Center for Women & Wealth

In 1998, Goodwin, then a regional Boston law firm, offered Regina Pisa the chairman’s office. Pisa was elected with a mandate for change, and after a decade of strategic redefinition, laser focus on industry specialization and incredible drive and perseverance, she set Goodwin on a path of growth that would see the firm transformed. Under her strategic leadership, Goodwin grew from a regional law firm of approximately 300 attorneys to a leading international firm with more than 1,000 attorneys in 10 locations across the United States, Europe and Asia. During Pisa’s tenure, revenue at the firm increased fivefold. Today, Goodwin is well-known as a leader in its service to clients in industries such as financial institutions, technology, life sciences, private equity and real estate capital markets and has received accolades for its outstanding client service and commitment to innovation.

The shy only child of an immigrant carpenter with big dreams, Pisa is no stranger to overcoming obstacles by reaching far and driving hard. As the first woman to lead a major U.S. law firm, a passionate advocate for women and children and an active philanthropist, Pisa is a catalyst for transformational change. We set out to learn more about what makes her successful and ask her advice for other women building their own careers and leadership skills.

On Girls Developing Confidence: The Importance of Strong Role Models
My father had a big influence on who and where I am today. He was outgoing and gregarious, and his mission was to push me while providing me with the security of knowing that if I fell, he would pick me up. He encouraged me to raise my hand, stand up and speak out. When asked how to develop resilience in children, I always think about what my father did for me. He used to say, “Reach far because you’ll never go farther than your own reach. And if you fail, don’t worry, I’ll be here.” He instinctively knew what it took to give a shy young girl the confidence to take risks and to equip her with the resilience to face the prospect of failure head on, because failure and disappointment are inevitable in life if you want to make real progress.

On Leadership Qualities: Courage Is Critical
My shortlist of leadership qualities includes: vision, drive, courage, resilience, confidence, humility, compassion and a bias toward action. You have to be a great storyteller and paint a picture that makes people want to follow you. You also have to have grit and be able to persevere through the inevitable ups and downs. You cannot afford to have a bad day because there are people relying on you to succeed so that they can put food on their table and provide a future for their children. Shouldering that kind of responsibility takes real courage.

On Giving: Impactful Philanthropy
My personal philanthropy is centered around causes affecting women and children. For me, giving back is all about providing access and opportunity to disadvantaged children and empowering women. I once had a client ask me why I was on the board of Franciscan Children’s Hospital when there were other, more prestigious hospital boards that I could join. I told him that it was because they needed me more, and I could have a greater impact. I have always been attracted to promoting the underdog.

On the Importance of Women’s Education: Developing Leaders
One of the things I am proudest of is my work with Simmons College, where I am in my second three-year term as chair of the board. Simmons is committed to educating women in its undergraduate college. Most women’s colleges in the country are experiencing declining enrollments at a precipitous rate. Simmons was experiencing this three years ago as well. At that time, we retained a consultant who was charged with interviewing high school students to find out what they were looking for in a college. What we learned was that, all things being equal, high school students would prefer not to attend a single-sex college. However, what trumped that preference was a college that prepared them for leadership or was committed to social justice.

Armed with that insight, Simmons set out to revamp its entire undergraduate curriculum to focus on preparing women for leadership – not just what it means to be a leader in the C-suite, but what it means to be a responsible citizen, a leader in the community and a champion of social justice. When we went out to recruit our next class of high school students with this new curriculum, our first-year enrollments jumped, and we have now had three consecutive years of record enrollments.

On Failure: Disappointments Are Inevitable – Do Not Let Them Get in Your Way
When I first applied to Goodwin as a summer associate, I was rejected. The next year, I approached the firm again saying that I wanted to return for another set of interviews and that while I was rejected the prior summer, I believed this was the firm where I should be. After my interview, I got an offer and joined Goodwin following law school. Many years later, my mother found the original rejection letter and framed it next to the announcement of my appointment as chairman and managing partner of Goodwin.

I share this story with our younger attorneys because I want them to know that they should not let disappointment stand in their way – life is full of disappointments. What distinguishes a successful career – indeed a happy life – is not an absence of disappointments, but how one deals with them. If I had been too timid to approach Goodwin again, I would have lost what I consider to be the opportunity of my career.

During our conversation Pisa, also shared the top 10 leadership lessons she has learned during her career. Read them here.

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