• by Kaila Colbin , Featured Contributor, November 20, 2020

Let me tell you about Greg.

Officially, Greg is a salesman. He works for a computer company, securing significant corporate contracts for data centers. He is very good at this job.

Unofficially, though, the value Greg brings is not his ability to talk features and benefits. It is his ability to serendipitize.

When you go out with Greg, magic happens. He goes to get another round of drinks -- and finds a new customer. He heads to the bathroom -- and comes back with sponsorship for your charity event. A few years ago, a group of us got a T-shirt as a gift for a friend with cancer; Greg happened to have it with him when he bumped into the All Blacks (the New Zealand national rugby team) in a hotel lobby and got them all to sign it.

Greg does all of this spontaneously, irrepressibly. You can’t stop him spotting opportunities any more than you can stop him breathing. It’s not about his KPIs or the bottom line, although these are definitely important to him. It’s about the delight he gets from making connections, about how useful he feels when he can bring people together and know that everyone is better off because of it.

To be effective, Greg needs a reasonably free rein. He needs to have his head, to be able to say, “What? A random pro-am golf tournament? Sure, I’m in.”

Fortunately, he works with people who understand this, who realize that -- Greg being Greg -- far from having a blow-off waste of an afternoon, he'll more likely than not end up getting partnered with the former professional golfer-turned-tech company CEO who happens to be looking for a new data center.

His luck also relies heavily on randomness. These opportunities arise precisely because Greg does not have a routine. If you always travel the same path, the only opportunities that show up are the ones that come to you. But by consistently straying from the well-trodden path, Greg regularly stumbles upon situations overflowing with fortuitous coincidence. He engineers these occurrences, inasmuch as they can be engineered. He is a serendipitist.

I suppose in the Venn diagram of “jobs that people understand” and “jobs that generate unpredictable value,” there’s a reasonable overlap between salesperson and serendipitist. But there’s no rule that says the function has to be performed by a salesperson, and there are lots of opportunities beyond closing deals.

A visionary organization understands the delicate balance between planned execution and openness to the unknown. Survival and growth call for periods of stability and jolts of transformation, predictable progress and quantum leaps that require two different approaches and are both essential to the long-term viability and vibrancy of a company.

If you have one of these people in your midst, acknowledge him. Celebrate her. Articulate the role. Your Chief Serendipitist could well be the source of your company’s next transformative leap. And, sooner or later, you’ll need one.

Have you had the pleasure of working with a Serendipitist?