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Purpose: The purpose of this research was to explore a program’s approach to preparing school leaders for teacher evaluation to address concerns about leaders' competencies in this role. Methods: This case study of a school leadership preparation program unpacks aspects focused on teacher evaluation. Sources included documents, observations, and interviews/focus groups with candidates and faculty members. Findings: Authentic experiences that helped prepare candidates included: (1) faculty member and aspiring school leaders’ prior experiences, (2) authentic experiences including clinical practice (i.e., required course activities such as the mock evaluation) and internship site visits. Implications: This study contributes to research on school leader preparation for teacher evaluation offering a more nuanced understanding about authentic experiences including, but not limited to, clinical practice.