Lessons from a Life in the Law

Following a bone marrow transplant in 2013, I remained in virtual isolation for a month at Brigham & Women’s Hospital in Boston. I spent much of my time with a group of devoted and talented nurses and medical technicians. I spent hours asking each of them about their education and training, their families and hobbies, and their aspirations. We talked about everything from their career paths to their kids, family recipes (one of which I later tried successfully), and how to negotiate for the purchase of a house. Thanks to these discussions, I was able to avoid spending my days thinking and talking about my precarious condition. In addition, I received a valuable education about the myriad careers in the health care sector, and, occasionally, I was able to provide a little advice that I hope led no one astray.

Looking back, I now see that I questioned and learned about my nurses in much the same way I have interviewed litigation clients and witnesses. Indeed, upon reflection, and as I transition to a new career in the public service arena, I realize that there were a number of important life lessons learned over the course of my legal career that have application well beyond cross-examining witnesses, writing briefs, or any other specific litigation skills. These lessons and learned behaviors have helped me not only as I’ve grappled with illness but also as I sit in board meetings, advise nonprofit clients, or talk with friends about their challenges. Five in particular come to mind.

Dealing with Unexpected Setbacks

In the corporate law firm setting, our cases typically span several years, often with hundreds of millions of dollars, the fate of a major company, and people’s careers at stake. Powerful judges of varying abilities and temperaments preside. In this environment, the only prediction one can make with confidence is that, at some point, bad, unforeseen things will happen that will radically alter the case and force you to change course: Incriminating documents surface belatedly, particularly in a world where people fire off ill-advised emails (or even tweets!) in haste or anger, a key witness unexpectedly gives harmful testimony, or a judge issues a damaging decision that cuts the legs out from under your case and forces you to come up with a new game plan.

Although I never recognized it as a “lesson,” what years of absorbing these unpredictable blows taught me was to take setbacks in stride, to look ahead (and avoid harping on what had been lost once it was clear that nothing could be done about it), and to devote myself instead to coming up with a new game plan that would make the best of the new reality. So, upon reflection, I realize that the answer to my friend’s question is that my experience as a litigator instilled, or at least solidified, the single most important habit that carried me through my medical roller coaster.

Leading Teams by Forgiving Mistakes

Our cases are staffed with teams that typically include a few partners, a group of associates and paralegals, representatives of the client, and often lawyers from other law firms. When such a large group works under intense time pressure over a period of years, it’s inevitable that mistakes are made, even by talented people. Sometimes the screwups are big.

My experience as a lawyer reinforced a lesson I’d learned playing high school team sports decades ago: People feel bad when they make a mistake that hurts the team. So the last thing a leader should do is come down hard and make an otherwise competent team member feel worse. Rather, showing sincere support, while also teaching, at this moment of vulnerability yields dividends, including helping other team members feel secure and bonding the team going forward. I have tried to follow the same practice in other contexts—whether learning at a board meeting that the chief executive officer (CEO) or some valued staff member has made a mistake that has caused a problem or listening to a promising mentee reveal that she received, and deserved, a bad performance evaluation. While there will sometimes need to be consequences, responding to missteps in a forgiving manner helps ensure that the inevitable future mistakes will be disclosed in time to address them, and find solutions, before the problems mushroom.

Unleashing the Young

In important respects, the most junior members of our teams know the most: They review the thousands of documents in which the critical facts of the case—good and bad—are buried, and they do the legal research. As a result, they are often aware of looming pitfalls and have ideas that haven’t occurred to senior partners. But many are afraid of saying something stupid and being forever branded as a result. I remember having these same fears in my days as a fledgling law firm associate.

Over the years, I’ve learned to seize opportunities to positively recognize younger people when they volunteer reasonable suggestions, particularly in group settings or when a junior team member pushes back on an idea or plan of mine. The goal is to create an environment in which everyone on the team feels free—and indeed is encouraged—to speak up and challenge the status quo, whether to identify minefields or suggest a new, creative route, even if it’s ultimately not the route taken. I now strive to create such an environment when participating in nonprofit board meetings or committees—especially when younger people, often from diverse backgrounds, make presentations to a board of older, predominantly white, ostensibly high-powered professionals.

Interviewing by Listening

Listening well is essential at every phase of a litigation. Whether you’re questioning a witness at a deposition, conducting a cross-examination at trial, or advising a client in a crisis, the raw material you need to succeed more often comes out of the other person’s mouth than your own.

In order to obtain information worth listening to, however, I’ve found it important to first break the ice and help the individuals I’m interviewing feel comfortable sharing information that’s often personal, which may involve conduct of which they’re ashamed and for which they or their employer could face serious consequences. As a result, I’ve gotten in the habit of starting an interview by talking not about the case but about some noninvasive topic that will be easy for the other person to talk about—often something we have in common or something interesting or commendable he or she has done.

The habits I’ve developed over the years for asking questions are shared by many good lawyers. Rather than conducting an interview by posing a series of pointed questions, I tend to ask short, simple, open-ended questions, and then give the witness space to talk while I listen carefully. My follow-up questions are derived from the witness’s answers, and often those follow-ups aren’t questions at all; rather, they are reflections that attempt to sift through and distill what I’ve heard the person saying or thinking, in order to highlight the points worth pursuing (e.g., “It sounds like you’re concerned that. . . .”). Those reflections and follow-up questions lead to more expansive answers that go deeper into the heart of the matter as the witness grows increasingly comfortable. At that point, in a low-key, sincerely supportive tone, I can often directly ask, and get honest answers to, the most sensitive questions. And, although I am often fearful that some of those questions may offend the other person, I’ve found that they rarely do if I’ve taken the time to lay the groundwork thoughtfully.

Getting back to my bedside chats in the hospital, these are some of the habits I used to learn about my doctors and nurses during my medical odyssey. These habits are also the same ones I use constantly now as I advise CEOs on matters having little to do with law, talk to friends about their challenges, or meet strangers and learn their life stories—whether at a dinner party or while talking to a taxi driver. And the more I’ve morphed into the role of senior advisor, the more I’ve learned that my listening, not talking, is paramount.

Our Strengths Are Our Weaknesses

Perhaps the most basic but important lesson I’ve learned during a career participating in litigation teams and in the management of a global law firm is that, for every one of us, our strengths and weaknesses are on the flip side of the same coin. The groundbreaking visionary is often a poor manager of today’s operations. The meticulous thinker who thankfully spots every flaw and potential problem may have trouble pulling the trigger and deciding to move ahead with the least bad option. The confident, decisive (and often arrogant) leader may be prone to charging ahead in disregard of serious lurking problems that will doom the mission or undermine the morale of the team, or both.

As Jeff DeGraff, one of the county’s top leadership coaches, teaches, while some people who are extremely successful in one regard think they’re great at everything, very few of us actually are. The key is to know both your strengths and your weaknesses, and then to surround yourself with those whose strengths will compensate for those you lack. I try to keep this in mind when I evaluate leadership teams and counsel people in other contexts.

For example, I recently listened to a terrific young CEO I’m coaching criticize herself for being too slow to fire an executive who was underperforming but who had been loyal and valuable in the past. I reassured her that this “weakness” was shared by one of the best CEOs I know (of a global public company) and is a by-product of the fact that she is a compassionate person—which is among her great strengths and one of the reasons she has been such an inspiring, successful leader. Bottom line: Everyone comes as a full package.

Seize Your Opportunities

Reflecting back on my career, I realize that truly major opportunities—whether to gain important new clients or great trial experience—did not come often. I’ve taken advantage of some, and they propelled and shaped my career. But I also missed at least a few. I missed them because I was not sufficiently assertive or persistent in pursuing those opportunities in the face of obstacles or because I was unduly hesitant to promote myself aggressively, or a combination of these. In recent years, I’ve been less reticent. When I see a good opportunity, I pursue it more boldly and persistently than in my younger days—and time and again, I’ve benefited. So my simple advice to those at the other end of the age spectrum: When your big chances come along—whether to garner a client or pursue a personal relationship that could evolve into the love of your life—be sure to make the most of them. And don’t worry about failing!