Tips for traveling with your boss

Traveling with coworkers can be tricky, and that can be multiplied exponentially if you are traveling with your boss. On trips 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 to your wardrobe. Here are a few tips to look calm, collected, and like you know what you’re doing.

  • Don’t check your bag. This is always my standard advice, but even more so when traveling with your boss. If there is any way you can avoid checking your bag, carry on. You don’t want to be the reason for any delays upon arrival! Know the airline’s guidelines so 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, keep in mind that anything you read is a reflection on you. Perhaps look at a magazine that you could show your grandparents: Real Simple, In Style, something in that vein. 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”. If you don’t have a Kindle this is a great excuse! No one knows what you’re reading.
  • Choose your seat wisely. Don’t feel like you have to sit next to your boss on the flight unless there is a work-related reason. My experience–and the experience of many readers–is that co-workers generally don’t expect to sit by each other. Feel free to blame the airline if you need an excuse.
  • 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 and 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 overindulge! 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, 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, 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!

Readers, is traveling with your boss something you do? Any tips?


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  1. Some of these tips work backwards. For example I have a boss that checks a bag on every flight, even a short 1 night stay. I’ve had bosses in the past that liked to drink…a lot. That can be a problem as well.
    The other thing I’d add is to avoid gossip. They may draw you in to talk about your co-workers so think this through before you travel. Keep the gossip as tame as possible. For example if your boss says “You know your co-worker Suzy just isn’t doing a good job, dresses bad, looks bad, etc.” then say something like “I hadn’t noticed” much or “I wasn’t aware”. First it looks unprofessional plus they may just be baiting you so see what you say or how you are.

  2. @DaninMCI that’s a great point. Maybe it’s better to say, follow your boss’s lead with checked bags. I just hear so much about the stereotypical young high maintenance woman that has to check her bag slowing down a group traveling together! But if your boss doesn’t check their bag, I would try not to check yours.

    It’s always a good idea to avoid drinking too much with your boss, but I agree it can get sticky when your boss drinks too much. And yes, totally agree about not gossiping! That is a recipe for disaster.

  3. I got stuck sitting next to my VP – my boss’s boss – for a 14-hour flight to China a few years ago. He was perfectly nice, and we pretty much ignored each other for the duration of the flight, but I realized immediately that I wasn’t wearing any of the company’s merchandise (I work for a luxury retailer, handbags and jewelry). So my advice: if your company sells something, have at least one with you.

    And don’t worry about trying to sleep next to your boss on a flight like that – I felt much better after I caught him watching Beyonce music videos 8 hours into the flight!

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