Simon Taylor | Crain's Boston

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

Simon Taylor


Comtrade Software provides IT infrastructure management solutions and specializes in data, system, network and application performance. The company is headquartered in Boston, with offices in Sunnyvale, Calif., and Slovenia.

The Mistake:

One of the first managerial roles that I took, was at a financial services tech company. I was asked to go out and basically hire someone who was going to run our marketing operations. It was my first experience getting out there and interviewing a wide range of candidate and going through that whole recruitment process. What I found was I had this natural affinity for very extroverted, execution-oriented people.

What I realized much later is that the people I had the greatest affinity for were the people that reminded me most of myself. Of course when you hire somebody that is very similar to yourself, you end up with two sets of the same skills. Especially in a smaller organization where you've got to wear a lot of hats, you want to find somebody who is maybe not your polar opposite but somebody who certainly has a very different set of skills.

[This came into play when] we were designing a market communications strategy for a new product. We had a lot of great ideas, but when it actually came time to take that strategy that was created around the table and go out and find the actual events that made sense for us to get at the actual collateral that needs to be done, suddenly the individuals I had hired said, "We need to hire some other people to do that, too!" So you end up in a situation where people are less excited to go out and do the job you actually might need them to do.

What ended up happening is we'd have wonderful brainstorming discussions about how to change the world with this technology, and how to fix massive problems. But at the end of the day the execution and the holes I needed to plug when I did the hiring never got plugged.

I really want everybody on my team to be smarter than me.

The Lesson

You can get a lot more out of a team that has a diverse skill set. Today when I go out—and I'm constantly hiring people—what works for now are people who have very different skills than myself. As you become more confident as a manager you start to say to yourself, "I really want everybody on my team to be smarter than me." There's this old expression that you'd much rather have 1,000 people thinking for you than for you to be thinking for 1,000 people. What you really want on your team is people who are brilliant at the things that you're not.

I think you have to make a clear separation in your mind between cultural fit and a natural sort of liking of a person. Your emotional response to how much you like someone is actually rather irrelevant to whether or not they're going to succeed in a job. What is very important is that they not only have the skills to do the job, but that they're also a good cultural fit.

What you have to get good at is understanding the culture that you work inside of, and making sure that any candidate is going to be a great fit for that culture and most importantly that they've got the skills to do the job you're hiring them for.