The Qualities That Make Up an Outstanding Boss

September 12, 2016

Perhaps no one on earth has spent more time researching what makes a great leader than former professor and writer Sydney Finkelstein.

For his book Superbosses, Finkelstein spent more than a decade investigating what a great boss looks like. Through research and more than 200 interviews, he uncovered the characteristics of “super bosses” – i.e. people who are not only outstanding bosses themselves, but also developed dozens of people who went on to be great bosses in their own right.

A perfect example is Larry Ellison, CEO of Oracle. Obviously, Ellison is a strong leader himself, turning Oracle into the multinational corporation it is today. But also, from 1994 to 2004, nine of the 11 executives who worked closest to Ellison that left the company without retiring went on to become CEOs, chairs or COOs of other companies.

Hence, not only is Ellison a great boss, he also helped develop many other great bosses.

So what were Finkelstein’s findings? What qualities did these so-called “super bosses” share?

Unsurprisingly, it was that they were great at both hiring and developing their people. Here’s their strategy behind both:

Great bosses employ “unconventional” hiring methods.

Finkelstein found that great bosses have hiring processes he described as “unconventional.” By that, he means these four things:

  • They seek out “unusually gifted people”.

To paraphrase a Game of Thrones speech, great bosses don’t hire people who are spokes in a wheel. They want people who break the wheel.

In other words, great bosses don’t look for the exceptional – they look for the transformational. They want people with such outstanding gifts, they change the market they operate in.

  • They take chances on people from a wide variety of backgrounds.

Great bosses pay little credence to degrees or experience. Instead, they focus on finding people with those unique qualities described in the previous section.

An example Finkelstein cited – super boss and billionaire Tommy Frist ran the health care giant HCA. There, he would occasionally put physical therapists on a path to an executive position, simply because he spotted something extraordinary within them.

  • They build their organization around great talent, instead of the other way around.

Great bosses don’t create a system and then look for people who fit within it. Instead, they look for great talent, and then build a system that talent will flourish in.

My favorite example Finkelstein cited was former San Francisco 49ers Coach Bill Walsh, one of the greatest football coaches of all time. While coaching offense for the Cincinnati Bengals, Walsh’s starting quarterback got hurt, and in his place was a man with a weak – but accurate – throwing arm.

Rather than have the new quarterback adjust to his system, Walsh designed an offense featuring an array of short, precision passes – exactly what the backup could do well. Walsh used the same system with another quarterback with similar skills, Joe Montana, when he went on to coach the 49ers, which compelled them to five Super Bowl titles.

The point? Walsh wasn’t stubborn. Rather than doing things his way, he did what would maximize his employee’s ability.

  • They accept that great people will leave.

One thing Finkelstein found was that great bosses do not expect their great talent to be around forever. In fact, realizing they are so talented, great bosses accept that their people will eventually leave for a bigger opportunity. In fact, great bosses took pride when their people went on to bigger and better things.

Great bosses believe in “hands-on” leadership.

Finkelstein found that great bosses tirelessly work to develop their people. They accomplish that by doing these four things:

  • Great bosses set really high expectations.

Finkelstein described great bosses as having the attitude that “perfect isn’t good enough.” Instead, they constantly demand greatness out of their people, which forces their employees to be excellent in all aspects.

  • They aren’t afraid to delegate, although they monitor closely.

Finkelstein found great bosses are great delegators. He found they are eager to give out tasks, as opposed to running everything themselves.

That said, throughout the process super bosses closely monitor projects and provide coaching and direct feedback to their people. Finkelstein compared it to a master-apprentice relationship, with the super boss playing the role of master.

  • They will build the right person’s career, quickly.

When a great boss sees someone they like, they actively work to grow that person’s career – and fast.

For example, Julian Robertson, billionaire, former leader of Tiger Management and super boss, took a liking to a young employee named Chase Coleman. Within three years of hiring him, Robertson gave Coleman $25 million to run his own hedge fund.

The point is that when a great boss sees someone they think is worth investing in, they invest in them – without worrying about seniority or politics.

  • They stay connected, even after their people leave.

Great bosses will stay committed to people, even after they leave the company. They build relationships for life, not just for the time the person works for them.

An example cited by Finkelstein is Lorne Michaels, who runs Saturday Night Live. After one of his players leaves SNL, Michaels maintains strong relationships with them, and sees where they could collaborate again in the future.

That allowed Michaels to partner with his departed talent years after they left his show. Two perfect examples are Tina Fey’s 30 Rock and Jimmy Fallon’s The Tonight Show, two hit TV shows by SNL alums. Michaels served as executive producer for both.

*Image from Schreibvieh, Wikipedia Commons

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