The 5 Habits of Spectacularly Successful Bosses

What you can learn from leaders who aren't afraid to seek out and embrace change.

learn more about Sydney Finkelstein

By Sydney Finkelstein

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The imperative to innovate is greater than ever, but what should bosses and executives do to amp up creativity? Over the last ten years, I've studied how the world's best bosses create wonderfully fertile environments that foster industry-shaking innovations. No two of these bosses are exactly alike, but my research reveals five actions the world's best bosses all take to generate exciting new thinking in their organizations.

1. They foster innovation.

They mostly do this by removing the anxieties that often prevent people from trying new things. Legendary film producer Roger Corman was known for letting his actors improvise in front of the camera -- even if that particular shot didn't work. Without their boss breathing down their necks, employees feel free to take chances and they frequently do. Great bosses in general trust employees and believe in their talent, and this enables them to feel secure enough to try something new. When employees do fail, these bosses usually re-frame it as an opportunity in disguise.

Related: 7 Things That Make Great Bosses Unforgettable

2. They encourage employees not to rest on their laurels.

"You always get the sense," talk show host and former Saturday Night Live writer Conan O'Brien said, "That the show is almost like a shark that's constantly on a mission to find what's new, what's hot, what are people into now. And chomp its teeth into it." Such proactive novelty seeking was quite intentional, spurred onward by SNL's legendary producer Lorne Michaels. As he remarked, "The show must change. I know it's supposed to be "must go on,' but "must change' is important also."

Related: The 5 Secrets of Great Bosses

3. They exploit opportunities to adapt their businesses.

The best bosses eagerly jump on promising new ideas as soon as they arise. Initially Norman Brinker had planned to establish a friendly Mediterranean-themed restaurant combining features of fine dining and fast food. But then he saw the classic film Tom Jones and was mesmerized by a scene in which two characters eat a voluptuous dinner in an eighteenth-century English tavern. An idea came to him: that setting was a more enticing atmosphere for ordinary diners. So Brinker pivoted, abandoning the Mediterranean theme midstream and constructing the first Steak & Ale restaurant. The reason more entrepreneurial companies are usually the ones doing the "pivoting" is that bosses in more established businesses value stability over change. And that's a losing formula.

4. They're always hunting for the next great innovation.

When J. Crew CEO Mickey Drexler gives lectures to students, he doesn't just deliver wisdom -- he uses the occasion to run an informal focus group. "How do you like your Ludlow jacket?" he'll ask of a student wearing J. Crew merchandise. "Where did you buy it? Do you find it matches well with our chinos? How many of your friends have Ludlows?" Drexler is perpetually looking for nuggets of information and windows into ways J. Crew might improve what and how they sell.

Related: 5 Key Ingredients for Corporate Innovation

5. They encourage constant risk-taking and rule breaking.

They don't just want their employees to do it, they practice this behavior themselves. When Cincinnati Bengals' quarterback Greg Cook was knocked permanently out of action in the 1980s, celebrated NFL coach Bill Walsh, then an assistant coach, devised an entirely new offensive scheme. Since the team could no longer rely on Cook's raw athletic talent, Walsh's new approach emphasized mobility, accuracy and intelligence -- all of which were strengths of the team's backup. The risk paid off: Walsh's new system -- the now legendary West Coast Offense -- propelled the team to its first division title. The episode sent a message to all of Walsh's subsequent hires: when it comes to new thinking, everything is fair game.

There's no formula for divining the next great idea, but what you can do is develop a series of habits that increase your chances of an innovative breakthrough. You can set the stage for creative thinking, taking actions to make sure that when the next great idea swims past, you're ready to bite. The world's greatest bosses do this. So should you.

Sydney Finkelstein

Professor at Tuck School of Business at Dartmouth College.

Sydney Finkelstein is the Steven Roth Professor of Management at the Tuck School of Business at Dartmouth College, as well as Tuck’s Director of the Center for Leadership. He is a consultant and speaker to senior executives around the globe, as well as an executive coach, focusing on talent development, corporate governance, learning from mistakes, and strategies for growth. He has published eight previous books, including the Wall Street Journal bestseller Why Smart Executives Fail.

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