How to Become a Principal: An Interview With Derrick Kimbrough

Last year, we interviewed Principal Derrick Kimbrough of Jahn School of Fine Arts to learn about his journey to becoming a principal. He is an active participant in our programming — including Leadership Bridge, Professional Learning Communities, and the Summer Design Program — and has an interesting story to share. This interview has been edited for clarity and length.


The Fund: Tell us about yourself and how you got into education as a career.

Principal Kimbrough: I started as the new principal of Jahn School of Fine Arts on July 1, 2022. [It was] my 18th year in education. Education, to me — I think it was something I always knew I wanted and somewhere I needed to be. Initially, I joined the United States Environmental Protection Agency here in Chicago. I worked mainly in the Office of Public Affairs, where I did community and media relations. About eight years into my career, I realized I wanted to do something different. So I started thinking about it, and I decided to get my substitute certificate. I decided to, at least, take a stab at being a substitute teacher. On my first day, I knew it was what I wanted to do. So from there, it was a matter of figuring out how I could get into teaching. I had no education degree and no experience whatsoever. Eventually, I found an alternative teaching program and got accepted into it. That’s how it all started.


The Fund: How did you find the Jahn School of Fine Arts?

Principal Kimbrough: Jahn actually found me, to be honest with you. I was quite comfortable in my assistant principal position, but I knew at some point I wanted to move into a principalship. Working with The Fund, I had done Leadership Bridge, and that helped me figure out where I was going. I even worked on a Professional Learning Community for assistant principals. I was comfortable at Skinner North [Classical School]; I was happy I was doing work that I thought spoke to the needs of the community. I was doing work around equity, which really is a big driver for me. Then, a member of the Jahn Local School Council reached out. I guess they saw the things that we were doing at Skinner North. I applied, did a number of interviews, participated in a public forum with the finalists, and eventually was offered the role of principal, in which I now sit.


The Fund: Tell us about your time at Skinner North and your transition to Jahn.

Principal Kimbrough: Skinner North, interestingly enough, is one of the few selective enrollment elementary schools in Chicago. Our students come from all over the city and have to test into the school. Something I appreciated during my time there was my work around distributive leadership, really learning that the work of leading a school can’t necessarily be done by the administrators alone. It takes a lot of calling on and pulling on members of your staff to actually help do that work. And interestingly, that has carried over into the work that I’m doing at Jahn.

The first thing that I wholeheartedly did with my staff was reach out and say, “Hey, I am new, but this work is not going to be done by administration alone. I need you guys to step up.” And overwhelmingly, the staff have definitely risen to the occasion, doing everything from helping figure out what professional development week is going to look like, to revitalizing our instructional-leadership team, to leading interviews for open positions within the school. They have really jumped out there and taken the lead on what needs to happen to move the school forward beyond the actual leadership of the school leader. So that has been something that I could wholeheartedly say has been brought over to Jahn, as well as a lot of work around equity I did at Skinner North.


The Fund: Can you tell us a little bit about your time in Leadership Bridge?

Principal Kimbrough: I think the Leadership Bridge program really did so much for me. And the good part about it is that it provided me, first and foremost, with a continuous opportunity to be a part of a triad to grow as a leader. That triad consisted of my principal at the time and my leadership coach from the University of Illinois Chicago. So while I had some opportunities to do that on my own, Leadership Bridge gave us the chance to come together more often as a team and really build upon the principles and ideals that we learned during our meetings. We could take what we learned from those sessions and actually apply it. It really assisted me in laying the groundwork for thinking about what my next moves were as a leader.


About Leadership Bridge

Leadership Bridge supports the leadership development and career growth of assistant principals (APs) so that they are ready to assume principalship in the next one to two years. It aims to ensure that Chicago has a robust, high-quality, and diverse pipeline of school leaders. Through on-the-job professional development and individualized coaching sessions from school leadership experts at New Leaders, the University of Illinois at Chicago, and Accelerate Institute, APs work in close collaboration with their principals to prepare for their future roles and to develop succession plans for their schools.

Since the inception of the program in 2019, The Chicago Public Education Fund has supported more than 60 AP and principal pairs to develop clear succession plans for their schools, and has seen more than 20 APs successfully become principals in Chicago schools.

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