School & District Management Leader To Learn From

In Chicago’s Rough and Tumble Politics, Schools Chief Rises Above the Fray

By Sarah D. Sparks — February 21, 2018 10 min read
Janice K. Jackson
Janice K. Jackson
Recognized for Leadership in Supporting Urban Schools
Supporting Urban Schools
Chief Executive Officer
Success District:
Chicago Public Schools
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If you are going to walk a high wire, it helps to have some tethers. Janice K. Jackson has spent her entire career weaving a net of support for improving the Chicago public schools.
This year, she will be drawing on every tie she’s made in a lifetime of education in Chicago—chief education officer, the head of a school network in the district, founding principal of two schools, a history teacher, a student, and a parent—as she steps in as the latest chief executive officer of the Windy City district.

In the CEO’s job—a position whose two previous occupants, Forrest Claypool and Barbara Byrd-Bennett, resigned amid scandal—Jackson will answer directly to Mayor Rahm Emanuel, who has control over the district.

“She’s grown up in the system,” said Mary Ann Pitcher, the leader of the Chicago schools research partnership at the University of Chicago Network for College Success, “and over the course of however many CEOs we’ve had, I think one of the biggest obstacles continued to be people not having any institutional memory or history or relationships. She’s been able to really capitalize on what’s been working and build on it.”

Lessons From the Leader

  • Develop Leaders: Build cohorts of future leaders at every level within the district’s structure.
  • Use Principals as Policy Advisers: Give principals an explicit voice in developing policy.
  • Cultivate Community Trust: Commit to ongoing, difficult conversations with parents, staff, and community members to explain policy structure and build support for changes.

Jackson, 40, a native Chicagoan and the city’s only schools chief in recent memory to have her own child in the public schools, argues the answer to the district’s financial and academic issues is the same: Build trust and nurture principals’ authority to make decisions.

She was in middle school when then-U.S. Secretary of Education William J. Bennett labeled Chicago schools the worst in the nation, and then-Mayor Richard M. Daley took over the system. “[Bennett] said back then it would take a man of steel to turn Chicago around,” Jackson recalled.

She said she disagreed both with Bennett’s dismissal of the district’s strengths and his prescription: “It takes not just one ‘person of steel,’ but all the leadership of all the schools.”

In her role as chief education officer between 2015 and the end of last year, Jackson dramatically expanded principal professional development, mentorships, and community involvement in district policy. She did all that while often acting as the public face of the administration during some of the district’s most contentious debates of recent years, from budget cuts and school closures to common-core-based testing.

Homegrown Leader

Perhaps Jackson’s strongest asset is her grounding in the community.

The 371,000-student Chicago district is the third largest in the country, with more than 90 percent children of color segregated by race and ethnicity and neighborhood among 660 schools. Although Chicago enrolls nearly 1 in 5 public school children in Illinois, it accounts for more than 40 percent of black students and more than a third of Hispanic students in the state, but only 10 percent of white students.

“She has an innate ability to engage all types of people: parents, politicians, educators, students. She was able to speak to the interests of all parties,” said Gregory Jones, the principal of Kenwood High School on the city’s South Side. “What has been successful for her in navigating the process and politics and red tape is people genuinely think she cares about children and has a passion for the work. So teachers are willing to work for her, donors are willing to give money to her.”

Jackson’s first dream was to be a college history professor, but her interest turned to school administration when she took her first job as a history teacher at South Shore High School, then one of the worst in the state. Jackson had graduated from Hyde Park High School, a top-performing, overwhelmingly black campus on the city’s South Side. “Sometimes I’m embarrassed to say this, but it was the first time I really realized there was an opportunity gap between what I’d experienced and what these public school students were experiencing,” she recalled. “My focus and drive really shifted quite quickly.”

She kept teaching while earning a master’s in education at Chicago State University and a doctorate in urban education at the University of Illinois at Chicago.

At 27, after only five years in the classroom, then-schools CEO Arne Duncan tapped Jackson to redesign and lead one of the lowest-performing vocational schools in the district—what became the Al Raby High School for Community and the Environment, a nonselective college-preparatory school. Within five years, the school boasted an 85 percent graduation rate—nearly twice the rate of neighboring high schools.

She went on to open George Westinghouse College Prep, a selective-enrollment school on Chicago’s West Side that has become one of the top-ranked high schools in the state, particularly for its world-languages program. At both high schools, and later as the head of the city’s 26-school Network 9, she regularly brought in and mentored those interested in becoming principals.

“I would say even as a principal at her own school, she always had a pipeline of resident principals and other teacher-leaders in her midst,” said Pitcher of the research partnership. “A lot of people have gone on to lead from her mentorship.”

One example is the Chicago Principal Fellowships, a partnership with Northwestern University. Each year, a cohort of 30 principals receives a year of executive-management training at the university, including a leadership evaluation, coaching, and monthly training by Jackson and other staff members to study and draft district policy. In return, principals commit to leading in the district for at least three years.

As chief education officer, she also brought in principals and teachers to restructure the district’s academic departments to better coordinate across different subjects and provide 22 content teams to provide curricular support and coaching to schools. The district also created an Independent Schools Program, giving more autonomy to high-performing principals, something school leaders had repeatedly requested.

“There’s an old adage that you’re not a leader if you don’t have any followers,” said Patrick McGill, the current principal at George Westinghouse Prep. “Well, she ascribes to the notion that you aren’t a leader if you aren’t developing other leaders.”

McGill, who was a resident principal under Jackson, said she provided specific opportunities and coaching not just in instruction and operations but also in how to engage with teachers, parents, and the community. “She has a way of being able to critique so it doesn’t feel critical,” he said. “It feels like you have an advocate helping you become better at your job.”

Leveraging Principals

In 2015, roughly 60 percent of Chicago principals didn’t make it past their first five years in the district; since the introduction of the new principal fellowships, leadership programs and networks, that turnover rate is down to 17 percent, well below the national average of more than 25 percent. A 2014 study found reducing principal turnover by that much can save millions of dollars in the long term.

“One thing I’ve learned was high-performing principals need autonomy, and need the district to be very explicit about it, because school principals can innovate faster than a large district,” Jackson said. “I think our principals feel more connected to the district now because they feel empowered to improve it.”

McGill credits Jackson with giving teacher-leadership teams more authority when she was a school network leader, and, as chief education officer, with creating principal-advisory committees to redesign the school-quality rating system and process to buy instructional materials for the district. She also teamed with principals and teachers to redesign district in-service training to ease Chicago’s transition to new curriculum based on the common standards.

“As a principal, I was always frustrated with policy and the lack of involvement of the people who are most impacted by it,” Jackson said. As more principals learn about and participate in policy development, “they become much more invested in and connected with how things work, why things happen … but they also understand the roles they can play as leaders in the field, implementing.”

“What I learned pretty quickly,” Jackson said, “was not only did mentoring others help me reflect on my own learning and improve my own practice, but it resulted in people working extremely hard for me as a leader.”

Political Minefields

Principals’ support has been vital while navigating the political minefields of Chicago’s education system. “When you are doing big and bold things, you need support, people who will back you up,” Jackson said.

Jones, the principal of Kenwood High, praises Jackson for leading the move to a districtwide high school choice program, with a common school enrollment application that allows students to rank their chosen schools rather than applying to each in person.

“It’s a massive project and undertaking, but as a principal, I’m noticing it allows principals greater access to families across the district and gives families access to schools across the district, not just in a three-mile radius,” Jones said.

When you are doing big and bold things, you need support, people who will back you up.

The district’s five-year graduation rate has risen from less than 70 percent in 2015 to 77 percent in 2017, with 89 percent of freshmen also now on track to graduate. A recent Stanford University study showed Chicago students are progressing faster academically between 3rd and 8th grade than their peers in 96 percent of all districts in the United States. Moreover, that rapid growth spanned across boys and girls in every racial group, in spite of Chicago’s overwhelmingly segregated schools.

“She has been [engaging] people in the research base for how you build collaboration and support teacher development in really targeted ways,” Pitcher said, noting that under Jackson’s leadership, the district has been working to pair teams of school leaders to observe and help each other, as well as to identify particular schools making exceptional progress to become districtwide models.

Yet, under Jackson’s helm, the district faces a state investigation of special education procedures, ongoing fallout from more than a billion-dollar budget shortfall, and scandals that drove two separate predecessors from office, leaving Jackson as the seventh schools CEO in the last decade. And while she has successfully helped negotiate rancorous union contracts, she’s still left with the residual effects of years of new curriculum and testing and controversial school closures that make for easily riled parents and teachers.

Rebuilding Trust

“Trust is something that is missing in a lot of public education around the country, and particularly here in CPS,” Jackson said. “Community perception and involvement is critical. … If people don’t trust or believe anything that our senior leaders say, then they don’t believe in the academic gains that we talk about—and that goes straight to the hard work our principals, teachers, and kids do every day in the classroom.”

“We have this mayoral control, and I feel like we’ve seen over and over again that there are these hard lines that [Jackson] has to navigate within,” said Jennie Biggs, a parent representative at Mark Sheridan Math and Science Academy in the city’s Bridgeport area. “You hope that since she’s an educator and came out of the schools directly and as a parent she sees schools from that angle, too, that she can really bring that expertise and make decisions that are child-centered and teaching- and learning-centered.”

The Chicago Teachers Union declined to comment on Jackson’s leadership, but union officials have said they are cautiously hopeful. Jackson stands by some of the district’s more-controversial moves, such as requiring schools to test students both with the state’s common-core-aligned exams and the district’s formative assessments and encouraging expansion of successful charter schools.

She has pledged to involve residents more in decisions about low-performing and underenrolled schools, following protests of school closures. She hopes the principal-advisory groups will help craft policies that are more useful for the classroom.

“I don’t mind spending the extra time, because it ultimately boils down to time … and being willing to have conversations that are uncomfortable, sometimes confrontational,” she said.

“When I walk into a room, I’m just as headstrong as any other Chicagoan, but I know if we are going to get something done, we have to compromise, and I always go in with that kind of posture.”

Coverage of leadership, summer learning, social and emotional learning, arts learning, and afterschool is supported in part by a grant from The Wallace Foundation, at Education Week retains sole editorial control over the content of this coverage.
A version of this article appeared in the February 21, 2018 edition of Education Week

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