Learn to Be a Superboss


Through collaboration with the Holdsworth Campus Leadership Program, educators from Klenk, Zwink, Kuehnle, and Vistas are focused on their personal leadership development.

During our week with Holdsworth in July, we learned from world-renowned leaders such as Sydney Finkelstein, author of Superbosses.

The luckiest of us can think back fondly on a leader who was a superboss. This is someone who developed and empowered us. Someone who gave us opportunities to take risks and supported our growth. I am extremely grateful to have worked alongside a number of superbosses. They have inspired me to continuously grow and improve as a leader.

I highly recommend you all read Superbosses. During our time together with Sydney Finkelstein, we took time to think about our past bosses. The purpose of the activity was to gain a greater awareness of a superboss’ practice.

I encourage you to take a few moments to reflect on your past bosses, just as we had the opportunity to do with Sydney.

  • Step 1: You’ll need a piece of notebook paper and a writing utensil. On one half of the paper, list the best bosses you’ve ever had. On the other side, list the worst.
  • Step 2: Think back on your career as an educator, your high school or college job, any sports teams you were on, and maybe even some volunteer opportunities in which you took part.
  • Step 3: Consider the most memorable behaviors and characteristics of your best bosses and think about the impact those behaviors had. How did the behaviors compare to your worst bosses?
  • Step 4: Now it’s time to reflect. Have you taken on the behaviors of your best bosses? Have you taken on some of the bad habits of your worst bosses?

This activity made me realize that I’ve still got plenty of work to do in the leadership department. I am still learning and growing. Sydney Finkelstein encouraged us to create next steps and to establish a goal of being more like our best bosses and less like our worst bosses. If you’re really wanting to grow as a leader, set aside time to reflect on this exercise 10 minutes a day for the next month. Use these 10 minutes to reflect on practices of your best bosses. At the end of the month, think about how you’ve done. Did you notice any changes as a result of focusing on these good behaviors and avoiding the bad ones?

Thinking about your past bosses is a great way to grow as a leader. Keep your focus on what makes a great leader.