Should You Buy a Holiday Gift for Your Boss?

by Kimberly Lew

In the midst of decking the halls and crossing things off my Grown-Up Christmas List, there’s always a slightly awkward question come this time of year: What should I get my bosses/supervisors for the holidays?

Do a Google search for “presents for bosses” or “etiquette for bosses present,” and there is no shortage of articles ready to dispense advice. On one hand, accepted etiquette through the years has been that presents in professional settings should flow down the command chain, not up. A particularly helpful reader from The Hairpin pointed me to Ask a Manager, which often advises not to get gifts for bosses (baked goods can sometimes be the only exception). On the other extreme, The Billfold also had a column last year about offices that go overboard with gift-giving, trying to rope people into spending more than they are willing or able for their bosses. Then there’s the year my supervisor gave me a Snooki bobblehead and I gave him a keychain that made laser noises — so clearly there is also a lot of gray area in between.

All these possibilities made me think about the myriad ways people approach giving gifts to their bosses (if they do at all). I was especially curious about how people determined what was appropriate, how much they spent, and how these things changed depending on industry/work environment. So, I had some people anonymously submit anecdotes about their gift-giving approaches, and here are some of the responses I received:

Producer at a media production company

I work at a digital media company, and every year the employees all pool in to buy the founders/CEOs something nice. Two of the girls in our company sent out an email reminding everyone to chip in. We could either physically give them cash, or “email” them the money via Square Cash. I’d never used it before, but it is SO cool… it’s not even an app or something you sign up for, just a way to email people money. The email chain where the girls reminded everyone to pitch in also served as a place for all of us to throw around gift ideas, but nothing’s been finalized yet. We’ll present the gifts at our office Christmas party.

Writer for an international magazine

I have never given Christmas gifts to any of my superiors. Firstly, in the companies where I worked this was not part of the culture, and secondly I strongly believe that, if any Xmas giving is to be done, it should be done the other way around — unless it’s a small outfit where everybody is “family” and giving a gift comes naturally. In the corporate structure, it’s the boss who has been “serviced” all through the year. An appreciation gift should come from him/her to me. Not vice versa. Which is not to say that I wouldn’t give a gift merely on principle. If I had a great connection with my boss and a great idea for a gift I’d get it.

Also by definition, it’s the boss who has the dough and can afford to be generous to whatever degree. My bosses used to be company owners or high executives who made oodles of money — one of them didn’t even have health insurance — he just paid whatever he needed in cash. What do you give a guy like that? Oh, yes, I did give his wife a small gift … we were friendly and she was in charge of buying a gift for me. But, again, that was different. Gifting here came naturally.

Digital Strategist in social media advertising

Last year, I didn’t get my boss anything because my favorite boss left and my new one was an undiagnosed alcoholic who played seriously inappropriate favorites.

This year, I’m getting my boss makeup. I don’t know what the gift-giving protocol is quite yet at my new company, but I do appreciate how my boss has guided me this year. There was a great offer on Gilt City for a high-end makeup line (which felt gift-worthy but not over the top). I noticed once that my boss wore this nice shiny cream/silver colored eye shadow one day, and I thought I’d try to get her something similar so she’d actually use it. It was $16, originally $26. Something reasonably priced that still feels like a luxury. Hopefully it conveys that I appreciate what she’s done for me but doesn’t seem too brown-nosey/over the top!

Rights associate at a publishing house

I think the key, whenever possible, is to team up on bosses’ holiday gifts. Not only are you pooling monetary resources, you’re also pooling multiple perspectives on what your boss would find most appealing, suitable, etc. Plus, there’s wisdom in setting things up to either succeed together with your coworkers, or not be alone in feeling like you missed the mark.

In terms of WHAT to get, I’ve always been most comfortable with something somehow related to the shared work experience or environment. Something for the office that’s nicer or more unusual than your boss would get for him or herself helps narrow options, and keep things thoroughly appropriate.

Systems manager in hospitality/travel

One year working for a hotel, I bought the General Manager a Coach leather travel folio. He was a Japanese nationalist and once worked for Japan Airlines. I thought he would appreciate using it on his travels. We had little in common, but he supported my project plans.

I’ve also given champagne or wine for the holidays. Also chocolates/cookies, theme ornaments (Hallmark), soaps, and movie tickets.

Former analyst in investment banking and current start-up co-founder

I worked for my old boss for three years, and he always gave me super extravagant Christmas gifts and I never gave him anything. To be honest, he made my life completely miserable, and I genuinely believe he gave me crazy fancy looking gifts (huge bags, huge boxes, tons of tissue paper) in order for his bosses to see him “appreciating” me. Also, none of the juniors ever gave their managers gifts in my group, so I never really felt any pressure to give him anything.

I left that terrible job to co-found a start-up, which is awesome, and it’s a total pleasure to show up to work every day. My partner and I don’t give each other gifts, because I think it would be kind of weird. On the other hand, we’ve recently hired a few people and I’m considering having some company stuff (hats? T-shirts? stress balls? unclear) made up for them for Christmas this year. So, maybe there’s more pressure to do gift stuff when there are more people in the office?

Administrative assistant for a university

I’ve always been told that you don’t need to get gifts for superiors/bosses and that it’s inappropriate for them to expect them. If you were in the type of office that did holiday gifts, then it would be from the top down, rather than the other way around. I was always told this was for a few reasons: partly because it can be coercive, in that you might feel you need to buy a gift for your boss or that not buying one would affect your performance review, partly because they probably make more money than you and you might not even be able to afford a gift, and sometimes (depending on your position/the office structure) if you’re already doing work for them/that benefits them (especially if you take care of a lot of the busy work/drudge work), it’s just another thing to add on top of that. I actually learned this perspective from my father who manages a bunch of people and will do nice holiday stuff for his staff but wouldn’t be comfortable if that were reversed.

Worker at a social services non-profit

Last year, I gave my boss a vase set. It was really pretty, and there was a big vase and two small ones. She likes flowers a lot, and her husband always gets her roses, so I figured that was what she wanted. My budget was under $40, but I was open to spending more. She usually drives me to my bus stop in the winter, cause it’s far from our job, and it’s not such a good neighborhood. She also always has my back when we’re going head-to-head with our bigger boss.

Former gardener and current grad student

Once I bought my gardening boss a shank of meat for Christmas. He was really into meat. (Who isn’t!?)

The reason I picked out the meat shank is because my boss and my fellow gardeners would go to the Union Square Farmers Market every week to pick out new peppers and herbs to plant. We would pass the meat stands and George — who really appreciates a good cut of meat — would stare in awe at the shanks. So when gift time came around, we all chipped in $10 (so about $40 in total, I guess) to buy him a really freaking awesome shank.

Associate working in accounting

I personally do not believe in buying your boss gifts unless it is a group effort. Not only do you seem like a kiss-ass, but in my opinion it also seems a bit weird, especially if your boss doesn’t get you anything in return (awkward). The only exception to buying your boss a Christmas gift is if you are a personal assistant. Outside of that, a simple “Merry Christmas,” topped with a “Happy New Year” is enough.

Assistant in TV ad sales

I work as an assistant to three “account execs” (sales reps), and I got each of them $12-$16 bottles of wine. I had a little fun with it and tried to match their personalities. The fiery Latina got a bubbly with a fashion-forward label. The boisterous Mr. Nice Guy got a big, bold table red. And a really classy pinot noir went to the quiet but well-liked third. They all really appreciated it and said I didn’t have to get them anything, but I’m pleased to work for them and I love gifting so it was perfect!

Legal Assistant at a corporate law office

I generally purchase gifts for bosses/supervisors at Christmas. Although, it is less about the holidays and, rather, it’s the end of the year thank you — generally reflecting on the past year and getting ready for the new one. While I have not given gifts to all bosses/supervisors I have had, I think it is a nice gesture for a boss/supervisor who’ve helped me out, has been accommodating during a difficult time, went out of their way to help me develop professionally, or offered me opportunities for overtime because they knew I could use the extra money. A lot of my positions have involved a lot of long hours and these are the people I spend the most time with.

Kimberly Lew is a published playwright and blogger who writes about the publishing industry and theatre. She once gifted cookies to her office made from a mix and didn’t say anything when everyone assumed it was from scratch.

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