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This paper explores key developmental issues and considerations that emerged over a three-year qualitative, longitudinal study as school leaders, tasked with supporting the enactment and development of collaborative data practices, engaged in diagnostic work to support practice development and concurrently received development to strengthen diagnosis. Four key developmental issues and considerations are explored, which warrant attention by those seeking to support the enactment of collaborative data practices as well as those seeking to enhance the diagnostic approaches and skills of school leaders tasked with the support on collaborative data practice development. This paper advances existing literatures on school leadership preparation and development and evaluation/diagnosis/monitoring. Study findings should also prove particularly instructive for those who prepare, support, and develop school leaders.