Gift Trap

We always chip in $100 each for a Christmas gift for our boss. Do I have to?

A hand giving money to another hand in an office decorated for the holidays.
Photo illustration by Slate. Photos by Getty Images Plus.

Few people are as knee-deep in our work-related anxieties and sticky office politics as Alison Green, who has been fielding workplace questions for a decade now on her website Ask a Manager. In this week’s Direct Report, she answers readers’ questions about holidays at work.

Dear Direct Report,

My co-workers in my department like to give one another gifts for various events and holidays, like birthdays. It is a nice thought, and typically the contributions are small ($5 to pitch in for one gift card), but for Christmas, we all chip in to buy a gift for our boss. It’s a minimum contribution of $40 but often comes out to be $100+ per person, and I am starting to feel a bit resentful.

Is there a way that I can politely decline to contribute to the gift for our boss, or should I cough up the money? My team is small—only five members—so it will be very obvious if I do not partake.

I wasn’t as bothered by it in the past, although I did think it was ridiculous, but right now I am really pinching pennies as I am in a tough spot financially.

—Not Flush With Cash

Dear Not Flush,

One hundred dollars per person for a gift for your boss? Good Lord. That’s more than many people spend on family members. Your boss should have put a stop to this long ago.

The etiquette rule for gifts at work is that it’s OK for gifts to flow downward (from your manager to you), but they shouldn’t flow upward (from you to your manager). That’s because of the power dynamics inherent in the relationship; otherwise there’s too much chance that someone will feel pressured to buy a gift for the person who controls their paychecks, and it’s unseemly for a manager to benefit from the position in that way. What’s going on in your office is a good example of this: People are chipping in for pricey gifts for the boss but no one else, and at least one person (you) feels pressure to participate.

Can you nudge your co-workers to reconsider the tradition altogether? I bet you won’t be the only person who’d be relieved to have one fewer purchase to make at this time of year. You could say you just read an etiquette column on this (hell, send them here) and would rather do a simple card.

But if not, it should be fine to bow out by saying, “It’s not in my budget this year.” If you want, you can add, “I could chip in for something much smaller, like our usual $5 contributions. Would everyone be up for that instead?” (And again, I’d bet money someone else on your team will be glad someone else is speaking up. This might be like the Emperor’s New Clothes, where no one wants to be the first to say something, but everyone is secretly thinking, “WTF?”)

Dear Direct Report,

I’m the director of a 100-employee office of a multisite organization. Our employee engagement team, with support from our corporate office, planned the holiday party months ago. It’s appropriate enough—snacks and drinks and optional escape room activity, employees only, after work on a Friday. It’s also at the end of a week that will be unusually busy and stressful for my family for nonwork reasons, and I’d much rather spend the evening with my spouse and young kids. Can I sit this one out without looking disengaged and uncaring? If I decide to skip it, am I better off trying to frame it as “everyone will have more fun without the boss around” or simply stating my desire to see my kids before bedtime?

—Partied Out

Dear Partied Out,

As a general rule, most people should put in an appearance at the office holiday party. Yes, they’re allegedly “optional,” but in a lot of offices, not showing up will get you marked as less committed or less engaged. This is absurd but still the way of the world (in many places at least).

That said, if you have a truly unmovable conflict, that’s different. Reasonable workplaces won’t expect you to change airline flights or reschedule surgery just to attend an office party. But when the reason is “I don’t want to” … usually you’re better off if you suck it up and put in an appearance. I find that incredibly annoying, but so it goes.

And all of this is especially true for you because you’re the head of this office. Your absence will be far more noticeable than nearly anyone else’s, and not going risks looking like you can’t deign to socialize with underlings. It’s once a year; you should be there.

However, I do have some good news, which is that you don’t have to stay for the whole thing. Show up for an hour, circulate, be seen, and then head home to your spouse and kids. You’ll get the points for attending without losing the whole evening.

Dear Direct Report,

I manage a big team—27 staff members. Until last year, I only had 10 direct reports, and I gave individual gifts to each of them over the holidays. Nothing fancy, think $10–$15 range. This money does not come from the company’s budget: I buy these gifts with my personal money to show my appreciation for my awesome staff. However, my team is so big now that individual gifts will require me to spend a lot of money. So this year I was thinking of ordering a big gift tower of assorted edible items and bringing it to the office so everyone can share it. Do you think this is rude? Should I skip employee gift-giving entirely or suck it up and buy individual gifts?


Dear Overwhelmed,

A massive tower of edible items isn’t rude! Food is an excellent approach to holidays at work in general, especially for managers of large teams like yours. In fact, a lot of people will prefer a spread of shareable food over individual trinkets, which can be hard to match to recipients’ taste when you’re not very close to them.

Do try to take into account any allergies or other food restrictions on your team, though. It’s OK if you don’t find one thing that works for everyone, but in that case, make sure you supplement with other options so everyone can partake. (For example, if you’re getting a bunch of cheeses, getting some fruit and fancy dark chocolate for your vegans will make them feel taken care of.)

Dear Direct Report,

My company has announced it will close at noon on Christmas Eve and New Year’s Eve. Employees will be required to use a half-day of vacation time to cover the afternoon.

I feel like this is a cost of business being passed on to employees. I think a better policy would be still requiring use of an entire vacation day if you take the whole day off, but being paid for a full day if you come in. Is this worth pushing back on?

—Protective of My Vacation Time

Dear Protective,

Yeah, that’s a crap policy. If the office is closed, it’s closed. What are you taking vacation from? There’s no office to go into.

But it’s also not a terribly unusual practice. A lot of offices handle early closures for holidays this way. Some companies that close the whole week between Christmas and New Year’s even make employees use vacation time for that period.

That doesn’t mean you can’t try pushing back, though. It’s reasonable to point out that employees may have that vacation time allotted for other uses, and if the office is closing, it’s a bit like asking people to use vacation time for Presidents Day or another day the office is closed. Try to get a group of co-workers to join you in this push; as with many things, you’re more likely to succeed if a bunch of you make the case.

Dear Direct Report,

I was instructed to plan our company party last year, so I reserved tables at a local restaurant where I have been a regular because they have excellent food and service.

NO ONE SHOWED UP ON TIME EXCEPT ME. No one. To the point that they could not continue to hold the tables. I did convince them to let me (and the co-worker who arrived 15 minutes after me) have a table, and as everyone else trickled in, they added chairs. This was an enormous inconvenience for the restaurant—the last member of our party was 90 minutes late—and was hugely embarrassing for me as a person who had gone out of her way to benefit an awesome local business and was now the face of a wildly inconsiderate group of people. As a result, I refused to coordinate this year’s holiday gathering.

Am I out of line? I feel like I can’t rely on my co-workers to honor timelines, and I don’t want to be the person responsible for that!


Dear Embarrassed,

It’s possible your co-workers weren’t clear on the nature of the arrangements you’d made with the restaurant. A lot of holiday functions have pretty loose start times. So if people weren’t explicitly told this was a sit-down meal that would start at a specific time, their late arrivals could have been simple miscommunication rather than flagrant disregard for you and the restaurant.

That said, if you have the option to decline the party planning this year, go ahead and decline! Planning parties tends to be a thankless job anyway, and despite taking a lot of energy to do well, it’s not usually the type of work that gets you raises, promotions, or higher-profile projects. As long as your job description doesn’t specifically include party planning, it’s reasonable to say you’d like to pass the torch this year.

If it is your job to manage the holiday party, flatly refusing might not be in your best interest, or even an option. If that’s the case, and you don’t think last year’s fiasco was due to a miscommunication, plan an event where it won’t matter if guests show up on time. For example, you could consider having catered food brought to your office or a rented venue, which would make it far less problematic if people trickle in at their own pace.

Dear Direct Report,

I am currently a contractor for a large tech company. I know that I am being underpaid for my level, and I want to start job searching. However, should I hold off given the proximity to the holidays and the likelihood that people will be out and interviewing would be difficult to schedule? Since I am thankfully not in a situation where I need to get a job imminently, would it make more sense to wait until January?

—Impatient Job Searcher

Dear Impatient,

Job searching around the holidays can be weird. Some places have everything on hold until the new year because of interviewers’ vacation schedules and a general December slowdown. But other places are still hiring, and with those you might even have a leg up because much of your competition is focusing on shopping and eating pie rather than applying for jobs.

You can’t tell from the outside which companies will be in which category, so if you’ve got the time this month, go ahead and start applying. Companies that are moving slowly right now either won’t be advertising anyway or will get back to candidates in January, but plenty will still be moving forward at a mostly normal pace. Good luck!