How to use structure to create spontaneous group social interactions remotely

For the past 2 months, I was part of a circle of Endeavor entrepreneurs who come together every 2 weeks to share about our challenges and help each other out. I had myself organised such circles with fellow CTOs before, and though it was a great bonding experience, the sessions became a little too fluid and unstructured after a while, and eventually petered out due to a lack of interest.

And that was pre-Covid, when we could meet in person and draft off each others' energies. Recently, in a recent survey conducted with our leadership team, we realised that folks don't know each other well enough beyond work. This was expected given that half of them joined after we went remote, but the solution was anything but obvious. That's why I was curious how this Endeavor entrepreneur circle will be pulled off, given that we all hail from different parts of the world. I have to admit I had my doubts given my past experiences, but nonetheless went in with an open mind and a willingness to commit and give. Now that I have experienced 2 sessions, I'm convinced there is a way to make such group bonding work. I personally came off feeling a strong sense of connection and meaning with the group.

First thing that caught my eye was that they didn't use Zoom, Teams or any of the mainstream video conferencing software. It was a newer software designed by one of the Endeavor entrepreneurs designed for interactive group sessions. Instead of squares lined up in a grid, our faces were circles grouped around in a circle, kinda like a real-world campfire huddle. There were some cool features like group hugs, fireworks and embedded documents, which definitely added to the experience, but I'd say wasn't the main reason why it worked.

There are 2 main reasons it worked - structure and facilitation. There was an agenda to these sessions, even though it was meant to be casual, open and non-work. The agenda was designed to break the ice in the first session, and subsequently, to have everyone help out a selected entrepreneur with his/her challenge for that week in a non-judgmental, respectful manner. The questions and prompts were purposefully crafted to draw out personal sharing comfortably, with follow-up question and answers to make the person sharing feel heard. I still distinctly remember the first time we shifted to fully remote group meetings and feeling like I was talking to the void in a Zoom call with 0 responses. Our lovely facilitator, Carmen, struck a delicate balance between keeping everyone on the agenda and time limits, while giving us space to express. She also set a strong example for the exercises by going first.

It was also helpful to have team norms spelt out explicitly, which in our case was commit, contribute and be on time. There were many times when I joined a new social group where I wasn't quite sure what the norms were, and thus defaulted to being a quiet observer. Those were times of great anxiety, compounded by a remote setting where you can't read social cues to know if you are being accepted by the group. Having them spelt out makes the rules clear and eliminates this discovery period.

Though this structure might appear to be too rigid for a social interaction, in practice, it was immensely helpful because it removes the cognitive load from the participants to decide what is socially appropriate to do next. In most cases when you put people from different cultures in a video call, the default is dead silence, or stilted conversations that end abruptly. I think as a whole, we hadn't quite figured out the mainstream way to deal with a group video call dynamics that is inclusive (like how do we engage with quiet participants who keep their camers off), so deciding the flow upfront significantly reduces those cognitive barriers.

While still not quite the same as in-person meets,  I think these structured social meets are one of the best I have personally experienced online, and would be implementing these structures for my own leadership and engineering teams.