Secret Santa at the office: How to choose the perfect gift

Twinkling lights lining the streets and glittering trees in shop windows are a few telltale signs that the holiday season has arrived. You may be spending this special time of year with your loved ones, but nothing’s stopping you from spreading a little holiday cheer at the office. So, why not organize a Secret Santa? This quaint tradition has strong roots in the workplace and can be a great opportunity to show your appreciation to your work family this December. If you’re not familiar, the rules are simple: Each employee draws the name of a coworker and buys them a small gift with a set budget. Depending on your office culture, Secret Santa can be the time to make a meaningful gesture with a thoughtful present or lift spirits with a hilarious gag gift. However, what happens when you draw the name of someone you’ve never spoken to, or worse, your boss? Check out our guide to gifts for all different kinds of working relationships – and you can make sure no one goes home empty-handed this year.

Your boss

Ouch, that’s the luck of the draw. Even if you have a great rapport with your manager, it can be stressful to find the perfect gift. If you know them well, try to get something thoughtful but not too personal. Choosing something meaningful or funny – without crossing any professional boundaries – can be tricky, but you also don’t want to snub them with something too generic. One unfortunate worker told us their coworker “gave the director of purchasing the thong from the Borat movie. He blushed and left the room in silence…” So, save the funny gifts for next year. A box of chocolates or a houseplant can be a nice, neutral gift. You may not win any awards for creativity, but you won’t risk an awkward situation.

The person you never talk to

Maybe they’ve just joined the company, or maybe you just never had the opportunity to work together, but you have no idea what this person likes. The best thing to do is talk to your colleagues and see if there’s anyone who can give you some insight into their personality, or suggest a potential gift. Like this worker, you could even use this as an opportunity to make a new friend at the office: “I had drawn the name of someone with whom I’d had very little contact. Someone from his team told me about his passion for literature and theater. The shop beneath my apartment was selling used books and I found a 1930s edition of a classic for a few bucks. I found out later that she wasn’t a fan of the author, but she was touched to see I was interested in her and that I made an effort to find something meaningful. We still don’t work together, but she’s become my best friend at the office!”

The office clown

Do they pull pranks, speak too loudly, and make the office laugh all day? You can really let loose with this one. The office clown knows how to take a joke, and will love a gag gift. Get them something to make them laugh, or if you’re feeling mischievous, a new tool to cause more office hijinks.

Your nemesis

There’s one in every office, and this year you drew the short straw. Are you racking your brain trying to think of what to get for someone you don’t like? If you’re really struggling, you can try convincing someone to exchange names with you. Maybe they have a friend in the office who would be happy to get them something, but if you’re stuck with them you’ll have to think hard. Just like shopping for your boss, it’s best to get something that won’t fan the flames of your office rivalry. However, sometimes pettiness can get the best of you as it did with this person: “Last year, the person whose name I drew slut-shamed me. I couldn’t help myself, I gave him a box of chocolates… filled with wasabi.” Yikes!

The creative

Do they spend their time during meetings doodling in the margins of their notebook? You may be shopping for a creative. Whether they’re a web designer, a graphic artist, or even a stylist, they’re a talented worker who will appreciate an original and beautiful gift. Go for a nice drawing pad, an art book, or even art supplies. To impress them even more, you can make it personalized, “I thought this lime-colored mug would really fit your unique style.”

The hipster

The hipster is a unique character that we love to hate. Luckily, they are easy to please. Go with something out of the box and it will surely be a hit. Vintage glasses or a pair of funky socks could be just the ticket (or anything with the words “artisanal” or “organic” on it). In short, authentic gifts for an authentic person.

Your work bestie

The Sam to your Frodo, the Robin to your Batman, what should you get for your best friend in the office? For this one, the sky’s the limit. You can surprise them with something that represents a shared interest, references an inside joke, or even something completely ridiculous to catch them off guard. In short, you probably don’t need our advice for this one! You can’t go wrong when you’re lucky enough to draw your bestie’s name during the season of giving. Secret Santa is meant to be a bonding experience, so if you already have a good relationship, why not just have fun with it?

Gifts to avoid

Maybe you ran out of time or couldn’t think of an idea, but you can still avoid disaster. So, here are some areas to avoid entirely when choosing your gift:

• Tactless gifts (toothpaste, deodorant, underwear, etc.), anything a person should buy for themselves
• Anything with the clearance sticker left on it
• Expired food or candy
• Anything with political, religious, or sexual connotations (no need to ruin the holidays with a meeting with HR)

If you work in an office, Secret Santa can be a great way to kick off a great holiday party with your coworkers. It can break down office hierarchies, and give you the opportunity to get to know people you don’t work directly with. Just remember, when in doubt, it’s better safe than sorry when it comes to giving a risky gift!

Photo: Welcome to the Jungle

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