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A millennial’s guide to finding a ‘superboss’

Former host Jon Stewart in a segment about fast food on “The Daily Show.”Comedy Central

Bosses can make or break your career. A good boss can be a crucial mentor, a great boss can shape the rest of your career, and a horrible boss can make work – and even your personal life – miserable.

Great bosses roll up their sleeves and work closely with their employees. They are ambitious, drivers of change, interested in the message of the company, and willing to delegate authority. After 10 years of research and over 200 interviews, Sydney Finkelstein, a Dartmouth College professor and a management consultant, thinks he found an entire class of amazing bosses. In his book “Superbosses” and in speaking with me, Finkelstein described what he thinks makes some leaders exceptional.


What’s a superboss?

According to Finkelstein, people like designer Ralph Lauren, comedian Jon Stewart, and coach Bill Walsh are not only highly qualified and successful in their own right, but they’ve created highly qualified and successful employees who’ve gone on to do great things. Lauren helped launch Vera Wang. Walsh boosted the careers of so many other future football coaches. Stewart, despite not wanting to be thanked, is largely responsible for the successes of comedians like Stephen Colbert and John Oliver.

Superbosses are geniuses at helping other people accomplish more than they thought possible, and they focus on generating talent on a continuous basis, says Finkelstein. They want to see you leave and do well; they optimize talent flow, not talent retention. They find unlikely winners to hire. They don’t care about traditional resumes.

But not all superbosses are the same. Finkelstein says there are three groups: iconoclasts like Jon Stewart who are so obsessed with their jobs that their dedication motivates others; glorious bastards like Larry Ellison of Oracle Corp. who are driven by a desire to win and know they need talent to do so; and nurturers like cosmetics queen Mary Kay Ash who simply like helping others get ahead.


When looking for a boss, if you are motivated by the type of work you do, go with the first type. If you care more about helping others, go with the third. If you’re highly competitive, in it to win it, and care more about money and prestige, an Ellison-type may be a good choice.

Finkelstein suggests that bosses either have what it takes or they don’t. While they can develop their skills in some areas, being a good boss is part of an innate personality. Even highly successful, well-liked people like Steve Jobs just didn’t have all the traits. But he was also adamant that superbosses are found everywhere, not only in famous circles.

So how do you find an amazing boss or maybe even a superboss?

In your interview, here are some questions to ask:

“What are the greatest flaws and strengths an employee could have?”

Pay attention to what your boss wants. Is the priority teamwork or following rules, creativity or analysis? If he or she thinks loyalty is the greatest strength, the job may not encourage change or growth. Is the office culture one where big assignments are delegated to subordinates or is there a lot of hand-holding? You want a boss who does both, says Finkelstein.

“How often do people leave your team and where do they go? Is there a strong alumni network?” Bosses should share several examples and they should be proud of their employees who have moved on, not look at them as disloyal. They should keep in touch (this, says Mr. Finkelstein, is crucial).


“Why did you join this company?”

Amazing bosses will believe in the message of the organization and share that vision with you. They’ll explain what they love about work culture.

“What are some of your frustrations with your work and what are your proudest moments?”

Good bosses will share how they worked through problems, and that their frustrations are team-driven, not personal. Their proudest moments will be watching people they’ve helped succeed and increasing the wins of the whole team, not big events they’ve handled or big money that they’ve made.

Other things to do: Notice what bosses have on their office tables in interviews. Do they have a sense of humor? A family? If diplomas are the only things on the walls, you’re probably in for trouble. Do they ask you about more than just work? Can they joke around? If bosses ask you about your creative initiatives, that’s a good sign. If they’re more curious as to how quickly you fulfill your tasks and whether you meet deadlines, that’s a warning. Good bosses are flexible.

Meet co-workers and ask them what some of the dos and don’ts of office culture are. Do they feel comfortable telling their boss they’ve had a family emergency? Being able to be honest with your boss is crucial. Try to ask your references what types of questions your future boss asked them. This will also give you a good idea of what they’re looking for.


Finally, how do you maximize your chances of landing a job with a great boss?

Good bosses want unusual talent and quirks. Finkelstein describes how Ralph Lauren once hired someone to head women’s design because she just “got the clothes.”

So two great tips in interviews are: 1) leave everything on your resume. You never know when your boss will also be a figure-skater or care about animal rights. Amazing bosses want to you to try different things and will take chances on hiring people to do new projects that have little to do with their previous experience. And 2) be yourself in interviews. Good bosses are intuitive at hiring and they want to know if they click with who you really are.

Isvari Mohan can be reached at voice@isvari.com. Follow her on Twitter @IsvariM.