The colleague with the uncomfortable sense of humor. The client who has zero concept of personal space. The assistant who chatters non-stop.

When you find yourself teamed with someone whose work style—and, well, personal habits—couldn’t be further from your own, it’s tempting to just put your head down, and (as cordially as possible) tune out his or her differences.

And while this may help you get your work done without ruffling any feathers, it does nothing to help you build a connection. A better approach? Do your best to try and get on his or her wavelength, which will not only help you work together more effectively, it’ll impress everyone around you. Read on for the dos and don’ts of working with someone with a difficult personality.


Don’t Judge

By glossing over a difference in work style—or getting frustrated by it—you lose the opportunity to gain more insight into the person you’re working with.

Instead, try to take a step back, and instead of judging someone’s behavior, consider where he or she might be coming from. That colleague with the awkward sense of humor? Ask yourself why he might be cracking those jokes. To break the ice? To help illustrate a point? Just because? By stepping outside of judging his sense of humor and focusing on where the jokes find their way into conversation, you will be able to develop a plan of action to work together more effectively. On that note:


Do Give Them What They Need

It’s true that you can’t always change someone else’s behavior, but you can often change your own. So, once you know (or have guessed) where someone’s quirks might be coming from, look for ways you might be able to mitigate them. That meeting attendee who always speaks first and loudest? Perhaps she fears not being heard. By making an effort to listen extra carefully and using check-back-in phrases like, “I think you’re saying…” you can allay that insecurity and move forward.

As far as the assistant who is always chattering away about the latest celebrity gossip? She may simply want to build a beyond-the-9-to-5 relationship with her colleagues. Try adding some pop culture mavens to your Twitter feed and engaging in an exchange about Kimye’s wedding plans or Kate’s latest dress. After a few minutes of bonding, suggest you both get down to work.


Do Adjust the Circumstances

Still can’t figure out where someone’s coming from? Focus on how you can shift the environment you’re both operating in. If, for example, close talking makes you uncomfortable, don’t choose a crowded coffee shop for a meeting. Anyone who has an issue with auditory discrimination will need to be as close as possible to hear you over the music, the people ordering, the five tables around you, and so forth—so instead scout out a location that’s equally convenient but boasts a quiet atmosphere.

Or, let’s revisit the client with no sense of personal space who manages to take over your office when she comes in for a meeting. If you can’t get to your notes because they’re buried under the jacket she flung on your desk, find a polite way to mention it. Perhaps begin with, “Could I hang your coat for you?”

This can be applied to other scenarios as well. Ask yourself what you can do to make the overall environment as conducive to a comfortable work environment as possible—then do it.


Don’t Gossip After the Fact

Okay, isn’t one of the benefits of working with someone colorful that you get some great stories? And doesn’t a little water cooler gossip build camaraderie among colleagues? Yes and sure, but remember that any points you gain dishing about the other person’s eccentricities will cost you the relationship you’ve been working so hard to build with him or her.

If you do foster a great connection with someone legendarily hard to reach, your colleagues will likely be curious. Just go out of your way to avoid framing it as “I totally handled working with that person,” and instead choose, “I just learned that he’s not a fan of meeting over meals—and it’s definitely helped us communicate better.”



Working with someone who is known for being “difficult” doesn’t have to be, well, difficult. Be focusing on the other person in a positive way, you can make constructive strides in your working relationship—and your overall office happiness.


Photo of people working courtesy of Shutterstock.