Traveling With Your Boss

Recently, I did a guest post on business travel for my favorite blog, Corporette. Yes, it was a very exciting moment for me. One of the things that I was asked to talk about was how to act when traveling with your superiors. I had to think about it for a bit! I haven’t traveled with superiors in long time, but I remember it can definitely be tricky.

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.

Keep competence in mind with everything you do, starting with your suitcase. Be familiar with 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.

While on the plane, looking like you are 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), or 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”.

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. Yes, there was one time 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!!

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.

And 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 is not going to make the impression you want. (I saw this happen, and trust me, three years later we still talk about it.)

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, abstain. But this is a time that you can show how skilled you are in areas your boss doesn’t usually get to see–take advantage!



  1. Great post! I used to travel with my director a lot and my main goal was to not make him wait for me. He was a seasoned traveler and one of his pet peeves was taking too long to get through security. So I would always make sure I was ready to get everything in my bins and get through the line as quickly as possible.

    I also used to worry that I would get upgraded and my boss wouldn’t. It never happened but I definitely would have been a little embarrassed and would have probably tried to give my boss the upgrade. Have you ever been in this position and how would you have handled it?

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