Humor at work, under the best circumstances, is a delicate balancing act. It demands the very best interpersonal communication skills. Large issues, such as culture, language, and context define what is funny, who thinks it's something to laugh at, and when it's considered humorous.
You can't take these things for granted. Even the typical banter between friends involves a certain amount of joking at each other's expense; and it can only be done when everyone concerned knows and appreciates one another, and knows when to stop.
When one person doesn't understand these rules, you and those who work in your organization all have a responsibility to him or her to appreciate the differences between you. In other words, you must make allowances for the possibility that this person may misunderstand what is actually happening.
When you do that, it demonstrates that you have good interpersonal communication skills. When you don't, then when the tables are turned, and this person becomes the brunt of any jesting which everyone else believes is harmless, then he or she will take it personally.
Anytime employees won't talk to you about a problem, it's due at least in part to the fact that they are convinced that you won't take their concerns seriously. In this case, he probably thinks you'll just tell him to "lighten up," or make some other equally useless suggestion.
When you work with someone like this, you have to be careful. Keep your conversations strictly business and make sure that others do the same, even when you are with people who routinely joke around with you. Those who have strong interpersonal communication skills take into consideration everyone who is around them; not just those they like or who like them.
If you try to be friendly with some people and not with others for any reason, it can be perceived as favoritism and, as a result, you could have other problems on your hands.
All of us are insecure: some more, some less; but, those who have the best interpersonal communication skills are cognizant of what they say, especially in the presence of those who don't share their sense of humor. Through this one behavior, they show a degree of sensitivity and maturity that is uncommon.
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