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There is a widespread belief in the efficacy of school leadership development programs on school improvement. This study investigated the influence of school leaders and teachers, trained as Assessors of school quality, on their home school’s quality performance. Quality ratings in the key performance area, Leadership and Management of the internationally benchmarked Adhyayan Quality Standard (AQS), were analyzed for 123 schools, in India, with either multiple, one or no trained Assessors. Shifts in quality performance and Assessor reflections indicated that learning within school contexts positively influenced quality improvement. Attitudinal changes and quality consciousness enabled schools with multiple Assessors to develop collaborative leadership. This paper contributes to research on the influence of collaborative eco-systems on sustained quality improvement.