update: my boss wants me to ask a rejected problematic job candidate to volunteer

It’s “where are you now?” month at Ask a Manager, and all December I’m running updates from people who had their letters here answered in the past.

There will be more posts than usual this week, so keep checking back throughout the day.

This one is a double update. The same person wrote in to ask about a coworker who kept bringing her “problems” that weren’t problems (Emily) and, in a different letter, about her boss pushing her to ask a rejected problematic job candidate to volunteer (John). Here’s the update on both.

As many of the commenters picked up, management is kind of delusional here. In the past two years, every single position in my 8-person department has turned over at least once. I am very pleased that I just resigned yesterday after accepting a job elsewhere with a higher salary and significantly better benefits!

First, though, the updates. Emily is still here. Before the job was posted, Emily mentioned a few times that she was having a lot of trouble finding another job, and that her old workplace (shockingly) didn’t seem to want her back. My manager, I’ll call her Elaine, had not posted the role yet. Then, Emily came in one morning and gleefully announced that Elaine had asked her to stay. I was absolutely livid, and so, so confused. I immediately requested a meeting with Elaine, who avoided every question I asked about the situation. My other coworkers guessed that Elaine just didn’t want to go through the hiring process for a niche role, and that she really didn’t see Emily as a major issue because she just avoids managing her at all.

Emily continued to cause numerous issues, and her tone became increasingly confrontational. A few commenters asked about what kind of problems she caused. Shortly after my letter was published, another writer’s experience sounded almost identical to mine. Emily is very similar to the employee that letter is about.

Here’s a recent example of an interaction I had with her (think of this happening constantly, truly constantly, every day): I was hosting a low-key art program in an art studio (that I manage), and a few teens asked if they could paint. Everyone else had finished (so there was no one in the studio) and I had plenty of extra painting supplies. I let them paint for about 10 minutes. Emily lost her mind. While the teens were still in the room, she told me very loudly and rudely that I was setting poor expectations, that those teens were probably going to come back and want even more paint every single week, that we can’t be allowing things like this because then everyone is going to want to come in and paint all the time, and finally, that there were “probably other things [I] should be doing.” I calmly asked her to have this conversation at another time. She said that she needed to explain this to me in the moment, and continued saying that I was “setting poor expectations” by letting the teens use our (cheap, abundant) paint and paper. I gently guided her aside and said “Emily, this is an appropriate use of the art studio. They are being very respectful and clean, and we have more than enough supplies. We do not have to accommodate every request, and we can handle any future requests on a case-by-case basis. But I do think that allowing a few teens to paint is reasonable for an art studio. We want to create a positive impression of the space for every guest. Also, this is my activity, and I am not asking you to assist.” Emily continued arguing with me, to the point that I said “Emily, I am not going to continue this conversation. Please talk to Elaine if you want to discuss this more.” I then emailed Elaine, who assured me she would meet with Emily the next day to discuss her behavior. The very next week, I had a nearly identical situation, and Emily reacted even worse. I essentially gave up on Elaine’s management.

Other staff members became increasingly frustrated with Emily, as she continued to bring problems to them when I was unavailable. One close coworker knew I was job hunting, and she said that she would love to step into my position, but that she would not take the promotion solely because of Emily.

At the same time, under pressure from management, I reached the point where I was directly asked to have John volunteer as a presenter. I met with him to discuss the opportunity, and the topic he wanted to present was on a piece of technology I have used for over ten years. He brought me an article titled “[Piece of Technology] for Beginners.” I said “Oh, John, thank you, but I have been using this daily since 2010!” John said “Oh yes, I know, but you can always use more information, right?” So he has not changed a bit.

After that meeting, Elaine mentioned that she thought Emily would be a good person to host John’s presentation. I knew that they would mix like a match with gasoline, but I also knew that Elaine would push for it no matter what I said, so I agreed. I wasn’t working the night of his presentation, but I felt like I was there: Emily texted me 36 times about how awful and problematic John was. I hate to admit it, but I kind of enjoyed it. I steered it all to Elaine.

I am very happy to be leaving this toxic workplace. In addition to the John and Emily situations, there was a situation in which Elaine raised her voice to a coworker on the public floor, and that situation potentially involves racism. Upper management also put together an EDI committee, and of course, forced employees of color to be on it.

Thank you and your readers for advice on both of my weird situations!