So You Want to Be a Superboss

Protégés of Ralph Lauren, George Lucas, Bill Sanders, and other legendary leaders reveal how the great ones inspire greatness in everyone.

By Sydney Finklestein, Ph.D.

If you walked into the Bloomingdale’s on the corner of 59th and Lexington in New York City during the early 1970s, and proceeded past the racks of suits, slacks, and ties to the center of the men’s store, you might have noticed an attractive man in his early thirties inspecting the clothing displays. If you noticed him, chances are you saw another man dutifully assisting him by rearranging shirts on a shelf, or moving a display of ties from one spot to the next.

The young, good-looking guy checking his wares was none other than Ralph Lauren, who went on to become a fashion icon and billionaire several times over. Before Lauren came along, designers made either formalwear or sportswear; he combined the two into a cohesive collection that reflected a new, aspirational American lifestyle. The rest is sartorial history. 

But who was that man assisting Lauren? It wasn’t Joseph Abboud, Joseph A. Banks, or John Varvatos, although they all worked for Lauren at some point, as did Vera Wang. It was a young designer and merchandising specialist named Sal Cesarani. 

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Cesarani would go on to win multiple awards for his own designs, have articles written about him in the New York Times, and become known to some as New York’s Dean of Good Taste. Between 1970 and 1972, though, he served as Lauren’s top assistant, involved in all aspects of the design process, from fabric selection to showroom display to sketching Lauren’s design ideas. It was an exciting job, a wonderful learning experience—and, as Cesarani remembers, indescribably intense. 

He and Lauren would work late into the night and then walk home together discussing designs. Lauren was “always so soft-spoken,” Cesarani told me in a 2008 interview, yet he also managed to exert an incredible amount of pressure to perform—“demanding but in a non-demanding way.”

If Lauren asked you to do something, you did it because you wanted to please him, and above all, not disappoint him. “You felt the need to do it simply to receive his recognition, or because you knew it was the right thing to do,” Cesarani says. “He made you feel you were so much a part of the business.”

Some bosses inspire so much affection that employees are willing to do anything for them—even take the metaphorical bullet. Lauren was that kind of boss. If you were to talk to any other former Ralph Lauren employees, Cesarani says, “they would tell you the same thing: They would have given him their lives.”

Think for a moment how powerful this kind of motivation is. Many companies today measure how engaged or emotionally connected members of their workforce are. In all too many of them, engagement is disappointingly low. For superbosses like Lauren, engagement is the least of it. 

They know that to succeed they need the world’s best team, which doesn’t mean engaged talent; it means energized, supercharged talent. Having people like Cesarani working their hearts out to do the impossible was a big reason for Lauren’s success. His team wanted to excel and, as a result, they were able to blow past preconceived ideas of what they could do.

If you manage others, imagine what you might accomplish if all or even a few of your team members felt this internal drive to succeed. Consider millennials, for example. They’re the most highly educated and mobile-enabled generation ever. And in survey after survey, they say they’re not interested in a “job”; they’re looking for passion, the chance to be part of something meaningful. So how do you inspire that kind of motivation? How exactly do you become a superboss?

Perfect Is Good Enough

The first thing to know is that all superbosses, even the most supportive, drive their people exceptionally hard. Take legendary real estate strategist Bill Sanders, for example. 

“Everybody knew that Bill demanded results, and if you were going to work with him, you need to be prepared to make that the primary focus in your life,” explains Ronald Blankenship, the former CEO of the Verde Group and a longtime associate of Sanders. 

Or consider Tommy Frist, cofounder of Hospital Corporation of America. “You were expected to get done what needed to get done, and get it done in a timely fashion,” says Victor Campbell, senior vice president at HCA.

Comedian Andy Samberg says that after working for Lorne Michaels at Saturday Night Live, acting in movies was a “cakewalk.” “The pressure doesn’t really seem that high,” he says. “You’ve dealt with this thing that’s SNL, which is just this crazy, intense, beautiful pressure cooker.” 

Superbosses don’t merely want strong performance; they expect world-class performance. As one protégé remarks of Oracle cofounder Larry Ellison, his great strength is “to make exceptional people do the impossible,” accomplished in part by setting the impossible as a clear goal. 

That’s how Carmen Policy, former president and CEO of the San Francisco 49ers and Cleveland Browns, remembers the legendary head coach who won three Super Bowls. “Bill Walsh came to the 49ers with a hunger, a vision, and a strong desire to do more than just coach the team,” Policy says. “He wanted to create a dynasty.”

Same with Sanders, whose goal for his real estate investment company was to have the national footprint and reputation of Goldman Sachs. Anything less than extraordinary effort from his staff just wouldn’t cut it. “One of the things Sanders taught me was if you are going to be in the service business, if you are going to have clients or investors, good is not good enough,” says Don Suter, former managing director at Sanders’ Security Capital Group (SCG). “Perfect is good enough.”

What exactly does “perfect” mean? Suter tells about a time when he had to convince the CEO of a public company to buy into an important financing deal involving SCG. He spent three days preparing for a 45-minute meeting. It paid off when the CEO agreed to Suter’s proposal on the spot. 

But Sanders wasn’t happy. After the CEO left, Sanders went into Suter’s office and shut the door. “I thought he was going to give me one of those pats on the back,” Suter says. He had nailed the presentation, hadn’t he? Instead he got an earful because he had spoken too informally at one point, using the term “you guys” to describe the CEO’s company. “Sanders said if you ever use the term ‘you guys’ again in a meeting, I’m sending you back to Kokomo,” where Suter was from. “That is Bill’s obsession with making sure whatever you do is perfect.”

In setting ever-higher expectations, superbosses aren’t bound by last year’s figures, or by a sense of what “normal” performance would be for an employee in a given position. They’re certainly not bound by what employees may perceive as their natural limitations. Superbosses want to see how far people can go, to see how far they can bend. They treat staff like Olympic athletes, pushing them to the limit and beyond.

The Ladder of Confidence

Isn’t all this hard-charging, whip-cracking perfectionism ultimately counterproductive? Doesn’t it lead to employee burnout and disenchantment

In many traditional high-performance cultures, yes, that’s exactly what happens. Investors and boards apply pressure at the top of the organization, and the pressure cascades downward as bosses at each level tighten the screws. Managers are told they have a number they need to hit. But what happens when they hit that number? The target goes up the following year. When they hit that number, the target goes up even more. The demands never seem to end.

Some employees at superboss-led companies crack and drop out. But those who remain respond to the constant and continually expanding pressure by developing an even deeper emotional bond with the person at the top. That’s because even though superbosses keep the pressure up, they also inspire employees to aggressively push themselves. 

They understand that individuals—even the most driven and talented—accomplish so much more when high expectations come with a message of possibility. They get that people will work their hardest to become bigger, better, tougher, more resourceful, and more creative when they first see themselves as all those things. And they sense that it’s their job as leaders to instill self-confidence in their workforce.

Again and again, protégés told me that the greatest strength of their superboss was to make staff members believe in themselves. As I unraveled how superbosses did this, I found that they first modeled self-confidence. The gumption of a George Lucas, who stayed committed to Star Wars even when people predicted the franchise couldn’t be revived, rubs off on people. Protégés notice and feel elevated by it, more aware of their own greatness by virtue of their proximity to the greatness of the superboss. 

Lucas protégé Howard Roffman remembers that when he first took the position of head of licensing at Lucasfilm, Star Wars had already lost traction in the market. Roffman’s job was to sell people on the film again and get them excited about it. When he met with retailers, licensees, and other industry players, however, they weren’t buying it. “Every one of them looked at me like I was crazy,” he says. They told him Star Wars was dead.

Roffman feared having to deliver this message to Lucas. “I thought the wrath of God will come down on me,” he says. But Lucas just laughed it off, telling him Star Wars wasn’t dead. “It’s just sleeping. Give it some time. Someday all those people who saw it are going to have their own kids and are going to want to introduce them. We can try to make a comeback then.” 

Of course he was right. Today, the Star Wars franchise is arguably bigger than ever as a new generation embraces it.

The Power of Vision

We’ve heard a lot of talk in recent years about the importance of vision for organizations. Yet vision still tends to get lost at most of them. At best, people see it as something that managers transmit from the very top of the corporate pyramid, a notion that can be so far removed from their everyday work that it seems completely meaningless.

When I work with management teams, even relatively high-performing ones, I ask them about their organization’s vision. More often than not they can’t even articulate what it is without looking it up on the company website. Vision becomes mere window dressing, rather than what it should be: motivational, compelling, energizing. The idea that every competent boss needs to craft a unique vision for his or her own team is also nonexistent. And if vision plays such an unimportant role for managers, imagine how employees see it. I have to think that much of the time it barely even enters their consciousness.

Superbosses become talent magnets not only because of their track record, but also because they envision future possibilities in a way that’s utterly compelling. Bill Sanders struck colleagues as someone who could “see around corners.” R. Scot Sellers, a Sanders protégé who went on to become CEO of Archstone Properties, says that Sanders “would lay out his vision and he would say, ‘I would like you to be a part of it.’ You were so honored to be asked to be part of this great vision that you just wanted to jump in and say, ‘Sign me up!’”

Superbosses’ visions are without exception unique, authentic, and consistent. As one of his protégés excitedly related to me, George Lucas “changed the way movies were made with Star Wars.” Another emphasized that Lucas “was the guy who pioneered digital sound and digital imaging. It was all analog. He started Pixar. … He is not afraid to think of the way things might be and how different they will be from the way they are today.”

Still another protégé, Michael Rubin, the author of Droidmaker and a young member of Lucasfilm’s Graphics Group in the 1980s, recalls hearing Lucas talk about his transformational vision of technology. “I heard him explain what the future could be like and I was infected with that at age 22. I believed him. And it changed my career.”

Superbosses take for granted that employees buy into their visions. As a result, they don’t need to constantly monitor their employees to make sure they’re putting out their best. Alignment with the vision does that naturally. Many employees I spoke with reported being utterly riveted to their work for years, so much so that almost nothing could tear them away.

Joyce Goldstein, the James Beard Award-winning chef at Alice Waters’ Chez Panisse in the early 1980s, remembers that she was “there from five in the morning till six at night. I worked six days a week. I inventoried on Sunday and I did the ordering for both restaurants [the formal dining room and the café]. But I was in love with food. I discovered I loved the business and I never watched the clock. The only reason I went home is that I had three kids who needed to be fed.” 

Employees of superbosses never watch the clock, and they’re not in it for the fame, the glory, or the money. They’re in it because they see what the superboss sees. And it’s utterly irresistible.

It’s Hard to Go Back to Being Ordinary

Superbosses are geniuses at motivation. Unlike some bosses, they don’t want 80 percent of the attention and dedication of their people. They want 100 percent. And they get 100 percent. People know when they’re working for a special boss—someone who’s changing the rules every day, who’s unafraid to take risks, who cares deeply about achieving a higher objective, and who invites employees to be a part of it.

When a boss like that is giving orders—or, as is more often the case, pushing and inspiring you in a powerful way—you don’t perceive the pressure to perform as tedious or unwelcome. You perceive it as part of a gigantic, exciting, and unbelievably important mission. You thrive on this pressure. And just like your boss, you lose yourself in the mission. 

Superbosses’ combination of lofty expectations and aspirations enables the exceptional people under their wings to do impossible things. An upward spiral of performance takes root among their protégés, and as they grow accustomed to surviving and thriving in an intense environment, their ambitions only increase. 

They become so addicted to success that they seek out ever more challenging assignments. And they feel so great upon meeting or exceeding the superboss’s expectations that they want to do it again and again. They yearn to be even closer to the superboss, his inspiration, his energy. They’ll do what it takes to stay in his orbit.

This cyclone of pressure, success, acknowledgment, rising confidence, and then even more success makes the protégé, the superboss, and the superboss’s organization utterly unstoppable. As an employee of advertising icon Jay Chiat, cofounder of the Chiat/Day agency, sums it up: “He left something in people that makes it hard for you to go back to being ordinary. Once you feel it, you can’t change it.”

Getting Closer to Purpose

If you’re a boss who’s struggling to get superior performance from your team, maybe it’s time to stop doing what doesn’t work and try something new. Cracking the whip isn’t a leadership philosophy. Unless you instill a sense of possibility in your people, at some point the engine will grind to a halt.

It doesn’t matter what your position in an organization is. Vision isn’t just for CEOs. You’ve got to craft a vision that energizes your team, and you’ve got to spend lots of time communicating it effectively. As an exercise, try performing a quick audit of how you’re spending each day. How much time do you spend doing what superbosses do—asking opinions, affirming abilities, establishing employees’ status as members of an A-team, alerting them to the underlying purpose behind shorter-term priorities and objectives, and so on? 

If you’re already pushing people to their limits and you can’t push any harder, you might find that spending more time on the softer stuff—meaning, purpose, vision, identity—will result in even greater performance. Inspiring others is not an incidental activity for superbosses. Rather, it’s at the core of what they do.

In many organizations, the “why” of work gets lost as teams focus on the hard metrics of financial performance. Employees forget why they need to sell a thousand more service contracts, or extract $486 per customer interaction as opposed to $483. Getting those extra contracts or dollars might be a big deal to you, but what do they mean to your employees? If you find yourself thinking less and less about the fundamental purpose of the team and organization, chances are your employees are even more disconnected from the mission.

Ask yourself these crazy questions: Why does your organization exist? Why does your team exist? Can you communicate it succinctly and in a way that hits home? Can you connect it to specific items on your agenda for this year, this quarter, this month?

Any company can get energized around a purpose. Any department within a company can too. An internally focused, process-oriented department like accounting might seem especially far removed from lofty ambitions. Can managers really frame an inspiring vision for this department? Of course they can! 

A business needs to get its numbers right. Financial filings must be accurate and professionals doing the work must follow appropriate procedures. If an accounting team isn’t doing its job and mistakes happen, the whole company might be at risk, and with it, the larger purpose it serves.

Each team is linked to the organization’s calling. It contributes vitally to work that affects people’s lives. As a superboss-style manager or leader, your role is to explain this to your employees, underscoring how each of their specific jobs factors in and how they might innovate to do their job even better, and by extension to make the company better.

Whatever the case, now is the time to get your people fired up. Discover your greatness, so that they can find theirs.

Sydney Finkelstein, Ph.D., is the Steven Roth professor of management and director of the Center for Leadership at the Tuck School of Business at Dartmouth College, specializing in business leadership and strategy. He is also the author of 20 books, including Superbosses: How Exceptional Leaders Master the Flow of Talent.