Celebrating Principal Appreciation Month with an Exceptional Administrator-in-Charge

Ramona Outlaw wrapped up her decades-long career in Chicago Public Schools by serving as the principal of Harlan Community Academy High School. After retiring, she stepped away from education for a bit, but she notes that she started to feel a yearning to be around students again. 

So, she took advantage of an opportunity to rejoin CPS as an administrator-in-charge (AIC), a position that provides school leadership for schools during periods of transition. She’s served at a number of schools in this capacity, and her latest assignment is a full-circle moment—she’s back at Harlan. 

It’s the perfect opportunity to catch up with her about why she continues to serve students even after retirement, especially since it’s Principal Appreciation Month. Read more about her experiences below.

Has your time as an AIC been what you expected, or has it been more unexpected? 

Both. When I was given my first assignment, I expected to be fully prepared, since I knew that I would need to learn the school culture and be a partner to those already working there. However, my expectations were actually exceeded. Every single person in the building was a partner for me. 

I didn’t expect to have the same reverence that I did as a principal, since I saw myself more like a guest in the building, or a substitute principal, if you will. But I’m reminded that it’s still my job to coach and to lead. At the end of the day, you need to strive to make the school community a better one in partnership with all of the other entities at the school. 

How has it felt to be back at Harlan? 

I think back to when I came to Harlan for the first time. I was raised in this community, and it’s the reason I came to work here. I think it does help to be somewhere at least a little familiar when you’re in a role like this. School leadership is really, really rewarding. Something I realized recently is that the word community ends in -unity. That highlights how unity and cohesion with members of the school community are so valuable. 

Your entire career in CPS was serving high school students. How did it feel to be the AIC at an elementary school? 

I was always intimidated by the younger students, but after working with the little ones while on assignment, I feel differently now. My belief in the value of establishing trust with students by listening and learning about the “why” of what they do, instead of providing an immediate response with “how” they should do something, is so valuable in building a relationship with any student. While the style of communication is different with different age groups, the process of establishing trust is not. Leading with love is something every child understands.

What advice would you give to someone else who is starting out as an AIC? 

Your top priority should not be to change things. The school community is really in charge, and you’re there to support them. At the same time, the work is really gratifying. It is work that will let you be at the intersection of passion and purpose. 

What is your message to the students at Harlan whom you are currently supporting? 

School is a place you come to learn, to lead, and to become better people. Your time in high school should be a transformative experience. You should leave Harlan better than when you came in because you’ve been educated on how to be a good student, a good friend, and a good leader in your community.