"Should I Give My Boss A Gift?" And Other Holiday Gifting Questions—Answered

As if it wasn’t hard enough to shop for your extremely picky aunt. Let us unpack the politics of gift giving at work (and all of its nuances). Most employees get a little something from their boss around the holidays (a bottle of wine, an engraved ballpoint pen, a box of overpriced truffles) as a sign of appreciation, but does that mean you’re expected to give something in return? What about a colleague that surprises their whole office with Starbucks gift cards when all you had for them was a measly e-card with a dancing elf? And for remote teams, how does the whole holiday gifting situation work if you’ve never met your team IRL? With all of the conflicting advice out there, we asked two etiquette experts to give us the corporate gifting lowdown.

The Experts

Lizzie Post, co-president of the Emily Post Institute, co-author of Emily Post's Etiquette, The Centennial Edition and co-host of the Awesome Etiquette podcast

Juliet Mitchell, a certified etiquette trainer, business coach and the founder of Life Etiquette Institute

Do I have to give my boss a gift?

Short answer: Absolutely not. Post actually advises against it. “You really don't want to gift up the corporate ladder,” she says. Mitchell agrees. “Some people say, ‘Well, I just like giving gifts,’ but you have to be really careful about your position and the boss's position,” says Mitchell. By giving your boss a gift, it could look like you’re trying to outshine your coworkers.

There are only two exceptions to this rule. One of them is if you have a really close, special connection with your boss. Think of Carrie Bradshaw (Sarah Jessica Parker) and her assistant Louise (Jennifer Hudson) in the Sex and the City movie. Louise gives Bradshaw a DVD of Meet Me in St. Louis (because she calls herself Louise from St. Louis and Bradshaw had never seen the film). “It was low stakes, small but sweet and connected to something personal between the two of them,” says Post. Then, Bradshaw gives Louise a much more extravagant, higher-priced gift: a Louis Vuitton bag (which is ok when it’s from a leader to their subordinate, not the other way around). “It's a great gift exchange between two people who work very closely together,” she adds.

The other exception? If you give your boss a gift from the whole team. Ask the group if they want to contribute, pick a price point that everyone is comfortable with and present your gift as a united front. “You don't want to look like you are trying to gain favor by buying gifts for your boss,” says Post. One thing to be mindful of, according to Mitchell, is the employees who might not be able to contribute financially to the boss’ gift. Maybe they can sign the group card and still be part of the gift giving process—without feeling isolated.

If you’re a small company of say 10 or less people, where it's more of a tight-knit vibe and you're all really good friends, then you could do a gift exchange that includes the employees and the boss, advises Mitchell.

If I want to give my boss a gift, what are some appropriate ideas?

The general rule of thumb is: the smaller and more low-key, the better. And bonus points if there’s a personal connection, says Post. How well do you know your boss? What stage of their life are they in? It’s important to consider those things when choosing a gift, says Mitchell. Things like jewelry, clothing, designer items, lingerie (obvi), perfume, concert/sports game tickets or anything else extravagant and expensive are no-gos. Same with what Mitchell calls “dust collector gifts” like paperweights, branded water bottles or another “world’s best boss” mug.

You can’t go wrong with consumable items, like gourmet hot chocolate, a gift card to their fave coffee shop or a gift box of charcuterie ingredients (but be sensitive about dietary restrictions and allergies). You can also opt for beautiful glassware or ceramics like candle holders, a serving bowl or wine decanter. Or donate to a charity that’s important to them, on their behalf. Your best bet is to stick to a $25 to $50 price range—anything more than that might feel inappropriate.

“I would say cards are also really great,” says Post. “Using your words to express your intention is excellent.” A handwritten card is underrated—and more than enough to show your appreciation. It’s always best to include why you enjoy working with them and why they make such a great boss, advises Mitchell. “That means so much, sometimes more than a monetary gift.”

Still feeling stuck on what to get them? “Ask their administrative assistant, secretary or right-hand person who probably knows the boss more than anyone else,” says Mitchell.

Bonus Tip: Remember the three M’s: be mindful, meaningful and modest, according to Mitchell.

I work remotely and have never met my boss or colleagues in-person. Anything I should do differently when it comes to holiday gifting?

Again, it’s really up to you and the rest of the team. If everyone’s down to come together and coordinate a gift to be shipped to their house (like some artisanal drinks or a set of glass coupes), then great. But if it’s gonna feel forced and everyone’s not on the same page about their feelings for the big boss, then it’s best to skip a gift altogether. Virtual gift cards or a nice handwritten note from the whole team that gets delivered in-person is great too. Or, nothing at all! Just don’t Venmo your boss money—that’s weird (and has probably happened before).

Another idea? If you’re the boss, send everyone on your team a gift card to get some coffee or some baked goods, and host a virtual holiday celebration during work hours. That’s the time when you can thank your team as a whole, maybe play some virtual games where people can win extra prizes or host a virtual cooking class, and end Q4 on a high note.

What if my boss refuses my gift?

This can happen—and there’s nothing to be ashamed of. You can always check your companies’ gifting policy before you go out on a limb. Maybe your boss isn’t allowed to accept gifts—period. “Don't get too disheartened by it,” says Post. “It's okay if someone chooses not to receive gifts at work. Just say, ‘That’s ok! I figured I'd try. No hard feelings.’ And now you've got a gift to give to someone else.”

I’m a boss and want to treat my team with a holiday gift. How much should I spend?

The amount of money you should spend on your team’s gift depends on the size and the revenue of your company. No one is expecting a small start-up who is in the middle of their first round of funding to give their 50 employees plane tickets to Fiji. A good base level is $25 for each employee (and it has to be the same gift for everyone), according to Mitchell. “Some people give more than that, and some might give a coffee shop gift card depending on their staff and their budget.” Alcohol is also a common one, but it’s important to be mindful of those employees who don’t drink. “A heartfelt letter to the group is so powerful too, and it means so much,” adds Mitchell.

You can also opt out of gifts altogether and throw an in-person holiday party for your team. Use that gift budget for catering, drinks, decorations and a DJ.

Bonus Tip: Mitchell advises creating a gifting guideline to share with the team ahead of the holiday season. Budgets, appropriate gift ideas, whether or not it’s allowed to give your boss a gift, etc. It could help eliminate some of the guessing or awkwardness that comes with gift giving at work.

If I give a gift to my work BFF, am I obligated to give something to everyone else on my team?

You don’t have to get gifts for your colleagues if you don’t want to. But for that special work wife who you want to spoil, “give those gifts outside of the office, not during work hours,” says Post. “Go plan a coffee date with each other, and you can give them the gift then.” TL;DR: Be discrete about it. You don’t want to make any of your colleagues feel excluded from your gift exchange.

What if my colleague gives me a gift when I wasn’t planning on reciprocating?

Yikes. We’ve all been there… and it can be awkward as hell. But it doesn’t have to be. It’s more than ok to receive a gift without giving one in return. Instead of saying something like, “Oh, I forgot your gift in the car!” and running out to Macy’s on your lunch break to throw together a present haphazardly, “focus on the gift that they've given,” advises Post. “Don't go into your lack of a gift for them. You can always get them something in the future. But you don't have to talk about that right now.”

Need gift inspiration? Check out our gift guide for everyone on your list here.