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Insight

5 ways ed leaders can become ‘superbosses’

By Sydney Finkelstein, Steven Roth Professor of Management at the Tuck School of Business at Dartmouth College and director of Tuck’s Center for Leadership|December 2, 2019
Sydney Finkelstein, Steven Roth Professor of Management at the Tuck School of Business at Dartmouth College and director of Tuck’s Center for Leadership, is pictured during a Holdsworth Center session.
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Sydney Finkelstein is a professor, consultant, speaker, author, executive coach, and host of The Sydcast podcast. He focuses on talent development, learning from mistakes and how to craft a career and a life of impact. He is the author of 20 books and has shared his learnings with executives around the globe, including Holdsworth District and Campus Leaders. 


I have spent many years studying the behaviors of legendary leaders to find a common thread to their success. What I found is this: the hallmark of truly great leaders is the ability to create other leaders. To survive and thrive in the long term, any organization – school districts included – must be able to generate and re-generate talent on a continual basis.

Educators have big jobs. With children’s futures at stake, the pressure to get it right is intense.

But no educator is too busy to invest time into bettering themselves. Leaders in particular owe it to their students not only to become the best leaders they can be, but to teach others how to follow in their footsteps.

I dubbed these kinds of leaders “superbosses,” and set out to reverse engineer the habits, behaviors and philosophies that contributed to their success.

I lay it all out in my book “Superbosses: How Exceptional Leaders Master the Flow of Talent” and the accompanying Superbosses Playbook, which is full of exercises meant to help leaders strengthen their superboss powers.

An image of the book Superbosses, written by Sydney Finkelstein, taken during a Holdsworth Center District Leadership program session.

You may be thinking, “Schools aren’t businesses. We don’t operate the same way.”

While this is true, superbosses are not just CEOs and famous entrepreneurs. They are everywhere, in every organization and sector. It’s not about business, it’s about people. There is nothing in the superbosses playbook that educators can’t use to improve their leadership. With the critical role leadership plays in schools, educators should be on the front lines of this impactful work. If we know students thrive under great school leaders, why wouldn’t we do everything we can to continually grow outstanding leaders for the benefit of kids?

Interestingly, the superboss mindset often comes more naturally to educators than businesspeople. At their core, superbosses from all kinds of industries are teachers at heart. They are constantly reaching out to those around them, giving them challenges to tackle and pushing them outside their comfort zone. Sometimes they teach through modeling, other times through candid feedback. Like classroom teachers, some bosses are tough, but you know they care.

When I speak with educators, I hear a real hunger for deeper learning about leadership. They want to know how to up their game and are eager for a playbook with research-based practices to serve as a guide. Educators love curriculum! (I would know, I’m a professor).

So, what makes a superboss? Below are five things they do well:

  1. Recruit great talent – To be successful, you need incredible talent around you. There’s an old adage about hiring people smarter than you are: Everybody says it, but not everybody does it. If you are insecure, it can feel threatening, but the truth is that you will perform better and move up faster when you have better people around you.
  2. Create a world of high expectations – If you don’t ask for it, you won’t get it. Create a world in which you raise the bar, expect your team to succeed and reward those who perform well with more responsibility.
  3. Communicate a powerful vision – This is especially important in education, where teachers are not in it for the money. You must be able to inspire and motivate people with a compelling vision. People get excited when they’re around someone who is really shooting for the stars.
  4. Unleash creativity – The best teachers find ways for their students to shine. Superbosses do the same. If you micromanage people or stifle their creativity, you won’t keep them long.
  5. Customize your approach – If you’re a principal, you really have to know and care about each member of your staff. Figure out what motivates and excites each person. Investing time and energy in each individual who reports to you breeds loyalty and effectiveness.

With the right mindset and motivation, anyone can become a superboss, creating a legacy of talented leaders who will move their organization forward.

To learn more, and to take a quiz that will tell you where you sit on the superboss spectrum, visit my website.

Sydney Finkelstein, Steven Roth Professor of Management at the Tuck School of Business at Dartmouth College and director of Tuck’s Center for Leadership|


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