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The Trusty Oak Blog

How to Show Holiday Appreciation—Remotely

December 12, 2019

Remote employment is convenient, easy, and freeing. But as the Trusty Oak family have written about many times, it’s easy for remote employees to feel like an island. Not to sound like anyone’s grandparents, but the distractions of technology do sometimes make it harder to find the human connection we need.

As the holidays approach, many of us will prepare to celebrate traditions that honor our loved ones. In turn, businesses will try to do the same for their employees. But it might be a bit harder for those that employ remote workers. In fact, Harvard Business School did a study in which they found that remote employees often feel undervalued by the companies they work for. In short, they don’t feel highly prioritized. This time of year is a perfect excuse to show your remote employees that their work and presence in your company is valued, and we at Trusty Oak have some ideas on how to do this.

Throw A Remote Holiday Celebration

To quote our CEO and founder, Amber Gray, “There’s still nothing that can replace the benefits of in-person interactions.” Businesses around the country recognize this and throw end-of-year parties for their employees. Heck, even my previous manager at Subway would invite us over to his house for some seasonal poker and drinks. But how do you do this when your employees are scattered across the United States?

At Trusty Oak, we divvy up part of the budget for a remote holiday party. Since some of our VAs share a home city, they’ll get together with each other and video chat the rest of the company in their respective locations. For instance, my family’s from Boise, ID, so I’ll be attending the Boise Trusty Oak party, and we’ll video chat Amber and co. in Austin, Katie in Pennsylvania, and so on and so forth.

Remote Christmas party virtual assistants

The 2018 Trusty Oak remote holiday party with VAs and their families from Idaho, Texas, South Carolina, and Pennsylvania. 

It’s actually not too much different than other business holiday parties. There will still be adult beverages, I’ll probably bring my girlfriend, and we’re even going to watch a Christmas movie this year. Trusty Oak isn’t the only company to do this, and as remote opportunities grow I expect it to become commonplace. 

Holiday Games

A great way to build company culture and contribute to it yourself is to implement and partake in holiday games. If you grew up celebrating Christmas, or are a fan of the Office, you are probably aware of the holiday game entitled “Secret Santa.” In a work setting, each employee draws the name of one coworker out of a hat. They are then tasked with buying a gift for the person whose name they drew. 

A game like this is perfect for remote companies because you don’t actually need to be in close physical vicinity to one another to make it work. The fine folks at IMPACT have implemented this into their seasonal traditions and explained how it works in an article they wrote:

This year, we used to digitally draw our names. All you have to do is input the names or have people sign up with a custom link, and then with the click of a button, it assigns out all of the giftees… Since we can’t walk over to everyone and give them our gifts, we had to change to shipping everything directly to people this year. (You’re welcome for the business, Amazon.)

Of course, it’s important to have an established remote culture in place before a game like this can occur in your virtual office. The reason is that there’s no “one size fits all” Secret Santa gift. With remote employees, we sometimes find that the personal relationships built in offices don’t happen so naturally. The Trusty Oak blog has talked a lot about using communication tools to build a remote culture before, and IMPACT doubled down on this by having their remote employees share pictures of their gifts in a Slack channel. So keep in mind that while holiday games are moment-focused, company culture should be built constantly.

Company Gifts

I’m not the kind of person to expect gifts from employers. However, I always find myself being pleasantly surprised when I receive them, especially as a remote worker. There’s something about getting personal mail that makes me feel valued by others, and the holidays are a perfect time to do so for your employees.

If you plan on sending out a thank you card, some candy, or any other kind of gift to your team, I would challenge you to go one step further and tell them in writing why you appreciate them. Did they recently close a big deal? Were they particularly helpful on a certain project? Do what you can to make it more than just another Christmas card. Make it personal to them. This will let them know that you appreciate their role in your company and that they’re important to your success.

If you find yourself overseeing a lot of people and happen to have lower chains of command under you, then it may be good to delegate every manager to handle this for their own direct employees. This will make each gift personal and of higher quality, building company trust and remote community all around.

Related: 5 Holiday Gifts Ideas for Your Virtual Assistant

So this holiday season (do I sound like the commercial of a Hallmark movie?), consider the people that make it work. Don’t forget those out of your physical office space—they’re real people who desire to be appreciated just like you do, and you can’t do what you do without them. After all, that human connection is what the holidays are all about, right?




About the Author

Robert Lanterman

Robert Lanterman is a content specialist based out of Queens, NY. He loves the creative aspects of marketing and most of his career has thrived due to that passion. He graduated from the College of Idaho in 2014 with a Bachelor’s degree in Business and a minor in creative writing. Shortly after, he began working for an SEO firm as a link builder, doing both resource and directory work before shifting his focus primarily to content. All the while, he established himself as a freelance writer and began doing publicity for artists in the North American independent music scene. He absolutely loves writing and seeks to help enthusiastic entrepreneurs reach their goals.
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