We’ve all been there. You are at the company holiday party, and something embarrassing happens that makes everyone feel uncomfortable and uneasy. While you might think that virtual events would be exempt from such circumstances, the reality is that Zoom events have had their fair share of awkward moments.

To give you a sense of just how uncomfortable these virtual events can get, even The Washington Post had enough material to publish a compiled list of the cringiest Zoom moments.

At one mixology event, all the participants had to buy the ingredients for the artisan cocktail on their own, but everyone forgot to do so. Instead of paying attention to the facilitators and having fun, the Zoom grid was full of people wandering over to their liquor cabinets to drink whatever they could get their hands on.

Or better yet – a scavenger hunt where everyone in the group is assigned to smaller teams, but the organizers didn’t know how to use the “breakout room” feature in Zoom. Picture the chaos of 60 participants trying to coordinate with teammates in one large room.

And when one company hired a DJ for their virtual party, the event quickly turned into a snooze fest because everyone could only see the DJ’s screen. The DJ was trying to hype everyone up, but no one could respond to her or interact with each other. So, people started logging off early, feeling lonely and bored.

As you can see, the ways a virtual holiday party can go awkward are just as varied as with in-person events. Luckily, there are ways you can stay one step ahead of these kinds of uncomfortable situations.

Here are six tips for planning ahead of time to prevent things from going sideways. Following this helpful guide will ensure a more enjoyable experience for everyone.

1. Choose the Right Technology

After nearly two years of working from home, everyone is likely to have a solid computer setup and knows how to use the company’s preferred virtual meeting platform. However, attending a company meeting is a bit different from hosting a virtual holiday event. 

First and foremost, make sure that the app you are using to host your virtual holiday party can support the number of people you have invited. There’s nothing more embarrassing than having to tell your guests that they can’t attend the party due to your poor planning. 

Take time to test your entire technology stack. Ensure everything is working properly at least an hour before the event starts. Most importantly, check if your internet connection is stable enough to handle live streaming. You can do this by performing a simple speed test to determine if your internet is fast enough. 

Before the actual event, you should also take time to connect with your less tech-savvy staff members to ensure they won’t have any trouble connecting. This is especially important if you plan on using a different platform than the one you use for usual weekly video meetings. But no matter how well you prepare, technical difficulties may crop up anyway. So, have someone on hand who understands technology to help you minimize any awkward waiting around for things to start, skips in the video, or audio problems.

2. Limit the Number of People

If you run a small business, inviting everyone to the event isn’t going to be a huge problem. But if you are planning a virtual party for hundreds of staff members spread across different time zones, consider breaking it into smaller events or groups rather than trying to get everyone together.

With in-person holiday events, people can walk around and mingle, forming smaller groups to have more intimate conversations in the context of the larger party. But in the virtual space, it is far more difficult to have meaningful conversations if 200 people are speaking at the same time. 

Similarly, if most of your staff is just sitting around staring at the screen with their mics muted because there are too many people, they won’t feel connected, and it won’t be much of a party. Instead, make everything less awkward and encourage more interaction by having fewer people at any single virtual holiday event.

3. Have a Host

If you work in a small office, it might be tempting to just let everyone come in and mingle. While that might not be a bad thing, you still need to have a designated host to move things along. 

This person will be in charge of starting and ending activities on time, initiating conversations to get interactions going, and even helping push past any awkward moments. Having a single point person in charge of making sure things are running smoothly can help the entire event feel more polished and relaxed.

4. Set a Time Limit

Who hasn’t been to a Zoom meeting that felt like it was dragging on forever? Virtual holiday parties run the same risk, so make sure to set an end time to avoid the awkwardness of people looking around to see who will be the first to leave. 

And when it’s time to end the show, your designated host should wrap things up and terminate the feed at the appropriate moment, so no one has to play that awkward Zoom shuffle. Setting a clear end time also allows your employees to better plan around the party, ensuring everyone can stay for the duration of the entire event.

5. Make It Interactive

In this work-from-home environment, your staff will likely have their family at home during your virtual holiday party. Take advantage of the opportunity to get everyone involved. This is your chance to let the team interact not just with each other, but with the wider extended “family” as well.

To get your employees and their family members in the holiday mode, you could try out Virtual Gingerbread House Hunters. This fun and festive event includes a kit packed with all the materials and tools needed for fun decorating, and every person on your team will get their kit in the mail before the event. 

While at the party, each family will be given a theme for building their gingerbread masterpiece. Then, once everyone has finished, a virtual judge will declare a winner, and everyone will get to eat their creations. This is a fun way to have an interactive virtual holiday event that involves more than just team members staring at each other through the screen.

And if your team is all about learning and competing, consider the Oh What Fun! Holiday Team Trivia with customized polls, questions, and categories. It’s a great way to get everyone in the holiday spirit and having a good time while learning fun facts about different holidays. Another option is the Amazing Race Around the World – Festive Edition, which pits small teams against each other to complete interactive travel-themed challenges to earn points and win the prize. And, yes, Santa is involved. 

Organizing these types of engaging activities will help you avoid any awkward moments of people sitting around and not saying or doing anything.


6. Get Help from the Experts

Finally, if you want to throw an entertaining but, most importantly, less awkward virtual holiday party, consider bringing in experts who know how to properly organize and execute a virtual event. TeamBonding has years of event planning experience, both virtual and in-person.

With a wide range of holiday-themed activities to choose from, you can organize an event and theme that best suits your employees. Experts from TeamBonding can serve as the host, deal with all things technical, and make sure everyone has the right materials ahead of time. If any awkward moments do crop up, they will know exactly what to do to move past them quickly and get back to the fun. 

Anna Webber

Team Contributor


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