Holiday Survival Guide: 14 Do’s and Don’ts for Boss Gift-Giving

During the holidays, one of the hardest gifts on your list is always your boss. To get a gift? To not get a gift? Real talk—you feel like you’re going to lose either way, and it’s true. But you're always better off getting them a little something than being the only one who skimps out.

Perhaps your boss belongs in Horrible Bosses 3, or maybe you two are total besties who just get each other. Most of you are somewhere in the middle. So here are our Do's and Don’ts for boss gifting.

Don’t look like a total brown-noser by overspending, or by being the only person who pulls the trigger on the gifting. Make sure you ask around and use your best judgment. Check with your coworkers and see if they’d like to all chip in on something so no one looks bad.

Do assess your situation. Young start-up design firm is a different environment than white-shoe New York law firm, so keep company culture and your own relationship with your boss in mind, but in every situation err on the conservative side. Risqué gifts are not worth it.

Do choose something that says thoughtful, but not too personal. The easiest is food and drinks. Even your most Devil Wears Prada–esque boss drinks coffee or tea! Because unless your boss is Michael Scott, no one needs more tchotchkes on their desk.

Do and Don’t: Booze. This is often the go-to, so let’s get it out of the way. Do be very careful to check your company’s policy on alcohol and the workplace, as it is more and more common to have a zero-tolerance rule in effect. So long as you get the all-clear, a nice bottle of something you know your boss enjoys—such as a unique gin, a Vermont vodka made of fermented honey, or an older bottle of Pappy—is always a smart choice. With that being said, don’t choose a generic, easy-to-find bottle, which screams laziness.

Do go with a nice accessory if you know your boss loves wine or beer but the company policy is a big booze no-no. Don’t get wine charms. Try picking up a set of two or four very nice wineglasses instead, or a few Moscow Mule mugs; they're the perfect thoughtful, but alcohol-free, gift.

Do observe your boss in his or her natural habitat. What does he or she do for lunch? A gift card to a favorite corner café or a delivery service is a useful gift you know your boss will like and is easy to scale up with coworkers pitching in. If your boss brings lunch in every day, a container that has its own bamboo cutting board is ideal. Or, a sleek lunch bag if he/she is brown-bagging it all the time, and throw in a selection of gourmet hot sauces if climbing the Scoville scale is his/her lunch style.

Do consider their tastes and their indulgences. If your boss is always jonesing for a 3 p.m. snack, stock his/her drawers with some packages of sweet or savory bites like fancy Paleo-friendly beef jerky if he’s a CrossFit nerd, or the most dangerously delicious chocolate chip cookie from a baker who even makes her own vanilla. Even some gourmet granola bars like 18 Rabbits or Awesome Bars may seem like a lame gift, but they're both practical and thoughtful.

Don’t buy your boss a pen. Or a candle. Or a calendar. Ever.

Do keep the price of your gift appropriate. Your boss knows what you make; don’t go way overboard to the point that they’ll feel uncomfortable.

Don’t hand your boss a gift in front of your coworkers. It makes you look like an attention seeker and can make your boss and cubicle-mates feel squirmy.

Don’t give your boss the same gift that you gave everyone else in the office. Even if you made a batch of homemade granola for everyone on your acquaintance list, it is not appropriate to gift the same item to your boss.

Don’t give a practical/hint-y gift. It’s rude. I know she had gross coffee breath and that he complains about trying to lose weight, but the holidays is not the time to send subtle messages.

Last but not least: If you’re the boss, treat your team to a nice lunch outside the office.

Header image of The Office from The Moldy Canoli; copper mugs image from Williams-Sonoma; jerky image from Food52; Basic Granola recipe from CHOW

Vanessa W. Simmons is a former cook living in San Francisco, helping to run a food business. She's probably hungry, but if not she could eat.

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