Executive Education for Lawyers

Volume 4 • Issue 1 • November/December 2017
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Quiet Leadership

A conversation with Susan Cain

Susan Cain, best-selling author and cofounder of Quiet Revolution, and David B. Wilkins, faculty director of the Center on the Legal Profession at Harvard Law School, discuss leadership, collaboration, and belonging in the legal profession.

David B. Wilkins: Welcome, Susan. It’s so amazing to hear your voice again, after all you have been giving voice to so many others and to so many important things. We’re just thrilled to have you join us.

Susan Cain: Thank you so much, Professor Wilkins. I just have to tell you one thing, before we start. Yours was literally the first class that I attended at Harvard Law School. Every time I give advice to people, the favorite piece of advice I give comes from a lesson that I learned in your classroom: When you’re attending a meeting, and you think you aren’t such a great participator, think in advance of something that you might want to contribute and push yourself to speak up early, because if you do that, you start to feel more present in the room and other people start directing their energy toward you—and it becomes this virtuous circle.

Law school was the most intellectually stimulating year I’d ever had. And I loved it. But, at the same time, I did feel like I didn’t belong there…

I learned that from your class, because when I first got to Harvard Law School, as you can imagine, I was terrified of the Socratic method. I was terrified of being called on, and that strategy was so helpful. I started doing that, and each time I did, you kept referring to my one little comment and you would say, “Well, as Ms. Horowitz said…” It was just an invaluable lesson and has stayed with me ever since. And it’s a lesson I’ve now been passing on to thousands of people, thanks to you.

Wilkins: Wow. Well as you know, as someone who teaches for a living, there is no greater gift that you could possibly give me than such a wonderful story, especially when it is not just empowering for you, but for so many others. Thank you.

Let me start this interview where you began and ask you about what you were thinking and feeling when you came to law school. Why did you decide to go to law school? And can you talk a little about your journey through law school?

Cain: I was an English major, and I had wanted to be a writer since I was four. I came to law school for many reasons, but honestly, I think it was—as it is for many people—I wasn’t quite sure what to do next. At that time, I had concluded that being a writer was not going to be a practical way to support myself. So, I came to law school in that sort of default way. But the funny thing is, I absolutely adored it. I really loved it, especially in my first year­—before you get that intensely pre-professional vibe, when it still feels more like an intellectual exercise. Law school was the most intellectually stimulating year I’d ever had. And I loved it. But, at the same time, I did feel like I didn’t belong there, because I didn’t think I was really meant to be a lawyer.

Wilkins: You just said something very interesting, which is that you loved it but you didn’t quite feel like you belong there. You also mentioned earlier that it was kind of a terrifying experience. Looking back on that time with all the thinking you have done since, are there things that you wish you could tell your younger self or that you think students today should know about how to approach that experience, particularly if they are more on the introvert end of the spectrum or have had some of the same feelings that you had when you were in law school?

Cain: Throughout my time at law school, and during my first years as a lawyer, I thought that the main way to be effective in the law was to be the type of person that I was not. It was only later when I realized that there was this other model of being effective. I initially thought being an effective lawyer was being the kind of person who could effortlessly grandstand in front of a jury. But then I started to look around and realized there are these people who contribute in much more quiet and thoughtful ways—for instance, by raising a question or turning a question over in ways that other people haven’t thought of, or by listening to what everybody says and then thinking of a different angle on the problem. It’s a different role for everyone, but to expand your vision of the ways of making powerful contributions, I think, is a big thing.

Thinking about what the law school could be doing differently, the most emotionally difficult classes that I took were those three-week intensive trial preparation classes and those very intensive negotiation classes. Both of those classes presume that you are already the kind of person who’s extremely comfortable holding court—and I wasn’t that person! I was literally terrified, so I grit my teeth through them all and got something out of it, but it was very difficult.

It would be great to have a class during the January semester that would be “public speaking for people who are uncomfortable with public speaking.” After I graduated from the law school, I took a seminar for people with public-speaking anxiety. The class was based on the psychological idea of desensitization—that the way to overcome any fear is to expose yourself to it in very small and manageable doses. On the very first day of that class, all you would do is stand up, say your name, sit down, and declare victory. And then you come back the next time, and you would do a little bit more. You’d answer some questions about where you’d grown up and where you’d gone to school—simple things like that—and then you were done. Little by little by little, you would work up to it until the fear of addressing a crowd with people watching you became a little more manageable. I think having a class like that would be critical—not only would it give people the practical tools they need to address this stuff, but it would also be a way of the law school acknowledging that a huge chunk of the students are not comfortable with this stuff and giving them a socially acceptable space to say so instead of everybody kind of walking around with this silent feeling that they’re supposed to be comfortable with it. And they’re not.

I initially thought being an effective lawyer was being the kind of person who could effortlessly grandstand in front of a jury. But then I started to look around and realized there are these people who contribute in much more quiet and thoughtful ways…

Wilkins: That’s wonderfully helpful, and in fact we have started making progress in this area, though granted it’s not nearly enough. In the January term, we now have a course called the Problem-Solving Workshop. It’s a three-week, workshop-style course, but the goal is to introduce things like presentation skills or public-speaking skills or team-building skills. But I agree with you that we don’t do nearly enough around these areas, and a lot of the assumptions still are “Well, if you went to law school, you’re the kind of person who likes to do this or finds it comes natural.”

Cain: Exactly. If you’re not that kind of person, you feel you’re in a place where it’s supposed to be natural. It would be interesting to do a survey of law students, and just ask them how they feel anonymously, to ask them how comfortable they are in front of a crowd and get a sense of how many students do feel that way. My guess is it would be a significant percentage.

Wilkins: Let me ask about you about the transition to law practice, because you did go—as most of our graduates do initially—into a law firm, where you stayed around for six or seven years. And I take it that that was a formative experience for you, both positively and negatively. You survived and conquered Harvard Law School, though perhaps not always feeling entirely comfortable there, and then you moved into this new environment of the large law firm. What was that transition like?

Cain: I loved working at the law firm. For the first two years, I really loved it, in much the same way I loved Harvard. I didn’t feel like I belonged there, but to me, it was like traveling to a foreign country. It was just really interesting. My peers and colleagues were incredibly interesting and fun to be with, and I thought it was interesting to learn this whole new language of finance that I didn’t know anything about—that was the kind of law that I was practicing. So, I got a huge kick out of it for a good while!

But, at the end of the day, I’m not a corporate finance person, and that became clearer and clearer as the years went by. I had the same issues that everybody has in practice where you’re working 16 hours a day with no control over your time. You come in in the morning and have no idea what time you are going home that night, so you stop making plans, because it is just less stressful to not have to worry about whether you cancel them. It’s fair to say I had that kind of mix of emotions about the whole thing, as I think many people do.

Wilkins: Did you come away from that experience with a different view of the range of personality traits that lawyers had in practice? Are there things that you took away, either from observing them or being a part of that environment, that then helped frame for you some of the ideas that you began to write about when you left?

Cain: Oh yes—very much so. I came into the law firm feeling like I had at the law school. I had the idea that to be successful in the profession means to be the kind of person that I’m not. I just started off with that supposition, but then I started to look around me at the effective lawyers in my firm—more in the transactional practice, but you see it sometimes in litigation, too—and I’d see that some of the people were quiet, cerebral types who were good at thinking about the what-ifs of any situation. They were deeply thinking through things like: What if the transaction goes this way? What if it goes that way? What should we be thinking about? You know, and entering negotiations, responding in a very thoughtful way that was here in the discussion, away from getting cantankerous and more toward a constructive spirit. That’s when it started to open up for me in a real-life way that there are a lot of different ways to be successful and a lot of different ways to negotiate successfully.

At the same time, I had always been very interested in women’s issues, and I would sit around in these meetings on Wall Street with 10 or 15 people in a room and I’d be thinking about all the social dynamics. At the time I was going into it, the kind of language that I had for thinking about these things was through the language of gender. But then I started to realize that while that explained some things, it didn’t explain everything. A lot of what was going on was just a question of how introverted or extroverted people were, and that was shaping the way they behaved. Yet there was no language whatsoever for talking about this dynamic that struck me as profound. That was the experience that started me in this direction that I’ve now followed. It just felt like it was the great unnamed social dynamic.

One of the most powerful things that you can do is to identify a role model.

Wilkins: I think that’s such a deep observation because no one talks about it. Again, the people most likely to understand it are the least likely to talk about it for the very reasons you suggest.

Cain: Exactly. People often suggest things like, “Well, women are maybe less likely to speak up in a meeting.” And I would think, Well, that’s true, but then there are some women who are not unlikely at all to speak up. If they’re more extroverted, they’re not less likely to speak up. I just felt like there’s this whole narrative that gender is shaping us, but there are other factors as well.

Wilkins: And is that eventually what propelled you not only to leave the law firm but then to move into a writing career? Did you just decide for yourself, you know, there’s something here, and I want to write about it? Or were there intermediate steps in between before you began to write on a full-time basis?

Cain: I was lucky that at my firm, it was very common to take a leave of absence. So what happened was I took a leave of absence—I had been there about six and a half years at the time—and I think I knew deep down I wasn’t coming back. I had at that point forgotten that I had always wanted to be a writer, so I just thought I would relax and travel. But I found within 24 hours of being on leave that I was starting to write. I remembered that it was what I had always wanted to do. So, I signed up for a class at NYU in creative nonfiction writing, and I went to the first session about a week later, and it was like one of those cinematic epiphany moments of feeling like this is what I need to be doing. I never in my wildest dreams thought I could make a career out of it. But I tried to rearrange my life so that I could make that my hobby and have a lot of time to devote to it. I left the law firm, set up a little freelance business teaching people negotiation skills, and spent the next few years working and writing. I wasn’t writing about introversion: I wrote a play. I wrote a memoir. I wrote poetry. However, a few years into that process, I started thinking again about introversion and extroversion and started writing about it. And that’s the book that became Quiet.

Right now, people take the word collaboration to mean that we should be working in teams 24/7…and that’s actually the worst thing that you can do if you want to be greater than the sum of your collective parts.

Wilkins: One of the things we started over the last few years is a series of courses for professionals that focus on helping them to understand the challenges of leadership and to think of themselves as leaders—not just as lawyers—as well as understand their own leadership styles. Many find it challenging, partly because of the organizations that they are in. Many of them are senior leaders in law firms and others are senior leaders in in-house legal departments. Having thought so richly about these issues and written this profound book on introversion, what advice would you give those leaders about how they might better understand their own leadership styles and learn how to use those styles more effectively—both for themselves but also in their positions as leaders of organizations? How might they try to reshape those organizations to make them more open and accessible to people across the whole range of styles, from the most introverted to the most extroverted and everything in between?

Cain: In terms of how do you function at your best within your own style, one of the most powerful things that you can do is to identify a role model. It can be somebody in your firm or just in your orbit who has a temperamental style that’s much like your own and whom you admire. And you can study that person and see how they handle each of these situations because they’re very likely handling them in a way that would feel comfortable to you as opposed to trying to be somebody whom you’re not. So, finding that role model is really key.

In terms of being a leader to introverts, the first thing to think about is office space. My sense is that in recent years, law firms are starting to go the way of other offices in introducing more and more open spaces, and I would just be careful not to follow that trend too dramatically. This is for the extroverts as well as the introverts. I’m a big believer in quiet, private space where you can put your head down and get into a state of slow and not feel that you’re going to be interrupted or be subject to other people’s noise. There’s a ton of research on how much more effective that is for everybody, but especially for introverts.

I would also think that—especially in the law firm world, where we are used to thinking of people as either partners or associates—it is important to break down what the different ways in which lawyers contribute are. For some it’s being the rainmaker; for some it’s being the very extroverted, charismatic organizer; and for some, it’s being the person who cultivates a lot of expertise in a given practice area. And these aren’t all necessarily the same human being. Instead of looking for the human being who embodies all these things, rethink the model so that it’s a collection of different humans where if you pool those talents together, you’re much bigger than where you started.

Wilkins: I think one of the things that we really try to emphasize is just that last point—that the team is greater than the sum of its parts—but only if we think about each part contributing something different and reinforcing that in a way that allows people to contribute in their own ways and where everyone can see the benefit of the collaboration. Frankly, we don’t do that very well in law school where everything is an individual effort judged on an individual basis, and that’s exactly the opposite of the way the world works.

Two things you mentioned in the course of that last answer, which really goes to what you might think of as where the future of work is going. One is it’s going toward being more collaborative, trying to build people’s ability to work in teams and to work across different kinds of divides—cultural divides, personality divides, different styles of work. And the other is the way spaces are being transformed more and more to be open space, which some would say is for the purpose of ensuring collaboration, yet it may also make it more difficult for others to contribute. And I wonder, as you think about the future, do you have any suggestions as to how we might create a better workplace—either the way people work together or the design of it or the way people use technology—that could help make it a genuinely more welcoming place to people of all different types as well as create the kind of collaboration that you talk about?

Cain: I believe we need to redefine the word collaboration, or maybe even get to a new word. Right now, people take the word collaboration to mean that we should be working in teams 24/7—meaning the whole team should be out there together, the open floor, working together all the time—and that’s actually the worst thing that you can do if you want to be greater than the sum of your collective parts. And I’m looking at this now from the perspective of personality. The best team, from a personality perspective, is one where the extroverts are getting the social stimulation they need where there are plenty of opportunities to be interacting. The introverts, as part of that team, are also able to go off by themselves and put their head down for hours at a time, get into that state of slow that introverts love, and then be able to come back out of that and share what they’ve gleaned and what they’ve produced with the members of the team. It decidedly doesn’t mean that the team members are together all the time. A good team, rather, means we are taking into account all the individual preferences of each member of the team and negotiating together what each person needs so that we can all work at our best together.

Instead of looking for the human being who embodies all these things, rethink the model so that it’s a collection of different humans where if you pool those talents together, you’re much bigger than where you started.

As you extend that view to the use of space, it’s really the same thing. I will still, honestly, advocate for returning to the offices of old where everybody had their own private space, and then have lots of collective spaces within that. But assuming a world of more costly and limited office real estate, you at least want to make sure you’ve got space where people can move freely back and forth between the private and social spaces so that the people who want to work in the private space have access to it whenever they need it and the people who want to work in the social space can do that as well. And everybody gets to situate themselves in the way that each individual team member works best for the sake of the collective output.

Wilkins: Susan, that’s just incredibly thoughtful and timely considering the issues that law firms and other kinds of professional organizations, as well as lawyers of all types—public and private—are grappling with as they try to advance a profession that is based on a very old traditional model and is, at the same time, being subject to forces of change that are coming from many different directions. And this is a really important redefinition and reframing of how we think about collaboration, what this word really means, and how we can help everyone be a part of it in the way that’s best for them and ultimately best for the end product or output. Thank you so much for sharing these thoughts with us.

 


Susan Cain is the cofounder of Quiet Revolution and the author of best-sellers Quiet: The Power of Introverts in a World That Can’t Stop Talking and Quiet Power: The Secret Strengths of Introverts.

David B. Wilkins is the Lester Kissel Professor of Law, vice dean for Global Initiatives on the Legal Profession, and faculty director of the Center on the Legal Profession at Harvard Law School.

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Executive Education for Lawyers Volume 4 • Issue 1 • November/December 2017

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