A sort-of-crazy woman works with my kid. Should I talk to her boss?

Dear HTT,

My job involves interacting with a good number of volunteers. While most of these volunteers are lovely people invested in being helpful, one is so difficult to get along with that many of us suspect she has a borderline personality disorder. In person, she's more or less OK, if whiny; but in the 2,000-word passive-aggressive vitriolic e-mails she sends out at 4am, she complains of offenses against her, tosses out unpredictable insults, and threatens to remove herself forever from our workplace in a "goodbye cruel workplace" sort of way. Pretty much everyone is aware of her dysfunction, and frankly, more than a few of us would be happy to see her move on; but since the nonprofit I work for is in a rehab business of sorts, our jobs include letting her volunteer and helping her feel safe. We're all well practiced at turning the other cheek, and we're developing strategies for not getting emotionally punched out every time.

My problem isn't my workplace, where she's a volunteer, but her workplace, where she's a tenured employee who comes in contact with many children, including mine. As I wrote before, she seems OK in person, but it's those split-personality e-mails that have me worried, especially because I seem to be a convenient focus for much of her anger at the world (though others who receive messages from her also report being foci). In person, she doesn't seem like she'd take out her anger at me on my child, but I wouldn't put anything past her e-mail persona. Recognizing that she's likely only to be in occasional in-person contact with my child, should I nonetheless speak to her supervisor to request that she not be allowed to be alone with my child? I imagine her boss also knows about her idiosyncrasies, and I don't want to get her in trouble--I suspect she does her job pretty well, even if she bombs as a volunteer--but I also want to feel that my child is safe.

Sincerely,--What Would HTT Do?

Dear WWHTTD?

If you have any qualms about your child’s comfort and safety, you should talk to the woman's supervisor. But before you request that she not be allowed alone with your child—a request which is, let’s face it, an implicit accusation—why don’t you first simply express your concerns, calmly present what you know about this woman’s behavior, and see what the supervisor has to say? Phrase it just as you have here: “I don’t mean to get Ms. X in trouble. I suspect she does her job well, but I have witnessed some troubling behavior at her volunteer gig and I want to make sure there isn’t any spillover in her work with my child.”

It’s possible her boss will be able to put your fears to rest in any number of ways. If not, then ask that your child not be left alone in her care. If there’s only the occasional opportunity that he would be anyway, it’s not like you’re demanding any major changes or concessions.

You don’t want any niggling fears about your child’s well being, especially when this is one of the few situations in his life over which you’ll have some control. It’s good of you to turn the other cheek on this woman’s semi-abusive volunteer behavior, but I don’t think you need to be as tolerant while your kid is in her care.

Good luck!
HTT