how can I get my employee to stop condescending to me?

A reader writes:

I hired a promising junior employee who seemed polite and reasonable during his interview. However, now that he is my employee, he constantly condescends to me and says things that come across in a belittling way. Here are some examples:

Me: “Bob, I was going to train you on how to do X today.”
Bob, with a dismissive laugh: “Yeah, I was wondering when you were going to get to that.”

Me: “Bob, has anyone shown you how to do Y yet?”
Bob, with a dismissive laugh and a shrug: “How hard can it be?”

Me: “I just noticed an issue with the X documentation and wanted to make sure I corrected that so you have the right information.”
Bob, with a dismissive laugh: “Yeah, I was wondering what you meant by that.”

With everything he says, it feels like he’s trying to be smarter than me, or one step ahead of me. And he’ll always act like this stuff is easy and he’s the expert, but when he has to actually do it for the first time, he needs all the help he can get.

It has been all I can do to contain my irritation, and I have started to respond by becoming irritable, which I know is not excusable. Recently, he gave me the “I was wondering when you were going to get to that,” treatment, and I snapped back, “I can’t download my entire brain to you in one sitting!” He laughed, as though it was a big joke, but I felt terrible because I knew I had spoken in anger. I didn’t apologize, though.

I don’t think I can fire him over such a small thing, and I’m not sure it’s fair to nitpick someone’s personality just because it’s not compatible with mine. It’s not really a performance issue, because for the most part, he’s doing fine.

It’s possible he’s feeling insecure, but the way he’s expressing it is just not okay to me. Do you have any advice for this kind of conflict?

I answer this question  over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and sometimes updating/expanding my answers to them). You can read it here.

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