On Your Best Behavior: Traveling with Your Boss


Before you recline your seat, dip into your favorite book, and order yourself a double whiskey on your next business flight, think again, particularly if you’re sitting right next to your boss.

The first rule of traveling with your boss is this – you’re not on vacation now.

Granted, you might be out of the office, but you’re still working, you’re just in a different setting. So here’s how to keep up appearances while you’re traveling for work:

Dress to Impress

Consider work when you’re putting together your attire for the trip, making sure you’re not letting your professional guard down, even if you are flying somewhere exotic. Choose casual business wear rather than t-shirts and flip-flops, making sure you’ve dressed appropriately if you’re heading straight to a meeting once you land.

Ladies, make sure you’ll be able to survive those long walks to and from the airport, terminal, and hotel, perhaps taking a change of shoes you can slip on as you head to your first meeting.

Follow Your Boss’s Lead

If your boss settles down for a nap or starts reading a book once the plane takes off, this is a sure sign you can do the same. However, be prepared to look alert and professional if they do want to talk business mid-flight. Make sure you’ve got a notebook and pen or tablet in your travel bag just in case.

Prepare Yourself for Lonely Meals

You’ll need to make your own arrangements for dinner unless your boss suggests you all go together. You may need to fend for yourself if your boss has other plans, but these meals should be covered in your company’s expenses. Business-friendly hotels, like the Marriott Virginia Hotel, make sure dining alone isn’t awkward, or you may even like to order room service so you can really kick back and relax.

Work Out What Your Responsibilities Are

During the trip, what is your role going to be? Is it your responsibility to make all the travel arrangements, dinner reservations, and organize meetings, or will your boss be taking the lead? If you’re unsure, you should ask your boss what his/her expectations are so it gives you enough time to plan ahead.

Pay as You Go

As a business executive, you’ll probably be responsible for taking care of your expenses as you travel, including taxi fares and dinner bills. Make sure you’ve packed your company credit card along with your own personal card (in case your business card doesn’t work or there’s something you want to buy for yourself). Be aware that it might also be your duty to tip those who are helping you throughout the trip, so pack plenty of single bills you can use for gratuity. Doing this will help demonstrate how in control and prepared you are, which will definitely impress your boss.

For business owners, traveling with employees is a great way of observing how they represent the business when they’re out of the office. And for employees, retaining an air of professionalism at all times will help no end in showing your boss how competent and conscientious you are.

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