Risky business

Dave O’Brien has no problem laughing off concerns about handing over the reins to the next generation of talent.

After all, it’s the next generation that has helped Oswald Cos., the independent insurance brokerage firm where O’Brien is president, average 18 percent growth per year over the last six years. O’Brien and other leaders at Oswald set stretch goals for their 400-plus employees and expect their young talent to take risks.

“I treat them the way I wanted to be treated when I was their age,” O’Brien says. “And I was given those types of opportunities early in my career, so that was the natural thing to do. As long as they communicate back, there are very few problems they create that we can’t solve.”

Smart Business spoke with O’Brien about how to ignite young employees and why you have to tell people why they don’t want to work for you before you hire them.

Work with people to build intelligent risk. We’ve grown aggressively the last five or six years, and we expect to continue to grow. As we do, that will create new opportunities for people.

They need to understand what those opportunities may be and which ones they may be a good fit for, and then we put them on a track to get there. With those folks, we very much get them to set stretch goals for themselves to help them get to the next level.

They have to see that when they do that, they are achieving greater results, that when they do stretch and take a little risk and push a little further, it’s much more rewarding, and the people that are willing to do that here are very successful.

We help them draw that conclusion. You ask them questions. You challenge them to think through how it would work, what it would take to be successful, what might cause it to fail. We have a process people have to go through when they make these types of investments, and through that process, they draw their own conclusions.

The goal is to help them understand how the idea or the concept is or is not aligned to the vision of the firm.

People who take risks and try things, oftentimes they succeed, and sometimes they don’t. If we discourage them from taking that risk, it wouldn’t happen again. We understand that every risk that they take and everything that they try is not going to work. Our point is, all right, let’s learn from it and let’s try another one; it will be that much better because we tried this.

The best benefit we have is that our younger people have become successful people. Those are our future leaders, and in some cases, they are our current leaders, and they are our ownership perpetuation plan. When those people take on new levels of responsibility, we see good things happen. That’s what drives our growth.