am I really supposed to contribute to a “Boss’s Day” gift?

A reader writes:

Apparently October 16th is “Boss’s Day.” A person in my department at work has sent out an email asking for $5 from each of us to buy our manager a gift. While $5 isn’t going to break the bank, there are over 20 employees on my team, equaling $100 for a gift.

A little background: my company is especially proud of the charity work it does and consequently is always asking for donations and participation in charity drives. I’ve come to terms with it and do my small, albeit sometimes begrudging, bit.

This recent request, however, has frustrated me quite a bit. The team manager in question is new, they have only been here a month and has had no opportunity to be a “good” boss to us. I am also not particularly fond of them in general. One hundred dollars seems like an outrageous amount of money for someone who we don’t know very well and who already makes exponentially more than any of us on the team.

Is there any way to politely decline involvement? Can I just ignore this request for money? Am I making too big a deal out of this? Help! I feel like I’m constantly being nickel and dimed.

Well, first, let’s separate out “Boss’s Day” from charity drives. Charity drives in the workplace pose their own problems when people feel pressured to contribute to them, but at least they’re for charity. Boss’s Day, on the other hand, is just BS.

It’s a recently made-up fake holiday, most bosses really don’t want gifts from their subordinates, etiquette says that any gift-giving should be from a boss to an employee and not the other way around, and any sensible boss is going to feel awkward about their team celebrating this mock-worthy holiday (and doubly so if they’ve only been on the job for a month) because any halfway competent boss knows that the only kind of celebration of a manager that really matters is freely-given, unsolicited praise or thanks. Forced thanks compelled by an event like this is pretty cringeworthy.

You’d be doing the rest of your coworkers a favor if you speak up about how dumb this is, and you’ll almost certainly be joined by others. I’d “reply all” to the email and say something like this: “Most managers I’ve known have felt ‘Boss’s Day’ was silly and embarrassing and would rather their staff not spend money on them, particularly since they make more than their team. [New Boss] seems sensible enough that I’m sure she feels the same. If anyone really wants to observe it, let’s all sign a card, but let’s not put her and everyone else in an awkward position of taking up a collection for a $100 gift.”

Most people are thinking this, and it would do some good for someone to speak up and say it.

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