In 2012 Massachusetts implemented a new educator evaluation system designed to create a "cycle of continuous improvement" that includes self-assessment, goal setting, evidence collecting, and evaluation. This new system was supported by more than twenty years of educational research demonstrating that highly skilled teachers remain one of the most important factors contributing to the quality of student learning. As a result, federal and state educational policies have incentivized school systems to incorporate teacher evaluation systems that accurately measure teacher performance as well as promote teacher development. This study explores the role reflection plays in this evaluation system, as reflective practices can be attributed to ongoing growth in professional practice (Darling-Hammond & McLaughlin, 1995;Lewis, 2015). Survey data collected from school principals enable policy makers to better understand if the structures of this evaluation system generate the intended behaviors of continuous improvement. The major findings of this study conclude that a school principal's experience, demographic background, or school characteristics do not impact the frequency with which they engage in reflective professional practices. The principals also reported that the teachers they supervise are more likely to engage in reflective practices earlier in the career. Moreover, they report that the quality of teacher reflection frequently flattens out or even declines with experience. This finding aligns does not account for the effects that school-based professional development might have on teacher performance, as cited by Kraft and Papay (2014) and Kraft, Papay, and Chi (2020). Finally, data collected from this survey suggests a need to explore different models that can support continuous improvement for teachers and that reflective practices can contribute to this professional growth. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]