The 5 Most Awkward Conversations at Work

1. You asked your co-worker if she was pregnant, and she’s not.

2. You asked your boss of eight years if he enjoyed his Christmas, and he had to remind you that he’s Jewish.

3. Your co-worker is a touchy-feely type, and you just admitted it makes you uncomfortable.

4. A colleague just remarked on an unsavory habit of yours – like the fact that you bite your nails.

5. After going on about how much you dislike a new hire, your colleague informs you he’s her cousin.

Okay, so maybe these aren’t THE most awkward conversations, but they are certainly good examples. In fact, I am certain there is no shortage of truly awkward moments that could occur at the office. In order to make them less excruciating, here are some suggestions.

If Someone Made an Awkward Comment to You

Rather than acting offended or taken aback, keep your cool and be as gracious as possible.  Say something simple like “thanks for letting me know,” or even something moderately tongue-and-cheek, like “thanks for sharing.”  Then, proceed to change the subject and converse as if the awkward comment never happened. Recognize that the other person is probably still uncomfortable, so do your best to engage him or her in a discussion by asking questions and demonstrating body language that shows there are no hard feelings.

If You Made the Awkward Comment

Instead of standing there like you were the victim of a stun gun, make light of the moment in order to put both of you at ease. My go-to phrase in this situation is, “well, that was awkward.”  Smile and turn the conversation in a positive direction.  For example, in the case of the non-pregnant co-worker, you might say, “I guess you must be glowing for another reason.  What skin care regimen do you use?  I might have to try it.”

Now more than ever, it’s important to be mentally present for the person.  Don’t let yourself get distracted by technology or other people during the conversation, and genuinely listen to what she’s saying.  The more involved and attentive you are, the less likely you are to find yourself in the middle of another uncomfortable moment.

Alexandra Levit

Alexandra Levit’s goal is to help people find meaningful jobs - quickly and simply - and to succeed beyond measure once they get there. Follow her @alevit.

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