CHAPTER FIVE

Masters and Apprentices

If you aspired to become a successful artist during the fifteenth-century Italian Renaissance, there was one skill you needed to master above all others: the ability to draw. But where could you go to learn this? Master’s of fine arts programs didn’t exist back then, and you couldn’t very well just hop online and watch instructional videos. What you could do was go to a master artist and work for him as an apprentice. If you were just a beginner, you would receive training from the ground up; if you were already fairly accomplished, you would hone your craft by assisting with the master’s commissioned artworks.

Budding artists tended to flock to one master in particular in Renaissance Italy, a man named Andrea del Verrocchio. Beginning in 1460, Verrocchio operated a workshop that produced a variety of media for wealthy patrons, including painted, sculpted, and cast-bronze works. But Verrocchio was especially famous for his drawings, most of all for his ability to render the intricacies of the draperies commonly found in Renaissance paintings.1

Scholar Gigetta Dalli Regoli noted that Verrocchio was able to “recognize among the youths of his time the gifted and the imaginative, and [was] quick to obtain their collaboration.”2 Projects like the Medici Tomb in the Basilica of San Lorenzo, Florence (circa 1473) were complicated to execute, but thanks to Verrocchio’s expertise in assembling a talented group of apprentices, he and his team could complete them with ease, and on a tight schedule.3 In Verrocchio’s hands, the master-apprentice relationship also served as an immensely powerful structure for imparting skills and knowledge. Researcher Liletta Fornasari has characterized Verrocchio’s workshop as a veritable “school of design,” with Verrocchio teaching his pupils the rules of perspective and encouraging them to practice drawing from life.4 Experiments with drapery formed “a special branch” of his teachings, and Verrocchio also made plaster casts of figures and body parts, such as hands and feet, for his assistants to study and sketch.5

Verrocchio’s workshop must have been an exciting place for young protégés to work and learn: it was in the forefront of artistic technologies, such as the chemical preparation of pigments, new ways to handle tools, and innovative metal-casting processes. Verrocchio’s efforts also allowed him to become a superboss of his day. The artists who passed through his workshop were some of the most recognized of Renaissance Italy, including Pietro Perugino, Sandro Botticelli, Domenico Ghirlandaio, and Francesco Botticini.6 Verrocchio even spawned one of the greatest artistic talents in the history of Western art: Leonardo da Vinci.

With all of Leonardo’s genius, it’s easy to forget that he was, at one time, just another young artist learning his craft. As Leonardo expert Jill Dunkerton noted, “Behind all of Leonardo’s innovations as a painter lies an approach to the first steps of making an under drawing on the panel surface that has its origins in his training in the Verrocchio workshop.”7 Leonardo began his apprenticeship with Verroccio at the age of fourteen. After some time, however, it became clear that his skill had eclipsed that of his master, and that his talent was, in fact, extraordinary. Secure in his own capabilities and stature, Verroccio continued to rely on Leonardo’s genius in his shop, all the while taking the opportunity to also learn from him and further his own skills.8 Leonardo eventually became a master himself and secured his own commissions, going on to become one of the most famous protégés any superboss has ever had.9

Given how successful apprenticeships such as Leonardo’s have been over centuries, you’d think they’d still be everywhere in developed economies. In some countries, such as Germany, apprenticeships are relatively common (although less so for managerial jobs).10 Elsewhere, though, on-the-job training has largely disappeared, replaced by formal education at universities and specialty schools. Young people just starting out learn through internships, while older employees receive ongoing training from their employers, usually via formalized and highly structured programs and online courses.

So much of how people learn in the workplace today, from 360-degree performance evaluations to mentoring to coaching, has become bureaucratized and impersonal—a far cry from the personal relationship of learning that existed between Verrocchio and a protégé such as Leonardo. In 2003, there were fewer than a half million structured apprenticeships in the United States; by 2013, cost cutting in organizations had brought that number to below three hundred thousand.11 Moreover, the best, most competent bosses today generally don’t prioritize engaging reports informally in an immersive learning experience. Aiming for more certainty and clarity in their organizations, they promulgate rules and establish bureaucracies that distance them from employees. They also choreograph their days to assure that work gets done, leaving very little unstructured time for instructing or coaching. They certainly don’t use the word apprentice very much. The very concept seems quaint, the product of a bygone age.

Close, direct, on-the-job training worked wonders for a genius like Leonardo—imagine what it would be like for mere mortals, with such modern jobs as marketing manager, attorney, and sales rep? In the absence of such a personal master-apprentice relationship, employees may learn technical basics, but they don’t necessarily learn the subtleties and nuances of their professions, nor do they learn critically important “softer” skills that matter in any industry, such as networking, giving and receiving feedback, negotiating, or leading. Up-and-coming managers might be able to come up with the “right” answer to a business problem on their own, but they’ll often need personal coaching to learn how to communicate that answer, convince bosses of its viability, and inspire colleagues and subordinates to help implement it. They may even need help understanding that having the right answer isn’t worth very much if you can’t bring other people with you. When highly educated managers start a job these days, their bosses almost always assume they already have everything they need to excel. Quite often they don’t.

Unlike many of their contemporaries, but very much like Verrocchio, superbosses embrace the apprenticeship model wholeheartedly as a way of doing business. When they hire, they know they are giving an employee a chance to learn a craft at their feet. Staying in the trenches with protégés and serving as something akin to a player-coach, superbosses use this informal manner of instruction not only to convey knowledge but also to exert a powerful, almost parental influence on their protégés.

Today, most good bosses spend time teaching and mentoring the employees who work for them. They keep lines of communications open, ask questions designed to impart wisdom, accompany employees on sales calls, visit them on the front lines, and offer valuable advice. Superbosses, however, take such laudable practices much further than even the typical “good” boss does, effectively raising the bar. By apprenticeship-style management, I’m talking about workplace relationships that are more sustained, all-encompassing, intense, and intimate than the best traditional corporate “mentorships.” Although the boundaries of these relationships may be unspoken or undefined, superbosses take much deeper personal responsibility for the growth and development of employees than conventionally good bosses do, and apprentices in turn expect far more in the way of attention and instruction than their counterparts at other organizations. And they receive this attention and instruction, often by working with superbosses on a daily basis. Of course, they don’t work only with superbosses; again, it’s not that rigid or formal. Leonardo da Vinci would hardly have been able to accomplish what he did if all his time was spent with Verrocchio. Like any apprentice, protégés of superbosses need time to interact with colleagues and to acquire know-how, but they also need time to be alone, practice what they’ve learned, and invent their own ways of doing things.

It’s worth noting that some superbosses don’t necessarily take pride in the role of “master.” Glorious Bastards like Larry Ellison, Jay Chiat, Michael Milken, or Bonnie Fuller tend to shoulder the responsibilities of the master opportunistically; they’re not touchy-feely types who care much about how apprentices “feel” along their career journeys. What they care about are results. But as it turns out, results are precisely what the apprenticeship approach delivers. You don’t have to be attuned to employees’ feelings to be a superboss and to embrace the apprenticeship model. Operating as masters, all three varieties of superbosses forge remarkable connections between themselves and the people who work for them. Staff members often come away learning far more than they may have from formal training alone. They perform far better, pushing the superboss’s business to new heights and furthering their own careers. Like Leonardo da Vinci, some even go on to produce dazzling “masterpieces” and to become recognized masters in their own right.

Managing in the Moment

It’s eight thirty in the morning and you’re sitting in your cube, starting the workday. You’re sipping coffee, checking emails, maybe taking a quick peek at what’s happening with friends and relatives on Facebook. Just as you open an unfinished presentation you’re slated to give tomorrow, you sense a presence hovering over you. Looking up, you’re shocked to find your company’s legendary CEO smiling at you and saying hello. Hundreds of people work at your company’s corporate headquarters; you’re just a midlevel manager. Yet here he is. He introduces himself and asks what you’re working on. When you tell him, he says, “I’d like to hear more. Are you busy now? Can you come up to my office for a chat?”

If you were starting your career at Kraft during the 1980s, you might have had an encounter such as this with Michael Miles, the company’s then president and COO, and later CEO. In his varying leadership roles, Miles brought Kraft into the modern era of food marketing, transforming the company’s image from an unhealthy, fatty foods purveyor into one focused on healthier offerings. Kraft introduced line extensions such as “light” Philadelphia Brand cream cheese and low-fat and fat-free salad dressings, cheese, and ice cream. Between 1986 and 1988 alone, Miles oversaw the introduction of some 350 new products.12 Growth on several of Kraft’s brands increased from 1 percent annually to about 4 percent.13 Miles also formed a venture group to look into acquisitions that would complement Kraft’s existing product line, eventually buying consumer favorites such as Lender’s Bagels and Tombstone Pizza. Miles didn’t do all of this alone, of course; he had an uncanny knack for nurturing top-flight marketing talent. His list of protégés reads like a who’s who of American consumer marketing, including the future CEOs of Mattel, Young & Rubicam, Gillette, Sears, Heinz, Hershey Foods, and Quaker Oats. Want more? Add Marks & Spencer, 3M, CVS, and Campbell Soup to the list.

When I interviewed Miles’s protégés, I discovered that one of his trade secrets was making himself unusually accessible to employees. As longtime Kraft employee John Tucker told me, Miles was a “walk-around manager”14 who took time to get to know people throughout the company. He made a point of having lunch with employees two or three rungs lower than him, and he did so in the cafeteria, where other employees could see. He kept his office door open so that anyone could just drop by to ask questions or talk strategy. And there were also those impromptu morning conversations with younger staff. When Miles first arrived at the company, he picked someone at random every morning, brought him up to his office, and spoke with him for about an hour. Don’t be mistaken, though, these were not casual chats about sports or the weather. “His questions were very direct, very pointed,” Tucker said. “It was like taking a final exam.”15

Tucker speaks from experience. He was serving as head of human resources for Kraft’s global manufacturing group when Miles asked him in for a morning talk. Tucker apparently did well, because three months later Miles called him up again, this time to offer a huge promotion, to senior vice president of human resources for all of Kraft, reporting directly to Miles. “My first meeting with Mike . . . was the basis on which he offered me the job,” Tucker recalled.16 It’s not every CEO who will spend an hour chatting with a low – or midlevel manager. But Tucker’s promotion was just the beginning of his contact with Miles. For years thereafter, the two would talk on a practically daily basis, and a full apprenticeship under Miles would blossom.

The most basic and critical set of practices underlying the apprenticeship model concerns simply being there with employees, getting to know them, and letting them in. You can’t develop a personal approach to training staff if you aren’t there in person (or, if necessary, via communications technology), day in and day out. Yet most bosses don’t do this—in fact, they don’t even come close. The CEOs appearing on the hit television show Undercover Boss are, sadly, not all that unusual. Imagine resorting to impersonating low-level employees to find out what’s really going on in your own company. These clueless, distanced bosses are the complete antithesis of the superboss. Whereas many businesses today focus on getting closer to the customer, superbosses are very much focused on getting closer to their employees or team members. In deploying an apprenticeship mind-set, superbosses like Michael Miles let their employees know that they’re always available to be consulted.

As Dr. Paul Batalden, a former VP at HCA and professor emeritus at the Geisel School of Medicine at Dartmouth College, told me, his superboss, Tommy Frist, was “such an unusual CEO of a Fortune 100 or whatever the size of the company was at that time. You could always get to see him. He always had time.”17 On some occasions, Frist, who was also a pilot, would even fly his protégés to events in other cities, letting them sit in the copilot’s seat and talking business with them. The world-renowned conducting teacher Jorma Panula would spend all day with his students, and then he would invite them to a restaurant to talk even more.18 “There’s one very important thing that Mr. Panula has,” protégé Juhani Poutanen related. “He has time.” The Philadelphia Inquirer’s Gene Roberts was known to stay up until two in the morning talking to staffers—at his home. John Carroll, who went on to run the Baltimore Sun and Los Angeles Times, recalled that when Roberts wanted him to take on a new project, “he couldn’t just call me into his office and say, ‘John, I’d like you to do this.’ No, you’d end up spending the whole damn evening with him.”19

In the corporate world, employees who seek to speak with their bosses normally attempt to “book time.” They might send an email to an assistant, and the resulting “meeting” occurs outside of the “actual work” being done. Such practices seem to bring bosses and employees closer together, but in reality they distance and control the degree of contact bosses have with staff. While today’s hyper-scheduled executives obviously need to control their time, we often forget about what we lose when we run from event to event—the casual, ongoing contact in the moment that is essential for learning, serendipity, and building meaningful relationships.

More than just making themselves available for meetings, superbosses are often in the thick of it with employees—not just for a half hour once a week, but regularly and informally. Superbosses often work side by side with protégés, coaching them in unmediated ways. Remember how George Lucas collaborated with Ben Burtt to invent the characteristic bleeps of R2D2’s language? He gave him space and he gave him freedom, but he also stepped in for direct and often unannounced intense one-on-one discussions.

When I interviewed hedge-fund mogul Julian Robertson, he took a quick call and decisively instructed one of his young protégés on how to handle a business situation. As I heard from Samuel Howard, chairman of Phoenix Holdings and Xantus Corporation, Tommy Frist also “worked as hard as anybody else. When you asked him to do something, he would roll up his sleeves.”20 Michael Milken got up bright and early at four thirty and wrote notes to every member of his team, probing decisions they’d made and asking for opinions on pending business matters.21 Norman Brinker’s former CFO reported that she’d see him in restaurants picking up a dishrag and bussing tables.22

Traditional managers often talk about the importance of coaching subordinates, but they don’t actually spend their time that way. That’s because managers today tend to view work relationships as strictly transactional to them: “I’m giving you a paycheck, and in exchange it’s your job to get your work done, not mine.” If there is coaching, it tends to come from specialists brought in for limited purposes, such as helping members of a team get along better or preparing a young executive for a senior role. What you likely won’t have is a boss who coaches you day in and day out, and views coaching as a fundamental part of her job.

Superbosses, on the other hand, invert the classic boss-subordinate relationship—not entirely, but significantly. Superbosses think about strategy and vision, as we’ve seen, but they also think about doing. To a surprising degree, they join employees in getting their hands dirty with actual work, modeling behavior and guiding employees in the process. They can do this, in the first instance, because they are extraordinary subject-matter experts with deep reservoirs of lessons to impart. It’s an important precondition for the apprenticeship model: You can’t be a master to an apprentice unless you truly have mastered your craft. Protégés, for their part, walk away impressed by and appreciative of this mastery. Jorma Panula had “X-ray vision for the technical side of conducting,” remarked Eivind Aadland, chief conductor and artistic leader of Trondheim Symphony Orchestra. “His knowledge is extremely, extremely big.”23 Sid Ganis related how after Steven Spielberg and George Lucas screened the first Indiana Jones movie, Raiders of the Lost Ark, Lucas gave Spielberg “three hours of notes on the movie.” To Ganis, “that describes who he was and how he was.”24 Walsh, Brinker, Lauren—all were revered by the protégés I interviewed for their knowledge of craft, not just leadership.

Ultimately, though, many superbosses make it a priority to work side by side with junior staff because they’re convinced it’s critical to the successful operation of their businesses. Thomas Keller, a successful superboss-chef whose restaurants include the renowned French Laundry and Per Se, spends time with sous-chefs because “that’s our next generation,” the people who will one day be running his kitchens. Keller feels this way, even though he knows that staff members might eventually work for someone else. As Keller noted, you never know if talented staff members will leave and then return years later. It’s worth the risk to take the time to work with them now.25

“West Coast” Companies

Look around your workplace. Do leaders enjoy special parking spots, cafeterias, bathrooms, offices, and the like? Why do many bosses think of executive perks as the reward leaders enjoy for “making it to the top”? To most superbosses, the usual perks, distinctions, and hierarchies are just not that meaningful. In fact, they’re counterproductive. Superbosses are so focused on engaging with their people that they disdain anything that might create physical or even emotional distance. They want person-to-person involvement that enables everyone to make stuff happen. If all it takes to connect with a superboss is a quick phone call or knock on the door, that’s because a disregard of hierarchy is not merely tolerated—it’s explicitly encouraged.

Robert Noyce, creator of the integrated circuit26 and a founder of Intel, influenced so many tech entrepreneurs that he became known as the Mayor of Silicon Valley.27 The company he helped found before Intel, Fairchild Semiconductor, spawned a family tree of hundreds of companies, including Raytheon Semiconductor; Kleiner, Perkins, Caufield & Byers; Advanced Micro Devices; and Intel itself. Charlie Sporck, Fairchild’s manufacturing guru who later became CEO of National Semiconductor, said it well: “It is no overstatement to say that Bob Noyce made what Silicon Valley is today.”28

At Fairchild, Noyce became known for his “West Coast” management style (not to be confused with Bill Walsh’s “West Coast offense”), which was much freer and more egalitarian than the formal, hierarchical, “East Coast” way of running a company. The West Coast style has since become associated with any number of hugely successful Silicon Valley companies, suggesting that although superbosses influence their industry by unleashing cohorts of superstar individuals, their impact is often far greater.

Noyce dispensed with hierarchy because it just didn’t make sense for an entrepreneurial business. Just over thirty years old at the time, Noyce was one of the oldest people at Fairchild. He hired engineers fresh out of college and graduate school because “experienced” people didn’t exist (sound familiar in today’s Silicon Valley?)—the transistor was too recent a technology. Noyce got new employees acquainted with Fairchild by thrusting them headlong into the heart of research and development, expecting them to learn on the job, side by side with him. Intensity, not privilege or seniority, defined the culture. Writer Tom Wolfe described in Esquire how “a young engineer would go to work at eight in the morning, work right through lunch, leave the plant at six thirty or seven, drive home, play with the baby for half an hour, have dinner with his wife, get in bed with her, give her a quick toss, then get up and leave her there in the dark and work at his desk for two or three hours on ‘a coupla things I had to bring home with me.’”29

On a more basic level, the trappings of titles and distinctions eluded Noyce; it just wasn’t what he was about. As Gordon Moore, cofounder of Fairchild and Intel, and a legend in his own right, told me, Noyce was “a very down-to-earth guy” with “a beat-up old car. One of his technicians hung a sign on it saying, ‘Please park this in the back. It’s giving us a bad reputation.’ . . . No pretensions at all.”30 In one illustrative story Moore told me, the CEO of Fairchild’s parent company came out to California to check on Fairchild Semiconductor. He arrived in a limousine driven by a uniformed chauffeur. Noyce was shocked at what appeared to him to be an unconscionable indulgence. How could the CEO enjoy himself all day long while the driver sat in the car the entire time doing nothing? It just didn’t make any sense. “Bob just could not imagine somebody sitting around all day doing nothing,” Moore said.31

When starting Intel with Moore, Noyce made a point to again create a “flat” structure, banishing bureaucracy. There were no executive suites or special parking spaces; stock options were standard for most office workers and all of the engineers. Intel’s workspace consisted of one large room divided into individual “offices” by low partitions, and everyone, including Noyce and Moore, worked under these conditions.32 Noyce and Moore didn’t want any employee to feel that anything stood in his or her way of advancing. At least while Intel was still small, every employee had access to Noyce and to Moore. Under this model, all questions could be asked and all ideas voiced. Staff meetings were not the domain of a few select managers—all employees could attend and share their thoughts.33

The rules of the game were similar at so many other superboss-run organizations I studied. At Kraft, Michael Miles shook up hierarchy by declaring one day that all parking would be on a first-come, first-served basis, with no special treatment for executives. John Griffin, one of Julian Robertson’s “tiger cubs,” described Robertson’s office as follows: “Imagine a room. . . . Julian was plop in the center. No door, no [individual offices], no private conversation . . . mostly everything was open.”34 Jay Chiat instituted an open office as well, with everyone sharing desks separated by low dividers.35 According to Stevan Alburty, a manager at Chiat/Day, Chiat “felt that ideas should come from everywhere . . . that ultimately people will not change until you change their physical space and force them to change. It was a radical idea and people felt threatened and terrified by losing the trappings of power.”36

Any resistance some managers and employees might put up doesn’t dissuade superbosses. Archie Norman is a superboss in the British supermarket industry whose many protégés have gone on to lead companies such as Boots, HBOS, Vendex, Levi Europe, Royal Mail, Halfords, Cable & Wireless, and Sainsbury’s. In 1991, Norman became CEO of the British supermarket chain Asda, where a stultifying bureaucracy had taken hold. Norman’s turnaround strategy combined cost cutting with a series of moves to eliminate all formality. Cubicles were torn down in favor of open offices, meetings were held standing up, name badges with titles were removed, letters to the CEO from the rank and file were encouraged (Norman received forty thousand letters in the first three and a half years), and store visits from executives that used to be about ceremony (think ribbon cutting and entourages) were recast as learning opportunities. Meanwhile, Norman cast a wide net for young talent to take on leadership jobs.37,38

Some superbosses I studied took the abolition of hierarchy and bureaucracy even further than Norman did; they seemed to harbor an almost visceral hatred for any bureaucratic elements that might obstruct, impede, or diminish casual interactions at work. Can you imagine life without the ubiquitous memo? Former employees of Chiat/Day can: Jay Chiat banned memos for an entire year, calling them a “corporate disease that people hid behind.”39 Gene Roberts banned staff meetings and formal speeches.

Although they might complain about bureaucracy, many bosses still retain formalized practices such as standard memos, endless meetings, and formal titles because they fear that without them, uncertainty and chaos will reign inside an organization. You need organized processes and people who are clearly in charge, don’t you? Superbosses’ collective response appears to be “Maybe not.” To be precise, superboss businesses are not perfectly flat; the superboss ultimately does retain control at the top. But to superbosses, sacrificing a bit of order is well worth it if, in the process, you obtain the innovation, creativity, and dynamism that accompany informal relationships.

A relatively flat organization and unpretentious culture enable superbosses to enjoy close, unmediated, in-the-trenches contact with all employees, regardless of age or experience. In Verrocchio’s workshop, master and apprentice worked simply and side by side, with knowledge and expertise flowing back and forth between them. Though modern-day superbosses may run larger, more complex organizations and grapple with Kafkaesque regulations unheard of in the time of the Medicis, they, too, sense that bureaucratic processes and fancy titles are distancing almost by definition. They treat them as necessary evils to be used sparingly. To a superboss, the ultimate goal is never to be simply a manager to an employee. It’s to be a perceptive, responsive, authentic master to an apprentice.

“How Do You Do That?”

At middle age, conducting master Jorma Panula would seem fairly ordinary on first glance—short, a little heavyset, steel-gray hair, a long, rectangular face. But such an unassuming appearance belied his arresting personality. David Curtis, artistic director of the Orchestra of the Swan, a British chamber orchestra, told me of a teaching session with Panula in which about a dozen student conductors took turns leading an orchestra through a Brahms symphony while the other students looked on from the back of the hall.40 Unfortunately, one student was having trouble. He was not making the correct motions, and as a result, the orchestra was not accenting properly. Panula got upset, growling and grumbling. He tried to correct the student, but to no avail. Finally, he got up and stormed out, slamming the door.

Sometime later, he came back in, and the orchestra tried again with the student. The notes still weren’t being played with the proper accents, so Panula came up to the podium, stood behind the student, and growled some more. Once again, the orchestra played the offending section of the piece. At the precise moment where he wanted accents played, Panula “just sort of shrugged or put a fist down—not a big movement, nothing flashy. It was just a sort of bear gesture. You can imagine a grizzly bear just sort of looking at you and grrrr.”41

Somehow, that did it. “A huge sound came from the orchestra. Well, we all just looked at each other,” Curtis said. “How do you do that? The orchestra didn’t know he was going to do anything. The students didn’t know, nobody knew. He just made the typical Panula gesture and the orchestra . . . exploded. We just stood there looking at each other thinking, ‘Oh, shit.’”42

Curtis offered this story to illustrate just how intense Panula’s in-person presence was as a teacher. He related that Panula was effective because he not only conveyed specific points of craft (for instance, how to have musicians accent certain notes in an appropriate way) but also initiated a deeper developmental process in the minds of students. Panula’s idiosyncratic interactions seemed to help students improve by triggering a powerful process of self-examination. That student who wasn’t hitting the accents needed to become more aware of what he was doing as well as of the deeper assumptions or motivations behind his conducting actions. Behaving on stage without rigor or focus just wouldn’t cut it, and Panula’s feedback helped root out these often unconscious actions.

The ultimate lesson Panula had to teach was one of integrity as a musician. The intention of the conductor was everything, and Panula would suffer no bullshit of any kind. Panula would also explicitly coach his students to remove any trace of ego from their performances. The conductor’s ultimate objective was to offer a natural experience of the composer, not of the conductor: “It is about the music . . . about honesty and integrity . . . and if you’re going to stand up on the podium and show off, [Panula] is really not interested. He will just say, ‘Oh, yes, marvelous, marvelous . . . next.’”43

Protégés of all superbosses related similar powerful, career-shaping lessons they learned during the course of informal, apprentice-style interactions. How, precisely, do superbosses teach so efficiently? Panula’s methods were no doubt unique to him. But the other superbosses were equally idiosyncratic. No matter how many times I reviewed the thousands of pages of interview notes from my research, I could not discern a single teaching style or method employed by all superbosses. Sometimes they carved out specific times for group teaching, as Bill Walsh did during end-of-day sessions at training camp; other times, they worked one-on-one with protégés, as in the walks through department stores Ralph Lauren used to take with individual protégés. Sometimes they told stories, such as the one Gene Roberts would tell about a blind editor he once worked for who clutched his arm and said, “Make me see!” in an effort to get journalists to write in a vivid way that would evoke images in readers’ minds;44 other times, it was a phrase they coined that conveyed precisely the wisdom a protégé needed (Luc Vandevelde, former chairman at Marks & Spencer and Carrefour, told me that Michael Miles advised him to bring out the best in people by using “eliciting skills” and avoid “limiting skills.” “I’ll never forget those two words,” said Vandevelde. “It profoundly changed my management approach, creating an environment where people can be at their best”).45 Still other times—in fact, much of the time—superbosses asked questions of their protégés, forcing them to articulate a fresh idea in the moment, thus giving the superboss a new window into their way of thinking.

One reason superboss teachings are so memorable is because they are frequently delivered in intimate settings and in unusual ways. Over dinner, Gene Roberts would offer John Carroll “little hints” about how to handle certain situations; as Carroll remembered, these dinners were “the best seminar you could ever have.”46 Pianist Herbie Hancock once told a story (recounted to me by sound engineer Scott Ross, who worked with Davis) about how he and Miles Davis were recording, and Miles told Hancock to sit on his left hand and only play with his right: “For a piano player,” Ross observed, “that’s like having your hand amputated.” But it was Miles’s way of teaching Hancock how to control sound in a more deliberate way than he ever had before.47

Superbosses may convey ideas as “nuggets” of wisdom, but they just as often seem to teach by simply being themselves and letting employees observe. As saxophonist Bill Evans said of Miles Davis, “I learned the most from just watching and seeing how he did it.”48 Mary Sue Milliken, co-owner and chef of Border Grill in Santa Monica and Las Vegas, recalled looking to Alice Waters as an “inspiration” for how to have a career and be a mom at the same time. “When Alice had her daughter, Fanny, it really perked up my interest. I thought, I gotta watch and see if she was going to keep working and how does it all fit in?”49 Edward Stack, a former executive of HCA who left to become the founder of the Behavioral Centers of America (by spinning out HCA’s psychiatric hospitals),50 recalled that long before exercise became fashionable, Tommy Frist would jog to and from work, sending a message to the whole organization that staying healthy was important. Many executives subsequently got in the habit of running or lifting weights as part of their daily routine, but Frist “never said to anyone, ‘You ought to do this.’ He never made anyone that I was aware of feel uncomfortable if they didn’t do what he did. He would set an example, do the things, and allow other people the opportunity to do it.”51

Superbosses deliver multiple layers of lessons at once. First, they teach technical nuances about their business—insights employees can’t get anywhere else, as well as memorable reminders of the fundamentals that protégés are already expected to know. If you want to learn the finer points of running a newspaper, who better to teach you than Gene Roberts? If you want to learn the secrets of starting a successful restaurant chain, who better than Norman Brinker? Director Roger Corman was known to teach an array of useful filmmaking precepts, including “prioritize your shots; rehearse while the crew is lighting the set; chase the sun; use foreground objects to enliven a dialogue scene; bring in movement to stimulate the eye; and above all, wear comfortable shoes and sit down a lot.”52 Actor Jack Nicholson remarked of his old boss that “with Roger, you learn the basics, good basics and tough basics; you never really forget it.”53

Just as valuable is a second layer of lessons, the make-or-break advice superbosses impart on how to run businesses and lead organizations. Billionaire entrepreneur and designer Tory Burch credits Ralph Lauren with teaching her “the importance of having a complete vision for a company, from product to marketing to store visuals.”54 Alice Waters taught Gayle Ortiz, now chef and owner of Gayle’s Bakery in San Francisco, how to “pay attention to detail and demand perfection” in all aspects of a restaurant’s operation, a lesson that became “my main focus of the way that I looked at business.”55 Michael Miles taught his protégé Richard Lenny, former CEO of Hershey Foods, how to develop strategic initiatives that would deliver superior shareholder value.”56

One business lesson we would expect all superbosses to impart is the importance of talent. And they do. Superbosses don’t simply urge their protégés to “hire well,” they emphasize the importance of hiring genuinely unusual talent as well as the importance of helping that talent fulfil all their potential, and then some. Doug Conant worked for about six years under Michael Miles before becoming the CEO of Campbell Soup. As he told me, “It’s hard to have extraordinary performance if you don’t have extraordinary talent. . . . The importance of this is what I really learned at Kraft. When I went on . . . I was much more aggressive on talent management than I would have been had I not had that Kraft experience.”57

Some of the most valuable and enduring lessons employees glean from superbosses fall into a third category, what we might call “life lessons.” A recurring lesson superbosses teach, for instance, is discipline—the importance of working hard to perfect your craft and to stay true to your values, beliefs, and vision. A hedge-fund manager learned a thing or two about discipline one day while watching Julian Robertson consider whether to buy a stock. Robertson had spent a lot of time researching before deciding to invest $100 million in the company’s shares. He placed the order, but in the meantime, he still wanted to consult a few people to learn about the company and its industry. He made his calls, and the information he obtained suggested that perhaps the stock was not as attractive as it had first seemed. Another manager might have rationalized a way to stay in the deal, especially since pulling out would have cost 10 percent of the transaction ($10 million!). Robertson didn’t care about taking the loss—he pulled out anyway. As the protégé recalled, “He never looked back. I am not sure if it worked out or didn’t—it didn’t matter. Because what that told me is when the story changes, get out, you can always reevaluate.”58

Such intellectually honest behavior leads us to another core lesson superbosses impress on their people: the importance of cutting away the nonessential and prioritizing what is real, even if this requires that protégés behave independently and flout social conventions. “I think the main message we got from him,” conductor Esa-Pekka Salonen said of Jorma Panula, “was to question all the basic axioms of culture and society and just try to develop integrity.”59 There is, at bottom, a simplicity to what superbosses do, whether it’s Ralph Lauren tailoring the image of his brand, Norman Brinker staying true to his concept of a casual restaurant, or Roger Corman pursuing his model of how best to produce a low-budget film. In their daily contact with superbosses, protégés feel the burden that such simplicity entails but also experience and are inspired by the richness of its results. It’s a lesson they never forget.

The life lessons superbosses share often stick with protégés, informing forever the way they conduct themselves. As David Curtis told me, “Every time I get on the podium, I’m thinking that if Panula were sitting there at the back of orchestra watching, what would he be thinking?”60 One well-known hedge-fund manager who worked for Julian Robertson for years confided that, on occasion, he considered an investment that just didn’t feel exactly right. “I will just hear Julian’s voice: ‘Big guy, don’t do that, think about it, wait a week and see how you feel in a week.’ And I think, ‘That’s right.’ And I will wait a week and say, ‘Stupid, why did I think I wanted to do that?’”61 Accounts such as these testify to the extraordinary impact superbosses have as teachers. Some bosses have trouble getting employees to do anything unless they’re standing over them; the minute they leave, employees revert to old habits. Protégés of superbosses internalize their teachings and make them their own. They mobilize these lessons again and again during their careers. As David Murphy said of Chiat, “It wasn’t until Jay died that I realized what a significant impact he’d had on me as a young executive. That it was okay to risk, it was okay to ask questions, that it was about the result of the work you were doing and to take it seriously.”62 What greater tribute could Murphy have paid to his boss than that?

Teaching like a Superboss

Apprenticeship might sound like a crazy idea for organizations and bosses to adopt. In our fast-moving, twenty-first-century economy, it may not seem helpful or even realistic to go back to the fifteenth century when dealing with something as vital as talent. Yet the track records of superbosses speak for themselves; theirs is a proven playbook. In workplaces where organizations or individual bosses adopt superboss-style approaches (remember, superbosses exist in even larger numbers in the middle of many companies and nonprofits), we find that employees really do benefit. In schools, for instance, the best principals are typically those who spend time in classrooms with their teachers, as opposed to playing the “CEO role.”63 In Teach for America, an internship program that offers young, inexperienced teachers an opportunity to cut their teeth at tough, low-performing schools, research shows that participants whose principal is actively involved in coaching them are more successful.64

Most good bosses today understand the importance of face-to-face contact. Management experts have coined a term for this: management by “walking around.” Yet management by “walking around” as it has long been practiced doesn’t begin to encompass the constant, deep collaboration that exists between superbosses and protégés. Despite most managers’ best intentions, apprenticeship-style management doesn’t actually happen. Calendars get filled up so quickly. Executives feel pressured to perfect the strategy and leave the execution to their subordinates. Hierarchies and bureaucracy remain firmly entrenched. Under these conditions, it’s the rare manager who would accompany protégés and lower-level employees, coaching them as they actually do what they do.

If you’re a manager, you cannot and should not just toss out formal training programs. You can’t spend all of your time interacting one-on-one with people—keeping some sense of control and order is important. But coaching in the moment is important, too, and deserves higher priority. The good news is that you don’t need to do away entirely with personal assistants, Outlook calendars, meetings, or other elements of bureaucracy. Remaking processes and structures incrementally so they’re closer to those of superbosses can yield significant results. See if room exists to dial back formality or to spend more unstructured time with your people. The point is not to allow hierarchy and bureaucracy to dominate. Let structure influence how you organize workplace relationships, but don’t let it constrain them unduly.

The apprenticeship model doesn’t need to be a substitute for what you’re already doing, but rather it can be an enhancement, part of a rebalancing that might occur in how your workplace operates. Training programs can and do teach the kind of basic instructional knowledge that superbosses expect their protégés to possess. So keep training programs, but don’t make the mistake of thinking such programs are all you need.

A good place to start is to revisit some of the assumptions you bring to the workplace. We get in the habit of not interacting closely and personally with subordinates; we see management as “just a job.” Likewise, we look upon the idea of “pitching in” as a negative, a sign that our subordinates may not be up to the task. Superbosses don’t want to do their subordinates’ work for them, but they do want to remain deeply engaged. Try to think about your relationships with reports in a less transactional way. They’re not only there to “get the job done,” nor are you only there to oversee them. You’re both there to get the job done and come up with bigger-picture ideas that will help drive the business forward.

As you modify your thinking, take stock of what you currently do and how you might improve. How much time do you actually spend with your team members? If that time turns out to be considerable, does an imbalance exist, with too much time spent on formal interactions, such as meetings or filling out performance evaluations, and not enough time on informal, one-on-one interactions? Think of the specific things superbosses do: Are you performing any of these actions already? Are there ways to perform more? Try experimenting at first with having more direct contact with one person or a couple of people in your organization, and encourage your reports to do the same. Do you see any positive results? Galvanize people in your organization to reorganize processes and eliminate red tape. Are there ways to streamline decision making? Are there ways to make communication easier throughout the hierarchy?

Don’t forget technology in all this. I’ve compared modern business practices to Verrocchio’s fifteenth-century practices, but in some ways, we’re better equipped today to incorporate the apprenticeship model into our organizations. We’re so good at communicating with strangers on Facebook, Twitter, and LinkedIn; why can’t we get better using these tools inside organizations? Bosses and employees in today’s global corporations are often separated by multiple time zones, but technology easily effaces that distance. It could allow for far more regular and consequential contact—if we’re willing to prioritize it.

We all need to perform well and make our numbers; to that end, what superbosses do is critical to observe. But there’s a higher benefit. Think of how meaningful it is to personally impress upon someone lessons they may carry with them throughout their lives. Think of how satisfying it is to share your passions with someone. Think of how incredible it is to help someone along, the way you were probably helped along. We all remember our best bosses . . . and our worst. It turns out we have a choice about what kind of boss we’ll be. When you teach and coach people the way superbosses do, your people will come away feeling fulfilled, fortunate, and grateful. Chances are, so will you.