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Research purpose included giving aspiring school leaders an opportunity to discuss how they built skills in teacher evaluation adding to literature on what it takes for school leaders to effectively evaluate teachers. In a qualitative case study of school leader preparation, I looked at program aspects focused on teacher evaluation through document analysis, observation, and interviews/focus groups with aspiring school leaders and faculty members. Findings included how aspiring school leaders developed an understanding of teacher evaluation and their perceptions about skills needed to evaluate teachers. This study contributes insight about nuances of leaders’ role in teacher evaluation, a critical function of supervision and instructional leadership, pointing to needs for preparation programs and K-12 settings to collaborate on developing needed skills.