Effective principal leadership contributes to improved levels of student learning, teacher satisfaction, and teacher retention. Effective principals can improve instruction by building capacity through teacher evaluation and dismissal, and professional development. However, there is a lack of effective principal leadership, particularly in low performing schools where principal turnover is high. Despite the important role that principals are positioned to play in improving teaching and learning through new educator evaluation systems, research has shown that principals are not being adequately prepared and they are receiving only limited preparation in how to conduct teacher evaluations. Using a single descriptive case study design, this study investigated how participation in a university and district-based professional development program, grounded in situated learning theory, influenced the participants knowledge, skill, and self-efficacy regarding leadership practices associated with educator evaluation as well as their capacity for executing the practices in the context of their current administrative role. This program consisted of four community of practice sessions and three school-based coaching sessions for each participant. Data were collected in the form of artifacts, observations, and interviews. Eighteen participants and six expert/mentor principals participated in the program. Findings from the study support the use of a situated learning framework for principal professional development programs. Participation in the professional development program led to increased knowledge, skill, and self-efficacy of the participants due to the challenging and supportive learning environment. This increase was not only an improvement in the technical ability to perform observations and evaluations, but it also reflects a change in mental model regarding the use of observations and evaluations to address adaptive challenges. Finally, while both the community of practice sessions and the school-based coaching sessions were recognized as valuable the relationship between the expert/mentor principal and the participant greatly impacted the effectiveness of each component for each individual. [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.]