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From Tipping the Scales: Bill Sinnott: Being “Comfortable with Chaos” and Leading by Example

Bill Sinnott serves as the Corporation Counsel for the City of Boston.  In representing the City, Bill’s clients include the Mayor, all City Departments, including the Police and Fire Departments, and the Boston City Council.  He oversees the Law Department and a staff of approximately sixty attorneys, paralegals and administrators. Bill was previously an Assistant District Attorney and then an Assistant United States Attorney and prosecuted narcotics, gang, and money laundering cases for the New England Organized Crime Drug Enforcement Task Force. At the BBA, he served as a Council member from 2009-2012, and has been a part of the Diversity & Inclusion Section, the Joint Audit Committee, and several selection committees.

  1. How do you manage the stress of working in a government environment with political pressures?

First of all, you have to be comfortable with chaos. Government lawyers, especially those in a position similar to a general counsel, engage in a lot of legal crisis management, and dealing with the political side of the job is just part of that. It helps when you have clients that understand your role and the constraints of the law and legal ethics. I am fortunate to work for a chief executive who values lawyers and understands what lawyers do. That has lessened any political pressure I might feel. When all’s said and done, you have to make decisions based on the law coupled with the best interests of your client. That means not always providing answers your clients want to hear, but you’ve got to do your job.

In this business, friction is a constant. It may be more apparent at some times than others, but there’s always an undercurrent of conflict. We can’t make everyone happy, and you have to remind yourself of who the client is. That makes decisions somewhat easier. So long as you stand by your legal responsibilities and the decisions that flow from those, you’re going to be in the right and have the confidence of knowing you’re doing your job.

  1. What are some of the most critical leadership dos and don’ts?

The most important leadership trait or ‘do’ is to lead by example. You can’t expect your personnel to do things that you wouldn’t do. Frankly, as the leader of a legal operation, your expectations of yourself should be even higher. Beyond that, consistency in how you deal with people is essential. Employees and staff may not like a particular directive or practice that’s put to them, but if they understand it’s being applied consistently and is devoid of any personal animus, then they will accept it and perform.

As far as “don’ts” — never lose your temper in front of your staff and attorneys, never embarrass anyone publicly, and treat your staff the way you’d want to be treated.

  1. Why is it important for you to volunteer your time and experience to an organization like the bar association?

I learned soon after I assumed my current position as Corporation Counsel that the BBA and the City had a longstanding partnership. This was evident in many forms, but most apparent in the large number of community service programs managed by the BBA in which the focus was the city of Boston, especially Boston Public School children. It was easy for me to become involved with the BBA, and as I became more involved, I came to appreciate even more the role that this organization plays in the bar and the community in Boston. Plus, it’s a terrific group of people. I’ve really enjoyed working on the BBA Council, the Committee on Legal Services for Veterans, the Audit Committee, Diversity Committee, and other groups where everyone seemed to be devoting a lot of their personal time and professional talent towards some very worthy goals. The great thing is that there are people with very different outlooks, political perspectives, and very different practice areas – yet under the umbrella of the BBA’s efforts, they come together and work together and enjoy working together for a common good. The BBA was the vehicle for this collective effort, and that’s why I’ll continue to stay involved. It’s a great feeling to be part of an organization that embraces that collaborative effort. Finally, it’s allowed me to meet legal professionals whom I probably would not have dealt with in the course of my duties for the City, and I’ve become friends and admirers of many of them.

In particular, I think the BBA has a special role in teaching the ropes to younger lawyers, and I’m thrilled at the efforts that the BBA has made on behalf of  law students and aspiring attorneys because that’s the future of the bar in the greater Boston community. And we’ve had some talented young lawyers and students looking for that direction and the signal from those of us who have been practicing for these many years that they are valued and their input is welcome. The BBA has taken on that responsibility and really excelled at it.


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