver, and, of course, me. She certainly wasn't following anyone's lead with her behavior, as all of the other passengers were friendly and a pleasure to have onboard. But it did stand out to everyone on the flight. Funny, I flew with those exact executives several more times... but I never saw her again.
4. Don't be difficult, picky, or ask for special favors. When you go out for business dinners you will have to go with the flow, even if its not your kind of food. This means not requesting that your food be gluten-free (unless you have a serious allergy, of course) or asking whether the sauce is made with cream. It also means not complaining about your room or acting as if being along for the ride on this trip has magically granted you some kind of privileged status.
5. Be neat and well dressed in appropriate business attire. Even if it means sacrificing a certain degree of comfort. And especially of your boss is always well dressed, take that as a cue. You wouldn't (I hope) arrive at work unshaved, so you shouldn't arrive at the airport with a five o'clock shadow. Remember, if you're with your boss, you are at work -- only the venue has changed.
6. Never drink too much. Some people would say never drink at all, but if you're at dinner and everyone else is ordering a cocktail or a glass of wine, I don't think there's anything wrong with that -- so long as you monitor yourself and know your limit. Remember, because of the thin air, every drink in-flight equals two on the ground, so pace yourself. The goal is to always act professionally and appropriately. So if no one else is drinking, you shouldn't be either.
7. Just in case... have an "out." Don't let your boss lull you into behaving unprofessionally just because he (or she) is. Be prepared with a list of three or four non-company "safe" topics (food, restaurants, sports, etc.) you can immediately use in case the conversation starts to take a turn that makes you uncomfortable. And don't allow yourself to do or say anything that makes you uncomfortable just because he or she is your boss.
8. Be discrete. Keep your cell phone out of sight, and if you must leave it on, put it on vibrate. If there's a call you feel you absolutely have to take, excuse yourself and go outside or someplace where you can talk privately.
9. Never lose your temper Don't cry, or otherwise lose your cool, no matter what happens. If your luggage is lost, figure out how to calmly resolve the problem (if you check your suitcase, always have enough clothes/supplies with you in case your bags are lost). If everyone else gets the fabulous deluxe suites, and the hotel is oversold and you get the regular room with twin beds, a "dumpster view" with screaming alley cats, handle it with decorum.
It's in these moments of stress that your boss can accurately see how you handle yourself, so you need to rally and be a champ. There's always a way to transcend a situation, and your boss shouldn't ever feel that he or she has to take care of you.
As I said in the beginning -- if you are traveling with your boss, you're supposed to be part of the solution, never the problem.