Festive Season Icebreakers For Remote And Hybrid Teams

It’s almost the most wonderful time of the year, or so the song says. December is a month that’s filled with celebrations, whether it’s Christmas, Hannukah, the past year ending or the new one beginning. Which also makes it the perfect time to get to know your teammates and colleagues a little better.

Everyone celebrates this time of year in different ways (or may not even be celebrating at all), and it’s a great opportunity for learning a bit about what December means for those around you. With this in mind, we’ve put together a few icebreakers to open up conversations around the festive season.

Why Are Icebreakers Necessary?

Some people hate them, others love them. But whether you’re on one side of the fence or the other, icebreakers are a necessity in a world that’s becoming ever-more digital.

Remote and hybrid work environments may do wonders when it comes to productivity, but it also means that the people you work with every day aren’t necessarily sitting in the same room as you. They could be across the city, across the country, or across the continent, which makes it difficult to connect with them. Because, let’s be frank here, connection is always easier in person. A video call over Microsoft Teams may be the next best thing, but there will always be a sense of disconnect from the person at the other end of the screen, and conversation doesn’t necessarily flow as easily.

This is where icebreakers come in. They can be quick questions that everyone answers at the start of a meeting, just to put people in a positive frame of mind, or they could be deep and meaningful questions that can lead to engagement, conversation and understanding. Or they could fall anywhere in between the two.

Icebreakers just give the opportunity for connecting to one another as humans for a few minutes at a time, and introducing them into meetings on a regular basis can be a huge boost to company culture.

When Should You Use Icebreakers?

At Solid Systems, we try to use simple icebreakers at the start of each of our Microsoft Teams meetings, especially when more than two humans are on a call. Our go-to throughout the year is asking each other about our best personal and work moments from the past week, though around December, this tends to naturally lean towards how our plans for Christmas, Hannukah or New Year’s are progressing.

But it’s not just digital meetings where icebreakers can help to… well… break the ice. On the days that our humans come through to the office, we encourage connection, and a simple icebreaker can kick off a discussion that lasts throughout the day, week or month.

Examples Of Ice Breakers

Now that you know why icebreakers are important and when they can be used, let’s jump straight into some icebreaker examples that particularly relate to this time of year. And they can, of course, be tweaked to be relevant year-round.


Quick Icebreakers

These are quick questions that can be used to kick off any meeting. They come in particularly handy when there are a lot of people in a room or on a call – because they are short and sweet, everyone will get the chance to give their answer without taking too much time away from the meeting itself.


Festive Themed This Or That…

This or that questions are the shortest of the lot. Simply ask your team to choose between two popular answers, and let the chaos ensue. “Who would prefer TRIFLE over mince pie? That’s just insane!” and other such utterances will see you learning more about your colleagues, all while laughing together and having a bit of fun.

And if you want to turn these questions into longer discussions, ask each person to explain why they have chosen their answer. You may be surprised at how much you’ll learn along the way.

  • Trifle or Mince Pie?
  • Fireworks or Streamers?
  • Holiday Lunch or Holiday Dinner?
  • Go Out And Party or Stay Home And Relax?
  • New Year’s Eve Celebration or New Year’s Day Relaxation?


First Thing That Comes To Mind

Another very quick icebreaker, particularly if you limit it to one or two words. Ask your team members what comes to mind when they think of a specific word or phrase.

  • Christmas carols
  • Secret Santa
  • Giving gifts
  • Boxing Day
  • New Year’s Resolution


Longer Icebreakers

While quick icebreakers are a great way to get conversations flowing and see your humans participating in discussions, sometimes you want something a little meatier to push that connection further. This is where longer icebreakers are handy, especially when you’re dealing with smaller groups or breakout rooms in Microsoft Teams. Here are some questions relating to the festive season to start more meaningful conversations over December:

  • What is your favourite thing to do in December?
  • Are you taking extra time off (on top of public or banking holidays), and what are you planning to do with your free time?
  • What do your festive celebrations look like?
  • Who do you celebrate with in December?
  • What does New Year’s involve in your household?
  • Do you make New Year’s Resolutions, and do you stick to them?
  • What has been the highlight of the past year for you?
  • What are you looking forward to most in the year ahead?


Icebreaking Events

There are times when a single icebreaker is just what you need. But there are also times when you are solely focused on connection, and for many businesses, end-of-year functions are the perfect opportunity to not just break the ice, but crush it.

While planning a year-end event doesn’t always need to include icebreakers, having a few in your pocket, or even planning an entire day around getting to know each other better, can go a long way towards relieving awkward silences and keeping conversation flowing.

Icebreaking events are especially fun for team members who work entirely remotely. They rarely get to experience the camaraderie of being in the same physical space with their co-workers, and if they’re based internationally, then they may have entirely different ways of celebrating the festive season, since December may be summer in South Africa, but it’s winter in the UK and the USA. So while you may be celebrating Christmas with a poolside braai, your colleague in London could be lighting their menorah with the snow falling outside their window.

What kinds of icebreaking events are there?


Scavenger Hunts

What better way to get to know your colleagues than to see their surroundings. Scavenger hunts, where your humans are given tasks to complete around their home, neighbourhood or city, are sure to see your teams laughing together and sharing more than you may expect.

We personally ran an indoor and neighbourhood scavenger hunt for our own remote team recently, and it was sensational getting to learn more about our humans’ homes, their routines, their likes and dislikes and, since it was a year-end function, what Christmas looks like in South Africa, the UK and India. The items that our teams needed to find in their homes included:

  • Their favourite drinking vestibule (coffee mug, tea cup, wine glass or otherwise)
  • Something unusual from their fridge or pantry
  • An item that holds a great deal of meaning for them

And once the home-based portion of the scavenger hunt was complete, they took to their home towns to take photographs that included:

  • A picture of the building they live or work in
  • A piece of ‘art’, which could be interpreted in any way they liked
  • A busy street (or whatever counted as busy for where they live)
  • Something unique to their city


Escape Rooms

There’s something about being stuck in a room together that boosts connection. You get the opportunity to learn so much about the people around you, including their strengths, weaknesses, and how they react under pressure. And while physical escape rooms are certainly experiencing a spike in popularity, they aren’t the only option available to you. Online escape rooms are just as popular, making them a useful icebreaking activity to get to know new team members, or to celebrate the end of the year.

Tools That You Can Use For Icebreakers

While asking icebreaker questions over a Microsoft Teams call works well, there are a few tools that can help you to simplify the process.

For example, did you know that when people raise their hands in a Teams call, you can view a list of the order in which their hands went up? This makes it easy to keep track of who gets to speak and when, and makes going through icebreaker answers a lot simpler.

Putting together polls over Teams is easy as well, but if you are asking more than one icebreaker question at a time, I would recommend using Slido. Sign up for a free account, and you can ask up to 3 different questions, or put together a quiz with multiple questions and answers that people can vote on.

Ready To End The Year In The Right Way?

We hope that these icebreaker ideas for the festive season will come in handy and help you to put your company culture first and foremost. If you’re looking for other ways to boost your company culture, we’ve put together a guide for Being Human In A Digital World – our own take on company culture, and the guidelines that we follow at Solid Systems. Feel free to head on over to our resources page and download it. And, as always, if you want to find out more about how Managed IT Services can see your teams becoming more connected to each other, and to your business, we are always here to help – get in touch with us today to chat to one of our IT consultants.

Michael Claxton

Michael Claxton

Co-Founder and CEO of Solid Systems | I am a father of two, and a mentor of many. My calm focus makes me a natural leader, both in and out the office, and I have a unique skill in nurturing leadership qualities in others as well. But most of all, I understand the true value of time and the ways that technology can optimise efficiency within a business and see humans making the most of the time available to them, both in terms of productivity, and in terms of personal growth. 

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