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Effective principal’s impact on student achievement is nearly as large as that of an effective teacher. However, information available on principal evaluations is exceedingly thin and inconsistent. The purpose of this mixed methods, convergent parallel case study was to gather an understanding of the data types considered, and analyses conducted by principal supervisors when evaluating their principals. Findings suggest principal supervisors do not show preference towards subjective or objective data-types when evaluating their principals. Additionally, principal supervisors took into account student achievement data and artifacts, support systems that principals provide to teachers and principal supervisors provide to principals, conversations and discussions with principals, and equity as evaluation considerations.