6 Tips for Traveling with the Boss

Business travel can be stressful.

You have enough to worry about simply attempting to adapt to working outside of the office.

You’ll be spending a lot more time with your coworkers than usual, and this can make for some awkward situations.

The most awkward of all situations will likely be your away-from-the-office relationship with your boss.

It’s a tricky social landscape to navigate, and it may not be clear exactly how you should handle certain situations. Developing an etiquette code for yourself ahead of time will keep most surprises from popping up.

1. Have a Financial Plan

Talking about money can create some unpleasant situations. Before you head out, understand how the business is covering your travel expenses.

Keep your company credit card handy, and know when you’re supposed to use it. Make sure you take the right amount of cards and cash to handle your personal expenses, and also be sure you understand what things are considered personal expenses rather than business expenses.

The business may cover more than you think, and you need to be sure you understand the budget.

2. When in Doubt, Mimic

If you’re ever unsure of what you should do, it helps to play follow the leader. If your boss is content with relaxing during certain times, it’s probably okay for you to do the same.

No one will be as rigid as they are around the office, but there’s still an unspoken code of conduct to follow. Be ready to shift things around according to your boss’ schedule.

3. Dress for Success

Work travel is not a vacation. Your boss isn’t going to walk around in cargo shorts and a tank top, and you shouldn’t either.

When packing, go for business casual. Street clothes are a no-no in nearly every situation you’ll encounter away from the office. It’s okay to dress comfortably, but there’s a difference between comfortable clothing and leisure clothing.

4. Watch the Alcohol

You may enjoy a glass of wine with your dinner, and that’s fine. If your boss doesn’t, you might want to enjoy that wine in private.

Most bosses will generally be accepting of a beer at a business dinner, but limit yourself to one. Your boss will probably understand having a beer or a cocktail to take the edge off of a long business day, but he or she won’t be nearly as understanding if you get drunk in a business setting.

5. Prepare to be Independent

Everyone will want breaks from each other, and that space will make the trip easier. Don’t expect that you’re going to have every meal and run every errand together.

There will be times where everyone is left to fend for themselves, and you should enjoy the peace and quiet.

6. Know What You’re Responsible For

Everyone will play their own roles during a business trip. Responsibilities are delegated to avoid the burden of everything being placed on one person’s shoulder.

There are some things you’ll be responsible for that pertain to the entire group (such as meal reservations) and things you’ll need to arrange yourself (such as getting a rental car). Showing up unprepared leaves a lasting negative impression.

If you have anything you’re unsure of, clarify it before the flight is booked. Your boss would rather answer questions than help you fix a mistake.

Your boss can be using this trip to evaluate your performance in a variety of situations. If you perform just as well away as you do at home, this could boost his or her opinion of you as an employee.

If you want a bright future with your company, make sure you’re on your best behavior during any trips you may take.

(Photo by Dan Evans / CC BY)

Will Norquay is a frequent business traveler who shares his experiences and thoughts writing for Stayz. Stayz is Australia’s No. 1 holiday rental website.


  1. Kamal on the 19th November

    Thanks for the awesome advice.

    There is a small mistake in the article. Instead of #6 you wrote #7 after #5
    “7. Know What You’re Responsible For”

    • Rebecca A. Watson on the 20th November

      Kamal! Thank you for your eagle eyes 🙂 I have fixed the mistake.

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