1. What do Chicago Public Schools administrators see as the greatest roadblocks to school improvement?
2. How have the top roadblocks perceived by administrators changed over time?
3. How do administrators differ in the breadth and depth of concern they experience about various roadblocks?
This brief provides insights in to what administrators in Chicago Public Schools (CPS) see as the greatest roadblocks to school improvement, based on surveys developed and administered by the University of Chicago Consortium on School Research (UChicago Consortium). Responses from the 2017 survey were analyzed and compared to previous years to determine how such roadblocks have changed over time. While no two administrators’ responses were the same, clear districtwide trends surfaced: the emergence of financial concerns as new top roadblocks for schools; the increased saliency of roadblocks concerning human resources in both charter and non-charter schools; and increased concern over social challenges in the community. In addition, patterns of administrators’ responses to roadblock items indicate that respondents fell into three roughly equally-sized groups that differ distinctly in breadth and depth of concerns, from those facing limited roadblocks to those facing considerable roadblocks. We identify factors that increase a leaders’ chances of falling into the “considerable roadblocks” group, and conclude by sharing what implications our findings may have for practice and policy.