Policy analysts have advocated for better licensure assessments to determine leadership candidate quality and improve readiness for school leadership roles. Through a professionally guided design team process, California Commission on Teacher Credentialing (CTC) developed initial leadership assessments [three cycles of the California Administrator Performance Assessment (CalAPA)]. This article uses the design team committee work and candidate and assessor feedback through the pilot study to explore the design considerations for performance assessments in leadership. It evaluates the feasibility, utility, and relevance issues in developing a valid assessment system. The findings offer insight for developing performance assessments elsewhere for leadership preparation and licensure.