Your Guide to Meaningful Holiday Celebrations with Your Team

It’s the most wonderful time of the year. With the holidays approaching, you may be thinking about how you’ll celebrate with your team. Investing in workplace rituals creates a sense of unity, meaning, and connectedness. Figuring out how to bring people together, whether you’re in person or not, is important. After all, a team exists to achieve more than any individual could alone. As a leader, this is your opportunity to help your team members feel valued for their individual and collective efforts at work. Here’s your ultimate guide to gift giving and gatherings at work this holiday season. 

Gift Ideas 

Navigating gift giving at work can feel overwhelming. Who on my team should I give gifts to? (A leader should give a gift to their direct reports and assistant. I give gifts to everyone who reports to me, direct or indirect.) Do I give a gift to my boss? (Generally, you don’t have to gift “up,” and I’ve always chosen to give gifts to my bosses. If you’re inclined to give a gift, you could consider going in on a gift with your colleagues to make it more comfortable.) How much should I spend per gift? (Though your team is priceless, set a reasonable budget for gift giving. Also remember you’ll be setting a precedent for future years, especially as your team grows.) Above all, focus on gift giving as an opportunity for showing appreciation and do what feels authentic to you. 

If you’re looking for some inspiration for your team members, colleagues, or boss, here are some of my favorite gift ideas that will work for most anyone:  

Subscriptions – Extend the joy of your gift by having it be something that happens more than once. There are lots of options to consider, ranging from floral arrangements delivered monthly from Poppy Flowers for someone who loves arranging flowers, to an HBR magazine subscription for someone who is always sharing the latest leadership articles with the team, to Audible subscriptions for the one who loves to listen to books on their commute. 

Books – Share the joy of learning by gifting a book or a book gift certificate. I learned Bookshop.org offers gift certificates, so you can support independent bookstores while you bring joy. 

Coffee – Whether your team members are remote or working in the office, there’s always a coffee shop nearby. Find a gift card for their favorite location. Add in a reusable travel mug for the gift that keeps giving. (I ordered personalized Yeti mugs for my whole team last year and they were well received!) 

Classes – For the team member who loves to try out new things, gift them a class pass. You can gift Masterclass for the person who wants to level up her skills in a particular area. Airbnb offers online experiences on different topics ranging from wine tasting to improv. (You might even consider using this as a holiday party gathering for your team.) 

Community – For the person who has everything, a gift to a charitable organization that is near and dear to their heart is always appreciated. The organization will often send a notification or personalized card to let the recipient know they’ve been honored. You can also consider gifting to an organization like Kiva, which is a microlender that supports underserved communities by providing access to financial capital, and your gift recipient can choose which entrepreneur to support through their gift. 

When you’re thinking about gifts, don’t underestimate the power of a handwritten note expressing sincere gratitude. Take time to appreciate your team member’s individual strengths or a specific example of something they did over the last year that made the team stronger. These are the gifts that honor who they are, which research shows will help them feel more connected to their purpose and their work. 

Gatherings 

Some offices are in person, some remain fully remote, and there’s a whole lot of in between. The goal of a holiday gathering is to help people feel connected. The moments when you’re not working on projects or deadlines, but showing up as people, create community. Remember, one of the fundamentals of building trust is connecting with your colleagues as their authentic selves. Plus, being together like this gives you a chance to connect people across teams and at all levels of your organization. This, in turn, breaks down silos and also gives everyone exposure and inclusion.  

The holiday luncheon has been a beloved ritual for many organizations. If you’re planning to celebrate in person, over-communicate what your safety protocols are, so your employees don’t have to wonder what to expect. If you’d like to bring everyone together, but want to respect physical distancing and masking guidelines, you could consider hosting a holiday open house in the office or a special location where your team can spend time connecting with each other and have to-go bags of treats to enjoy when they get back home. 

Not everyone will be ready to be back in a large group with colleagues or inside a restaurant, so get creative about your gatherings. As we’ve learned throughout this pandemic, you don’t have to be in person to create meaningful connections. Have a special meal or snack box delivered to all your team members to enjoy together while you gather virtually. Send team members a cookie decorating kit in advance and decorate them simultaneously on Zoom. (Don’t forget the prizes for best creation!) Host a virtual secret pals or white elephant gift exchange. Mail gift boxes with all the necessary ingredients for a recipe, and have a chef teach everyone to try it out at home. 

You can also bring the gathering to your team. Last holiday season, I personally delivered holiday gifts to each team member’s home. Even for just a few minutes, we were able to connect and share joy with each other. More than the gift I delivered, I wanted to show my commitment to them as people by meeting them where they are and personally saying thank you. 

Making the Holidays More Inclusive

For some people, the holidays may be a hard time, whether because missing loved ones or recalling sad memories. Be mindful of this when planning activities at this time of year. Plus, people don’t all celebrate the same thing or the same way. Make an effort to include decorations and music that represent multiple holidays—or there doesn’t have to be mention of any specific holiday at all. The spirit of generosity, kindness, and gratitude are always inclusive! 

Keep in mind you can create your own holiday observances for your team. December can get overly hectic between work and personal commitments. Why not host your annual holiday party in January? It will give everyone something to look forward to after they return from their vacation and start the new year.  

When the world moves so quickly and days blend together, rituals help us keep track of what we value. As leaders, we recognize what matters most are our people. Keep this at the heart when you’re planning for meaningful celebrations this year and always.

Shanna A. Hocking