The Boston Design Thinking Meetup came together on a crisp Monday night in November, at General Assembly Boston’s lovely new location, perched on the thirteenth floor, in the heart of downtown. The theme for the night would be Storytelling. It is my long-held belief compelling stories lead to lasting memories. When we sit and talk to each other, we are storytelling. When we tell jokes, we are telling a story. When we create a report to hand to our boss, we are telling a story.

The night started out as the Meetup normally does. Everyone gets into one big circle and we count off. I like to know how many folks showed up, and secretly, I like to try and test myself on familiar faces (I’m not great with names but I never forget a face). As we go around I notice a lot of new faces. More than ever, perhaps. “How will this go over?” — It’s an inner narrative that plays in my head throughout every meetup. Everyone was tasked with creating a “six-word” story, and reading it aloud to the group. “For sale: baby shoes, never worn” is the famous, or infamous, example I like to use. Mainly, because it’s very compelling and emotive, but also there’s a good story behind it.

Small teams are formed and I ask them to play a game, where you are given a fake nickname and you have to tell a true story about yourself as to how you got that nickname. This is a great way to get people to tell a story about themselves that they would not normally tell someone upon first meeting them. It takes you out of the “first date” area and into the obscure parts of your life, where the good stuff lives. It has another interesting effect; you will be remembered by your nickname — just ask Rusty, Fancy Pants and Cornbread.

Next, teams would go off and create stories for some famous works of art. They then had to share these stories with other teams. The diversity in the stories was vast and intricate. Some teams came up with amazing narratives that dug into deep details about areas of these paintings that might normally go unnoticed.

At the end I like to bring the entire group together and ask them a few questions that will hopefully stoke an interesting conversation. I try to be provocative at times, to get a reaction from the group.

“What if we stopped creating reports, and started telling stories?”

There’s was much spirited debate and many shared insights around creativity, collaboration and ways of communicating. I hope to see more familiar faces next time — and plenty of new ones too.

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