A reader writes:

I work in the HR department in payroll for a medium-sized company. My coworker (and his wife) want to have a child. They have already tried the conventional way, drugs, IUI, IVF, and surrogacy with her eggs/his sperm. They have not had success. Adoption OR surrogacy for a non-biological child is not an option for them because they both have past addiction issues and criminal records, although they have since turned their lives around.

They want to try IVF again, but since it was unsuccessful before and multiple doctors have told them his wife will never be able to conceive or carry a child, insurance will no longer cover it. And no doctor will attempt surrogacy again, given the history. They have turned to crowd-funding to raise the money.

Ever since the funding started, my coworker will not stop asking everyone for money. I don’t mean he once casually mentioned the fund and then dropped it. I mean he brings it up multiple times a day, send emails about it, prints copies of the fund page from the internet and hands them out, and flat out asks people for money “so we can make our dreams come true.” Giving money won’t deter him because one of my other coworkers did donate, and he still gets asked and emailed same as the rest of us. It makes everyone uncomfortable because he isn’t taking no for an answer.

Their past fertility struggles are written on the funding page and my coworker mentions them all the time. He even tries to show us paperwork from the doctors to “prove it isn’t a scam and we really are going to use the money for IVF.” I don’t think it is any of my business to know about their past attempts and medical issues, but he discusses them as casually as one would discuss traffic or the weather. He won’t take no for an answer and if anyone asks him to stop he will get upset. He will leave but act like we are personally trying to hurt him. The next day it starts all over again.

He isn’t a manager or supervisor, but he is by far the most senior person here so some people are afraid to speak up because he isn’t a peer. How do we get him to stop? Our boss retired right before the fund started and we are being remotely managed from another location until a new manager is hired and none of us have met our new management because they are largely hands-off. We are in our slow period so it might be a while before a permanent new manager is here. We are all getting sick of this. What would you advise?

Stop worrying about hurting his feelings

He’s being a jerk. He’s not taking no for an answer, and he’s ignored requests to stop. That’s jerk behavior. And yes, it’s stemming from a personal situation that’s presumably difficult and painful, but most people who are dealing with difficult and painful situations do not run roughshod over their coworkers and refuse repeated requests to stop.

So stop worrying about hurting his feelings by telling him to stop. You’re not saying something that’s actually hurtful; you’re making a request that’s beyond reasonable, and that anyone who cared about your feelings would have respected.

I get that it can be tough to push back on someone who’s senior to you at work, but this isn’t about work stuff. This is about personal behavior — very personal behavior — and you do have standing to assert yourself there.

You can start with kindness, but if that doesn’t work, you’ll need to escalate from there. Here’s what that escalation can look like:

The next time he hits you up for money, say this: “You’ve asked me about this a lot. It was fine to ask the first time, but I told you my answer was no, so I don’t want to keep being asked. Thanks for understanding.” If he gets upset and leaves, that’s fine! It’s okay for him to be upset. Don’t be manipulated by that.

If he continues to bring it up with you, then you need to escalate in firmness: “I asked you not to raise this with me again. You’re making me really uncomfortable.” Or simply: “No. Like I’ve already said, don’t ask me again.”

And if he brings it up after that: “Dude, no. I’ve told you multiple times that I’m not open to this. It’s really inappropriate for you to do this at work. If you’re not going to stop, I’m going to escalate this to (manager). Please don’t make me do that.” (And I get that your current manager is remote and hands-off, but this really does sound insanely disruptive and like something you could escalate after a bunch of attempts to deal with it yourself don’t work.)

That’s the professional approach. But frankly, in a lot of offices there would be room for a bunch of you to just yell, “Fergus, STOP ASKING FOR MONEY” the next time he raises it. Sometimes there’s room for social shaming when someone is repeatedly being a jerk.