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Superbosses: How Leaders Guide Generations of Success

“The delicate balance of mentoring someone is not creating them in your own image, but giving them the opportunity to create themselves.” –Steven Spielberg

You’ve likely encountered various leaders during your career–some with whom you worked well and others who were the impetus for leaving a job. Truly exceptional leaders–those whose brilliance in their field inspires the next generation of leaders–remain a rarity.

Sydney Finkelstein, Steven Roth Professor of Management at Dartmouth’s Tuck School of Business, shares his research on exceptional mentors in the book Superbosses. Finkelstein’s research began with thousands of articles and hundreds of interviews, from which he identified eighteen definite superbosses and several dozen likely superbosses who became the subjects for his study. These leaders include Bill Walsh, George Lucas, Lorne Michaels, Miles Davis, Ralph Lauren, and Oprah.

Finkelstein defines “superbosses” as leaders whose success extends to a future generation of leaders they mentored. Leaders in many industries–from investment banking to professional football–have worked for the same well-known leaders. 

While they share some personality traits, including confidence, imagination, and a competitive edge, superbosses also utilize the coach and mentor competency and coaching strategies similarly. These practices include unconventional hiring and hands-on leadership.

When recruiting and hiring, superbosses value intelligence, creativity, and adaptability and seek out people with these qualities. They often select people who could excel in a range of positions, not just one specific role, and will tailor a job to a mentee they see something in. And they’re willing to take risks on hires with unconventional experience or education.

Superbosses also consider the quality of talent more important than long-term retention. Instead of assuming the best people will stick around, they foster “talent flow” as a key organizational value, instead of talent retention. In this way, turnover becomes an opportunity for growth, as superbosses keep in touch with former employees and these employees’ reputations continuously bring talent to the superbosses’ doors.

When cultivating talent, superbosses set high expectations and utilize strengths in inspirational leadership to rally mentees around their vision. This innovative vision lies at the heart of their success, yet they remain eager to adapt and make changes as long as their core vision is not diminished.

Superbosses achieve a balance between hands-on management and delegation. They effectively delegate and give their mentees autonomy and space to fail. Yet they also keep an eye on progress, offering direct and timely feedback. As necessary, they shift to teaching mode to help their mentees learn new skills. When their mentees flourish under this guidance, superbosses will often create customized career paths and opportunities for advancement. 

Above all, superbosses view coaching as a long-term process that extends beyond a single job or organization. They offer advice and initiate networking opportunities long after a mentee has left their organization. This can give rise to future business partnerships. And as the superboss coaches new talent, they, too, join this network of resources and opportunities.

Experiment with the Practices of Superbosses

Becoming a superboss may feel unattainable. But you can begin by taking small steps to implement the practices of superbosses into your own life.

Superbosses often have strengths in emotional intelligence, particularly in adaptability, influence, coach and mentor, and inspiration. Honing these competencies can make a crucial difference in your ability to make a lasting, positive impact on a mentee.

If there is a specific superboss you admire, try implementing one of the methods or practices that set them apart and thus make them effective. This could range from experimenting with an unconventional hiring process to delegating more responsibility to a young mentee. However you incorporate the practices of superbosses, keep an open mind and seek the opportunities that arise from change.