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Top Five Tips for Traveling with Your Boss

Feb. 2, 2015
Traveling with your boss on business can be stressful, but with a bit of planning and preparation, you can make it a great opportunity to advance your career.

Business travel can be stressful, with unfamiliar people, places and situations keeping travelers on edge. If your boss is coming along for the trip, that can crank the anxiety up even further.  But with a bit of planning and preparation, a business trip with your boss can be a great opportunity to advance your career. Here are five tips to help you turn a business trip with your boss from an angst-inducing scenario into a professional plus:

  1. Define your roles before you leave. Don’t make assumptions – make sure you know up front what your boss expects during the trip. If she expects you to deliver the presentation to the client, you don’t want to find out in the car on the way from the airport to the customer’s office. Also sort out more minor travel coordination roles in advance, such as who will make dinner reservations, arrange taxis, book and drive the rental car, etc. Offering to handle those details can earn you some points, but be prepared to follow your boss’s lead.
  2. Look sharp, travel light and get to the airport early. You don’t want to start the trip with your boss frantically searching for you at the final boarding call or arrive at your destination and keep your boss waiting while you retrieve your luggage. If possible, travel with a carry-on bag only, and get to the airport first. You’ll want to arrive at least an hour early for domestic travel and up to three hours prior to an international flight. Also, dress professionally; a flight delay might mean you have to go straight to a meeting from the airport.
  3. Be prepared for action when you arrive. Nothing makes you look like a pro more than being prepared for any eventuality – even some situations your boss might have overlooked. Make sure you have mobile devices charged up and all connectivity cords ready to go so you don’t run out of batteries at an important meeting. Print out or save screen shots of destination directions, presentations, confirmations and other important information in case you lose cell service or are unable to access Wi-Fi onsite.
  4. Never forget that you aren’t on vacation. Traveling with your boss is a good time to make a great impression, so even if your boss watches a movie during the flight, show that you’re a go-getter by getting some work done or brushing up on your professional skills by reading. Also, exercise caution around cocktails. If your boss is indulging, it’s okay to have a drink or two to be sociable, but don’t go overboard – no matter how many drinks your boss throws back.
  5. Get to know your boss better while respecting boundaries. Some bosses are chatty while others would rather focus on work during flights and trip downtime. Follow your boss’s lead on that, keeping chitchat to a minimum if your boss is reading or working. But carve out some one-on-one time for dinner or drinks if you can, even if you’d really rather be relaxing at the hotel. A business trip can be a great time to impress your boss with new ideas.

Not everyone is a natural at business travel, and those who travel less frequently for business are typically more nervous about it, especially if their boss is coming along. But knowing what to expect, understanding what is expected of you and being prepared can go a long way toward reducing your jitters. By following these five tips, you can put the best foot forward on your next business trip – and set yourself up for success while on the road with your boss.

Dan Ruch is the co-founder and CEO of Rocketrip, a New York City-based business travel management platform that enlists employees in saving costs.

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