Planned Serendipity

“There are only four reasons to meet: to bond, learn, create, and decide. If we’re not gathering to achieve at least one of these goals, we don’t need to gather.” 

— Adam Grant, Vibe

Yes, I’m still reading and reflecting on Adam Grant’s latest book. This week, one idea in particular stopped me in my tracks: planned serendipity.

At first, the phrase sounds like a contradiction. Serendipity is supposed to be a happy accident, the chance conversation or unexpected connection that changes everything. How can you plan that? Grant’s answer is that while we can’t script connection, we can design the conditions that make it far more likely to happen.

He begins with an example from history. Thomas Jefferson was intentional about the conversations at his dinner parties. Rather than leave the evening to small talk, he prompted his guests to focus on healthy debate about the major issues of the day, and he even prohibited side conversations. Jefferson understood something many of us forget: a gathering’s value doesn’t come from simply putting people in the same room. It comes from what we invite them to do once they’re there.

Grant’s own contribution to planned serendipity is an activity called the Reciprocity Ring, which he credits to entrepreneur Cheryl Baker and sociologist Wayne Baker. The setup is simple. Sticky flip charts are placed around the room, and each person writes a request on a note: something they want or need but can’t get on their own. Then everyone moves around the room reading others’ requests and offering help, resources, or connections. There’s only one rule: you have to be willing to help others fulfill their requests.

What happens next is remarkable. People discover that the answer they’ve been searching for is sitting a few chairs away. Someone has the resource, the contact, or the experience that solves a problem another person thought they had to tackle alone. Beyond the practical help, the research shows that the activity builds a culture of gratitude and generosity. When people see that asking for help is safe and giving help is expected, the whole group starts to operate differently.

I can’t stop imagining what this could look like with the 20 or so site administrators in a district. Picture the requests on those flip charts: I need a better system for managing student supervision at lunch. I’m looking for a mentor who has navigated a difficult staff reorganization. Does anyone have a strong family engagement plan for a multilingual community? So often, administrators carry these challenges in isolation, each believing they’re the only one struggling. A Reciprocity Ring turns a room full of individual leaders into a network of shared expertise. It would hit three of Grant’s four reasons to meet at once: we would bond, we would learn, and we would create solutions together.

That brings me back to Grant’s quote, and to an uncomfortable question for every leader: how many of our meetings actually meet his standard? How often do we gather out of habit, to share information that could have been an email, or to sit through updates nobody will remember? Every meeting we host spends our people’s most precious resources - their time and attention. They deserve gatherings that are worth it!

So here’s my invitation. Before your next meeting, ask yourself: Why are we gathering? Are we here to bond, learn, create, or decide? If you can’t answer that question, consider canceling it. If you can, design for it intentionally, the way Jefferson designed his dinner conversations (think explicit norms!). And the next time you bring your team together, try leaving room for a little planned serendipity. Ask people what they need. Invite them to help each other. You may discover that the most valuable resource in the room was there all along: each other.