Bob Boudreau | Crain's Boston

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

Bob Boudreau


Bob Boudreau is CEO of WinterWyman, a staffing agency based in Waltham, Mass., that is among the Northeast's most recognized talent-acquisition firms.

The Mistake

In 1999 Dave Melville, WinterWyman's chairman and founder, talked to me about my next step in the company, and I expressed an interest in starting up another new organization. I figured I'd just throw my hat into the ring even though I was happy in my role as CFO. And he said, “What do you think about Keystone?” I'll be honest, I was a little disappointed because I wanted something brand new that would have my thumbprints all over it. But this was a good opportunity, so I gladly accepted the role of CEO.

I ran into a difficult situation with strong personalities involved, looking at some of the strategic direction in changing the businesses from a marketing and product development side. I'd never been directly responsible for those areas, and I thought I'd just be able to learn this on the job and muscle it out. I stayed in my own bubble versus opening myself up. It probably was a sign I wasn't ready for that job. My biggest struggle was managing people at that level and with that type of responsibility. I had never had to deal with the different conflicts that would create.

About nine months later, I was just miserable in the job. I wasn't sleeping; I was worried about everything; I couldn't relax; and I really wasn't thinking that clearly. I went on vacation with my family that summer, but I was just trying to wrestle in my own mind with all the responsibilities I had and the things I wasn't getting done. So I told Dave Melville, “I don't think I'm the right guy for this job. I don't feel I'm making the right decisions, and I'm not moving the ball forward. I was thinking about this over the weekend, and I think I want to resign.”

Dave was writing things down as I was saying all this, and I just reached over to put my hand over his hand as he was writing, and I said, “Dave, can we just do a reset? I'd like to continue to do the job. I just need your advice on how you would handle some of the things I've been going through, and I realize I shut you out — I stopped seeking your advice.” And he said, “Yeah, you did. So if this is going to work, we need to set this up with weekly meetings and to be more open.”

It totally changed [things] for me. A lot of that had to do with my demeanor, my approach, my clarity of thought. My confidence was a big part of that, too. It helps to have a mentor. Dave showed me what to do better, and he assured me I was doing a better job than I was giving myself credit for.

Now I view people asking for help as showing a sign of strength, not weakness.

The Lesson

Now I view people asking for help as showing a sign of strength, not weakness. I should have asked Dave Melville for help when I was having trouble, because he was my mentor.

I've always thought that it's not important to be the smartest person in the room, as long as you get the right people in the room. I was trying to be perfect with my team, and I stifled them. You need to let go a little bit, or delegate and stay above the details. You have to take a step back and give the authority to the people you've entrusted with it.

WinterWyman is on Twitter: @WinterWyman.

Photo courtesy of Bob Boudreau