When someone asked Sir Laurence Olivier what makes a great actor, he responded, “The humility to prepare and the confidence to pull it off.” This is the paradox of teaching for me: being humble enough to work hard at designing a potentially great class, and believing in my abilities so that I can turn that potential into reality.

To illuminate this paradox, I’m going to share my journey as a student and observer of teachers. Let’s start with some of the first lessons I learned.

On Becoming a Risk-Taking Teacher

I was enthralled with Mr. Walter Stickel and Mr. Ray Snively, my seventh-and eighth-grade teachers at Hosford Elementary School in southeast Portland, Oregon. They always wore nice suits and white shirts, and they smelled as if they had just smoked cigarettes. I loved the smell. I loved how they told stories. When Mr. Snively told a story about the Revolutionary War, I remember holding my breath with excitement. In high school, Mr. Jack Dunn and Miss Roberts could hold my attention for hours (or so it seemed).

I became aware of the huge difference between great and terrible teachers—how I resented the latter and worshipped the former. When I went to college, I had a number of inspirational teachers. I wondered why Stephen Covey could hold my attention in Organizational Behavior 321. I focused as much on his teaching approach—how he told stories, how he paused, how he lowered his voice, how he asked questions in large lecture halls—as I did on his content. It wasn’t just what he said, which was great, but how he said it, which was even greater. When Covey spoke, I felt this deep connection with myself. It was as if time stood still. Not to become overly spiritual about it, but it felt like someone was filling my soul with the purest nourishment in existence. As you might imagine, I was thrilled when I became Covey’s teaching assistant as a graduate student for the next two years.

I became a close observer of his and other teachers’ classroom styles. I was amazed by how teachers differed—how some could anger students by disdainful, disapproving looks while others could bring a classroom to tears by the way they told a story that in lesser teachers might come across as mundane. After my doctoral work at Purdue University and an appointment as a visiting scholar at MIT, I began looking for university teaching jobs. Brigham Young University (BYU) had a compelling draw, given that I knew the school, I had relatives nearby, and my wife wanted to establish her practice in the area as a marriage and family therapist. Most important, I didn’t like the other offers I had received from other universities. I ended up signing on to teach in BYU’s School of Education rather than their Business School (since the Business School wasn’t interested in hiring me). This was the beginning of a pattern—of taking big risks and then hunkering down and making those risks pay off—that would become increasingly apparent over time. Those risks in hindsight don’t seem like big leaps. But they were.

Driven to Self-Analysis and Risk

I left my master’s degree program early to pursue my doctorate. My wife and I drove a U-Haul truck across the country before I had been accepted into my preferred graduate program. I convinced myself that if I demonstrated my commitment by the long drive without formal acceptance, the admissions committee at Purdue would recognize and reward my resolve. We had no way of making money, no jobs waiting for us, and no friends sitting by the hearth counting the minutes until we arrived. Still, we drove. And I was accepted.

I went to Purdue University because there I could study both organizational behavior and family therapy. I didn’t take the typical path to obtain my doctorate—another risk—which resulted in a mixed degree of sorts. When I accepted a postdoc appointment at MIT’s Sloan School, I was one of the only postdocs in the program. Once again, I was studying on the margin of a program.

And why did I continue to get more education? Because I operated under the assumption that if I obtained one more degree, I would feel more competent, more settled internally. Yet after achieving each rung on the educational ladder—and later, each rung on the professional one—I felt strangely anxious. I wasn’t prepared to get on a professional track, settle in a community, and raise a family. But I never felt like I had a choice—I acted, took risks, and agonized about them reflexively. As we’ll explore in more detail in the next chapter, this was my pattern: to act, to risk, and to agonize about it.

BYU’s School of Education followed. One friend told me I had sabotaged my own career by joining a university that wasn’t considered among the elite. As a newly minted assistant professor, I was self-conscious about working under the aegis of a college with relatively little prestige (compared with the Ivys, for instance). I was defensive. I didn’t want to look people in the eye when I told them where I worked.

From my first day on the faculty at BYU, I wondered if I could not only pull off being a professor but carry out all the roles I felt needed to be accomplished simultaneously—a father of two, a good partner, and an active church member. There were also all my worries—about the retirement and care of my parents, about my oldest brother having a near-death experience hang gliding. It all felt like too much. I remember the first morning of my first class that met the day after Labor Day, 1979. I was so anxious that I thought I was having a panic attack. I ran to the restroom and washed my face and breathed deeply, trying to calm myself. Two students asked me if I was OK. I lied and told them I would be fine. Within fifteen minutes, I wandered back into my office, picked up my manila folder, and headed to the classroom, half-hoping no one would show up. I clung to the short-term goal of making it through the day.

What I feared most was running into former professors at the Business School who I was sure were disappointed that I had come back to BYU after attending the school for a master’s degree in organizational behavior. I did whatever I could to walk away from their Marriott School of Management. When I did see those former professors—Paul Thompson, Gene Dalton, and Bill Dyer—I was ashamed. There was nothing ever said to me, nor do I know that any of them were embarrassed that I hadn’t secured a more prestigious job. But I felt it internally. I would go home and be quiet throughout the evening and ruminate about where I had gone wrong and why I had returned to BYU. My mind was filled with self-critical thoughts.

But the actual work of being a professor suited me. Even though I was a new professor, I realized I could hold students’ attention. I could tell good stories. I could learn names easily and use them in the classroom to establish connections with students. At the same time, I also was aware of my flaws as a teacher. I didn’t ask good follow-up questions. Connecting abstract ideas in front of the class was difficult for me. My board work was often disorganized.

As you probably have noticed, I was a fierce observer of myself. Outside of class, I noticed that my one-on-one skills counseling students seemed to work. Students usually trusted me immediately. I also observed how my moods changed before teaching and after class was finished. My family was trying to figure out how to deal with these mood swings, not knowing whether I would be exhilarated or depressed based on how class went that day.

I was more obsessed about teaching—about how I affected my students and how they affected me—than were any of my colleagues. I understood very quickly that my obsession had to do with wanting to be the best teacher at the school.

Robert Kegan at the Harvard Graduate School of Education discovered that some individuals remain in what he calls the “interpersonal stage.” This stage is defined by activities and actions that are based on how much you please others and define yourself based on how many people you convince of your competence. Life is about accomplishing more tasks than others accomplish. It’s about selling others on yourself through your myriad activities. The more tasks you cross off your to-do list, the better person you become.

I related well to this interpersonal stage. It was one of many frameworks that helped me start to make sense of who I was. With hindsight, I became more aware of why I behaved the way I did and taught the way I taught. Let’s look back on my journey from West to East, from BYU to Harvard, and my search for a leader who inspired me.

Go East, Young Man

While serving as Brigham Young University’s associate dean of Undergraduate Education, I received a call from the associate dean at Harvard Business School asking me if I would be interested in filling in for a professor to teach the second-year Organizational Behavior course Self-Assessment and Career Development.

I received the call while on a motorcycle trip in southern Utah. We had just pulled into the Bryce Canyon Lodge; my wife and I had taken the trip with my parents, who were almost seventy and riding on my father’s Harley. My anxiety level was high—I was concerned about my parents’ welfare as they navigated the roads leading to Bryce. When we reached our destination that evening, I was relieved we had made it in one piece. That relief lasted until I called home and received a message to get in touch with Harvard’s dean Tom Piper in Boston. When he extended the invitation to teach, I thought immediately that someone was playing a joke on me. When it sank in that it was no joke, I told Tom I would call him back in a few days. From that moment on, my stomach started churning and I couldn’t sleep. Should I take this risk? I had never taught using Harvard’s case method. I didn’t know the material. But people at Harvard had been aware of my research on career theory. I had gained a measure of academic notice through my validating of Edgar Schein’s career anchors theory: that each person possesses an anchor consisting of values, motives, and self-perceived talents, and through career experiences refines what is considered important. My research focused on creating a psychometric instrument that identified career anchors.

Harvard was willing to take a chance on me because of what I had accomplished in this area. I figured if they were willing to take a risk on me, I should be willing to take a similar risk on them.

Four months later, after I received permission from BYU to take a leave of absence for a year, our nine-year-old daughter, Sara, and I headed east from Provo, Utah, in our 1977 Buick station wagon pulling a trailer carrying my Harley Davidson. My wife and two other daughters would fly and meet us a bit later in Boston.

From the very beginning, I had doubts. What made me believe I could teach at a school that attracted the best professors in the world? On January 4, when classes began, I hadn’t slept in two days. I had been sick to my stomach throughout most of the holidays.

What will happen if I fail at this? What if I embarrass myself in front of these very smart students? How can I face my colleagues back home if I return a failure? I couldn’t shut off the internal noise. When I walked into that first class on a Monday morning, the room was half full; students could shop classes for the first two days. A couple of students got up during my introduction to the course and left the room. Was I losing the class? What had I done to offend? Was I really that boring? What will I do or say if students begin jumping overboard?

I finished the first class. The students filed out. During the fifteen-minute break between this class and my second one, students began trickling into the room. And then a few more. A second-year student introduced himself and asked if he could add the course. Then another. As I began the second class, not only were all the seats taken, but students were sitting in the aisles. No one left the class. More entered. When the class ended, I walked slowly to my office in 435 Baker Library, closed the door, and sobbed with relief.

I knew I could do it. I knew there was hope. Though the self-doubt continues off and on to this day, I realized in that moment thirty years ago that I could stare down fear and win. The process had been agonizing, but I knew the fear could be put back in the bottle.

I sobbed a second time after the year was completed, and we packed up to head back out West. I had survived and thrived in my year of living dangerously. Nothing would ever be the same again.

Returning to the West, I remained there for five more years. But it might have been forever if not for a chance meeting on a plane from Salt Lake City to New York. I was practicing a speech I was scheduled to give when the person sitting next to me asked me to speak up. He introduced himself as John Mack, newly appointed president of Morgan Stanley. One year later, our family moved to New York.

It was a bold decision—leaving a secure academic position for a post in a field and a corporation for which I had little experience or training. Was I nuts? I didn’t know the difference between JP Morgan, Morgan Guarantee, Morgan Stanley, and Stanley Morgan (a receiver for the New England Patriots). I was giving up a deanship, a church community in which I felt valued and accepted, close friends, my family (my father had just passed away and my mother was living nearby), and a reputation as a great teacher. I was leaving the Teaching and Learning Center I had cofounded at BYU, which was involved in the training of faculty and graduate students. I was leaving the prestigious university promotion committee. I was leaving a perfect setting located at the base of the Wasatch Mountains. I was leaving the best motorcycle country in the world. I was leaving access to southern Utah, where my father’s roots ran deep.

But I left because I had faith in John Mack, because he felt like a leader. He could teach me about culture and motivation and commitment. So I took a leap of faith to Wall Street with little to no experience in the world of financial services. I realized soon enough that I was just like Dorothy in The Wizard of Oz when she looked around at her new surroundings and said, “Toto, I have a feeling we’re not in Kansas anymore.” I was no longer in the shadows of the Rockies, nestled at the base of Rock Canyon.

I’ve Come Home

The first day I walked on the trading floor, located at 1221 Avenue of the Americas, I felt like I was home. The characters who occupied this cavernous trading space moved with bravado laced with anxiety. I had never worked with people who were so revved up. David McClelland, in his lengthy and powerful research on motivation, described people who were obsessed with achieving, with accomplishing tasks. At Morgan Stanley, the people were focused myopically on nailing ambitious objectives.

With my academic perspective, Morgan Stanley became a lab to study professionals who had self-selected a work environment in which everyone was a high-need-for-achievement clone. This population informed my interest in and passion for understanding this personality type. Of course, I’d been studying this individual every time I looked in the mirror. Driven, smart, impatient, successful, autonomous, overscheduled, and committed were words that described me, too. From intensely personal experience, I knew this type couldn’t achieve all the agenda items on his list of responsibilities and action items. I knew that when this personality type felt overwhelmed, guilt (over things left undone) was an emotional reflex. This individual always came up short, no matter how much he tried. There was never enough time. Ever.

And having arrived at Morgan Stanley and witnessing employees all around me striving to achieve stretch goals and outdo the other person, I saw I was with kindred spirits. Home sweet home. Or so I thought until I realized what I had gotten myself into.

Failing to Fit

Why do I continue to place myself in situations that test my mettle? Because I relish challenges—even challenges that are difficult or impossible to meet. Morgan Stanley tested me every day. Could I have ten tough conversations daily during a rough week? Could I fire dozens of people? Could I manage hundreds of talent management experts around the world 24/7? Could I be a compass of sorts for John Mack, one of the most dynamic, intriguing, gifted motivators I’d ever met? Could I push back with him and other senior professionals who saw me as a competent social scientist but not “one of the boys”? Could I nurture and support my wife and kids as they suffered through the transition to a new place and a very different environment?

I thought I’d be better at being a manager than I was. I assumed I would learn over time not to take slights to heart and would be able to brush them off. But I couldn’t. John would say, “Just look at it as a game. You can’t take this stuff so personally.” But I did.

Observing John, I realized that the best leaders also possess qualities that make great teachers. John worked with me; he listened to me the way top teachers engage with their students. I don’t think I’ve ever met anyone who listened as well as John Mack did. I felt completely understood. There were moments he would be frustrated with me. There were times I wasn’t sure I could trust him. But just as I had faith in him, he had faith in me.

Like the best teachers, John was able to compartmentalize and focus on the task at hand. Unlike some leaders, he didn’t just talk at you. Instead, he concentrated intently, asking good questions and making comments appropriate to your concerns. He made you feel like the most important person in the company, the same way some teachers make each student feel like he or she is the most important one in the classroom.

As a teacher, I always want to make students feel psychologically safe. John has the same effect on his people, and they were encouraged to take reasonable risks without fear of making mistakes.

In fact, John modeled this behavior and took a chance with me. I had made my preference known early on: an office next to John so that I would have some referent power, given that I wasn’t a banker. Soon I had a target on my back. Other senior leaders were jealous of John and my relationship. Most were intimidated by John, and they didn’t like that this new naïve guy, an outsider no less, had John’s ear.

I felt I was disappointing a boss I revered and sometimes feared. It seemed as if I had swung for the fences and come up short. When John and Phil Purcell, former CEO of Dean Witter, announced that the two entities were merging, I knew I had to leave. I didn’t believe in the merger. I didn’t believe in my own abilities. I didn’t believe in Phil Purcell. I couldn’t understand how John could believe in him. How had he and I lost our moorings in such different ways?

Being Open to the Mysteries of Chance

Earlier that year, Kim Clark, dean of Harvard Business School, had been visiting Morgan Stanley offices to meet with our chairman, Richard Fisher, who was a noted alum of Harvard Business School. Kim had been a friend of mine through our church affiliation. We ran into one another in the hallway on the thirty-ninth floor of 1585 Broadway, headquarters of Morgan Stanley. We spoke for two minutes. He asked me to give him a call in the next few days. From the minute he asked me to call, I couldn’t think of anything else. I lay awake at night wondering what he wanted to talk about. I fantasized that Kim would be my way out. I found myself breaking my cardinal rule of never running from or to something. I was imagining doing both.

When I called Kim two days later, I flashed back to the moment I phoned Sally Iverson, the first girl I fell for as a freshman in high school. I had dry mouth. I was sweating through my shirt. I knew Kim. I trusted him. Why was I regressing back to old feelings of not measuring up? Of being rejected? When Kim and I connected, he mentioned that the Business School was experimenting with bringing practitioners in to help connect the faculty with the real world. We would be expected to teach a full load, write cases, and bring intellectual capital to the game. He asked me if I would be interested. I would need to interview with members of the Organizational Behavior (OB) Department; they would determine if they wanted me to join their group for a trial run.

I spent a day in Boston interviewing. From the lack of universal enthusiasm during the interviews, I could sense that not everyone was keen on the idea of bringing me in as a practitioner professor. As I was heading off campus to grab a taxi and go back to New York, I bumped into Len Schlesinger, an old friend and head of the service management area. When he heard why I was on campus and I explained my OB Department interviews, he asked if I would be interested in teaching in his group. I knew little about the field of service management, but didn’t dismiss his suggestion out of hand. A few days later, I heard from the OB group that they didn’t see a fit. They had a number of faculty who were researching careers, and there was too much overlap with other faculty. The next day, Len called to see if I’d come up to Boston and interview with his group. I did. And we clicked.

Kim Clark and Len Schlesinger were two excellent leaders, and I observed them in action. They both had clear goals and enthusiasm for the school—the faculty and students. Len Schlesinger would try anything, believing anything was possible. I was amazed, and continue to be amazed, at his lack of self-doubt. Kim was dean for eighteen months, and he told me that he was having a great time being dean. He could have been speaking Chinese. I couldn’t fathom how anyone could thrive and love having so much responsibility. Len felt like he could be the president of the university and do it comfortably. I was in awe. I was also experiencing those old feelings of inadequacy during this transition. Why was I so filled with self-doubt? Five months later I joined the faculty, commuting from New York.

Office Assignments and the Case Method

The cards and letters and phone calls kept pouring in from friends and family far and near, expressing excitement about my appointment to the faculty of Harvard Business School. During the winter, I had been sitting in on classes in Boston. I watched Jim Cash, Gary Loveman, Linda Hill, Jeffrey Rayport, Len Schlesinger, Jim Heskett. After every class, I noted what I learned from each teacher. And with every learning came more fear and self-doubt. Each teacher possessed a strength that eluded me. Loveman had command of the class; he didn’t even need notes to teach—he was so strong he could just rely on his brain. Len brought enthusiasm and support and positive confrontation. Rayport pulled concepts out of thin air and synthesized the student responses magically. I watched and perseverated. And I wouldn’t teach until the fall, five months away. I had plenty of time to nurture my fear. But I realized that observing others was a key strategy in figuring out our own teaching style. While sitting in on others’ classes took time, and at times made me uncomfortable, I knew that this comparative processing of how the case method was done by others would give me more courage to try other approaches.

Let me describe Harvard’s case method here and explain how it affected my teaching. As its name implies, the case method involves teaching through stories and narratives. Typically, instructors use the Socratic Method to help students think about the managerial challenges the cases present and respond to them. The Socratic Method consists of the teacher asking a question to a student, having the student reply, followed by a subsequent question. The design of the teaching plan basically follows this question and response sequence. The method consists of asking questions to students, followed by a response from the students, followed by another question from the professor. Guided by teachers, students create solutions to case-related problems. At other universities as well as in high schools and other educational settings, teachers use variations on the case method (though they may not refer to it as the case method). Stories are a universal method to convey knowledge.

The case method has had an effect on my class preparation. My preclass focus on tone of voice, for instance, became crucial to my teaching, because the case method relies on stories and metaphor to pull the students into problem situations that need to be solved. As for any good storyteller, how you begin your story is critical.

I learned that at Harvard Business School, we would tell our stories in front of a semicircle of eighty students—it’s referred to as “teaching in the pit”—and facilitate discussions about the case. The first part of a class is typically about “sense making.” What’s the case about, what’s the analysis, who are the players? The second part of the class is about “choice making.” Given the information we’ve discussed, what should we do? What are the actions or nonactions that would make sense for this situation? The discussion throughout the eighty-minute time period is a give and take between the teacher and students, and between the students and each other.

It took me a while to develop this particular approach to case method teaching, but watching other faculty members use it was instructive, as was my proximity to so many masters of the method.

David Garvin, a gifted professor at the Business School, had the ability to organize his thinking in a way that was precise, clear, and straightforward. His blackboards were well thought out, and he had perfect handwriting. David spoke slowly and enunciated every word. He was in no hurry. He mesmerized me with the way he constructed his sentences and his clear, methodological approach to his teaching style. Observing him was frightening because of his ability, but it soon became exhilarating. At first, I reminded myself that “I will never be able to do what he does.” Yet his love for teaching was apparent, and it relaxed me so that I could pay attention to every nuance of his teaching.

When I walked to my new office, I noted that one adjacent office belonged to an internationally known Organizational Behavior faculty member. Michael Tushman was recognized for his innovative approaches to research in organizations. He wrote books and journal articles. And he wrote a lot. Later, when I visited his home, I couldn’t help but notice that his house was perfectly decorated. The perfect residence for the perfect professor. Of course, I hadn’t written in the field for years. No books, no articles, no cases. What was I doing next to Mike? Seeing his office unoccupied during my first few days there, I asked his assistant if he was traveling that week. I was informed that he was at his summer home. One more reason to hate him. How would I be able to walk by his office and not feel inferior, not compare, not get overwhelmed with the road ahead?

The good news? The occupant of the office on the other side made me forget about my jealousy of Michael. Bob Merton won the Nobel Prize at age forty-six, having discovered with his colleagues the financial trading model called Black-Scholes. Bob dressed very well, cared about appearance, drove a Jaguar, and loved playing poker. He was naturally quiet, funny, and gracious. Most important to me, he was brilliant.

Sandwiched between Mike and Bob, I couldn’t get to my office without being reminded that I had come up short in my life and career. Bob was writing papers I could barely decipher. He had noted scientists and scholars visiting daily. I spent my time making sure my pencils were sharpened and that I had plenty of my favorite pens in both black and dark blue ink. I fluctuated between hiding in my office after duct-taping the door shut when I knew Mike and Bob were in the office and leaving it wide open so that someone would stop by and welcome me to the fold. It was a bimodal approach. Bob, Mike, and I were all the same age. Both of them were teaching in executive education courses, while I would focus on a second-year elective course centered on understanding leadership in the context of professional service firms. I knew they would have large audiences.

From my earlier experience teaching at the school, I was aware that I would need to earn a reputation and generate student interest through my own devices. I had no reputation as a teacher. I would be competing with Michael Porter, Rosabeth Moss Kanter, and Clay Christensen. More importantly, I would be competing with my own internal narrative of self-doubt, my belief I may not succeed.

It struck me that the first class would make or break me. The students could come and go during class and assess whether or not they wanted to spend a semester with me as the teacher. Would I be able to remember Laurence Olivier and how he defined great acting? Would his definition empower or cripple me? How would I be able to summon my best self to show up for the first day of class?

No doubt, most teachers in new and challenging situations pose these types of anxious questions to themselves. What I was to learn is that these questions reflect particular patterns—patterns that may provide insights for teachers and leaders.