Traveling Together: You and Your Boss

Adding your boss or coworkers to a business trip can be fraught with issues. Traveling Together is a series on Road Warriorette about avoiding the pitfalls that crop up when traveling with others.

Traveling with coworkers can be tricky, but that can be multiplied if you are traveling with your boss. If you are traveling with your boss, you have to be on your best, and most competent, behavior. You want to come across as low maintenance as possible, and this can extend from your suitcase to your dinner orders (remember When Harry Met Sally? Don’t be Sally!!) to your clothes. Here are a few tips to look calm, collected, and like you know what you’re doing.

  • Be competent! This touches everything you do, starting with your suitcase.Know the airline’s guidelines so that if you are carrying on, your bag is within the correct size requirements. Also, make sure you can lift it into the overhead bin without throwing out your back or making weird noises.
  • Be productive. While on the plane with your superior, working is never a bad thing. If that’s not an option, look at a magazine that you could show your grandparents: Real Simple, In Style, something in that vein. (Not People or Us Weekly, please! Unless you’re sure that your boss shares your obsession with Brangelina.) Another option is to read a book. You don’t have to try to come across as a pseudo-intellectual, but please don’t read anything that looks like a trashy romance or something called “How to Get Your Boss’s Job”. This is a great excuse to finally get a Kindle! No one knows what you’re reading.
  • Know where you’re going. When you arrive, make sure you know where you are going and have a plan for getting there. You don’t necessarily need to do anything above and beyond what you would do when traveling alone. Just make sure, for example, you know the address of the office, what car rental company you are using, and the general location of your hotel. Long ago, I was traveling with a coworker and I couldn’t remember the name of my hotel, I just knew it was some kind of Marriott. I had to call all over the city to find my reservation (because I didn’t have access to my Rewards number or my confirmation code), and then it turned out my hotel was literally on the airport property. Way to look competent!!
  • Look professional. During any downtime that you spend with your boss, wear something comfortable but cute and well put together. It’s pretty unlikely you’ll have to wear a suit to dinner (unless of course you’re going straight from the office), so maybe a pair of slacks or dark jeans, a nice top, and cute shoes. Don’t wear anything that would make someone think you are going to a bar: nothing revealing, no too-tall shoes, etc.
  • Don’t get drunk! I hope this would go without saying, but just in case. Please, please watch your alcohol intake. Getting drunk and throwing up in a cab with your director looking on makes an impression, just not the one you want. (I saw this happen, and trust me, four years later we still talk about it.)
  • For more reading….. Check out the discussion on whether or not to give your boss your upgrade, just in case that situation comes up. Also, all of the tips from last week about traveling with coworkers still stand, and are even more important on trips with your boss.

The goal is to exude confidence and competence at all times. I know it doesn’t seem fair that someone could be judging you during “off” times, but that won’t stop them from subconsciously doing it. If a behavior could even remotely be considered questionable, don’t do it. But this is a time that you can show how skilled you are in areas your boss doesn’t usually get to see–so take advantage!



  1. What she said…

    One of the first times I travelled with my boss, it was on an overnight flight to Europe. Talk about uncomfortable! I had tried to move my seat ahead of time so that I wouldn’t be sitting next to him, but there ended up being an empty seat next to me and he moved to it! Ugh.
    But, I survived and we worked together for 11 years. Still, a trip I won’t forget.

  2. I am new on the job and in a week must travel with my boss and a co-worker on a 16-hour (total) airline trip, and I am nervous about it. I am thinking of calling ahead to make sure that I’m not seated near either one of them. I’m not anti-social or anything, but I value my privacy regarding sleeping, hygeine, eating, entertaining myself, etc. Is this unusual, or is it OK to not want to overshare on such a long and physically uncomfortable trip?

  3. @Mimi It is totally appropriate to ask not to be seated next to either of them, as long as you don’t actually say it in front of them. In all of the plane rides I have taken with coworkers, I have only sat next to one of them one time. My experience has been that people expect to not sit with their coworkers on a flight.

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