Making our city work for us: A conversation with LeadBoston founder Dick DeWolfe

Beth Chandler, President and CEO

For over twenty-five years, LeadBoston has provided Boston’s brightest mid- to senior-level professionals with the leadership skills they require to understand and address the city’s most pressing social, civic, and business needs. YW Boston acquired LeadBoston in 2011 from its founding organization, the National Conference for Community and Justice (NCCJ). Mr. Richard (Dick) DeWolfe, alongside other NCCJ leaders, noticed a need for cross-sector leadership programming that connected social efforts with business outcomes. From humble beginnings, LeadBoston has grown to serve over one thousand alumni from diverse sectors and backgrounds.

On September 12th, I had the opportunity to sit down with Mr. DeWolfe to learn about the early days of the program. From him I learned how he knew Boston needed this program, and why LeadBoston continues to be an important program for the city. Take a peak at our conversation below:


Beth Chandler: First, would you mind sharing a little about your background?

Dick DeWolfe:  I started off with a small residential real estate company, and built an enterprise that covered five states and employed 2,000 people. We took that company public in the early 90s, and then in the 2000s, it was acquired by a major New York firm. I began a new direction associating myself with John Hancock as a corporate director and subsequently with ManuLife, the company that acquired John Hancock. The last five years, I’ve served as the chairman of the board of ManuLife/John Hancock.

Beth Chandler: So, tell us, why did you decide to start LeadBoston? I know there were LEAD programs in other cities – what was the impetus behind bringing LeadBoston here?

Dick DeWolfe: Back in the time when NCCJ chapters were prevalent in the Northeast, there were very few organizations that attempted to forge common ground between race and religion in the city of Boston. NCCJ was the closest thing to that. In the process of trying to forge a direction for the Boston chapter of NCCJ, we became aware there were very few programs that actually sought to develop younger professionals in terms of the leadership challenges of the urban environment. We saw programs in Chicago and Atlanta and a number of other cities. We thought that if we could use some of the funds that we raised at NCCJ dinners to seed this program, perhaps we could get this off to a good start. So that was sort of the nugget that was planted.

We began to develop the outline of what a leadership program should look like. There would be eight different programs. We developed what the profile would be of the individuals we would try to attract and what we would do afterwards. We put together the program and circulated it among two dozen communities and nonprofits, and tried to get a good mix of government, business, and nonprofits. I think we ended up with 30-35 people in the first class.

Beth Chandler: Why was it important for you to have a mix of sectors?

Dick DeWolfe: Well it was a dual exercise. The first part was: We want to expose you to eight different sectors of life in Greater Boston, and the leadership challenges each of these areas has from policing to housing. It was equally important to bring people who were from different sectors of life together so that they could begin to appreciate what each other does every day and to build a fabric of relationships. The objective is to understand the problems of the city, and the challenges of the city, and in reality, it was their own challenges as well.

I always found there is a disconnect between people who provide so much of their energy to the nonprofit sector and find themselves outside the business community. Likewise, the business community sees in many cases a philanthropic responsibility on their part, but they don’t know where to take the money and how to apply their own time and talent. So it seemed to me that if you could bring these people together like this on a repetitive basis, you could begin to build relationships. They’ll know who to go to. As people find their way in their careers, they provide access points to each other.

The first group formed an alumni group right away, and the alumni part of it was actually very successful. As a result of individuals being exposed to certain areas of leadership concern, they identified with causes they didn’t know anything about. They subsequently might become the directors and leaders of those efforts later on. Keep in mind, it was also a time in the life of Boston, that there was a net outflow of management talent and a net outflow of key companies. Boston went from being this independent beacon of liberal thought and action to being a branch office of [New York] city, and people just had trouble trying to reconcile, what are we going to do about that? How are we going to solve that problem?

Beth Chandler: So, given the impetus for starting the program almost thirty ago, what things do you think remain that make LeadBoston still relevant for today?

Dick DeWolfe: I think there are a number of things that have changed. First of all, the business community has changed dramatically. It was very concentric, focused on the big banks and hospitals and insurance companies. They were the policy makers, and they were the decision makers, and they were the opinion makers. It was a pretty taut, sometimes very tenuous relationship between city government and the business community, but the nonprofits were just a group of scattered people who very seldom actually even identified with each other.

Today, the business community is far more scattered. I think the nonprofits are clearly much more sophisticated than they were in the past, but with respect to their approach to funding, not a lot has changed. Everybody is still trying to find corporate sponsors for their programs and the people in the business community. All of that said, with all of the changes, the fact that Massachusetts, and Boston in particular, has become a real hot bed, a very attractive place which has the potential of being competitive with any city, there is still this notion of, “Wait a minute. Where do the leaders come from?”

I don’t think any city in the United States has the resources that we have. By the same token, we suffer from the same kinds of extraordinary problems that even the smallest communities have. Whether we are talking about the opioid crisis or we are talking about the cost of healthcare itself, and how you bring some sanity to that process. Transportation, you know, has always been an issue in Greater Boston. The problems, in many cases, have been magnified from where they were thirty years ago and yet, I don’t know if we have launched programs that have magnified the intensity – that are able to take people and show them the mountains that need to be climbed. If we could enthuse people with the possibilities, they could be part of the solution.

Beth Chandler: How did you get companies excited about LeadBoston almost thirty years ago? It is not so much about wanting to be a good citizen for the city. How do you explain the return on investment?

Dick DeWolfe:  It was essentially saying to the company first and foremost: You have lots of young talent working for you. You can’t test that talent simply by putting them in the workplace and hoping they’re going to work more than 40 hours for the same pay. You want them to be broader based, you want them to be able to see opportunity. You want them to be, in a sense, rewarded by your confidence in them as individuals. Pick one of your people that you know could really be special. They just need to be rounded out, they need to be evaluated, they need to see a broader picture. Pick one of them and say to them, we are going to sponsor you to enter this program. This is a really small investment to reward one of your people, and in return, that person is going to be able to bring back to you is a sense of where opportunity lies, where problems lie.

Beth Chandler: If you were talking to a business leader today and they said to you, “What would be some things I should consider if I want to send somebody?” What might be the things you would say? Here’s why you should do LeadBoston:

Dick DeWolfe: I would say the quality of life in Boston has everything to do with the health of the culture of Greater Boston. How do we manage that? How do we get inside and take a look at how healthy that culture is? How do we measure ourselves against other people who have similar kinds of things, except to create an opportunity to get face to face in a discussion to actually listen to what other people have to say.

We have an obligation to get in there and create this soup. Let’s see if we have to right ingredients in there. Let’s listen to each other for a bit. If we could pick 50 people who we know all have aspirations and who have opinions and put them together, at the end of the day they would all come away richer for it. That program produces people who become directors, people who are willing to take risks, and people who give money.

Beth Chandler: Can you say more about why Boston needed LeadBoston, specifically?

Dick DeWolfe: Let me call your attention to Boston, Massachusetts in the 1960s. Digital Equipment and WANG and hundreds of other companies were generating jobs to meet demand and economic success. What happened to it? It collapsed in a nanosecond. Why did that happen? No one was really paying attention to anything except the economic success. No one was really understanding that, in order to sustain a truly magnificent part of civilization, you need to have all of the elements. You need to evaluate whether we have all of those elements present, and whether we’re nurturing those elements which give us the strength and sustenance. In the 60s and 70s, it was all high tech and no one really saw the other aspect of technology coming. As a result of that, they lost their way. We are in a different position now, with an economy that has medicine, education, technology, finance.

Look, you have about thirty seconds when you first meet a client to state your case in a way they can understand it. Thirty seconds to tell them why Boston is so much better for the families of the people who work for your company. You say, “This is our belief system as a city. It may not all be perfectly shaped up, but the momentum that these things take on is a clear indication to people. Yes they do really care about whether the harbor is clean or not. People really do care about these issues.” Look you are enjoying the fruits of this frothy economy. You have an obligation to pay back in time, talent, and treasure. If that means dedicating a few of your folks annually to become part of this program, we will all be richer for it.

Beth Chandler: I agree.  That is exactly what we aspire to at YW Boston – creating organizations that will sustain everyone in Boston. What we’re doing is building organizations that are inclusive, particularly for people of color, women, and women of color, but it takes all of us.

Dick DeWolfe: That’s a good thing to hear. To the extent that you narrow the focus of what you are doing, you’ll definitely achieve success.

Beth Chandler:  That’s what we decided to do. We had to put a stake in the ground. Our work is all focused now on building inclusive organizations. So we have our Dialogues program that works with groups of people in organizations, because you have to get people within organizations to understand why they should care. Help them figure out a project they can do together to move forward. Then it is helping to create those change agents within organizations, and that’s where LeadBoston comes in. Now here are individuals that are mid- to senior level executives. How do we support them around cultural competency so they can understand what the bigger issues are and how they impact the organization and how they can make change? Through the LeadBoston program we work so they can look inward, answer those questions, and make change in their workplaces and communities.

Thank you so much for speaking with me today. It is so rich and informative to learn about the beginning of LeadBoston.

Dick DeWolfe: Thank you. It was nice speaking with you.


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