Top Tips For Traveling With Your Boss

Hitting the road with your boss is a great opportunity to show them what a rock star employee you are – so it’s important to bring your A-game. The next time you head out on a business trip, keep these tips for traveling with your boss in your back pocket.

 Do's and dont's for traveling with my boss

Be early and be prepared.

Make like a Girl Scout and always be prepared. Before you leave, clarify with your boss exactly what is expected of you on the trip. Once you’re there, have cash on you to pay tips or pick up the tab for dinner, and be ready to figure out local transportation on your own if need be. It’s likely that your company will have you covered in situations like these, but the last thing you want to do is assume and then find yourself in an embarrassing situation. Be a few minutes early for every appointment, flight, and event on the docket. Make sure your boss never has to wait for you when it’s time to catch a flight or meet in the hotel lobby to start the day.

Keep your “office face” on.

Casual moments on the road can feel miles away from the office, but that doesn’t mean you want to treat your boss like a vacation buddy. This doesn’t mean you can’t have fun, but know that your behavior is always making an impression. It’s pretty simple: don’t be a jerk, don’t get wasted (more on that in a minute), and don’t embarrass your boss.

 Business travel with boss tips

Learn a bit about local customs in your destination.

Ideally this is something you do every time you travel, but it’s especially important on a work trip. Learn basic business etiquette and ways to show respect in the country you’re visiting, and make sure the way you interact with your boss in front of international contacts reflects those customs.

Watch how much you drink.

Okay, back to the drinking. In our unscientific estimation, the majority of business trip blunders happen when people accidentally get smashed. (Hey, it happens to the best of us.) Obviously, alcohol is often a big part of networking and building rapport. If your boss orders a drink, it’s generally fine for you to do the same – but the key is to know your limits, and to avoid touching them even with a ten-foot pole.

Try to catch yourself if you’re going through more drinks than usual to keep up with the pace of your boss or colleagues. The last thing you want is to get drunk, make a series of snide comments about your boss’s leadership capabilities that seem cleverly subtle to you in the moment, and wake up the next day to an early morning termination meeting. (Seriously, we have seen this happen!)

How to travel with your boss on business trip

Let your boss set the tone.

Follow their lead on how casual – or not – your habits on the road are going to be. If your boss is intently focused on their laptop your whole flight, follow suit. The same goes for conversations. If your boss shares a bit about their life outside of work, feel free to do the same. Just make sure to avoid spilling your guts or gossiping about your coworkers. (But you already know not to do that one, right?)

Use your travel experience to make an impression.

As every traveler knows, the fastest way to see a person’s true colors is to be with them when something goes wrong on a trip. As a frequent flier, you have an advantage in impressing your boss, because you’re used to rolling with the punches when hiccups arise on the road. Not everyone in the workplace can say the same, so let this part of you shine.

When hurdles come up, keep a cool head and offer calm solutions. Be adaptable, and keep your team’s attitude positive when delays put a wrench in your plans. If you can show that you take crises in stride, you’ll be more indispensable to your boss than even their morning double espresso shot.

Bento Bag Restock

Shop This Story

Come along with us on this adventure.

  FOLLOW US ON INSTAGRAM AT @NOMADLANE

share your photos with the hashtag #NomadOnTheGO

View Gallery arrow