A Sneaky Elf’s Guide to Hosting an Anonymous Secret Santa Office Gift Exchange with Coworkers

Godiva chocolate gift box
A scrumptious gift box of chocolates | Image courtesy Amazon seller GODIVA Chocolatier

This time last year, I had just started in a new department at work. Along with my orientation package came an invitation to participate in the office Secret Santa gift exchange. I was hesitant because I didn’t actually know anyone in my new office, but my boss encouraged me to take part—and I’m so glad I did! This fun office tradition truly helped me become a part of the team.

On the day of the gift exchange, I arrived at work and found a beautiful notepad, cute mug, and delicious box of chocolates waiting on my desk. I was delighted with such a thoughtful gift—what a great way to start the work day! My anonymous gifter must have noticed my love of fancy stationery, and dependence on the office coffee machine.

The thoughtfulness of the gifts gave me such a sense of being welcomed and accepted in my new role in the company, despite the fact I had absolutely no idea who gave it to me! I loved that added bit of mystery, and the fun of trying to figure out just who my Secret Santa really was.

So, to bring merriment and mystery to your own colleagues, I offer these four simple steps we use at my own workplace:

Step 1: Make Sure Name’s Are Top Secret

christmas wrapping paper
Image flick’r user Hade2K

The whole point of Secret Santa gifting is just that—to keep it a secret. I love spending the few weeks leading up to the gift exchange wondering who’s busy putting together a gift for whom. There’s a giddiness that takes over the office when we all receive a name of a coworker and start planning out their gifts. Everyone’s excited and, as hard as it is to keep our lips sealed, we know it’ll be worth it in the end.

In order to keep our Secret Santa truly anonymous, my office utilizes an online Secret Santa tool that distributes the names for you. Bonus: the online system has the master list of names in case someone, like my forgetful co-worker Laurel, forgets who her recipient is.

Step 2: Put Your (Sneaky) Elf Hat On

Here comes the fun part: “Operation Undercover Christmas.” You get to put on your elf hat and covertly find out exactly what your coworker would most love to receive for Christmas.

designer notebooks
Designer pocket notebooks | Image courtesy Amazon seller B-THERE

Here are a few great ways to get into spy mode:

  • Dig into their wish list: Many online gift exchange services will offer the extremely helpful option of having participants fill out a wish list. This was a lifesaver for me last year because I was new in the office and had no idea what my coworker Bryan, whose name I drew, would most enjoy. From his wish list, I learned that he was a huge coffee lover—something we definitely had in common.
  • Try to learn about their interests in casual conversation: This approach is a bit trickier, and should only be reserved for the sneakiest of elves, because, if you mess up, you could be found out! Luckily, I had a good “in” with Bryan. Upon learning we were both coffee lovers, I made it a habit to join him for a mid-morning coffee break, and we’d talk while the pot brewed. During these chats, I learned that Bryan and his family were gearing up for a tropical getaway over the holidays—information that came in handy later.
  • Do an office stake-out: But… make sure to keep your elf ears pointed up so you don’t get caught! Last year, I think my Secret Santa swung by my desk and noticed that I was using a boring company mug from the staff kitchen for my many, many cups of joe. They probably also laughed at the fact that all of my training notes were written on post-its, and realized that I could desperately benefit from a real notebook.
  • Gather intel: If you’re still stuck for gift ideas, it’s time to take your mission to the next level and bring in some reinforcements—it takes more than one elf to keep the toy shop running! So, ask around. If you don’t know your recipient well, but have some friends in common, covertly get their take on what would make a great gift. Throw them off the scent by getting gift recommendations for a few co-workers, not just your recipient. That way, you’re still able to maintain an air of mystery.

Step 3: Don’t Let Little Details Blow Your Cover

a self stirring mug
A fun gift mug | Image courtesy Amazon seller OliaDesign

By this point, I had the perfect gift all ready to go for Bryan, but I wanted to make sure I didn’t give anything away in the final stretch. I picked a unique way to wrap his gift using a map of the Caribbean island where Bryan and his family would be spending the holidays. I was sure he would enjoy the extra effort, and that the map of his vacation island would have him dreaming of sandy beaches and blue waves.

But, I didn’t want Bryan to catch me walking into work with wrapping paper he would later recognize on his gift. So, I made sure to hide the present in a plain bag so he wouldn’t suspect a thing as I dashed to my desk.

While I was pretty sure Bryan wouldn’t be able to recognize my handwriting, I didn’t want to take any chances. To keep things super secret, I typed up my card and was sure to keep my name off of it so even once he’d opened his gift, he would still be clueless that I was the one behind it. Adding a few extra steps to make sure the gifting stays secret is definitely worth the effort!

Step 4: Successful Delivery Should Be Followed by a Festive Fête

Luckily, last year my Secret Santa got to work before I did and was able to drop a gift on my desk anonymously. Or, if you’re one of the last ones at the office, you could leave your gift the night before to be found in the morning.

Every party needs a gingerbread house | Image courtesy Amazon seller Wilton Enterprises
Every party needs a gingerbread house | Image courtesy Amazon seller Wilton Enterprises

However, my boss had an even better option for this year’s Secret Santa. She renamed our meeting room “Under the Christmas Tree” and even went so far as to cover the table in a tree skirt. Instead of trying to drop off our gifts to our coworkers’ desks directly, we’ll bring them to the meeting room throughout the day, leaving the wrapped presents on the table. That way, they won’t catch us in the act—or discover who their Secret Santa is. I can walk Bryan’s gift in the plain bag into the meeting room before taking it out of the bag, and he’ll never know it was me who brought it!

At the end of the day, we’ll all gather in the meeting room with the pile of anonymous presents waiting for us. I’m really excited about this idea because not only does it maintain the surprise, but it enables all of us to open our gifts together. My favorite part of Secret Santa is watching my giftee open their gift—and I can’t wait to share that experience with the rest of my colleagues.

Plus, since we’ll already be gathered up, we’re just a few snacks shy of an office party. So now our Secret Santa gift exchange is going to double as a mini office Christmas celebration. I’m helping to arrange a potluck of snacks and baked goods to be brought in, spending the afternoon decorating the meeting room, readying my festive playlist, and even bringing some gingerbread house kits.

Getting to know, and love, your coworkers is the true gift of playing Secret Santa—to find a new coffee break buddy in Bryan, or learn the recipe for Cassie’s scrumptious scones. So why not sip a little eggnog and chat with your office mates as you open anonymously gifted presents? Because a thoughtful gift becomes all the more meaningful when you get to spend time celebrating with the ones who gifted it to you.

Let us know how you’re keeping the “secret” in Secret Santa by connecting with us on Facebook, Twitter @Elfster, or Instagram @Elfster. And, for extra inspiration, check out our Coworker Gift Guides.

About Jeni W 20 Articles
Jeni is a music-loving, crafty boy mom of 2. When she's not crawling on the floor after her toddler, she can be found DIY-ing up a storm, coffee cup in hand—there's always a reason to party in her world.