Chicago’s Fight to Keep Top Principals
2015 School Leadership Report

About The Chicago Public Education Fund

The Chicago Public Education Fund (The Fund) is a nonprofit organization working to increase the number of great public schools in Chicago by supporting talented principals and enabling effective educator teams to reinvent classroom learning. Our current efforts seek to more than double the number of top principals in Chicago’s public schools by 2018 and to enable the city’s best educators to redefine what’s possible for our schools and students.

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A Letter from
Heather Y. Anichini,
CEO of The Chicago Public Education Fund
(The Fund)

We must create an environment that allows our best leaders to learn, grow and stay.

One Big Goal:

Chicago as the Best City in America for School Leadership

In late 2013, The Fund raised $20 million with the goal of increasing the number of top principals in Chicago from 150 to 350 by 2018. At that time, we believed that our core challenges were a lack of great candidates and failure to hire the very best talent into principal roles.

While it’s true that Chicago does not recruit, train or hire enough great candidates to meet the city’s needs, a larger issue quickly became apparent: Chicago’s principals are disappearing. Our data show that principal performance peaks around year five, but Chicago loses 6 out of 10 principals before this milestone. The systems that surround, support and retain principals are broken. That’s bad for our students, teachers and families.

To address this issue, we broadened our strategy. In addition to supporting quality recruitment and hiring, The Fund is now also working to significantly improve the conditions in which principals lead schools. We published our 2014 survey of Chicago’s district and charter principals School Leadership: A Baseline Report. It highlights principals’ widespread desire and need for more differentiated leadership development opportunities and increased flexibility in their roles. These insights built momentum for the second year of the Chicago Principals Fellowship and helped spur Chicago Public Schools’ recent creation of a new Independent Schools Principal Program.

This summer, we surveyed principals again. This time, we heard even more voices from across the city; 423 principals answered us. This represents 65 percent of Chicago’s public schools and is a 50 percent increase over our 2014 survey. The results suggest similar themes, and they provide a deeper look into how we can keep and empower great principals to lead growth and change in their schools.

We have a long way to go: despite high levels of general satisfaction, principals overwhelmingly tell us that their jobs are simply unsustainable. More than 40 percent of top Chicago principals plan to leave in the next three years; 25 percent in the next year. Informed by principals’ own ideas, this report outlines the actions we can take as a city to begin reversing this troubling trend.

Over the next year, The Fund will continue leading this work. Along with members of the Donors Forum Leadership & Human Capital Group, we are renewing our call for principal leadership to be a central focus of Chicago’s education community. We are encouraged that Chicago Public Schools has recently convened a Principal Quality Working Group to examine this issue. The Fund is prepared to consider future investments that align with and advance the Working Group’s recommendations.

To achieve our city’s shared goals for public school excellence, we must make Chicago the best city in America for school leadership. The next step on that path is keeping our top principals for longer. Equipped for the first time with details about what principals need, and ideas on how we might work together to provide it, we believe this goal is within reach.

If we are serious about providing world-class public schools for all of Chicago’s students, we must create an environment that allows our top leaders to learn, grow and stay.


Heather Y. Anichini,
CEO, The Chicago Public Education Fund (The Fund)


Executive Summary

Chicago is losing its best school leaders. Four out of every ten of the city’s top public school principals tell us they plan to leave in the next three years. History says we should take them seriously; that number is consistent with the number of principals who did leave in the last three years.

Rapid principal turnover has real implications for all of us – especially our students. Principal departures are associated with declining student achievement, which can persist for up to two years.1 Like leaders in all industries, principals are also uniquely influential in the retention or turnover of their best team members. Even through times of transition or resource reduction, great principals keep great teachers.2 This benefits students, schools and communities.


So how can we ensure great principals stay longer?


Get out of their way.
7 in 10 principals say reducing compliance is one of the top three ways to improve their job satisfaction.
Principals are the instructional leaders of their buildings. They want to spend their time coaching teachers, observing learning in classrooms, and working with students and families, but they are often bogged down by paperwork and slowed by district demands. Spending more time on teaching and learning can help principals improve their schools;3 it can also make them happier – and more likely to stay.


Help them leverage the tools they already have.
40-50% of principals feel unable to organize school resources in ways that advance school goals and priorities, despite having the authority to do so.
State and district policies grant Chicago principals significant control in creating a school budget, schedule and curriculum. Too many principals feel unable to meaningfully use the flexibility they have, and this leads to frustration. More actionable tools and targeted coaching can help all principals lead change in their schools and help newer principals experience success sooner.


Support their individual development.
Principals are 3 times more likely to rate a development opportunity as “excellent” if they choose the activity.
Like every other professional, principals need personalized support in order to develop and learn new skills. Unfortunately, the current professional development model too often follows a one-size-fits-none approach. Principals find this demoralizing and demotivating: less than 25 percent rate current offerings as “very good” or “excellent.” When asked for suggestions on how to improve, principals’ most common request is for more responsiveness to their individual needs. By personalizing professional development for principals, we can increase their satisfaction and help them become more effective.


Challenge them to stay.
6 out of every 10 Chicago principals leave before the end of their fifth year – around the time data suggest principals reach their peak effectiveness.
Currently, only a few dozen Chicago principals are recognized for their excellence and challenged to expand their impact each year. If we want our principals to stay – through year five and beyond – we must act urgently to grow programs that keep top leaders engaged. Expanding leadership opportunities to new schools or new roles and creating meaningful chances for peer-to-peer learning can help top leaders stay and redefine what’s possible for students.


How we define top principals:

We start with student outcomes. We look at principals with at least two years of experience whose students grew on standardized tests more than those at similar schools. School culture matters, too. We identify strong learning climates based upon the Consortium for Chicago School Research’s 5Essentials.




Who Are Chicago’s Principals?

Diverse, mid-career professionals with significant responsibility



70% are between the ages of 36 and 55.


90% hold master’s degrees, 
and 1 in 20 has a doctorate.

The top three degree-granting institutions are:

1 Chicago State University
2 Northeastern Illinois University
3 University of Illinois at Chicago


46% are in their first three years as a principal; 62% are in their first five years.




In school year 2014-15, the median principal was responsible for:



Source: Available citywide data for 2014-15 school year.


The median principal salary is $132,036.

Why They Lead


About This Report

In 2014, we began surveying all of Chicago’s district and charter school principals with one goal in mind: to understand what they need to continue improving and stay engaged in their jobs. We complement these surveys with principal focus groups and exit interviews, ensuring we hear detailed suggestions and grasp the intention behind the feedback offered.

Over six weeks in the summer of 2015, we conducted our second citywide survey of principals. This report summarizes what 423 of them had to say.



Who Took Our 2015 Survey?






A Challenge for Chicago: Keep Our Top Principals


A Challenge for Chicago: Keep Our Top Principals

Over the last three years, almost half of Chicago principals quietly disappeared. Without fanfare, they made the decision to retire or resign from their roles. Among current principals, 44 percent – many of them top performers – plan to go just as quietly in the next three years. If this pattern holds, it will cost the 150,000 students and 7,000 teachers in their schools dearly. What’s more, it will undercut the progress our city has made to ensure every school is led by a great principal.

Since 2013, the number of great principals in Chicago has increased by 33 percent – from about 150 to more than 200. With the right investment of time, talent and resources, the city remains on track to 350 principals by 2018. This is the result of the hard work of so many in the school, nonprofit and funding communities; uniting to recruit stronger talent, to help high-potential principals develop and achieve more, and to encourage principals to pioneer innovations that redefine what’s possible for the students we serve.

If we want to accelerate our progress toward 350 and move beyond it, we must address the urgent challenge of keeping our top principals in schools for longer. Short of that, we’ll merely replace existing strong principals with new ones, unable to advance from a place where little more than half our students have access to great leaders in their schools.

To serve every student well, we must minimize the time principals spend on compliance, help them leverage their school resources, meet their individual development needs, and provide challenging opportunities that keep them engaged. That work cannot be done alone.

But it can be done.

Chicago can be the best city in America to lead a public school.

The future of our public schools and the fabric of our great city depend on it.

How You Can Help:

Parents and community members can recognize great principals in their schools. Thank principals for their tireless work or ask how you can support them – no effort is too small.


Nonprofits can continue to improve professional training and resources for principals. Modify your offerings to ensure all principals receive the personalized support they need.


CPS and charter networks can remove unnecessary burdens on principals’ time, recognize principal achievement and growth in meaningful ways, and plan for effective succession of school leaders.


Philanthropies can accelerate principal quality efforts. Build on investments in principal training by expanding funding to include individualized support and retention efforts.


We would especially like to thank Fund team members Nelson Gerew, Matt Lyons, Destiny B. Ortega and Lauren B. Rapp for their contributions to this report. Additionally, we are grateful to the principals featured in this report and to all of the principals who participated in our 2015 Principal Engagement Survey.



Tyre, Peg. “Why do more than half of principals quit after five years?,” The Hechinger Report (2015). [September 26, 2015].


New Leaders. Leadership Matters (2015). [April 5, 2015].



Bryk, Anthony S., Penny Bender Sebring, Elaine Allensworth, Stuart Luppescu, and John Q. Easton. Organizing Schools for Improvement: Lessons from Chicago. Chicago: University of Chicago Press, 2010. Print.


Unless otherwise cited, all data in this report comes from analysis of CPS data and/or The Fund’s surveys and focus groups.

Great leadership is required for world-class public schools.
Copyright © 2015 The Chicago Public Education Fund
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November 2015