Education reform is the focus of many of the political agendas today. The research is clear that the best way to increase student achievement is by having highly effective teachers in the classroom. As a result of prior research, both the state and federal governments have created mandates and legislation aimed at achieving that goal. One of the areas where transformational change is occurring is in the way teachers are evaluated. Evaluation, once a tool to document competency, is now a tool to promote professional growth and assist in personnel decision-making. The focus of the evaluation has turned from teaching to student learning. This change in focus will require principals to acquire a new set of skills in order to be effective teacher evaluators. This exploratory study surveyed principals from Upstate New York to determine what they perceived to be the best forms of professional development to help them hone their skills as teacher evaluators. The results of the study revealed that there is was a difference in perceived readiness between genders and years of experience. The findings of the study also discovered weak to moderate correlations between reported professional development and perceived readiness to conduct effective teacher evaluations. Principals have often been the coordinators of their own professional development. This study shows that principals desire a change and want to be able to collaborate and work with their colleagues. As a result of the findings of this study, it is recommended that system leaders create a transitional step by taking an activity principals previously did in isolation and making it a collective process aimed at increasing principals' skills and readiness to be effective teacher evaluators. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]