ask a boss

‘Should I Give My Boss a Holiday Gift?’

Photo-Illustration: by The Cut; Photos: Getty Images

Every year around this time, my inbox fills up with questions about handling the holidays at work. Are you supposed to give your boss a gift? What about your co-workers? How mandatory is the holiday party, really? The employee handbook rarely covers these questions, leaving everyone to figure it out for themselves. Fortunately, we’ve got answers to your questions below.


‘Should I give my boss a gift?’

Before my boss hired me back in February, I’d freelanced for years, so I’m out of touch with how offices handle holiday gifts. But I think she’s a great manager, and I’m grateful to her for taking a chance on me when I’d been out of this part of our field for so long. She’s also been really accommodating about letting me stay remote even though she and some others have returned to the office a few days a week.

Should I mail a gift for her to the office? And if so, what’s an appropriate boss gift? Or is that not a thing people do?

It’s a thing some people do, but ideally they wouldn’t. Etiquette says that gifts at work should flow downward, not upward (meaning that your boss can give you a gift, but employees shouldn’t be expected to give gifts to their managers). That rule exists because of the power dynamics at play. Otherwise an employee might feel pressured to purchase presents for a manager, and it’s not okay for managers to benefit from the relationship in that way.

A holiday card, though, is absolutely fine, and it would be lovely to include a note about how much you appreciate working for her.


‘My boss wants an expensive gift!’

The company I work for has about 12 employees. The owner asks our manager to go around and collect $60 from each person to then get a present for her. Around this time, she always makes comments about the type of jewelry she likes, or a new watch she saw.

I have kindly let them know that it is simply not in my budget this year as my spouse changed jobs a month ago and times are tight. When I told them that, they said that it’s mandatory and no one is allowed to not participate. I simply don’t have the $60. My spouse and I aren’t even exchanging gifts this year. Am I causing drama for no reason, or is $60 a lot to ask of an employee?

Your company owner is a terrible person, and whoever is trying to make this mandatory is out of their gourd. Frankly, even insisting on $5 donations for a gift for the boss would be out of line — but demanding $60 from someone who says it’s out of their budget is a whole new level of awful.

How firmly have you said no? If you soft-pedaled it in an effort to be polite, be more direct: “I literally do not have the money to give. I’m not even exchanging gifts with my spouse this year. It’s not possible for me to come up with money that I don’t have.” You might also consider seeing if some of your co-workers are annoyed by this, too, and if so, pushing back as a group. This kind of practice is harder to maintain when a bunch of employees speak up and say, “We’re not okay with this.” If all else fails, escalate the issue to HR.


‘Our holiday party is mandatory, but I don’t want to be around unmasked coworkers.’

My office is hybrid now, with each team in one day per week. I’m still being very vigilant about masking because my mom, who lives with me, is immunocompromised and undergoing chemo. So on the days I’m in the office, I’m careful to eat in my office with my door closed so that I’m not around anyone while I’m unmasked. However, we’re having a holiday party and we’ve been told that everyone will be required to come into the office that day. There will be eating and drinking, so people will definitely be unmasked — indoors, for several hours, without great ventilation, during a period when COVID cases are supposed to be surging. The idea of a mandatory party is weird enough already, but throw in the health risk and I’m really unhappy to be required to be there. What do I do?

Even “mandatory” work events aren’t always mandatory when people have valid reasons for missing them — like if they’re sick or traveling. Keeping your mom safe will qualify with any reasonable manager. So the most straightforward option is to simply say to your boss, “I can’t safely attend the holiday party because my mother, who lives with me, is immunocompromised. I can’t risk bringing something back home to her from an unmasked gathering.” Note that that’s not asking for permission to skip it; it’s letting her know you’ll need to. If she objects to that, she can say so, but if you frame it this way, she’s unlikely to. If for some reason you think that won’t go over well (like if your boss is wildly unreasonable), you always have the option of waking up “sick” that day and having to send your regrets “so I don’t spread this to the whole office.”

Alternatively, if you think there are professional disadvantages to not attending, you could go and keep an N95 or KN95 mask on the whole time. That means you wouldn’t be able to eat or drink — which won’t make for a particularly enjoyable party experience — but you could put in an appearance, get the points for being there, and then leave after an hour or so, having stayed masked the whole time.


‘My company gives terrible gifts.’

Every year, my company (with around 70 employees) picks out one corporate gift and sends it to all of us. Every year, it is terrible. One year they delivered hams to our homes, despite us having a fair number of vegetarians and Muslims on staff. One year they sent us all branded hoodies, which would have been fine except that they seem to have just guessed at people’s sizes (which is already weird, right?) and got them really wrong in a lot of cases. Mine would probably fit my toddler, but it doesn’t fit me. In 2020 (when no one was dining out because of COVID) they sent us all gift certificates for a restaurant that was far away from where most of us live. I’d rather receive nothing than these vaguely insulting gifts that seem to indicate no care went into picking them. Is it worth saying something, or is it rude to complain?

It’s rude to complain about a gift given in a social situation, but this is work, and the rules are different. Your company is sending gifts in the hope that it will increase staff morale and make people feel more connected to the company. If they’re failing at that (or, as is the case here, achieving the opposite), it’s useful for them to know.

So yes, if you have some political capital to spend, speak up to whoever coordinates the gifts! You’d be doing the company a favor, and you could probably find co-workers who would be happy to speak up with you. Start by acknowledging that it’s hard, if not impossible, to find a gift that 70 people will all love. Then let them know that they’ve been sending gifts that are unused by a disproportionate number of your staff, and ask if they’d take feedback about what gifts would be most appreciated this year. (But if they don’t budge, please write back and share what they end up sending this year, because I am eager to know what they come up with next.)


‘My co-worker gives me a gift every year – should I be reciprocating?’

I work on a small team where everyone is pretty friendly. Usually for the holidays, my co-workers and I exchange cards or leave baked goods in the kitchen for people to share. But one of my co-workers gives me a gift every year. It’s nothing extravagant — a candle one year, a book she thought I’d like another, and so forth. But I’m feeling awkward that I’ve never reciprocated. Honestly, I’d prefer not to! I have a small gift-buying budget that I’d rather spend on my family, and I don’t want to encourage the expectation that we’ll all give each other gifts. But now that it’s clear she’s going to give me something every year, am I being rude by not returning the gesture?

Some people give gifts to co-workers and some people don’t, and you don’t need to feel obligated to cross over to the gifting side if you don’t want to. It sounds like this has gone on for long enough for her to see the pattern and stop if she objects to being the only one offering a gift; she hasn’t, so I’d assume she simply derives joy from continuing to do it. A sincere “thank you” is all that’s required.

That said, if you feel awkward about not reciprocating with something, a card with a warm note inside is a good middle ground.


‘Is it appropriate to give my intern a gift?’

I have a graduate-level intern whose placement is required for her degree. She works directly with me. When I did required internships at both the BA and MA level, I received anything from small gift cards ($5 to $10) to the same holiday bonus as the full-time staff (a $100 check from the company). Is gifting to someone who is technically your “student” appropriate? I’m thinking about going the $5 to $10 Amazon, Starbucks, or Target gift-card route, but what are your thoughts?

A small gift card is a great gift if you make sure you know she likes the place it’s for. Every year I get letters from people who are mildly annoyed at receiving gift cards to restaurants that only exist two states away from where they live, or for coffee when they only drink tea, or other evidence that a gift was given without much personal thought.

Also, keep in mind that the $100 check you received was a bonus that came from the company, not from your manager personally. People don’t expect extravagant gifts from their managers, even if the company itself goes a more luxe route. And frankly, managers don’t need to give their staff gifts at all, though it’s a thoughtful gesture if you choose to.

Order Alison Green’s book Ask a Manager: How to Navigate Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work here. Got a question for her? Email Her advice column appears here every other Tuesday.

‘Should I Give My Boss a Holiday Gift?’