Kathleen Pitts was hired as an elementary principal with the intent of diversifying the educator ranks in a town with growing racial, economic, and cultural diversity. Upon starting her new position, Kathleen faced resistance from the staff and community. In addition, she received little support from her administrator colleagues as she forged ahead with implementing new curriculum. This case explores the critical intersection between building capacity for entering a school community, supporting new administrators, and fostering responsive and inclusive environments for staff and students. Discussion questions and activities provide a platform for exploring the complex nature of both school and district leadership, especially in contexts experiencing change.