Traveling with a coworker can make a boring trip way more fun. The flip side is that it can also make an otherwise productive trip really, really awful. In almost a decade of business travel I have experienced both ends of the spectrum and everything in between.  Here are tips for avoiding the potential pitfalls of traveling with coworkers.

Don’t overindulge. Finishing a long day with a glass of wine (or two, or three…) can definitely be fun. But don’t get sloppy! It doesn’t look good, and can lead to all sorts of bad stories (that will follow you until the day you leave your company. Trust me.). Not to mention, it can make the next day really painful, or even cause you to miss your flight home. 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 for days on end 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. It just feels, well, awkward running into that person in the breakroom a few weeks after your trip.

Maintain boundaries. On a trip a few years ago a coworker got pretty drunk drunk and told me long stories about marital troubles, going on in detail for a while. As we had just met the day before, I found it excruciatingly awkward. 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. Also, it sounds weird but don’t feel compelled to overshare in return. A friend of mine once confessed that whenever someone tells her something too personal she feels like she needs to balance the scales with a confession of her own. I promise, you don’t!

Get your work done. Just because someone is traveling with you doesn’t mean your working obligations just go away. You still need to check email, finish documents, and prepare for the next day. Make sure you’re not sacrificing work (or sleep!) for socializing.

Find a reason to sit separately on flights. There is no rule requiring coworkers to sit together on flights. One option if they are trying to force the issue: find out if your coworker likes the aisle seat or window.  If they like the aisle seat tell them you actually prefer the window seat and see if they would be ok sitting apart in order to make the flight comfortable for both of you.  Worst case, see if the gate agent can separate you. I’m sure it isn’t the first time they’ve gotten that request!

Know your company’s policy for who pays for expenses.  Company policies vary widely for who pays for meals, car rentals, gas, etc. Make sure you know what’s expected of you before your trip to avoid violating policy and risking not being reimbursed.

Being stuck in a car with a coworker has its own set of issues that can come up, especially when it’s a trip with someone you don’t particularly like. Here are a few driving-specific tips.

Plan talking topics ahead of time. I know this seems a little bit weird, but if you’re concerned about awkward silences plan some conversational topics ahead of time. Maybe ask them about their background—where they are from, where did they go to school, why they majored in what they did, what are their hobbies, etc. Or have specific items in mind regarding the work you’re about to do.  And while it sounds crazy, I have been asked numerous times about my salary and have found it helps to have something prepared.  If a coworker asks me how much I make I’ve found this reply to be the most honest but least awkward way to answer: “I’m not comfortable sharing that much detail, but it’s standard for the industry and my experience level.”

Turn on music. Maybe if you discover a shared love for a particular band you won’t dislike your coworker as much. You can also try talk radio but I would be careful with that because it can get controversial.

Tune them out. Worst case, stop listening and just look at the scenery, or pull out some work to do. The old “I have to finish this report by today,” thing would work just fine.  If you are able to schedule a conference call at some point during the drive it helps to pass some of the time.

Offer to let them drive. Unless you know they are a terrible driver, ask if they want to drive. This lets them feel like they are in control, regardless of whether they end up driving or not, which some people really need.

Know your route. Before you go, look at a map and make sure you know where you’re going. Getting lost is bad enough with someone you really like! It can be hell with someone you don’t get along with.

Readers, what are your tips for traveling with coworkers?

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