Rob Wilson, October 01, 2020
Even before the pandemic forced us to retreat to the safety of our home offices, creating team unity at Calendly took time, energy and dedication. Becoming a team, in the sense that we all support one another and pull in the same direction, isn't as simple as grouping us together on an org chart and calling it a day.
To work in harmony, we need to know one another on a personal level and understand how to think and collaborate together, which is why every quarter, Calendly’s R&D team—consisting of engineering and product design—meets offsite to ideate and reconnect.
As an Engineering Manager at Calendly, one of my responsibilities is to plan these offsites. This quarter’s event was to be our third, with the most recent one being in-person in January. But the world changed so much in such a short time that I had to find a new way to bring my team together.
I didn’t want to lose the spirit that made our first two events a success: they were engaging, impactful, and personal.
We settled on an idea called the Charity Challenge. To participate, each team member proposed a charity they felt passionate about, then submitted a video of themselves doing something funny or sharing a secret talent. For every submission, Calendly put $30 into a pool that would be donated to one of the proposed charities.
On the first day of the Challenge, we only had one or two submissions. I remember thinking to myself, “this is gonna flop.”
By day two, submissions came pouring in. In fact, the response was overwhelming—my original goal was to raise $300, and we doubled it!
What was truly priceless were the responses from my teammates. We managed to connect through humor, vulnerability and authenticity during a time when it can be hard to crack a smile, let alone laugh.
Eddie James sings Elvis's "(Let Me Be Your) Teddy Bear"
Once the submissions were completed, I blindly drew the charity that would receive the $600 donation. In the end, the winning charity was the Equal Justice Initiative—which felt extremely fitting, considering the current social justice movement sweeping the US.
The Equal Justice Initiative is an organization that works to end mass incarceration and excessive punishment in the United States. Their 150 passionate staff members are committed to challenging racial and economic injustice and protecting the rights of vulnerable people.
As a team, we were proud of the way we’d come together to bond and raise money for a powerful cause. But we were stunned when our CEO Tope Awotona, upon learning about our fundraiser, decided to match our donation with another $600 on behalf of Calendly.
It can seem impossible, during the pandemic, to truly feel like a team with your coworkers. After months of only ever seeing their names pop up on Slack, our “offsite” fundraiser was exactly what we needed to boost morale—and bring some good into the world while having fun.
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