Serendipity Dinners

Over the years, I have periodically hosted dinners with a handful of people — most of whom I knew, a few I didn’t — as a way of bringing smart people together for good conversation. I have also attended countless small group dinners, often at conferences. These events have been almost uniformly enjoyable, often productive, and sometimes even pretty profitable.

I have also enjoyed larger group events that seek similar outcomes — like my friend Bryan Person’s Social Media Breakfast series. These, too, are great but they lack the intimacy of a smaller dinner party.

In recent months, however, I have come around to thinking that I need a better system for the group dinners I host. They have been too infrequent and often require s significant amount of legwork on my part, often leading me to go for the “easy out” by inviting fewer people or sticking mostly to friends. They can still be good, but I feel like they have more potential.

So I have come up with what I’m calling the Serendipity Dinner format, and I want your feedback on the approach. (Note that it could also apply to a breakfast, lunch or even cocktail get-together, but I generally find dinner to be a bit more relaxed and thus more productive.)

Here’s how I plan to structure these Serendipity Dinners:

• A goal of 6-8 attendees. I have generally found that smaller groups can be too intimate unless the bonds are already really strong among participants; larger than 8 is simply unwieldy and often prevents some participants from actively engaging with each other.
• The dinners would have two co-hosts (me and one other person). We might know each other well — or not — but we would be the core organizers. We would settle on a date that works for both of our calendars first.
• The two co-hosts would then each invite one other person, preferably people that the other co-host does not already know really well, if at all.
• The co-hosts’ guests would each then be asked to invite 1-2 friends to join the event. In this way, the target number of 6-8 people would be met.

This format has the advantage of everyone having at least one “buddy” at the event, which should help make even the shiest participant comfortable. At the same time, by working off of this family tree style format, it maximizes the opportunity for new connections to be made. It also minimizes scheduling burdens because each person only needs to work with 1-2 people on calendaring rather than centralizing that effort with a single host.

So what do you all think about this format? Any suggestions for tweaks? Am I way off base? (Oh, and if you’re interested in participating in co-hosting or attending one — especially if you are in the Northeast Corridor of DC-NYC-BOS — then shoot me an email.)