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3 Superboss Strategies That Will Transform Your Managers

Sydney Finkelstein

Udemy for Business instructor and author of Superbosses

February 21, 2019

Ask a CEO in 2019 what their top concern is, and chances are, they’ll tell you that they need to figure out how to find and retain the world’s best talent. But if you asked a CEO the same question 20 years ago, they would have said the same thing. Doing the same thing we’ve been doing for the past 20 years can’t be the solution. I believe the answer is in redefining what a high potential is, and learning how to create these people in your organization.

I’ve done extensive research on managers who are able to create extensive networks of exceptional talent, build tremendous organizations, and transform their industries. These men and women go beyond just being good bosses—they’re superbosses. People like Alice Waters, George Lucas, Miles Davis, and Ralph Lauren are exceptional leaders who help other people accomplish more than they ever thought possible. Contact with this person, especially working for him or her, seems to put people on a fast track to success.

In my Udemy for Business course, The Superboss Playbook for Managers, I identify many of the practices that superbosses have in common. Let’s look at some of these practices—recruiting unusual talent, energizing and motivating employees, and unleashing creativity, to understand how they might help transform your managers into superbosses.

1. Look for ways to recruit unusual talent

One of the characteristics that sets superbosses apart from others is their keen ability to recruit unusual talent—and to do so in unorthodox ways. Virtually all superbosses place an emphasis on having everyone around them be as smart as possible, and they suss this out not only through interviews but by also observing people closely during on-the-job trial periods.

Superbosses make their own rules when it comes to hiring. For example, they often eschew traditional job descriptions in favor of people who demonstrate creativity and brilliance. Style icon Ralph Lauren looked for a kind of “fashion intelligence.” He wanted everyone who worked for him, even in the most menial roles, to have a fashion sense and be able to say interesting things about clothes. Lee Clow, one of advertising mogul Jay Chiat’s closest associates, emphasized that Chiat “didn’t hire off the conventional portfolio/resume—he looked for people who did things creatively.” The way Clow himself was hired illustrates this principle: he created an ad campaign featuring slogans, bumper stickers, T-shirts, mailings, and more about why Chiat should hire him. He persistently followed up with Chiat’s firm until they hired him. At Chez Panisse, rather than poring over someone’s resume, owner Alice Waters asks potential new hires to come work in the kitchen to demonstrate their abilities.

What superbosses appreciate is that it takes unconventional hiring practices to get people with unusual talent. This means they take a personal, intuitive, bold, inventive, opportunistic, and passionate approach to hiring.

To put this in practice at your organization, help your hiring managers learn to resist the urge to automatically eliminate prospective hires solely on the basis of their past credentials and experience. Job descriptions don’t need to be eliminated, but they also shouldn’t be treated as checklists. The formal job interview can also be loosened up to incorporate new elements. Consider how hiring managers might create trial periods or give prospects the chance to show off their skills.

2. Create opportunities to energize and motivate employees

Superbosses understand that they need more than just engaged talent: they need energized, supercharged talent. Survey after survey indicates that millennial employees want to feel like they’re part of something meaningful—when they don’t believe a company shares their values, they’re more inclined to leave. They don’t just want a job—they’re looking for passion. This is why it’s critical to think about how to bring superboss motivation and inspiration to your people.

One of the strategies superbosses employ to achieve this is to insist on perfection and push employees beyond what they thought they were capable of. Lee Clow said Jay Chiat was “always demanding of everyone to do something better than they very often knew or thought they could or were capable of.” Similarly, of Ralph Lauren, Kenn Thomas, former Polo employee says, “Ralph was fantastic at giving opportunities to people who didn’t even know themselves what they were capable of.”

Superbosses understand that sending a message of possibility is the way to encourage people to work their hardest. Showing people that they already are creative, resourceful, and tough is one of the ways superbosses instill self-confidence in their teams.

To help your managers achieve this, I recommend putting together a highlight reel to convince your employees of their greatness. Managers can use stories about their teams, their accomplishments, and adversity they’ve overcome to create a strong group identity. It’s possible for managers to create the highlight reel on their own, but involving their teams will further engage and energize them. I also recommend reinforcing this story over time to remind everyone of the importance of what they’ve achieved and motivate them for continued success.

3. Organize work in ways that unleash creativity

Superbosses excel at promoting creativity and innovation. They understand that the working environment they establish is critical to achieving these goals.

A willingness to learn and improve is an essential characteristic all superbosses possess—and they encourage this growth mindset on their teams as well. Superbosses don’t think about failure the way most people do. They are masters at reframing failure as an opportunity in disguise. By turning failure into opportunity, superbosses remove the fear from failure and give their team members permission to take chances.

In addition to reframing failure, superbosses like George Lucas also allow their employees to be truly creative and innovative. Ron Gilbert, who worked in the games division of Lucasfilms in the late 1980s and ‘90s, explains that unlike other games designers who were bounded by their sophisticated understanding of consumer tastes and habits, the creative environment at Lucasfilm “just produces very interesting and different ideas; it just kind of makes you feel that it is okay to explore.”

Superbosses aim to inject creativity into their daily work, not just through big initiatives or occasional creativity sessions. This is what I call microcreativity. It doesn’t take a lot of time to foster this, but it does take a great deal of focus. There are a few different techniques managers can use to foster creativity on their teams. For example, they can spark more frequent creative thinking by asking their team for new ideas in the moment, rather than waiting for more formal brainstorms. They can hold brainstorming meetings every few weeks instead of just when there’s a specific problem to solve to keep the creativity flowing regularly. And they can show that they are open, inquisitive, and bold to encourage similar behavior in their reports.

One of the things that’s so powerful about superbosses is that the extraordinary practices that contribute to their success are teachable. That’s why I’ve distilled them into my Superbosses Playbook for Managers course, so that you can help all your managers hone these skills and build your own organization of superbosses.

About the author:

Sydney Finkelstein is Professor of Leadership at the Tuck School of Business at Dartmouth, a speaker and consultant to global organizations, and the author of the bestselling book Superbosses: How Exceptional Leaders Master the Flow of Talent, which LinkedIn Chairman Reid Hoffman calls the “leadership guide for the Networked Age.”

About Udemy for Business:

Udemy for Business is a learning platform that helps companies stay competitive in today’s rapidly changing workplace by offering fresh, relevant on-demand learning content, curated from the Udemy marketplace. Our mission is to help employees do whatever comes next—whether that’s the next project to do, skill to learn, or role to master. We’d love to partner with you on your employee development needs. Get in touch with us at business@udemy.com

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