Corey Thomas | Crain's Boston

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

Corey Thomas


Corey Thomas is president and CEO of Rapid7, a cybersecurity firm headquartered in Boston. Rapid7 reports $110.5 million in revenue and an international workforce of more than 800 employees.

The Mistake:

You want people that are highly motivated and committed. One of my mistakes was I undervalued that. I wanted commitment, but in some ways I wasn't willing to spend the time, the currency to get that commitment. 

When I was at Microsoft, I was leading a launch. It was one of those great opportunities that gets you out of the everyday to do something very impactful for the larger company. I was thrilled, I was excited, I was young and ambitious.

But before the project was even over, I ended up being asked to step aside from my leadership role. I may have been aggressive and assertive but I didn't do a very good job of actually working with others, of communicating. The mistakes that I made were numerous, including taking people for granted. It was sort of the classic project management playbook—I focused on the things we needed to get done, and not on the people doing them. I ran meetings but didn't get input from the group, and I didn't spend enough time on the joint activity of determining what should be done together. People want to be engaged and I wasn't doing that.

Another problem was communication. It's relatively easy to actually say, “here's what we decided.” What's a lot harder to do is explain how you got there. One of the things that I was rated very poorly on was helping people understand the why behind the things that we were doing. For me personally, that was one of those major learning moments.

This was a global product launch. Well, I did a very good job of communicating what I believed the new marketing message was, but there was not nearly enough why. So that led to people in countries around the world not being able to do their jobs effectively. They didn't have enough of the substance behind the messaging strategy and why we were doing it. Only the highest level got translated down, and that led to a lot of back-and-forth about the decisions that were made, because they didn't have the context. Also, decisions without a concept tend to be executed very slowly.

Decisions without a concept tend to be executed very slowly.

The Lesson

You have to spend time talking with your team, in reconciliation, to get that team alignment. You need to give them context about why what you're trying to do is important to what the organization is trying to accomplish, why it matters. Then people can apply their own creativity and ingenuity to get it done. If you don't do that, you're only getting a partial effort from the team. If you want the full effort, you have to invest in that team alignment. Those are relatively expensive endeavors in terms of time, but they're well worth it.

Photo courtesy of Corey Thomas.

Follow Rapid7 on Twitter at @rapid7.

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