I wanted to be a lawyer since I was about nine years old because I wanted to “help people,” and lawyering was the only profession I could think of whose main function was to help people, and that played to my love of competition and words. From that time until the summer before law school, though, the only lawyer I “knew” was Perry Mason. Consequently, in my mind, litigation was what lawyers do. Fast forward a few decades to 2021, when I became the executive director of Lawyers Concerned for Lawyers, Massachusetts, a lawyers’ assistance agency, and I find myself doing the very work I had set my heart to doing at age nine. When I dreamt of helping people all those years ago, I had no idea my dream would bring me beyond the practice of law, to LCL, much less to a leadership role in the legal profession.
Taking on a leadership role, especially as the head of an agency, is a humbling, and at times terrifying experience. And because fear makes you question, I find myself pondering my preparation and skill to be a leader. Leading other humans who may lack vision, or may be fearful, angry, or are simply counting on you is not for the faint of heart. Even as I know in my bones that I am a leader, I find myself needing to summon courage by trying to make my nine-year-old self proud of her audacity to have a vision.
I know that I didn’t get here overnight; I find that as I read and listen to the stories of others, I gain clarity and perspective on myself and my leadership journey. I also have a story, and I mine my history for tips and strategies, as well as places to grow as I continue to build out the vision for myself as a leader and the strategy for my new agency. Here are some things I have learned and am learning about being a leader.
“Leadership Never Happens In a Straight Line”
I am a child of the 70s, born to parents who came of age during the civil rights movement. Neither of my parents has a college degree, which given their respective intellects, I have always taken to be the result of a discriminatory system. I grew up with several mantras from my mother. One of them, I am sure similarly used by other Black mothers of her time was, “a Black man’s ‘A’ is the equivalent of a white man’s ‘C,’” and, this was often followed closely behind with the admonition that my path would be even harder because I am female. From very early, I was competitive. I recall clearly thinking in elementary school, when such a thing was not a foregone conclusion, that I had to go to college because my mother could not. Somehow, my mother’s sermonettes set in my heart a desire to lift others, in part, by striving for a platform. The groundwork for leadership was laid.
My father often talks of his flight home from dropping me at law school, when a woman asked him whether he was traveling for business or pleasure. He told her that he had dropped his daughter at law school, so both. The woman responded by asking if he was a lawyer, and he replied that he was not. Not satisfied, the woman then asked, “What makes her think she can be a lawyer?” My father replied, with an impish grin (at least he tells the story with one), “I raised her to believe she could be whatever she wanted to be.” Countless other times, in countless situations, people have asked me, “Have you ever done that before?” My answer has usually been some version of “No, but I’ve done (some related thing) and I figured I would give it a try.”
Each leader has a place from which the inspiration for their leadership emanates. This is both an argument and an encouragement. No mathematical formula or single pedigree forecasts great leadership. At its core, leadership is simply a way of being that requires courage and performance. The courage involved in leadership is the ability to go against the grain, whatever that grain is, to envision an outcome that is not presently visible. While it is true that past experiences prepare us and demonstrate a capacity for future endeavors, the requirement that someone has had “C-suite” level experience will only get you more of the same, both in culture and gender. A transformative leader needs vision, courage, and resilience. Those skills can be obtained in a variety of settings and demonstrated in a variety of circumstances, often without a title or authority.
When I went to law school, I had no idea what type of law I wanted to practice. Since I didn’t know any lawyers, I had no idea what my choices were. The culture of law school seemed to promote big law as the path to success. I sat for several interviews with big law firms. I often felt awkward and none of the firms offered me a position. Instead, I left law school headed for the local public defender’s office and for trial work.
I had observed that the lawyers who seemed to do best were doing what they loved. I knew I needed to find what I loved. I did not understand that the uncomfortable turns were part of my leadership journey. But I now realize that each role and the experiences in it taught me something that is part of my leadership style.
While in criminal defense, I honed strategic thinking. I coached, I mentored, and I taught, all things that I love about practicing law. Eventually, I left criminal defense litigation, first to become a clinical instructor, and then to become a bar regulator, a disciplinary prosecutor. I went into bar discipline to become a better lawyer, and specifically a better litigator, another thing I love about practicing law.
While serving as a bar prosecutor, I continued to hone my strategic thinking, coaching, mentoring, and teaching; I became a better litigator. But more importantly for this discussion, during that time I caught hold of the vision that improvement of the legal profession was an inroad to the dream of my nine-year-old self, and that improvement of the legal profession was bigger than bar discipline. That vision led me to my role as executive director of Lawyers Concerned for Lawyers, MA. I had found what I loved.
“In Charge:” One phrase, three roles
Part of the challenge to our profession is a lack of leadership. Law school does not offer leadership or business training. When I moved to a leadership role, I was put “in charge,” but I quickly learned this simple phrase meant as the leader I had to take on three distinct roles: administration; management; and leadership. Administration is the skill of administering the structures that are necessary to conduct business. Management is the skill of exercising control to produce predictable and foreseeable outcomes. Leadership is the skill of inspiring others to move in a certain direction, even through unanticipated challenges. As we know, each of these can be a full-time job in an organization, and leaders will often lean heavily on any of the three, rather than seeing them as tools to be used in concert.
As I approached my leadership role, I found it helpful to think about what kind of leader I wanted to be. I spent time thinking about people to whom I had answered. My mother had another saying, that until I began thinking about leadership styles, I hadn’t thought much about since I was young. She worked at an elementary school, and used to say to the students, “I’m as nice as you let me, and as mean as you make me.” My father would say, “Don’t take my meekness for weakness.” A more widely known phrase is attributed to President Theodore Roosevelt: “Speak softly and carry a big stick.” For me, in a real sense, these sayings embody the push/pull of leadership and management. In short, leadership is inspiration, and management is control.
I will always remember my basketball coach once saying, “The more rules you make, the more there are to break.” And indeed, I learned working with pre-teens in the summers of my college years that the more I tried to control them with rules and systems, the harder my days were. I still recoil at the thought of working under some managers who seem to have no idea how to inspire cooperation, but instead demanded it with constant deadlines, remonstrations, and performance standards. Their methods stifled creativity and bred resentment.
To exercise true niceness, meekness, and softness, leaders need confidence, and courage in their vision, as well as respect and regard for those they lead. A leader who lacks these vital characteristics will compensate by leaning on controlling management techniques, often making employees miserable. To be sure, effective leadership has these three qualities in balance. A leader who thinks too highly of himself or herself will run roughshod over others. A leader who considers the comfort of employees to the exclusion of hard decisions will cause discouragement. A leader who sees courage in refusing to consider alternate viewpoints will drive disconnection and division throughout their organization.
Determining when and how to lean into leadership or management depends on the circumstances as they exist and your capacity for creativity in achieving your goals. The lower the capacity for creativity, the greater the need to rely on management. The capacity for creativity is situational, bound by time, and relies heavily on habits of mind. Faced with a split second to make a decision, habits of mind will take over. All of this suggests that good leaders should cultivate creativity and empathy, as these will build the confidence needed to exercise courage, as well as habits of mind for a healthy perspective on themselves and those they lead.
All three roles, administrator, manager, and leader, require skills that can be learned. Administration and management require substantive knowledge, are the most static of the three, and can, to some extent, be outsourced. Leadership also requires substantive knowledge, but is very much an art, the expression of which is highly personal. Each of us can decide the type of leader we want to be and hone our leadership craft to become who we envision.
Admitting Imperfection Leads to Innovation
As a child, with my mother’s mantra ringing in my ears, I learned that correcting mistakes and iterating were bricks on the road to victory. Literally. When I was in the second grade, she taught me how to play Scrabble, a strategic word game, and she NEVER let me win. I played and played, and I watched as she and her siblings played. And, finally, I won. When I won, she was a good sport about it, congratulating me. My mother was the same way about my work. With that approach, I always took her challenges as a sign of respect, rather than needing to avoid the work of fixing the problem.
As a new executive, I have felt the temptation to know it all and do it all. The terror of leading causes doubts about being good enough. Yet fear of inadequacy, being a know-it-all, and doing it all, will only breed distrust. These mindsets are a form of perfectionism, and perfectionism breeds shame. Most employees will do anything to avoid feeling shame, including proving that you, as the leader, are not perfect. Imperfection is reality and shows where we need to grow. Allow room to grow.
Perfection is a myth. In the fairytale of “The Emperor’s New Clothes,“ everyone, including the emperor, knew he had no clothes, and yet, because of ego, none would admit it, not even the emperor. Leaders who are unable to admit their mistakes impede their own growth and the growth of their employees. In a world of “cancel culture,” shame, and blame, humility takes courage. The courage that underpins the ability to admit mistakes is the knowledge that we are not defined by imperfection as much as perfection is delusion. Admitting failure creates the opportunity to do a postmortem analysis, which leads to growth and innovation.
Instead of having all the answers, ask good questions. A good question is one that reframes thinking. It focuses on what can be done and urges collaborative study of the problem. Asking questions when you already know the answers causes frustration and can feel like “gotcha!” Good questions show respect and inspire innovation.
Leadership is the art of inspiring others to take up a vision. It is a delicate balance of standing upfront and getting out of the way, and it requires confidence and self-effacement. Training in the art of leadership begins early, long before you sit down for the first time in the ‘big chair.” And as with art, it takes courage to put leadership on display. Sometimes, though, it takes finding the right place to display it.
About the Author
Stacey A.L. Best is the executive director of Massachusetts Lawyers Concerned for Lawyers, the lawyer assistance program in Massachusetts.