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The Problem

My coworker is very self deprecating to the point where several of my colleagues are worried about him. He will make negative remarks on the quality of his work, and even himself, saying things like "my work sucks", or "I'm stupid". Additionally, he's taken to complimenting me in a way that is simultaneously self deprecating to him (for example, implying that I will one day replace him).

At first I tried to encourage him not to say these kinds of things, but as time went on, and my (short) patience wore off, I'm just annoyed by him. This sort of behavior is annoying to most of my colleagues, but especially me, as I'm a pretty disagreeable and argumentative person, and this kind of behavior is particularly annoying to me (due to things in my past that are too lengthy for me to get into).

I've had several conflicts with him in the past, where I attempt to confront him about this sort of behavior, but I've failed to handle these confrontations in a productive way.

These confrontations basically play out as me asking him to stop making these sort of jokes, and him saying that it is a problem with the way I perceive the jokes, and not the fact that he is making the jokes in the first place. That's the short of it, but the way these confrontations actually play out involve a lot of frustration from both him and me. I'm at least a little rude during these discussions, and he is very defensive, so we get nowhere.

Although I agree that I'm taking these jokes more poorly than most of my coworkers, I don't agree that these jokes are okay to make. They reduce confidence in him, reduce team morale, and make him difficult to work with.

The question

What is the best way for me to deal with this coworker? I have a lot of difficulty dealing with people I dislike, at least for long periods of time (such as someone I work with every day). The best I've come up with is keeping my interactions with him as short and professional as I can, but I have difficulty doing that without also making it clear that I want to talk to him as little as I possibly can (i.e., I'm worried that I'm still coming off as rude). Is that the best I can hope for, or is there another solution?

Management is aware of the problem, but I'm not sure how much, or what they can actually do.

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What is the best way for me to deal with this coworker?

[keep interaction short and professional]...or is there another solution?

A good course of action might be adressing the issue on both sides, both your and your colleagues (let's call him Adam).

His side

Adam might see a lack of skill compared to you and your coworkers. This could either be from him being a slow learner or just because he's rather new in the company. In both cases you could try and build up his confidence and attitude by pointing out his improvements. Of course you'd also want him to know that by keeping these remarks to himself he's contributing to the teams morale.

You could have a meeting with a relaxed setting in order to take pressure of the topic, prepare coffee/tea. Try something like:

Hey Adam, I'd like to talk about our work relationship. You always point out how inferior your work is and how we're dragging you along. From my point of view you have improved in A and also in B, ever since you and I worked together. There is no neccessarity for self-deprecation - you're doing quite fine and should not be concerned of your shortcomings. If you focus on improving your attitude you could instead boost the morale of our team, including yourself.

Adjust to your needs, work and team environment.

Your side

Be open for change. The remarks he makes might just be his way of complimenting your work. It could only be your perception that elevates the issue to its seriousness. Changing your attitude takes time and openness. Be open. You don't want to get Adam (or youself) in trouble because he's kind of a pessimist.

Adam: Here's the code for review. Might not be as good as if you'd written it, sorry 'bout that.

You: Thank you for the compliment, but I don't perceive you or your work to be any less worth than mine or anybody elses here. Keep it up.

Bear in mind that change takes time. Lots of it. At first the change of behaviour might feel arbitrary but eventually it becomes natural.

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There's a couple of ways to handle these sort of people, and there's also a couple of different reasons why this person may be making those "jokes".

People's first instinct when someone makes a self-deprecating joke is to answer sympathetically:

Him: I suck at this. You will probably replace me in a few months.
You: Aww, don't say that. You do a good job!

Sometimes this behavior is born out of honest insecurity, and some people do need to be encouraged to recognize and reach their own potential. This, of course, requires a lot of patience, and is not really the responsibility of one's coworkers to manage, but you can step up with helpful comments every once in a while, etc.

However, other times people will use self-deprecating humor in a more underhanded fashion to fish for compliments. In other words they may be the sort of person who craves the approval of others, and may have noticed that behaving in this fashion gains him supportive, and sympathetic comments from others. This happens startlingly often.

And the reason why I suspect this to be the case in this situation is because of how negatively he reacted when you encouraged him to stop beating on himself. Most people would welcome someone saying:

Hey, there's no need to say things like that! You're really good at what you do!

Instead, he accused you of not taking his jokes in stride. This tells me that this person is perfectly capable of defending their choices and actions when they want to. If he were utterly lacking self-confidence he would simply crumble under the weight of your accusations - but he does not. He stood up to you in no uncertain terms. So why not defend his programming experience and decisions? Why deflect the subject by asking for your sympathy?

And the answer looks to be that he has no interest in doing the second, while the first brings him some sort of benefit. Like a child who knows to cry on command in the candy store because then mommy and daddy will buy him what he wants.

And so, how do you handle this?

One way is to avoid this person as much as possible. However, you're still running into situations where you have to deal with him. And so, react in such a way that his behavior backfires:

Him: I suck at this. You will probably replace me in a few months.
You: Who knows? OR Yea, probably. OR Time will tell, buddy.

The second you stop giving him what he wants, he is incentivized to cease that behavior (at least with you). Don't make your comments in a baleful, or venomous manner. Adopt a casual, matter-of-fact attitude. Act like your comments are as much a part of the act as his own self-deprecating attitude.

I believe you'll find him far less likely to engage with you in this fashion once you've taken the fun out of it.

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