Jay Dearborn | Crain's Boston

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Jay Dearborn


WEX Inc. is a payments technology company based in Portland, Maine.

The Mistake:

At a certain point in management it's not about the content—it's about the people.

About eight years ago I was a project manager at McKinsey. We were working with a very large industrial site and I had weekly one-on-ones with the general manager of that site. We were about six months into a project, and in preparation for one of those meetings I was there with a partner for McKinsey. 

I'm saying to that partner, “This is how this is going to go, this is what the agenda is, here is the role that I want you to play, and here are the things that he could say.” I'm trying to orchestrate everything in my head to be prepared for every contingency, and I'm only thinking about the content of the meeting, not the person I'm meeting with.

As we're about to be called in, the manager's assistant says he's going to be about five minutes more. So we say, "OK," and the partner looks at me and says, “Let's go for a five minute walk. And during that walk you think about one thing: think about this manager's day, what he's dealing with, where he's coming from, and how to connect with him as a person and not about the content of the meeting.” I was a bit confused by that.

I took the walk, came back, and when the meeting started I asked about the manager's day, and it immediately went off the rails. For 20 minutes he was talking about how bad his day was. There was a near-fatality that had happened on his site. I thought at first it was a disaster, but we ended up partnering with him over how bad his day was, and all the things going wrong that we could work to fix. We formed a relationship. It made me human and it allowed him to be human with me.

It's amazing when you create space for that personal relationship.

The Lesson:

It's something that I think of now, and it's really shaped how I became a leader.

It's amazing when you create space for that personal relationship. Positions of leadership can actually be quite lonely. The worst case is when they say, “My day's been just fine, let's jump into the content.” ... If someone shares that they're having a tough time with management, well, I actually really need to understand that to help you break through so that we get the right outcome.

It's around getting people to not only engage in the content. Sometimes you have to let them be people before you can engage in the content. Recently I had one of our big partners call with a concern that he had no obligation to tell me, but he was looking out for my back in the marketplace. And the only reason that partner did that is because we have a relationship where there's a bit of camaraderie between us. Easier said than done in the world of business, particularly in your young career when you're used to just putting wins on the board.

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​Photo courtesy of Wex.