Superbosses aren’t afraid to delegate decisions

Superbosses embrace a number of specific behaviours and beliefs that enable them to trust their subordinates more deeply, and delegate decision-making more aggressively


Photo: iStock
Photo: iStock

The answer to excessive micromanaging, we’re often told, is to learn to trust our reports, empowering them to make decisions for themselves. Yet that sounds far easier than it actually is. In practice, many bosses fail to delegate because they haven’t cultivated a set of underlying mindsets and practices.

Over the past decade, I’ve studied the world’s greatest bosses, extraordinarily successful leaders who have also unleashed vast pipelines of talent. These “superbosses,” as I called them, spanned dozens of industries and included legendary figures such as fast casual restaurant magnate Norman Brinker, packaged foods titan Michael Miles, tech mogul Larry Ellison, hedge fund pioneer Julian Robertson, media icon Oprah Winfrey, and a host of others.

Analyzing these leaders’ careers and business practices, I found that superbosses were expert delegators, ceding degrees of authority and control that would send chills down the spines of ordinary bosses. Would you hand a 20-something $25 million in seed capital and tell him to go off on his own to manage it? Julian Robertson did. Would you task a young protégé with generating the main strategy for a new real estate development—only two days before a big presentation with investors? If you’re real estate legend Bill Sanders, the answer is yes.

I wondered how superbosses could place such trust in protégés. After reviewing thousands of pages of published sources and interviewing over 200 people, I concluded that innate and unshakable self-confidence certainly played a major role. Yet I discovered an even more important factor. Superbosses embrace a number of specific behaviours and beliefs that enable them to trust their subordinates more deeply, and delegate decision-making authority more aggressively. (Take this assessment to find out if you’re a superboss.)

Superbosses live to learn and invent

They’re die-hard opponents of the status quo. As superboss Lorne Michaels told me: “The show must change. I know it’s supposed to be ‘must go on,’ but ‘must change’ is important also.” Superbosses are constantly pushing themselves to innovate, and they expect employees to work independently and take bold creative risks. As a protégé of advertising legend and superboss Jay Chiat remembered, “Doers were rewarded and anything was possible. If you came to Jay with an idea for how things could be done better, he would say, ‘Go ahead and do it.’” But what if protégés failed in their experiments? The leaders I studied weren’t overly concerned. Kyle Craig, who worked with Norman Brinker at Burger King in the 1980s, remembered the superboss openly acknowledging his own failure with an earlier venture, Brink’s coffee shop. “He was never unwilling to admit his failures and mistakes, which puts people around him very much at ease.” If you accept that you will fail from time to time, and that your employees will fail too, it’s far easier to relinquish decision-making responsibility—and still sleep at night.

Superbosses really know their employees

They aren’t distant bosses, like the hapless leaders on the TV show Undercover Boss. Rather, they’re what we might call “hands on delegators.” Norman Brinker would show up in restaurants to bus tables with his employees. Newspaper editor and superboss Gene Roberts would invite staffers to his home and stay up until two in the morning talking shop. Deeply committed to coaching and development, these leaders spent a disproportionate amount of time interacting with employees, observing them on the job, and providing valuable feedback.

Regular contact with employees puts superbosses in a perfect position to “trust and verify,” as the old motto goes. They can monitor decision-making and enforce accountability on a real-time basis because they’re there. “You just knew when you were around Brinker expectations and accountability were givens because of the way he conducted himself,” one member of his inner circle recalled. But superbosses’ commitment to highly personal coaching affords another advantage when it comes to delegating. They can also “pre-approve” employees for increasing amounts of responsibility. Superbosses know protégés’ first-hand. They understand their strengths and weaknesses. They’re aware of how much progress their people have made and what responsibility they’re ready to shoulder, and they’ve taken the time to craft customized development plans for them. Delegation thus becomes a far more informed and careful choice than it typically is. In the hands of superbosses, the old motto becomes: “Observe, coach, and trust. And then verify.”

Superbosses place clear boundaries around delegation and decision-making

Rather than let employees make decisions willy-nilly, these leaders articulate uncompromising visions that they expect employees to internalize and follow. During the execution of work tasks, employees enjoy extraordinary authority over everything except the vision. And superbosses generally stay clear, intervening only to ensure that decisions employees make support their visions and don’t conflict with them.

At Lucasfilm, superboss George Lucas trusted his team to define the characters, set designs, and sounds of the original Star Wars movie. He didn’t micromanage. But he did check in periodically and personally to test employees’ inventions against his vision. Because he was so clear about what really mattered—his vision—he could more easily cede control over all else. This is yet another reason why every manager should craft a compelling vision for their teams, no matter where they are in the corporate hierarchy. If you struggle to devolve decision-making onto your team, don’t just commit to trusting your employees more. Follow superbosses in creating the preconditions for trust.

Embrace a general mindset of constant experimentation and change. Stay close to your employees and become a “hands on delegator.” And hem in decision-making by forging and communicating a clear vision. If you lay the groundwork, delegating decisions ceases to be nerve-wracking. It becomes what it should be: natural, exciting, and value-creating for boss and employees alike.

Sydney Finkelstein is the Steven Roth Professor of Management and Director of the Leadership Center at the Tuck School of Business at Dartmouth College. His new book is Superbosses: How Exceptional Leaders Manage the Flow of Talent (Portfolio/Penguin, 2016).

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