Chalkbeat Chicago

For Nicole Spicer at Chicago’s Bronzeville Classical, news that the district’s CEO, Janice Jackson, plans to step down stirred anxious questions: Could the city enlist a leader with the experience, education chops and mettle to replace her? What would it take to draw that kind of leader to the traditionally high-pressure job at an especially high-pressure moment?

Finding a successor will be “a huge undertaking,” said Spicer, whom Jackson handpicked as the founding principal for the selective South Side elementary in 2017. Spicer said her priority No. 1 for the next hire is someone steeped in education, like Jackson, who drew from her own experiences as a former Chicago student, teacher and principal...