On Teaching Leadership

M. Todd Henderson

Our school is embarking on a new experiment in legal education—introducing “leadership” as a significant component of our pedagogical approach. The change will not be a radical one, but will start by giving our students information about and opportunities to practice leading others. My objective in this essay is not to describe these new programs—they are discussed elsewhere in this issue—but rather to question the premise that teaching leadership is something law schools like ours should do. After all, a good Chicagoan should not just follow the latest fad or undertake an effort because it seems like a good idea—we demand our students support their claims with well-reasoned argument and analytical rigor, and we should expect the same from ourselves.

There are several reasons to believe we should not be in the business of teaching leadership, and I admit that was my initial reaction upon hearing about our new ambition. On reflection, however, I’ve come around to believe that there are things we can do at the Law School to improve our students’ chances to make a positive impact on the world as leaders. What follows is an account of the journey I took from skeptic to supporter of our new leadership program. Some significant skepticism remains, but I think it will help ensure our efforts meet our high ambition for everything we do.

The Case for Pessimism

There is no doubting that lawyers are leaders in every area of our society. Our graduates lead law firms, government agencies, universities, businesses of all shapes and sizes, and countless other organizations. Given that this happened without any concerted effort to train them as such, it seems inevitable that we will continue to produce leaders. If that is the case, it may make sense to provide some leadership training, especially if we can do so effectively and efficiently relative to the other places in which our students can obtain these skills. But there are many reasons to doubt teaching leadership at the Law School is a good idea.

First, law professors don’t generally have much experience as leaders. We work almost exclusively by ourselves and manage at most a few research assistants. Deans are leaders, but the typical law school is governed more by committee than a single individual. Deans obviously provide some leadership, but it is foreign and hidden not only to alumni and the outside world but even largely to faculty. My practical experience leading anyone during my eight years on the Chicago faculty is zero. We can hope that if push came to musket fire, there is a leader in each of us, but I’m fairly certain sitting in his Bowdoin office even Joshua Chamberlain couldn’t have imagined what he was capable of on Little Round Top.

Second, law professors don’t think much about leadership. Many law professors, myself included, think about leaders —presidents and CEOs, for instance—but when we do, we are generally more interested in external constraints, like laws or incentives, than internal factors that make great leaders. This is natural, since law professors are generally interested in law, and law is about the rules and forces operating on leaders, rather than what makes them leaders or what distinguishes good ones from bad ones. We teach the rules of the milieu in which leaders of all kinds operate, but we generally don’t teach the nuts and bolts of what it takes to be a competent leader of others.

For instance, I’ve written widely on the subject of executive compensation, a field interested primarily in the question of how to use contracts to get the most out of CEOs from the shareholders’ perspective. It is a field almost entirely about leadership. But the papers in this area assume CEOs are an undifferentiated group. Modern legal scholarship in this area, as in the political context, takes leadership skill as an exogenous, random variable, and assumes that good leaders will thrive and bad ones fail in any particular context. Leadership is therefore thought to be something we need not concern ourselves with. This may make sense when trying to identify the differential impact a particular compensation practice can have on the average CEO, but it leaves open large questions about how incentives and leadership interact.

Third, the legal literature is empty on the topic. Our faculty, the most productive in the world by far, produces several hundred articles in top law journals per year, none of which are on the subject of leadership. Although as a faculty we do not write about everything we teach, overlap is desirable since research informs instruction. A more general search of the Westlaw database reveals nothing interesting on the subject. The pages of America’s top law reviews are filled with research about every conceivable subject from agency politics to queer theory, but I found them barren on leadership, despite the fact that it is perhaps the most important subject in a range of private and public law fields. Without a literature to draw upon, a teacher is lost.

But perhaps there are lessons in the broader social sciences literature that could be valuable to our efforts. As it happens, Dean Schill asked me to write this essay when I was visiting my parents’ home in North Carolina. My father went to West Point, served during the Vietnam War, and eventually commanded a company of troops in the Ordinance Corps. After the army, he worked for decades in managerial positions at a large corporation, making him the consummate Company Man of the second half of the twentieth century. His office is stuffed with books, and given this experience as a leader, I figured he must have read some on the subject. So I went in search of some wisdom on leadership.

I found many books on “leadership,” written in every decade of the second half of the twentieth century. He had read to learn something about leading others. There were books written by generals, basketball coaches, CEOs, presidents, ancient Greeks, life coaches, religious leaders, and what seems like an endless parade of hucksters and charlatans. (A search for “leadership” in the Amazon book section yields nearly 95,000 hits! Apparently my dad is not alone in a search for the magical formula on how to be a good leader.) Over the course of my vacation, I devoured many of them. To call them undernourished theoretically, empirically, and otherwise would be overly generous. John C. Maxwell, who Amazon.com tells me is a “leadership expert” who has sold nearly 20 million books, is an example. Maxwell’s book The Irrefutable 21 Laws of Leadership: Follow Them and People Will Follow You includes the following rules of leadership:

  • Rule IV. The Law of Navigation: Anyone can steer the ship, but it takes a leader to chart the course;
  • Rule XVI. The Law of the Big Mo: Momentum is a leader’s best friend; and
  • Rule XVII. The Law of Priorities: Leaders understand that activity is not necessarily accomplishment.

Sadly, this is a leading text in the field. Other research is no better. One study I found looked at whether performance at West Point by Civil War generals predicted their success in the field. Looking at 32 generals who served during the war on both sides, the author concluded that there was no correlation with their importance ranking by an expert and their class rank at West Point. Even for a casual empiricist, the methodology is quite weak. My conclusion from reading my dad’s library was that the general literature on leadership, although voluminous, is fairly vacuous.

Fourth, there is some question as to what exactly “leadership” is, as distinct from, say, management or charisma. Without a clear view of what it is, it cannot possibly be taught. Management guru Peter Drucker takes a stab at a definition, claiming in his classic 1954 book The Practice of Management that leadership is “the lifting of a man’s vision to higher sights, the raising of a man’s performance to a higher standard, and the building of a man’s personality beyond its normal limitations.” He continues that leadership is not about “making friends and influencing people” but rather inspiration at a deeper level. Leadership is also not simply about optimization. Leadership is about vision; management is about efficiency. Although this is something, it isn’t much. I’m not sure with this definition I could go about constructing any course on leadership. When you think of great leaders, at every level of society, it is probably hard for you to tease apart leadership from charisma, sales, and even demagoguery. I know I do a poor job of it. “I know it when I see it,” is probably not enough here, and may in fact lead us astray.

If true, this leaves a would-be teacher with a problem. To teach something, one needs to define it, categorize its various forms, and articulate its key features, as well as be able to give practical advice for how best to develop and apply it. Based on my experience and the books I read on the subject, I’m quite skeptical there is anything approaching a science of leadership. There are just anecdotes in search of a theory.

Fifth, there is a widely held view that leadership cannot be taught. We could sum this view up with the aphorism that leaders are born, not made. Drucker held this view quite strongly, devoting a scant three pages to the subject of leadership in his most famous work on management. Drucker concluded that while “[t]here is no substitute for leadership … management cannot create leaders.” This school of thought has many adherents.

This view strikes a chord with my experience. On the playgrounds of suburban Pittsburgh, at Princeton, in ROTC, and at Kirkland & Ellis and McKinsey, the best leaders I saw were not coached or schooled in the art. Reflecting on leaders in all these phases of my life while preparing this essay, I could not identify any particular traits or characteristics these leaders shared—some were tall, some were book smart, some were handsome, some were the best athlete on the field, and some were first-born children. But many were none of these things.

To make this only slightly more rigorous, my research assistant, second-year student Lior Geft, and I collected biographical data on the managing partners of the 100 largest law firms in the United States. As expected, indicia of academic success, such as law review and judicial clerkships, do not predict leadership potential. Some law firm leaders went to top 10 colleges, but most (70 percent) did not. Some were on law review, but most (65 percent) were not. Some were near the top of their class, but most (70 percent) were not. Few were judicial clerks (only 20 percent), while less than 5 percent clerked on the Supreme Court. If one had to predict based on their resumes who would and who would not be a law firm leader, it would be mere guesswork.

One might argue that there are institutions that routinely produce great leaders. The military academies, General Electric, Harvard Business School, and others would certainly make this claim. Their claim is not inconsistent with the born-not-made view, however, because of a phenomenon economists call “selection bias.” West Point may in fact produce superior leaders not because of anything it does but because it attracts those with natural leadership talent. The same may be true of businesses and other institutions that “produce” leaders. If true, a focus on trying to teach leadership may be a wasted effort.

In sum, the case against adding leadership to the curriculum is strong. The faculty does not have the experience or the literature to draw upon, and it is not entirely clear what exactly leadership is or whether it can be taught. But there were things in my father’s library and in my own experience that make me have hope for the modest but important steps the Law School is undertaking.

The Case for Optimism

Although I came to this question with a strong prior belief that teaching leadership is unwise, there are nevertheless reasons to believe our new ambition is a wise one. Perhaps the best case for making teaching leadership part of our mission is the fact that these skills seem to be increasingly important as part of hiring and promotion decisions at the firms who employ our graduates. Our goal at the Law School is to give our students every possible skill they need to give to themselves the best possible chance at success. We hear that leadership skills are something our students need to achieve their full potential. If the market demands that we teach particular skills, it is our job to provide them. And, as noted below, there are skills we can provide.

In addition, our students may be particularly in need of lessons in leadership compared with competitors at peer schools. Writing in the introduction to David M. Dorsen’s excellent biography of Judge Henry Friendly, our own Judge Richard Posner noted (about Friendly) that “brilliant people sometimes have great difficulty making productive use of other people.” Not only are our students brilliant, but we tend to attract students interested in the most intense academic environment. The self-selection effect is therefore perhaps opposite of that at West Point—we may naturally attract more solitary types, thus complicating our mission.

We can do more to attract natural leaders. A possible and simple thing we can do is to give graduates leadership opportunities that others do not have. This is easy for West Point, but less so for Chicago: our graduates don’t get silver bars and legally enforceable command of tank platoons when they graduate. But there are other possibilities for educational institutions. Public interest jobs generally give students opportunities to lead that law firms do not initially, and subsidizing these positions can be thought of as a form of leadership training. This could be achieved through scholarships, enhanced clinical opportunities, or externships. We are making substantial investments in all of these areas and emphasizing putting our students in positions to demonstrate their leadership skills.

There is more we can do. Aspiring leaders do not sort solely based on opportunities, but also on rhetoric and culture. We can cultivate a culture that emphasizes leadership. Although “culture” is a squishy concept, there is some concreteness we may be able to hypothesize about. We have not generally talked a lot about leadership here at the Law School, and what we talk about is important. It signals to our students what we value and what we expect of them. We have not taught classes about it nor rewarded it when students demonstrate it, either curricularly or extra-curricularly. We have not gone out of our way to create opportunities for natural leaders to exercise their abilities or to help make these people aware of their latent skills. All of these things can be changed, and should be in my view. If we want to create leaders, we have to foster a culture that makes leadership salient. My sense is that West Point and GE have built not just a brand around leadership, but they also help bring the best leadership qualities out of everyone. This work is on the margin, meaning it is only incremental to the inherent talents of individuals. But this is true of all education, and if we want to make a difference, it is likely to be through these indirect means. Our LEAD program, as well as the Keystone program and the Business Leadership Program, are steps in this direction, as well. Simply announcing that we are interested in leadership will undoubtedly change the mix of students we attract, thus helping meet the market demand through sorting.

Aside from these sorting and branding efforts, my research and experience suggests there may be some aspects of leadership that can be taught, even by law professors. Let me give two examples.

First, there are simple but powerful lessons about leading others that are used by some businesses, but that we could incorporate into our educational programs. One of these is the Myers-Briggs Type Indicator (MBTI), based on the work of Carl Jung. The MBTI identifies individuals’ personality types based on answers to a series of simple questions. Individuals are identified as one of two types in each of four categories. (Mine was ENTP, for those who know the test.) Whether one believes the theory behind the test or not, one leadership takeaway I got obtains regardless. It is about the first characteristic, which is denoted “E” for some and “I” for others.

In any group or team setting, there are likely to be both types, since the population is roughly split between them. E’s, like me, tend to be outgoing, talkative, and quick to respond to questions; I’s, on the other hand, are quieter, more deliberative, and need time to think before answering. Before I knew this, I would have believed the quiet ones in a team problem-solving setting were lacking in ideas, indifferent, or worse. But once I learned about individuals’ hidden preferences, I adopted a completely different leadership approach. I’s need to be drawn out and to be given time and space to think; E’s need to be reigned in and directed so they do not overwhelm the team. This is a pretty basic idea of human equality and dignity, but our instincts have the potential to lead us astray in the absence of some important facts.

We are deploying the MBTI methodology, along with other ideas in our LEAD program. To what extent we incorporate the ideas into our program is an open question. The point of this anecdote was merely to convey the idea that there are some leadership lessons that can be taught. Second, while many of the books I read contain leadership lessons, they are often hard to distill or to put in a context that our students will appreciate. Law professors excel at helping students closely read texts and apply the texts to relevant policy issues. This is an area where we may be able to add some value relative to the next best alternative.

To illustrate, consider one of the books on leadership I pulled from my father’s library. The book Cyropaedia, or The Education of Cyrus, was written by Xenophon, who was a student of Socrates. It is a partially fictional account of the rule of the Persian king Cyrus the Great (reign 559–530 BC). It is a stirring history, even if it is not all true, and contains a profile of a very effective leader. It is regarded as probably the best book on leadership ever written. One comes away from it with a deep admiration of Cyrus, who stitched together an empire stretching from Istanbul to Almaty and earned widespread admiration among even conquered peoples. Cyrus was tolerant, curious, and reasonable. At crucial moments during his campaigns and governance, he faced problems of strategy, caring for his troops, motivation, palace intrigue, and balancing war and peace.

In sum, the lessons are significant, but reduced to quotes, they can come across as superficial as the Maxwellisms noted above. For instance, in one part of the book, Cyrus is discussing a coming war with his father. The way of leadership, his father tells him is “the way of sympathy; to rejoice with the happy in the day of good things, to share their sorrow when ill befalls them, to lend a hand in all their difficulties, to fear disaster for them, and guard against it by foresight.” Later in the account, Cyrus demonstrates this approach by showing tremendous empathy for his men and their condition. By knowing them well enough to appreciate their seemingly petty concerns, Cyrus won their loyalty and raised their performance to a higher standard. In the right setting, perhaps as part of a Greenberg seminar, we can contextualize these lessons to help our students better understand the world of law firms, business, and other leadership settings. For instance, I’ve seen the Cyrus approach practiced by lawyers to great effect. My favorite partner at Kirkland & Ellis stunned me by asking about and seeming to care about the details of my life—my family, my worries, my trivial cares and passions—when I was a lowly first-year associate. Whether or not he was sincere, I believe I worked harder for him than others because of this personal connection. To this day, he stands out as a role model for how to lead a team of lawyers.

This kind of soft skill is not something we emphasize, either formally or in our informal interactions with students or among the faculty. At the Law School, we take pride in emphasizing substance and getting right to the heart of the matter. (One of the two rules of our thrice-weekly faculty lunches, known as Roundtable, is “no small talk.”) But in doing so we may unnecessarily short change the value of personal connection that is a crucial component of leadership, whether it is of a platoon of soldiers or a team of lawyers. This is, to be sure, a tricky balance, and I’m worried that putting leadership first or even near the top of the list risks falling in the trap of teaching neither leadership nor substance. But the kind of change I’m imagining is not a pedagogical one as much as it is a dispositional one. Caring and empathy can happen and be demonstrated without sacrificing rigor. My sense of the content of the various programs discussed above suggests we are refining not revolutionizing our approach to education.

Another example stands out that can be translated from ancient Persia to the halls of Big Law. In another passage, Cyrus discusses the importance of leading by example: “if the campaign is in summer, the general must show himself greedy for his share of the sun and the heat, and in the winter for the cold and the frost, and in all labors for toil and fatigue.” Cyrus is depicted on the battlefield as leading from the front, sharing the worst work of his men, and not shying away from difficulties. Although lawyers do not generally need to pick up a javelin and shield, there is tough work to be done by lawyers and their teams. I spent plenty of nights as an associate pushing papers, double-checking documents, organizing files, and digging for precedents. Although associates rightfully pull the laboring oar on this work, I can say that from their position, seeing partners “greedy for [their] share of the sun and heat” has a positive effect on the morale of associates. I remember sitting side by side with senior partners sticking “sign here” labels to documents, double-checking court filings, and proofreading documents. These lessons of humility and self-sacrifice are important ones that can be communicated now at relatively low cost, rather than be learned on the job.

That said, it is difficult to describe why exactly Cyrus was a great leader, which was the point raised above about the difficulty in making a science of leadership. But perhaps the classics have wisdom, even if it is not something that we can reduce to a formula. One can imagine a “great books of leadership” component of a modern legal education. Requiring lawyers to read the life of Cyrus, of Winston Churchill, of Dwight Eisenhower, of Henry Ford, of Susan B. Anthony, of Martin Luther King, and other great leaders not only would signal to students that leadership matters but also may give them some insights on how to improve their own leadership skills.


After reading a dozen or so books on leadership, the Chicagoan in me was unimpressed. There is no science, there is no rigor, and there are many charlatans. In addition, the value of leadership instruction must be measured by its opportunity cost—what is the value of the thing it replaces—and by the relative efficiency of this faculty to deliver it.

But on reflection, it may be simply because I’m conditioned to reject any claims or theories that are not based on bulletproof analytical rigor. There is learning, however, this side of proof, and if we want to create the future leaders of our society, perhaps the easiest way to start is by telling the world this is our goal, by bringing leadership into our conversations, and by exposing our students to leadership in books and in practice. Our students master everything we ask them to, and I see no reason why leadership should be any different. Count me then as one who supports our leadership initiatives. I don’t expect us to be having students falling backwards into each others’ arms out on the Midway, but rather I anticipate a distinctly Chicago approach to teaching leadership. Lawyer as leader is a reality, and I’m confident there are things we can do to give our students help in deploying their incredible talents to helping improve the social condition.


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