Q&A with Gillian Lester, Dean of Columbia Law School

Gillian Lester is the Dean and Lucy G. Moses Professor at Columbia Law School, a position she has held since January 2015, after having served in various capacities at Berkeley Law School, Harvard Law School, UCLA School of Law, Georgetown University Law Center and Stanford Law School. She started her career in her native Canada, where she majored in Biopsychology before attending law school, and has focused her scholarship on contracts, employment law and social insurance law and policy. 

I recently sat down with Dean Lester to talk about leadership, role models and the importance of grit and empathy. This interview has been edited from its original format.

Q. Looking back at your career, from a summer internship at a law firm to becoming the Dean of Columbia Law School, did you always want to become a Dean?  

No, I didn’t imagine myself as a dean but I became curious from an early age about what an academic path might look like, and I was very attracted to the possibility of teaching. I was inspired early on by the idea of the university and the possibility of going to university. When I was six years old, my father took time away from his 20-year law practice to get a Ph.D. and instilled in me a sense that the university was a special place and that it was a privilege to be connected to it.

Q. In your case, did you pursue leadership positions early on, or was there a moment when you decided to actively pursue leadership positions? If there was a moment, what was it and what do you think prompted it? 

I think that I came into leadership in a sort of unexpected way. From an early age, I was always hungry to learn new things and to take on activities in every sphere of life. As a child in elementary school, I did so many different things: sports, music, volunteering, girl scouts, hiking and camping – many of these things as part of a group. When I look back, I realize I was always drawn to activities that involved working collaboratively with other people – being part of a team that was working together to try to accomplish a goal.

I never saw myself as the leader – I just wanted to be a really engaged participant. I eventually realized that being intensely involved, being somebody who was always seeking to learn and understand new things, and also to work with people and understand people was, in itself, a form of leadership. As an anecdote, when I was about 12 years old, I was awarded “best all-around student.” This came as a surprise because I didn’t see myself as the best at any one thing. I did a lot of things and persevered—and I always tried to be the most engaged participant I could be. It turned out that this was recognized by teachers and classmates as a form of leadership.

Q. You have two teenage children – to what extent has being a mother affected your career strategy?

When I look at the major shifts in my career, they tended to correspond with major moments in my life as a parent. I waited a couple of years after I had tenure before I had my first child, so that I could see life on the other side and understand what it looked and felt like and take the measure of it. The next juncture was when we moved from Los Angeles to Berkeley – that corresponded with our daughter’s completion of preschool. When I came from Berkeley to be dean at Columbia, the timing was structured so that it was when my children were graduating from middle school and elementary school, respectively, and entering into a new phase of their school lives. I have timed my major career choices around either the arrival or the transition of my children from one phase to another, when they would be experiencing a change in their social dynamic anyway, so that would be an opportunity for me to make a career change without unduly disrupting their lives.

Q. What do you think are the most pressing issues for the generation of women about to enter the workforce?

The issue that really stands out for me is about work-family balance. How women are going to be able to have it all. These are issues that are familiar to all women in professional roles and that continue to be one of the most significant challenges in my life: to be able to give enough to both my family and my professional life and feel like I’m able to maintain a sense of both being present and passionate. I think it’s the great common experience; it’s the great tie that binds women.

One thing I feel heartened by is that, increasingly, I am able to have these conversations with men as well, in which they lament their own challenges in work-family balance. I think we will continue to fight that battle until men start to fully engage with the family side of the work-family balance proposition and really understand the challenge of trying to be truly committed and equal partners in family-life while also maintaining their professional aspirations and ambitions. It will then become less of a women’s issue and more of a family issue – but at this point, I think it is still very significantly a women’s issue.

Q. Did you have mentors along the way? Could you talk about how much in common you had with them and how mentorship has made a difference in your professional and personal life?

My mentors were almost always teachers. My mother was a teacher. Teaching is a challenging vocation. To teach and to teach well requires an enormous amount of passion, of preparation, a deep sense of responsibility to your students, and sometimes just grit. And it’s one of the reasons why, from an early stage, the people who were my most significant mentors and role models were my teachers.

As early as I can remember, my teachers and coaches taught me perseverance in the face of challenge. They were people who, when I became discouraged, told me that it was important to keep trying and to take on challenges I hadn’t yet mastered; that if I were to persist and persevere, I’d feel a sense of satisfaction from having accomplished something difficult. I take that with me in everything I do in my life.

As to common ground, it is certainly true that seeing someone who shares some of your characteristics, who has gone on to do something you’d never imagined for yourself, can be one of the most powerful sources of inspiration. But I also think that learning empathy, learning to understand people who come from different backgrounds from yourself and seeing that they’ve been able to make strides that you can only imagine, has been increasingly a source of inspiration.

Q. What was the most difficult leadership lesson you’ve learned and the best piece of advice you have received on leadership and balance?

I’d say three things. The first is that when you come into a leadership role, you are often called upon to make hard decisions with conflicting opinions on the right answer. I’ve learned to trust myself. It’s important always to listen very carefully, to really hear what people are trying to help me understand, then to use the absolute best of my abilities to make a reasoned judgment. It’s very easy to second guess yourself, but if you start to doubt yourself, then others will doubt you as well – you have to do the best you possibly can and trust yourself.

A second lesson that I’ve learned is that you need to be bold as a leader. There is a reason you were chosen to lead, and that requires having courage and making uncomfortable decisions that sometimes bring about change. You have to learn to be able to make the bold choice rather than always make the safe choice. That’s hard to learn, because it requires being able to put yourself out there. But you can never move an institution forward if you are not willing to be bold.

The third lesson is that in many cases leadership roles can demand an almost singular devotion to the role, and you have to be careful not to lose the things that made you an interesting, balanced person. The first time I served as dean in an interim role at Berkeley, I threw myself into the job. I really worked hard to maintain my attachment to my family, my children and my husband, while also taking on the job, but I left behind other things I love to do, such as exercise, reading novels, working in the garden, going for walks with my friends, cooking, etc. I was having lunch one day with a friend who asked “what is going on in your life?” and I had nothing to say except about work. I realized that maybe I couldn’t pursue as many interests as I had in the past, but that I had to maintain some basic time for myself. So the third lesson is not to give up all of your interests. A leadership role can take everything you have to give to it, and you have to guard certain parts of your life to allow yourself to remain a flourishing person who has other passions.

Q. You’ve written in favor of paid family leave – where do you see the US in this debate right now?

I am very encouraged by federal and state governments’ continued incentivization of paid family leave – specifically, developing new programs for family leave. The 2016 federal budget contains $2 billion dollars for the paid leave partnership initiative to assist as many as five states that want to launch paid leave programs following the example of California, New Jersey and Rhode Island. I think there is still a strong desire at the highest levels of government to encourage experimentation and development of paid leave programs in states. I am very hopeful. I would love to see enactment at a federal level of a paid leave program; there have been multiple efforts for decades, but that has not prevailed. The most successful kinds of social change happen when both federal and state governments are involved, where the states are experimenting and are backed by the federal government.

Camila Amaral Surcan is an associate in Debevoise’s New York office. 

Comments? Suggestions? We’d love to hear from you. Send us an email at women@debevoise.com.