Robert A. Di Ieso, Jr.

Q: How can I push back against increasingly obnoxious requests to help pay for gifts for coworkers who are resigning?

Recently, two of my colleagues both gave notice. After the news was announced, our boss threw a small party during lunch hours that we all attended. Our organization ordered food and a cake, and we all said nice things about our colleagues and signed photo books for them. They were also presented with gifts.

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It has now been a week since the party, and my colleagues and I have received three separate emails from our boss’s secretary – each one firmer than the next, asking us to contribute towards the cost of these gifts:

Email 1: “Dear Staff — We have bought our colleagues two beautiful goodbye gifts. If you would like to contribute toward their gifts, please bring me whatever amount you would like to donate. Thank you.”

Email 2: “Dear Staff — It is completely voluntary, but if you are able to contribute toward the gifts for Jane and Fergus, it would be most appreciated. If you are going to participate, please bring your contribution to me. The amount is up to you. Thank you.”

Email 3: “Dear Staff – I haven’t heard from you regarding the gifts we bought for Jane and Fergus. Boss is paying out of her own pocket whatever isn’t contributed by the staff. We don’t want the entire burden to be on Boss. Please try to contribute something – anything will be helpful.”

The first email was sent to the whole staff – but the second and third emails were sent to just a handful of us – the ones who did not contribute — and not via bcc. Like a public shaming!

How do I handle this and what do I say? I firmly believe it is not my place to have to pay for a gift on behalf of my company. I didn’t choose the gifts, they are not what I would have chosen if I did (I actually took my colleagues out to lunch separately to say goodbye), and I find the whole thing really upsetting.

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A: Oh, this is obnoxious on so many levels — the ones you named, but also the claim at first that it’s “completely voluntary,” followed by making it quite clear in the next email that the meaning of “completely voluntary” is not the one that any reasonable person is familiar with.

You have a few options here:

* You can continue to ignore her. After all, she told you this was completely voluntary, so let’s take her at her word. If she approaches you directly and individually, you can say, “This is voluntary like you said in your email, right?”

* You can email her back right now and say, “I’m not able to contribute and wanted to let you know so that you can cross me off the list.”

* You can explain to her why this is so problematic: “You earlier said this was voluntary, but these emails are becoming increasingly high-pressure. I’m concerned that we’re being pressured to help pay for this after the fact, without any input into the gifts or their cost or whether we wanted to spend our money this way. I think it’s lovely if the organization wants to recognize departing employees, but none of us signed on to pay for those items and may not have room in our budgets for this.”

* You can send the above email and also include your boss on it. It’s possible she doesn’t know that this high-pressure collection is being done in her name.

* You can enlist other coworkers in speaking up as a group, which is often particularly effective because it makes it hard to ignore that people — plural — are irked about this. (And hey, you know exactly who to approach, thanks to your coworker’s third email singling out the non-payers.)

And really, once and for all: People, get your hands out of your coworkers’ wallets! Their money does not belong to you.

Q: Should I invite my boss to dinner at my house?

I’ve been thinking it might be nice to invite my boss and his wife to my home to have dinner — but I keep having second thoughts about it.

My boss is a vice president and I’m one of six directors under him. He’s met my husband and I’ve met his wife at company holiday parties. The boss and I occasionally chat about non-work-related things like travel or sports, but have not socialized outside of the office at non-business events.

Is dinner a bad idea? Or am I overthinking this?

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A: Well, some people do this kind of thing and all parties involved seem to enjoy it. So it’s definitely a thing that happens. But I still wouldn’t. Your boss might feel obligated to attend, or awkward whether he does or doesn’t. And it’s blurring the boundaries in a bit in a way that isn’t great — ultimately, this is a work relationship, not a social one. Your boss needs to be able to, for example, give you tough feedback and it’s going to feel a lot weirder to do that if he was a guest in your home a week ago. So I say no, and just continue to appreciate the relationship for what it currently is, which sounds pretty nice as it is.

These questions are adapted from ones that originally appeared on Ask a Manager. Some have been edited for length.

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