Dear Penny: Am I Cheap if I Refuse to Spend $25 on a Gift for My Boss?

A group of coworkers sit in a line with birthday hats with one person with their hat off.
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Dear Penny,

My boss’s birthday is coming up, and his executive assistant has informed each of us in the office we’re responsible for chipping in $25 for his gift again this year. We work in an office with eight people (including the boss) and everyone is expected to contribute. As his birthday approaches, his assistant will send out an email reminder to anyone who hasn’t contributed. Everyone just gives in and contributes.

The problem is, this isn’t just for his birthday. She’ll hit us up again for a National Boss’s Day gift and again for a Christmas gift. I haven’t had a raise since the beginning of 2022. Quite honestly, I’d rather keep my $75 each year for myself rather than spend it on the owner of our company. But I don’t want to be cast as the grumpy co-worker either.

What should I do? Please don’t suggest talking to HR, as HR is nonexistent at this company.

— Tapped Out

Dear Tapped,

Alison Green, founder of the work advice website Ask a Manager, has long said that workplace gifts should flow downward, not upward. Basically, it’s fine for bosses to give appropriate gifts for those beneath them on the corporate ladder (provided everyone is treated equally). But employees shouldn’t be expected to sacrifice part of their paycheck to give the boss a gift.

Putting this rule into practice can be challenging, though, especially if this is a long-held tradition in your office.

Dear Penny

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I’m not sure if the problem is that your boss has an overly pushy assistant (calling out individuals who haven’t contributed is especially inappropriate) or if it’s a symptom of a broader office culture that doesn’t respect your boundaries.

You could approach the assistant privately and say office gifts aren’t in your budget this year. Anyone with a shred of common decency wouldn’t pursue the matter further. But if she would hound you further, you can respond with a flat “I am not in a position to contribute. Please don’t ask me again.”

I’m guessing your co-workers feel the same way as you do on this one. Surely, they have better uses for $75 than spending it on the boss.

It may be too late to rally your colleagues ahead of your boss’s birthday. But there’s still time before National Boss’s Day (could there be a more ridiculous made-up holiday?) and end-of-year holidays.

Perhaps you could approach a couple of them and see if they’d be comfortable talking to your boss’s assistant together. You could suggest ending the tradition of soliciting money for gifts for the boss out of respect for employees’ financial situations. You wouldn’t want someone who’s struggling to feel pressured to give.

One option you could suggest (or approach your boss about directly) is budgeting a small amount, say $100 a month, for office celebrations. That money could be used to buy cupcakes or a small gift card for any employee whose birthday falls during a particular month, including the boss. For the holidays, that money could go toward organizing a lunch for staff.

There are plenty of egotistical bosses out there who make headlines for behaving badly. But the optimist in me believes that a lot of bosses don’t expect or even want gifts from employees. Sometimes, it’s the employees putting the pressure on themselves and one another.

If you’d encounter resistance on this issue, I’d suggest that your workplace culture is the problem. Anyone who hounds you for money after you’ve repeatedly said no has boundary issues. I’d be surprised if those issues didn’t bleed over into other areas of your work life.

In that event, it may be best to do what is easiest — which is give the $25 for the birthday gift and quietly update your resume and LinkedIn. I hate to let someone tell you how to spend your own money. But if office drama will ensue from your refusal to chip in $25, wasting your energy on the matter may not be worth it. Spend that time and energy searching for a workplace that respects your boundaries.

Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. Send your tricky money questions to [email protected].