Casual check-in activities are supposed to be low-stakes ice-breaking and team bonding moments. So can anyone tell me why both coming up with them and participating in them fills me with feelings of dread? I know it’s not that deep. Honestly, it seems like part of the tradition of check-ins and icebreakers is the communal act of groaning over them. But also, if I have to come up with one more “fun fact about yourself” or “highlight from the long weekend” a little part of me will wither away.

There’s also the piece about the real anxieties and fear many people feel about public speaking as well as feeling lesser than when life circumstances don’t align to have enjoyable things from free time to share. Usually there is an expectation to speak aloud in these moments so sharing that it’s a-ok to pass, give written responses in the chat or share delayed responses in Teams or Slack can better accommodate diverse access needs. Given inflation and rising cost of living, more and more people are using their “free time” to work other jobs rather than indulging in a weekend getaway.

Inviting your team to participate in connection building activities that they can feel more comfortable in that allows them to express themselves authentically creates space for those true moments of bonding.

1. Lighthearted questions

Questions are the bread and butter of casual check-in activities but it’s time to level-up your questions roster. Take a break from the cookie-cutter questions and start adding a bit of levity with ones that have a bit for personality. Building connections is a lot harder when it feels like the questions feel like a competition to see who is the most interesting.

Embrace some casual silliness and try out some of our tried and true favorites:

What’s a boring fact about yourself?
What emoji describes you today?
Would you rather attend a murder mystery party, an intimate dinner party or a rave?
If you turned into a plant what would you be?
What’s your favourite little treat?

Bonus: Sometimes there’s room for a bit more heart. I love this list of Check-ins for Connection and Care gathered by Denise Shanté Brown.

2. Enter the Woodwide Web

A “mycorrhizal network” is a below ground system that connects individual plants together to transfer water, nitrogen, carbon and other minerals. In healthy forests, each tree is connected to others via this network, enabling trees to share water and nutrients. People and things in our everyday lives can similarly support us. With this visualization activity you and your team will shine some light on the things that help you stay healthy and connected.

How to: Get set up in advance by using an online whiteboard application that allows for text and images (like Canva) and have the activity leader create a Woodwide Web.

The activity is done in two parts. The first part starts with the prompt: “What is taking care of you today?”. This is where your team will silently add written or image responses of what had proved them with care today. The connection building part of this activity is strengthened when these responses are not work related.

The second part asks: “What do you need from the ‘mycorrhizal network’ today?”. In this part, folks will add responses and images of what they feel they need. To close the activity, you can offer space for those who want to share reflections or keep it to a silent activity and allow a few moments to take in the network as a whole that everyone created.

Here’s a network our team created:

3. Take a (virtual) art gallery tour

During the early parts of the COVID-19 pandemic, lots of museums and galleries enhanced their online presence by offering virtual tours. This was the inspiration for our art-related check-in activity. Art is a great foundation for a deeper and more meaningful team conversation - it is especially powerful as it allows the opportunity to learn about non-Eurocentric art practices and traditions.

How to: Get set up in advance by using an online whiteboard application that allows for text and images (like Canva) and have the activity leader create a virtual gallery for your team.

To get started, ask the team “If you were to paint a self portrait today, which style best encapsulates you/your mood?” Team members can choose from any style (impressionism, cubism, futurism) or perhaps a technique (mosaic, tapestry, wood carving) or even a specific artist like Kehinde Wiley, Kent Monkman or Frida Kahlo. Give the team 5 minutes to find a picture and copy it into the whiteboard.

For the second part, send your team on a 10 minute virtual tour of an art gallery somewhere in the world. We narrowed our options down to the National Museum of Modern and Contemporary Art in Korea, the Phansi Museum in South Africa and the Museu de Arte de São Paulo Assis Chateaubriand in Brazil but there are so many more on lists like this one! Ask each person to choose 1-3 pieces in their chosen gallery and have them screenshot it then import it to your collective virtual gallery.

You can finish up by going round and sharing why those pieces resonated with you or how they will inspire you moving forward.

Here’s a virtual gallery our team created: