The search for the National Assistant Principal of the Year begins every fall as each state principal’s association selects its State Assistant Principals of the Year. From this pool of state award winners, a panel of judges selects three finalists.

2022 National Assistant Principal of the Year finalists

Philip Rossetti

Philip Rossetti
Windham High School
Raymond, ME

Philip Rossetti believes that people make mistakes, but it’s what they do after that defines who they are. He used this principle to transform how Windham High School manages student behavior, focusing on restorative justice to hold students accountable and repair the harm they caused their school community. This restorative approach has improved school safety and reshaped school culture, fostering stronger relationships between students and turning mistakes into opportunities to learn.


Randy Oliver

Randy Oliver
Van Horn High School
Independence, MO

Randy Oliver knows that relationships are key to educator and student success. He led the staff in creating a shared student-centered vision to guide their work with each other and their community during the pandemic and beyond. This vision propelled initiatives to meet this challenging moment, such as a Cultural Competence Team that ensured every student felt valued and a weekly Academic Time to check in on their individual progress. This emphasis on relationships helped move Van Horn from a 50% graduation rate to a present-day graduation rate of 89.4%.


Katherine Holden

Katherine Holden
Ashland Middle School
Ashland, OR

Katherine Holden moved Ashland Middle from traditional letter grades to a proficiency-based feedback system that helped students grow through precise and timely feedback. Holden guided her teachers through creating rubrics that are clear, explicit, and accessible to students, and engineering a schoolwide system which included development of new software to create a responsive gradebook. The data shows her work is leveling the playing field regardless of students’ race, gender, first language, socioeconomic status or support at home.