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About this Report

The Chicago Public Education Fund (The Fund) is a nonprofit organization that improves Chicago’s public schools by investing in the talented educators who lead them. At the end of each school year, we provide an update on our programming, the scope of our engagement, and additional context on the schools we serve. This report outlines our lessons learned in 2021-22 and previews our plans for investing in innovation and school leadership in 2022-23 and beyond.

Reflecting Back

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Leaders SERVED

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Students Impacted

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Heading into the 2021-22 school year, principal satisfaction reflected the pandemic’s heavy burden on school leaders. As measured by The Fund’s summer 2021 Principal Engagement Survey, 54% of principals were satisfied in their roles, down from 66% in 2020 and from the high point of 78% in 2019. Yet educators, students, and families were hopeful that reconnection and learning would define 2021-22.

Those hopes were quickly tempered; most school leaders spent significant time in 2021-22 navigating evolving health protocols, changing operational priorities, flipped classrooms, staffing shortages, and missed instructional days. Principals and their teams juggled it all while doing their best to center students and communities.

To support them, The Fund team remained adaptive and solutions-oriented. We met educator and community needs where we could, ultimately exceeding our annual goal of reaching 300 district and charter leaders
in our programs. In 2021-22, Fund programs collectively supported 315 principals and aspiring principals, including 115 Black and 42 Latinx leaders. Together, these leaders served over 130,000 students in 246 schools across the city.

This reach is only possible because school leaders value our support. Among Fund program participants, 93% reported being extremely satisfied or satisfied with their experience. Specifically, participants valued the set-aside time to focus on leadership development and the embedded peer learning. They also appreciated both formal and informal resource-sharing opportunities.

“What’s exciting about being a part of The Fund? The focus on adult learning and selecting topics for my development and that of others.”


That said, when reflecting on our impact and achievement, we also prioritize student outcomes. Complete data for 2021-22 are not yet available, but we will publish a summary of our program impact on both leadership strength and student learning in the first quarter of 2023.

Supports for School Leaders


We helped educator teams design solutions for evolving student needs and fostered a culture of innovation among school leaders. Our largest program was our Summer Design Program (SDP), which included Professional Learning Communities (PLCs) and design-thinking workshops.

As part of SDP, we partnered with Leadership + Design to host eight design-thinking workshops for 95 school teams. This work culminated in a virtual Design Challenge. Participating school teams received individualized coaching and up to $10,000 to reimagine a practice that could meet the needs of priority students. Our Innovation Showcase and a set of case studies released in June helped amplify these projects.

In the lead-up to 2022-23, we partnered with the Office of Teaching and Learning for Chicago Public Schools (CPS) to help schools launch 19 student-centered summer enrichment programs.

Our PLC participants deeply valued the opportunity to learn from their colleagues’ experiences and build community; 100% of PLC leaders shared that they would recommend serving as a PLC leader to a friend or colleague. In 2022-23, we will host 22 PLCs serving at least 275 school leaders.


We collected new data to better understand the assistant principal (AP) school experience and expand our AP-focused programming. Ultimately, we served 20% more aspiring principals than in 2019-20. 

We successfully launched our inaugural AP Engagement Survey, which received a 63% response rate from district APs. APs voiced a need for additional say in district decision-making and more opportunities to grow as leaders. We will deploy this survey annually to inform our work in strengthening Chicago’s school leadership pipeline.

In 2022-23, we will launch an Assistant Principal Leadership Acceleration Pilot to improve the pathway to a principal position for Black and Latinx leaders in CPS.

This pilot will focus on:

  • Strengthening and leveraging professional networks.
  • Preparing for the CPS principal eligibility process.
  • Navigating the interview process.

Our evolving program suite for aspiring principals provides new opportunties for leaders to obtain principal-like experiences.

Chicago Principals



The Fund has long been an important convener of key stakeholders on issues related to school leadership. We expanded this role in 2021-22. We held five bilingual workshops for 45 Local School Council (LSC) members representing 35 schools. LSC members participated in peer learning around elected leadership, community engagement, and the principal evaluation process.

In addition, The Fund team re-launched our Educator Advisory Committee (EAC), which created room for school leaders across networks and school types to pinpoint pressing issues. EAC members worked in small groups and identified tangible solutions to school or system challenges.

We also supported citywide conversations around the needs of Chicago’s youth. For example, we organized a discussion with the University of Chicago Consortium
on School Research, the Latino Policy Forum, and CPS
on best practices for teaching English Language Learners in May 2022.

Finally, we continued working with A Better Chicago, the Obama Foundation, and Thrive to create a Youth Opportunity Index to understand the community-level needs of Chicago’s youth based on metrics from birth through adulthood.

Looking Ahead

We were pleased to meet our program participation goals in a challenging year, to expand our efforts to remove barriers to leadership, and to deepen our stakeholder engagement. We also recognize that significant work remains as school leaders work to accelerate student learning. The 2022-23 school year is critical for principals, for CPS, for The Fund, and for all of Chicago’s youth.

In response, we are expanding our program capacity and launching new supports. In collaboration with citywide stakeholders, we aim to serve over 400 school leaders through our programs, with a focus on engaging leaders new to The Fund. We will continue reducing barriers for aspiring principals while increasing support systems
for leaders in the schools that need them most.

To learn more about our work with Chicago’s school leaders, please visit TheFundChicago.org.

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