How to Orchestrate a Serendipity Explosion

The ? Dinner

Bringing people together is one of life’s joys. Putting a diverse group of generous and curious people around of table where they can authentically share engenders community, idea cross-pollination, and lasting friendships. And a lot of serendipity.

Here are a few ways you can create your own Serendipity Explosions via a ? Dinner.


  • It’s a ?, because each guest is soooo ?
  • Strive for diversity; I try very hard to keep the group at 50/50, Male/Female ratio
  • Try to find people who don’t know one another (probably the hardest part)
  • Ideal group size is 8–10; that number allows for a table discussion but also smaller group ones
  • Picking a location with a private room or low music is Major ?
  • Aggressively remind your guests that the event is happening; people get busy and it’s important to have the aforementioned diversity

The Dinner Itself

  • Warn your guests ahead of time that for the first hour, you are not allowed to ask “What do you do?” or “Where do you work?”
  • Prepare a list of questions that will serve as “prompts” to get people to talk about themselves, but in an indirect way. It’s more personal than just having people “give bios” (which by definition would include “work talk”). I’ve included my questions below
  • At the end of dinner, go around and ask each person to describe an “ask” (i.e. how they could use help)

Prompt List

These questions are created to be vague and open to interpretation. There’s obviously no right or wrong answer, and if further clarification is needed, let the person answering define that clarification themselves. Here’s the questions I recently used:

  • What would you do if you weren’t afraid?
  • What’s an aphorism that “sticks”?
  • What are you working on, on yourself?
  • What is the most memorable concert?
  • What is your favorite word?
  • What’s your favorite question? [The follow-up being “Now answer it”]
  • What brings you childlike giddiness?
  • Describe a memorable photograph.
  • Who is a protagonist you associate with most?
  • Describe a recent serendipity experience

And Watch the Serendipity ?


My math is rusty, so I posed the following question to my Twitter followers:

and the Twitterverse came back with:

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