Traveling Together: Trips With Coworkers

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.

Sometimes traveling with a coworker can make an otherwise monotonous trip fun. Or it can make an otherwise productive trip really, really awful. These are all issues that I have personally experienced, but there are many other potential problems. A few tips for minimizing the things that could go wrong:

  • Don’t overindulge. Winding down at the end of a long day with a glass (or two, or three…) of wine can be fun. But don’t get sloppy. It doesn’t look good, and can lead to a multitude of problems and make the next day really painful. Plus you will be more likely to share too much personal information if you drink too much. Which leads us to…..
  • Avoid oversharing. Traveling with someone creates a sense of intimacy. Working together, flying together, and eating meals together can foster a sense of closeness that may not hold up once you’re back in the office. Remember, the person you are traveling with is still a co-worker, and just because you are with them for three days solid doesn’t mean they need to know that you and your spouse are trying to have a baby, or that your husband cheated on you, or that you’re looking for another job.
  • Maintain boundaries. During a trip this year, my coworker got a little drunk and told me long stories about marital troubles, going on in detail for a while. It was kind of awkward for me, to say the least. When you are the recipient of oversharing, exiting gracefully can be a challenge.  If it seems like things may be getting too personal, try to steer the conversation back to neutral territory, and wrap up as quickly as you can.
  • Get your work done. Just because someone is traveling with you doesn’t mean your working obligations just go away. You will still need to check email, finish documents, and prepare for the next day. Make sure you’re not sacrificing work or sleep for socializing.

Readers, what issues have you encountered when traveling with coworkers?


  1. I went on a long trip to Africa with my boss, whom I did not know well beforehand. (We worked for a non-profit concerned with agriculture.) First, she commented incessantly on the imagined sex lives of not only Africans, but also the sex lives of African animals. Our driver was a Muslim, and she chattered on (as he was driving) about Muslims and how strange she thought their customs were. Whenever she saw a wild animal, she would feign fright, shriek, and then laugh. I was mortified. I privately apologized to our driver after the road trip was over. I sure learned a lot about her on that trip – so much so that I soon quit and found another job.

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