Traveling with Your Boss: The Etiquette of Planning Ahead for Success

traveling with your boss, tips on traveling with your bossTraveling with your boss adds a new layer of complexity to any business trip. Instead of just worrying about yourself, you have to factor in the expectations and interests of your boss.   Some bosses expect their junior executives to take care of everything – from arranging transportation, setting up meetings, booking the hotel and securing reservations for dinner. Other bosses take the lead and expect you to keep up. Wherever your boss falls on the spectrum, these tips will help you make a great impression on the road or in the air:

  • Stock up on cash. Keep an ample stash of dollar bills readily available. You never know when you will need to tip someone – a valet, a skycap or the shuttle driver who assists you with your bags. This is your first opportunity to show your boss you are in control and prepared.
  • Pack with care – You won’t need a trunk-full of suitcases if you pack well and include several pieces that you can mix and match.  Don’t make the mistake of bringing more luggage than your boss. It will look like you are either a prima donna or a traveling novice when you show up to the airport with 3 more bags than your boss and have to pay extra because each one of your suitcases is over the limit.
  • Avoid medication on the flight. Even if you’re flying across six time zones and you would prefer to sleep through them all, it’s in your best interest to be alert in the event your boss wants to talk business on the flight. If he or she puts on ear buds and starts to snooze, you may do the same.
  • Dress business casual. Whether you are traveling by plane or train, select an outfit that projects a professional image. Don’t let your professional guard down just because you are not in the office.
  • Plan on eating on your own unless you hear otherwise. Follow your bosses lead. If he or she asks if you would like to get a bite to eat, by all means accept but if there is not invitation to dinner, assume you are on your own.
  • Keep your own itinerary.  Rather than following your boss from meeting to meeting, look alert and informed. Keep track of the overall schedule and don’t hesitate to confirm meeting times with your boss.
  • Drink alcohol with discretion. No matter how manydrinks your boss may consume, stick to a one to two drink limit. Switch to a club soda with a twist of lime or some other “mocktail” and remain engaged in the conversation, not the alcohol consumption.
  • Keep the company credit card handy. Unless your boss takes the lead, be ready to pay for expenses along the way: the rental car, the cab fare, the hotel bill. If you’re not sure how to handle the situation, simply ask your boss in advance how he or she would like for you to handle the expenses. It’s always better to be informed – safe than sorry.

The bottom line for traveling with your boss? Do everything you can to show your boss a confident, professional travel companion.

Safe Travels,


Diane Gottsman

Diane Gottsman is a national etiquette expert and modern manners professional, sought out industry leader, television personality, accomplished speaker, Huffington Post blogger, author, and the owner of The Protocol School of Texas, a company specializing in executive leadership and etiquette training. Diane is routinely quoted in national and international media including The New York Times, The BBC, CNN, Bloomberg Business Week, Kiplinger, Huffington Post Canada, U.S. News and World Report, and Forbes. She is the resident etiquette expert for two popular morning talk shows, SA Living and Good Day Austin. She has been seen on The TODAY Show, HLN Headline News, WGN Chicago, and CBS Sunday Morning. Her clients range from university students to Fortune 500 companies and her workshops cover topics ranging from tattoos in the workplace to technology at the dinner table and the proper use of social media.

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