A reader writes:

I have a predicament that I’m in and I’m not sure on how to approach the situation. Every day I have to pick up my son from school and bring him back to my job since they don’t provide after school care. This has all been approved by my boss. It’s been going on a couple months now and I haven’t had any problems until today.

I have a ex-supervisor (as in no longer my boss because of good reasons) who tends to overstep her boundaries, but I think this one tops the cake. Today, my son was sitting in the back minding his own business when she brings him some candy (no big deal as she’s asked before if I’ve minded and I said no). Then, she comes back and hands him something and tells him it’s their “little secret.” He comes over to my desk and hands me $20. I ask him where he got it and he said that my ex-supervisor gave it to him and told him it was their little secret.

How do I approach this with her? I want to explain that (1) she should never give money to a nine-year-old and (2) never tell them to keep it a secret, especially from their parents. I don’t want to cause any problems and not be able to bring my son back to work because this is the only alternative that I have. I also tend to avoid confrontation at all costs so being able to bring this up to her is definitely out of my comfort zone. Any help is greatly appreciated!

Go over to her with the $20, hand it back to her, and say, “Cecil told me you gave this to him and said it was a secret. I know you meant to be nice, but I don’t let him accept money from people, and I definitely don’t want anyone encouraging him to keep secrets. That can be really dangerous for kids. So we’re returning this!”

Say it cheerfully and in a kind tone. The tone and the “I know you meant to be nice” are there to smooth this over since you have to work with her and you want to avoid her raising any fuss about your kid being there (if she’s the type to do that if she feels slighted). She may indeed have meant to be nice or she might have some other agenda (which who knows, could be as mild as trying to buy your kid’s affection so she feels good about herself, or could be more worrisome, but “I know you meant to be nice” is a social lubricant here. The important thing is that you’re setting the right boundaries for your kid, and you’re signaling to her that you’re paying attention and will enforce those boundaries if she pushes them.

Don’t think of this as confrontation. Think of this more as “oops, we just need to fix this” — like if she inadvertently handed him something she didn’t know he was allergic to. You wouldn’t have a major confrontation with her about that; you’d just matter-of-factly explain the situation and assume that of course she’d understand. (And yes, some people would not understand because they’re ridiculous about other people’s allergies, but that’s the tone you want, because being very matter-of-fact often bewitches other people into responding in kind.)

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