Superbosses

Superbosses Plot Summary

Introduction

Imagine stepping into your office one morning to find the CEO leaning against your cubicle wall. Not just any CEO, but one of the most visionary leaders in your industry. She smiles warmly and asks about the project you're working on. When you explain, her eyes light up. "That's fascinating," she says. "Why don't you come up to my office and tell me more?" An hour later, you leave her office with your mind racing. She's just given you ownership of a major initiative, one that could transform the company's future. She believes you can do it, even though you're not sure yourself. This scenario may seem like a fantasy, but for the fortunate few who work for exceptional leaders - superbosses - it's everyday reality. These remarkable individuals don't just manage people; they inspire them to achieve things they never thought possible. What sets them apart isn't just their vision or business acumen, but their ability to identify, nurture, and develop extraordinary talent. They create environments where innovation thrives, where people are pushed beyond their comfort zones in ways that feel exhilarating rather than threatening. Most importantly, they build networks of success that extend far beyond their immediate organizations, spawning the next generation of industry leaders. Whether they're running restaurants, technology companies, hedge funds, or football teams, superbosses change lives and industries through their distinctive approach to leadership and talent development.

Chapter 1: The Art of Finding and Nurturing Exceptional Talent

In October 2012, a young hedge fund manager named Chase Coleman sat down for an interview in his Manhattan office. Though only 37 years old, Coleman carried himself with remarkable intensity. With a baby face and sandy brown hair swept across his forehead, he might have passed for someone a decade younger, but his focused demeanor told a different story. Throughout the conversation, Coleman spoke earnestly, chose his words carefully, and maintained an unwavering seriousness that suggested he was someone who took his work very seriously. Coleman's career trajectory was anything but ordinary. After graduating from Williams College, he went to work for Julian Robertson, founder of Tiger Management. Robertson had been one of Wall Street's most successful hedge fund managers until the late 1990s, when his refusal to invest in overvalued internet stocks during the dot-com bubble led to massive client withdrawals. By 2000, Robertson had closed his $22 billion fund and returned money to investors. But rather than fade into retirement, Robertson embarked on a brilliant second act. He identified promising young analysts who had lost their jobs when he closed his fund and provided them with seed money to start their own funds. These "tiger seeds," as they were called, could call on Robertson for advice and access his vast network of contacts. In return, Robertson would get 20% of their incoming fees. When Robertson spotted talent in 25-year-old Coleman, he handed him $25 million and essentially said, "Go build something." Coleman recalled feeling "highly anxious" but also "confident in my authority to execute." He was "very appreciative of someone having that level of confidence in me." That confidence was well-placed. Coleman's Tiger Global Fund yielded average annual returns of over 35% from 2001 to 2007, and in 2011 was the best-performing hedge fund of its size, returning an impressive 46%. What makes this story remarkable isn't just Coleman's success, but Robertson's ability to identify, nurture, and empower extraordinary talent. Superbosses like Robertson don't just hire smart people – they find individuals with unusual intelligence, creativity, and flexibility. They look beyond conventional credentials to spot that special "it factor" that indicates someone might become a superstar. And once they find these diamonds in the rough, they give them opportunities that might seem crazy to ordinary bosses, pushing them into challenges that stretch their capabilities to the limit.

Chapter 2: Demanding Excellence While Inspiring Loyalty

If you had walked into the Bloomingdale's on Fifty-Ninth and Lexington in New York City during the early 1970s, you might have noticed an attractive man in his thirties inspecting displays of clothing, with another man dutifully assisting him. The older man was Ralph Lauren, who would go on to become a fashion icon and billionaire. The younger assistant was Sal Cesarani, who would eventually become an award-winning designer in his own right and be known to some as "New York's Dean of Good Taste." Cesarani served as Lauren's right-hand design assistant for two years, working "literally all aspects" of the design process. The experience was both exhilarating and intensely demanding. Lauren and Cesarani would work late into the night and walk home together, discussing designs. Lauren was "always so soft spoken" yet managed to exert an incredible amount of pressure to perform – "demanding but in a non-demanding way." As Cesarani recalled, "You felt the need to do it simply to receive his recognition or because you knew it was the right thing to do. He made you feel you were so much a part of the business." The loyalty Lauren inspired was extraordinary. "If you were to talk to any other former employees of Ralph Lauren," Cesarani said, "they would tell you the same thing: they would have given him their lives." This wasn't hyperbole – Lauren's protégés developed a deep, almost cult-like devotion to him and his vision. When Cesarani eventually left because the "ungodly" hours were taking a toll on his family life, it was an excruciating decision. Lauren didn't yell, but he "would shake his head in disbelief that I would have betrayed him." Even decades later, the memory of leaving Lauren aroused sadness and regret in Cesarani. This paradoxical blend of extreme demands and profound loyalty is a hallmark of the superboss experience. Superbosses set impossibly high standards, pushing their teams to levels of performance that seem unattainable. "Perfect is good enough," as one of Bill Sanders' real estate protégés put it. They expect long hours, total commitment, and flawless execution. Yet rather than resenting these demands, employees typically respond with even deeper emotional bonds to their superbosses. They'll do anything to avoid disappointing this larger-than-life figure, not just because they've bought into the vision, but because they want to prove themselves worthy of the superboss's faith in them. The magic happens because superbosses don't just demand excellence – they inspire it. They inject a powerful sense of possibility into their workforce, making employees believe they can achieve more than they ever thought possible. Superbosses model self-confidence, create compelling visions that energize their teams, and connect employees' work to a higher purpose. They don't just want 80% of their people's attention and dedication – they want 100%. And remarkably, they get it, not through intimidation or manipulation, but by creating environments where people feel truly alive and engaged in work that matters.

Chapter 3: Unconventional Thinking and Rule-Breaking Innovation

When Ben Burtt was eight years old, he saw the 1956 film "Forbidden Planet" and was so gripped by its otherworldly atmosphere that he felt transported to an alien world. The electronic soundtrack particularly captivated him, sounding like both special effects and music simultaneously. Twenty-one years later, Burtt was offered a chance to work on another groundbreaking science-fiction film: "Star Wars." The film's creator, George Lucas, gave Burtt a challenging assignment. Lucas wanted sounds that were fresh and original, not borrowed from a studio library. Breaking from the convention of using electronic synthesizers for science-fiction sounds, Lucas asked Burtt to try a new approach: collecting recordings from the real world as raw material, then modifying them in the studio. Burtt embraced the challenge, recording kitchen appliances, freeway traffic, bears, and the sound of breathing in scuba equipment. His greatest challenge was developing sounds for the robot R2D2, who needed to communicate without speaking English. Lucas had a general sense of what he wanted – sounds that were "organic," not too robotic, expressing a humanlike personality – but he didn't specify exactly what this should sound like. It was up to Burtt to experiment and bring possibilities to Lucas for approval. Through trial and error, Burtt and Lucas discovered that the best approach was to begin with human vocalizations and then mix them with synthesized sound. "And you end up with two boys making sound effects together," Burtt recalled. "Something like you would get thrown out of third grade if you did it." Throughout the process, Lucas maintained ultimate control, never hesitating to say no to ideas that didn't work. Yet he also expected Burtt to develop "semi-complete" ideas of his own. "I had a chance to crystallize my own ideas about something and then see if they would work," Burtt explained. This story perfectly illustrates the paradoxical approach that makes superbosses so effective at fostering innovation. On one hand, they maintain an uncompromising vision of what they want to achieve. Lucas knew exactly what "Star Wars" needed to be, and he wouldn't settle for anything less. On the other hand, superbosses encourage their people to rethink virtually everything about how to achieve that vision. They expect creative thinking and rule-breaking, viewing it as a core job responsibility, not an occasional indulgence. The key insight is that superbosses protect the "why" of their business but constantly improve the "how." They have clear visions that energize their teams, but they're uncompromisingly open to new approaches for realizing those visions. This unique combination allows superbosses to build organizations that are "built to change" – places where innovation isn't relegated to special task forces or committees but is woven into the fabric of everyday work. Everyone at every level is expected to think, experiment, and improve, creating a continuous flow of new ideas that keeps the organization vibrant and ahead of competitors.

Chapter 4: Masters and Apprentices: The Learning Journey

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. To learn this craft, you would likely seek out a master artist and work for him as an apprentice. In Renaissance Italy, aspiring artists flocked to one master in particular, Andrea del Verrocchio, who operated a workshop producing a variety of media for wealthy patrons. Verrocchio was especially famous for his drawings and his ability to render the intricacies of draperies commonly found in Renaissance paintings. More importantly, he had a remarkable ability to recognize talented young artists and obtain their collaboration. His workshop functioned as a "school of design," where he taught pupils the rules of perspective and encouraged them to practice drawing from life. He made plaster casts of figures and body parts for his assistants to study and sketch. Under his guidance, apprentices learned not just technical skills but also innovative technologies such as chemical preparation of pigments and new metal-casting processes. One fourteen-year-old who began his apprenticeship with Verrocchio would go on to become one of the greatest artistic talents in Western history: Leonardo da Vinci. Even after Leonardo's skill eclipsed that of his master, Verrocchio continued to rely on his genius while also learning from him. Eventually, Leonardo became a master in his own right, securing his own commissions and establishing himself as one of history's most renowned artists. This ancient master-apprentice relationship might seem quaint in our modern world of formal education and corporate training programs, but superbosses intuitively understand its power. While other bosses might delegate training to HR departments or online courses, superbosses embrace apprenticeship-style management as a way of doing business. They stay in the trenches with their protégés, functioning as player-coaches who transmit knowledge through direct, personal interaction. Take Michael Miles, who transformed Kraft into a modern food marketing powerhouse in the 1980s. Unlike many CEOs who sequester themselves in corner offices, Miles was a "walk-around manager" who made himself unusually accessible to employees. He took time to have lunch with lower-level staff members in the cafeteria, kept his office door open for questions, and even picked someone at random every morning for hour-long conversations in his office. These weren't casual chats but intense learning experiences – "like taking a final exam," according to one executive. This hands-on approach extends to all superbosses, whether they're Nurturers like Miles, Iconoclasts like Miles Davis, or even the more demanding Glorious Bastards like Larry Ellison. They all forge remarkable connections with their protégés, working side by side with them, coaching them in unmediated ways, and often breaking down hierarchical barriers that might impede learning. Many superbosses create flat organizational structures without executive suites or special parking spaces, fostering environments where knowledge can flow freely between master and apprentice. The apprenticeship model yields profound results because it transmits not just technical knowledge but also deeper wisdom about leadership, values, and decision-making. Protégés don't just learn what to do; they learn how to think. As one conductor said of his mentor, "Every time I get on the podium, I'm thinking that if he were sitting there at the back of orchestra watching, what would he be thinking?" This kind of deep influence can't be achieved through formal training alone – it requires the sustained, personal engagement that defines the superboss approach.

Chapter 5: Hands-On Leadership and Strategic Delegation

In the traditional management playbook, delegation is often seen as an either-or proposition: either you micromanage your team, or you take a hands-off approach and let them figure things out on their own. Superbosses, however, have discovered a third path – what we might call "Hands-On Delegation." They maintain close involvement with their team's work while simultaneously giving them extraordinary autonomy and responsibility. This paradoxical approach is perfectly illustrated by Gene Roberts, who transformed the Philadelphia Inquirer from a corrupt, second-rate newspaper into one of the country's most respected publications. Roberts allowed writers and editors absolute freedom to follow stories as long as they adhered to certain quality standards. When reporter Don Drake proposed an ambitious project called "AIDS: A Day with a Global Killer," Roberts immediately said "go for it!" and authorized a dozen reporters and half a dozen photographers to travel around the world for the story. On the appointed day, the stories rolled in, and Drake and a colleague found themselves overwhelmed by the volume of material. Without any directive from Roberts, the entire newsroom spontaneously stopped what they were doing and pitched in, enabling the story to make deadline with seconds to spare. This remarkable display of teamwork wasn't the result of Roberts micromanaging the situation; it emerged organically from the culture of excellence and collaboration he had cultivated. What makes superbosses like Roberts so effective is their willingness to delegate real responsibility to their protégés. They trust their people to handle significant challenges, sometimes placing them in roles that seem far beyond their experience level. Bill Sanders, a real estate mogul, once gave an employee just two days to create a compelling strategy for a major development that would be presented to investors considering pouring hundreds of millions of dollars into the project. "He believed that if he gave me those marching orders, I would come back with something that was close enough to what he envisioned, that we would be able to sell it together," the employee recalled. The presentation was a success, leaving the employee with an incredible sense of accomplishment. But superbosses don't just throw their people into the deep end and walk away. They remain deeply engaged with the substance of the work, sometimes to an extent that verges on micromanagement. They articulate their vision, set specific goals, and then step back to see what happens. When all goes well, they let it ride, while still paying close attention. If they don't like what's happening, they don't hesitate to step in and course-correct. This balanced approach works because superbosses are true masters of their craft with deep subject-matter expertise. They know exactly what's going on in their businesses and understand the strengths and weaknesses of their teams. Their clarity of vision gives them the confidence to delegate, while their hands-on engagement ensures that work meets their high standards. The result is an environment where protégés feel both challenged and supported, with enough freedom to grow but enough guidance to succeed. Superbosses also expect their protégés to step up and take responsibility for their own development. As Tommy Frist, founder of Hospital Corporation of America, demonstrated to a colleague by sharing his daily goal-setting routine, superbosses believe that what happens in your career isn't random – it's the result of deliberate focus and effort. They want protégés who ask questions, seek out knowledge, try to improve, and actively pursue the next stages of their careers. Those who wait to be told what to do will find themselves left behind, while those who take initiative will thrive in the superboss environment.

Chapter 6: Creating a Culture of Collaboration and Competition

Many of us have never experienced the kind of transcendent teamwork that emerges when highly talented individuals come together in intense situations to achieve a common goal. But for the cast and crew of Saturday Night Live, this extraordinary phenomenon is a weekly occurrence. In just six days, they must create a show from scratch that will air before a live television audience of millions. Rachel Dratch, who joined SNL in 1999, found that the show's high-octane atmosphere spurred her to work at her very best. The producers didn't coddle her; they threw her into the deep end and let her fend for herself. Either she wrote good sketches with funny characters, or she sat on the sidelines watching each week's show. As executive producer Lorne Michaels explained, "There's something special about an environment in which nobody is more important than the show. On Monday, we face a blank page. Then, in six days, we're on the air. It's a task so difficult that it brings out the best in people." To get the job done, cast members and writers collaborate closely, often helping to refine skits that others wrote and would take credit for. Amid the chaos of production, deep emotional bonds form. "We were sort of trapped there," writer David Mandel recalled. "There was a bunker mentality. You know, there was the siege of putting the show up each week." Will Ferrell once said that what he would miss most about SNL were "the moments you'll never see" – the goofing around during rehearsals, the camaraderie of living "in a dorm—except that everybody is doing comedy." What makes this kind of teamwork so remarkable is that it combines intense collaboration with equally intense competition. Cast members compete for limited airtime, fighting to get their sketches produced and performed. Yet they also selflessly help each other succeed, knowing that the quality of the show matters more than individual glory. This combustible mixture – what we might call the "2-C principle" of collaboration and competition – dramatically boosts the performance of individual team members. Superbosses excel at creating this balanced dynamic. They establish a kind of insider sensibility among their protégés, constantly affirming that they are a uniquely talented group unlike any other. Ralph Lauren inspired his staff by saying they weren't ordinary designers or merchandisers, but an elite of "chosen people" – "the most talented people in the world were in this room." Bill Walsh explicitly worked with his San Francisco 49ers to turn disadvantages into advantages, comparing their challenges to "the desperate and heroic fights" of World War II soldiers. At the same time, superbosses deliberately introduce elements of healthy competition. Julian Robertson's hedge fund analysts competed for "airtime" during lunchtime sessions, fighting for capital and attention while also recognizing that making "the pie grow" was in everyone's best interest. Larry Ellison would sometimes set up competing development projects at Oracle, believing that internal competition was "an interesting idea." The magic happens when these two forces – collaboration and competition – reinforce each other, creating what we might call the "cohort effect." As Paul McCartney said of John Lennon, "If I did something good, he'd want to do something better. It's just the way we worked." Tennis coach Nick Bollettieri put it this way about his academy: "We have a lot of good players at the same place. You put the good against the good and you get excellent players, and eventually that becomes the best." By mobilizing both collaboration and competition, superbosses create their own "talent hubs" marked by intellectual and social ferment. This cauldron becomes an engine, powering exceptional performance and innovation. Individual employees grow beyond their wildest dreams, while teams achieve results that far exceed the sum of their parts. It's a powerful formula that transforms ordinary workplaces into extraordinary incubators of talent and creativity.

Chapter 7: Building Alumni Networks That Last a Lifetime

For years, Joanne Weir had been a valued cook at Chez Panisse, learning and growing under Alice Waters' guidance. By 1990, after almost five years at the restaurant, she decided it was time for a change. "I was ready to leave but didn't want to go," she recalled. "I knew if I didn't leave then, I might never leave. There were chefs that had been there for 10 even 15 years. I didn't want to be what I called a 'lifer'!" When Weir told Waters of her plans, something remarkable happened. Rather than expressing disappointment or trying to convince her to stay, Waters invited Weir to her house for a glass of wine. During their conversation, Waters came up with a perfect transitional role: tasting food at Café Fanny, an establishment Waters co-owned. This allowed Weir to remain connected to Waters' world while preparing for her next career step. But Waters' support didn't end there. As Weir went on to become a successful cookbook author, television personality, and restaurateur, Waters continued to champion her career. When Weir published her first book, Waters featured her as a guest chef at Chez Panisse. She appeared on Weir's TV show and wrote endorsements for her books. Weir, in turn, thanked Waters repeatedly in her cookbooks and continued to visit Chez Panisse whenever possible: "I just have to get a dose of it, even just to get dinner, just to be there." This enduring connection between superboss and protégé exemplifies how the best leaders build alumni networks that last a lifetime. Rather than viewing employee departures as betrayals, superbosses like Waters see them as natural stages of growth and development. They understand that their influence extends far beyond the confines of their immediate organization, creating an "extended family" of former protégés who continue to feel close to the superboss and to one another. These networks yield tremendous benefits for everyone involved. Superbosses tap their protégés for business opportunities, investments, and collaborations. Julian Robertson, for instance, funded his "tiger seeds" – promising young investment managers – and received a 400% return on his capital over several years. Protégés gain valuable connections, mentorship, and reputational capital. The Chez Panisse brand functions like an Ivy League degree for former employees, opening doors throughout the culinary world. "You go anywhere and somehow, someone knows somebody that worked there or they've heard of Alice or one of the cookbooks," one chef observed. "It even opens doors when you want to go cook in other countries." Perhaps most importantly, these networks serve as vehicles for continuous learning and growth. Because superbosses and their protégés often share common backgrounds, perspectives, and even language, they can collaborate with remarkable efficiency. When employees at The Daily Show meet fellow alumni, they immediately understand each other's experiences: "There's this thing where we can already start communicating about, like, 'Hey, have you ever had a field piece where the subject tried to walk out on you?' 'Yes! I know exactly what you're talking about!'" Superbosses also benefit from these networks by enhancing their reputation and influence. As their protégés succeed, superbosses become known not just as innovators but as preeminent "talent brands" – people who know how to develop the industry's next superstars. This in turn attracts even more talent, creating a virtuous cycle that ensures a constant flow of fresh energy and ideas into the superboss's world. The existence of these powerful alumni networks challenges conventional wisdom about talent retention. Most companies focus on keeping their best people at all costs, fearing what will happen if top performers leave. Superbosses take a longer view, recognizing that they can maintain meaningful connections with former employees that benefit everyone involved. As investment guru David Swensen's protégé explained, turnover created a "natural vibrancy" and was a "great recruiting tool" – a billboard proclaiming to prospects: "Come here and someday have my job, or a job just like mine."

Summary

Throughout this exploration of exceptional leadership, we've encountered individuals who defy conventional management wisdom to create extraordinary results. From Julian Robertson's ability to spot and nurture investment talent, to Ralph Lauren's skill at inspiring fanatical loyalty, to Alice Waters' gift for building lifelong relationships with former employees – these superbosses have revealed a different path to success. They find unusual talent in unexpected places, motivate people to perform beyond their perceived limits, encourage creative thinking and rule-breaking, teach through direct apprenticeship, delegate responsibility while maintaining high standards, foster both collaboration and competition, and build powerful networks that extend far beyond their organizations. What emerges is a profound insight about leadership: the greatest leaders don't just achieve personal success; they create success in others. They understand that their legacy isn't measured solely by their own accomplishments but by the accomplishments of those they've influenced. As Robert Mondavi, the pioneering winemaker who transformed American viniculture, discovered in his later years when former protégés lined up to thank him at a dinner, there is no greater satisfaction than knowing you've helped others achieve their dreams. This is the true essence of the superboss approach – recognizing that when we help others grow, we grow ourselves, and our impact multiplies beyond anything we could achieve alone. It reminds us that leadership isn't about control or status; it's about unleashing potential, fostering innovation, and building connections that endure long after we're gone.

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Sydney Finkelstein

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