Telling Stories With Telestrastions
A Delightfully Friday Junior Experience
Everyone loves stories. Stories bring us together. They help us find our common ground and give us windows into each other’s world. Stories define who we are, where we come from and where we are headed. They show us how much we have in common while highlighting our personal gifts and quirks.
In this new age of endless screens and boundless AI slop it is even more important that we create and share stories together as humans. Here at Flagrant we make sure to carve out regular time to do something creative and fun together. Since we are a remote team the goal is to find simple but effective ways to reach through the technological interface to reclaim our human connection.
A couple of weeks ago I came up with an online version of one of our favorite party games that we once played in person at a retreat called Telestrations. The game is a cross between Pictionary and Broken Telephone. Everyone starts by writing down a phrase which gets passed around and everyone alternates between drawing the caption and writing down what you think the previous drawing represents.
While this is certainly most fun in person, I found a Figjam template that worked pretty well over a video call. By duplicating the column to match the number of participants and pairing the length to match we had just what we needed to do a full round. Note that it is critical to remind everyone to hide the content using the closed eye icon when moving to the next column.
The round ends when the stacks make it around back to where they started and that is when the real fun begins. Now each person gets to tell the story of how their original prompt changed as it got passed around the room. Sometimes the storyline is preserved:

And sometimes it gets transformed into something imaginatively unimaginable:

And, best of all, sometimes you open up associative stories that uncover hidden details about the people you work with:

It turns out that Jim’s mother and many of his family members worked at Oscar Mayer in Madison, WI. One time they opened the plant for a Family Day so people could bring their loved ones to work and see how the sausage was made.
As a part of that experience they brought ~3-4 Weinermobiles and you could get inside and have a ride around the parking lot in them. If you give the logistics of the vehicle a little thought you’ll quickly come to the realization that there is not much space inside them. There are two side-by-side seats up from and the rest is like a narrow carpeted cargo van.
He was probably about 12 years old at the time and stuck his head out the door and a couple of people remarked he looked like little Oscar:

Try out telestrations at your next work or social event and let us know how it goes. Please also share your favorite parlor games and especially ones that you have adapted for remote work. We are always looking for fun ways to connect and learn more about each other and ourselves.
If you’re looking for a team to help you discover the right thing to build and help you build it, get in touch.
Published on October 23, 2026
