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Under Race to the Top, many states are implementing new teacher evaluation models. To understand principals within this reform, we examined how individual- and school-level factors predict principals’ (n = 452) perceptions of their knowledge and ability to conduct evaluation and the value of measures used in evaluations. Results indicate that principal experience (experience in evaluation more so than in the profession or in education), predicts self-reported knowledge and ability. School risk factors positively predict valuation of all measures of teacher effectiveness, with the exception of student achievement. Principals who self-report higher levels of knowledge and ability also place greater value on the importance of evaluation measures. Implications for principal preparation and practice are discussed.