Tom O'Brien | Crain's Washington D.C.

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

Tom O'Brien


The HYM Investment Group is a Boston-based real estate company that has been working on real estate ventures in the Boston, New York and Washington, D.C., corridor for more than 35 years.

The Mistake:

When I was 33 years old I was offered the job of director at the Boston Development Authority by Mayor Tom Menino. It was a great opportunity at that age. It's a pretty significant job in Boston. It involved helping to lead and manage the planning and development agenda for the city of Boston. I think there were about a thousand employees or so. And it also was a very public position. It was a total life-changing opportunity for me at the age of 33. I loved the job, but the mistake I made, looking back on it, was I assumed that as the director I needed to be everywhere and to do everything.

I essentially over-scheduled myself. So from 7 in the morning until 11 at night I was working away on everything from meetings to reviewing written documents to various phone calls to neighborhood meetings. It's tough on your home life, No. 1. My wife and I had a very young family at the time—at one point during the course of this job we had three children all under the age of four. Plus I think the fact that I was over-scheduling myself meant that I didn't do as good a job. I wasn't paying enough attention to big questions because I was consumed by smaller questions or smaller issues. I was focused on the minute details of the organization's budget and looking back I really should have tried to offload some of that onto a chief of staff or other staff members.

In the course of my tenure on the job one of my employees did something that had kind of gotten past me. Frankly, it wasn't something that I was aware of and it was kind of an ethical breach, unfortunately. It became a pretty major news item and it was one of these things where I kind of sat quietly with myself and said, “well this is a true lesson learned.” If you slow down and pay more careful attention to some of the big picture items that are going on and through that set a really clear tone of how the agency needs to be operated and how people need to conduct themselves, that's the key thing. I ended up leaving the job shortly after that.

Spend time thinking through the team and the players that you want to have on that team.

The Lesson:

As a manager you need to trust your team and take more time thinking about the future of the organization and try to set a good example of slowing down and then paying more careful attention to the big questions.

The key lesson learned was was to slow down. You can't help it, but you get in and you run. I ran 12 to 15 hours a day. Spend time thinking through the team and the players that you want to have on that team. Pay attention to some of the details but make sure that you can rely on your team.

Photo courtesy of Tom O'Brien.

Do you have a good story you’d like to share, or know someone we should feature? Email

And be sure to sign up for your local newsletter from Crain.