Q&A: Mary Herrington on Leadership and the Private Sector

Mary J.L. Herrington is the Executive Director of the Chae Initiative in Private Sector Leadership, part of The Tsai Leadership Program at Yale Law School.

The Chae Initiative in Private Sector Leadership prepares students for nontraditional leadership careers in business, finance, investing, management consulting, and entrepreneurship with a robust cross-disciplinary skill set. The Chae Initiative’s core philosophy is to empower Yale Law students to be ready and capable of translating theory into practice, to obtain a firm grasp of business principles, to be nimble in the face of complex business issues and innovation, and to engage in ethical decision-making.

Prior to coming to Yale, Herrington was a Director at Columbia Law School, where she managed its joint organizational leadership initiative with Columbia Business School, counseled students on private sector careers, and designed speaker series on legal practice areas, careers in business, investment banking, management consulting, and DEI initiatives. Herrington earned her J.D. from the University of Pennsylvania Carey Law School, her B.A. from Columbia College of Columbia University, and studied English Literature at Cambridge University.

Leadership is a complicated and personal concept. How do you define it? 

Generally speaking, I would define “leadership” as the action of defining, influencing, and marshalling others towards a common goal. While I don’t subscribe to the notion that there is a one-size-fits-all approach to leadership, I do believe that there are common traits and practices that allow for a leader to succeed. To me, successful leadership is one that consistently engenders motivation and inspiration in others to want to become better versions of themselves and bring these best selves to the shared pursuit. Leadership is being comfortable with the unknown, taking on and simplifying novel, complex, and unexpected challenges, all the while guided by ethical principles and a deep set of values. A great leader draws upon knowledge — gained through education and experience — as well as taking counsel from the knowledge and wisdom of others, building true teams, trusting the team, and strategically delegating tasks. Leadership should value transparency, tolerate the existence of contradictions, and welcome dissent. This can mean decision-making that fully embraces that there will be short-term setbacks, accepting that setbacks can lead to long-term profitable and more favorable outcomes. Leadership is also on a continuum — it is ever evolving — and great leaders will always believe they can do better. There can be flaws and mistakes, and that’s okay; a sign of a great leader is one who takes accountability, learns from lessons, and shows humility in improving flaws. Leadership can also take many forms. And some of the best examples are not even those that make headlines, but are those that — to quote my favorite novel, Middlemarch — are “unhistoric acts” by those who have “lived faithfully a hidden life, and rest in unvisited tombs.” To name the most impactful for me, these leaders would be parents, teachers, partners, and many colleagues who mentor and spark new ideas, yet may be behind the scenes.

What have you learned about leadership in your own career?

The two most valuable lessons I’ve learned about leadership in my own career — which has spanned law firms, media companies, entrepreneurial ventures, and higher education — are: one, that it is vital to be nimble and resilient, and two, that emotional intelligence (i.e., social awareness, compassion, interpersonal aptitude) is just as important as raw intelligence. To the first point, there will inevitably be setbacks and crises in one’s career, one’s organization, and one’s personal life. In the organizational context, what I have learned is that a leader who has already cultivated a strong culture of resilience within the organization and models those values, is the kind of leader who maintains loyalty through crises. As to the second point, a leader is by definition leading a group, not just oneself. A leader who embodies and enforces an optimal organizational culture with a consistent demonstration that personal ego is not a driving force will motivate people to want to be high achievers aligned with the leader’s strategy. When people feel valued, they want the leader to succeed because success will be their success. Some of the smartest people I have come across in my career did not necessarily become the best leaders; the best leaders were smarter in how they knew the right times to pause and listen, how they empowered others, how they always strove to be clear and inclusive, while expecting the best. I’m a firm believer that EQ can be developed and enhanced. The COVID-19 global health crisis has been a true test in leadership under both points. Leaders at all levels have had to be resilient as well as deft. It has also made clear how vital it is to provide leadership education to the next generation and learn from this very real and devastating real-world crisis.

What made you interested in taking on this new role at Yale Law School?

As a former student of the liberal arts and of the law, I have valued innovation in education as much as I’ve valued membership in institutions steeped in tradition and intellectual inquiry. Increasingly in recent years, I have also been fascinated by changes that I’ve seen in the legal industry and in other client-services professions, such as investment banking and consulting, in the face of the rise of Big Tech and the ethos of “do what you love.” The financial crisis and its aftermath saw law firms and other law organizations become much pickier in the hiring process as they assessed candidates for grit and professional readiness than they had ever done before. It has only become clearer that the demands of all professions are only getting more competitive. When I began thinking about next steps in my own career journey, I wanted to find a role and a place that shared the same values in embracing innovation and in pushing the envelope in legal education. Rather serendipitously, I was told of this opportunity at Yale. And upon learning of Dean Heather Gerken’s vision for The Tsai Leadership Program, it felt like the stars had aligned. Here was a program that valued both innovation and tradition. That would draw upon all my prior experience as a career advisor to law students, as a director of a leadership initiative, and my legal and entrepreneurial experience. And, as cherry on top, it offered the chance to be part of a vision with such depth and breadth at the most revered law school. Also, the sheer opportunity to work with and learn from the most impressive set of leaders, such as Joe Tsai ’90 and Michael Chae ’97, was also an opportunity that anyone interested in leadership development couldn’t possibly pass up.

What do you want students to know about The Tsai Leadership Program and the offerings of the Chae Initiative?

The Tsai Leadership Program will support Yale Law School in deepening a holistic educational experience for students. We are supporting Yale’s great tradition of producing leaders by bringing visiting faculty to teach new courses and designing workshops that will develop students’ professional skills and leadership frameworks. When you look at any successful leader, you will see a common thread: they are interdisciplinary thinkers and agile problem solvers. The Chae Initiative is offering a platform for students to develop holistically. To dive deep into corporate finance, accounting, statistics. To expand one’s thinking with deeper study into professional ethics, organizational behavior, psychology, econometrics. To apply the skills learned from professional development workshops into one’s own negotiations, public speaking, and management of difficult conversations. To learn about different perspectives and on-the-ground real world examples from talks given by Yale Law School alumni leaders. And to bring all these experiences into rich discussions in and outside the classroom.

We view it as incredibly important that preparing students for leadership roles means deep engagement with ethical questions, where answers are never simple, and that as leaders, they will need to work harmoniously with people who hold opposing viewpoints, perhaps even antithetical to their own.

The Chae Initiative will prepare students for both traditional law careers as well as careers that are outside the practice of law. In any field, including law, as one progresses and takes on more responsibilities, a vast percentage of one’s time and success on the job entails managing teams and navigating interpersonal dynamics. Leadership training can also help lawyers better understand the client’s ultimate needs and objectives. For those students interested in careers in the finance, consulting, and business sectors, or hoping to launch their own venture, they will learn the tools, as well as the theories behind such tools, so that they will be prepared for jobs straight out of the YLS gate and leadership roles in the future.

What are you most excited about working on over the course of the next year?

Everything! But I am especially excited to launch the Chae Fellows program later this year. This will be a community of student fellows interested in non-legal practice careers in the private sector and leadership development. We also value the power of mentoring in preparing students for any career. To that end, we will be implementing a meaningful mentor matching program. And what really excites me is the unique opportunity to meet leaders in various organizations through offsite intensives in New York City and the Bay Area.

I am also excited about the support we will bring in career exploration and interview readiness. We plan to host industry-specific events that will provide practical advice, examples of effective interviewing, and panelists sharing insights on the day-to-day of their jobs. We plan to leverage our extraordinary alumni base to bring leaders and experts for book talks, panels, and small group ask-me-anything fireside chats. We are planning a full day of leadership education and inspirational keynote speakers in the fall. Whether one was to pursue a career in law or career in business or other non-legal profession, all of these offerings will prepare students to be thoughtful advocates, managers, colleagues, and leaders.