columnist Alison Green answers questions about workplace and management issues–everything from how to deal with a micromanaging boss to how to talk to someone on your team about body odor.

I briefly worked at a terrible company where I was brought in to help fix problems with a team that had been underperforming. Soon after I was hired, it became obvious to me that the company was a mess and I chose to move on after six months.

One person on my team — Joe — was very difficult from the day we met. He was combative, rude, and insubordinate, and our entire time working together was a game of chicken, wherein he was daring me to fire him while making it clear that, for political reasons, he was sure that I did not have the power to do so (he was basically correct). He had been there for several years, by his own admission had hated it the entire time, and yet seemed content to stay and be a thorn in the side of every manager he had rather than move on or attempt to fix the issue.

This former company became insolvent and my current company is in the process of purchasing it. It will be under my management once the transaction closes. Most other competent people from the old company have already left, and so Joe is one of the few with any institutional knowledge — and this company was so mismanaged that a lot of key information is likely missing from the documentation that we’ll receive.

Normally, I’d want to hire someone from the former company to help us make sure the takeover is successful, and Joe is the logical option — the other people who are still there are either too junior or incompetent. Joe has made it clear that he would not accept a contractor position — it is regular full-time employment or nothing.

Several peers from my current company have been pressuring me to give Joe a shot. But none of them knew him previously, and right now he’s on good behavior because he really wants a job with us. Part of me agrees that we need him, but I’m hesitant to bring in someone who I know has a chronic attitude problem and who has stated in the past that he has no respect for me as a leader.

This feels like a no-win scenario. If I refuse to hire him and the transition goes poorly, people will say it was reckless not to bring Joe on. But if I hire him and he’s the complete jerk that I’ve seen him to be in the past, I will be severely distracted by dealing with a nasty, disrespectful employee who is a master of toeing the line in a way that makes him very hard to fire. What should I do?

Good god, no, don’t rehire someone whom you know to be a nightmare and who has directly told you that he doesn’t respect you. Maybe there are former employees who would be willing to consult, or you can find a third-party consultant to provide the guidance you need.

Meanwhile, you need to tell your colleagues at your new company why you won’t hire Joe so they have context for your decision. For example: “When I worked with him in the past, Joe’s behavior was chronically toxic and disruptive. He was abrasive and alienated most colleagues, disrupted meetings, quarreled regularly with peers and those above him, and regularly refused to do assignments (or whatever the specifics are). At any other company I would have fired him, but there he was protected politically. I would never knowingly invite that disruption on to my team. The value he brought was far outweighed by the disruption he caused.”

The only exception to this is maybe if you are very, very sure your current company would let you actually manage Joe this time — meaning that you could hold him to reasonable standards of behavior and fire him quickly if he doesn’t meet them. I don’t think you should do that, but if you want to consider it you’d need to clearly warn him beforehand what to expect. For instance: “I value the work that you do on X and Y and the knowledge that you’d bring on Z. However, I had serious concerns about your conduct when we last worked together. You were combative and abrasive with me and others, to the point that it impeded your effectiveness in your role. I want to be very clear that that’s not something I’d allow in this job. If the same problems came up again, we would quickly part ways.”

But before even considering it, you’d need to double and triple check with your new boss and your new HR department that you’d have complete authority to fire Joe and they wouldn’t stand in your way if it came to that. And, frankly, even if they give you every assurance of support in the world, I’d still strongly advise against it, given what you know about Joe.

Institutional knowledge is valuable. But people often overvalue it to the point that they keep on people whom they really, really shouldn’t keep on. If Joe weren’t interested in the job or if he disappeared tomorrow to live off the grid, you’d find a way to function, right? It’s hard to imagine that you shouldn’t just do that now, given the very likely price of hiring Joe.

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