This article examines the importance of caring in schools and school leadership. It analyzes the concept of caring and how it functions and introduces a model of caring school leadership situated within this broader exposition. The analysis and model are informed by literature including academic and professional works from education and education-related fields and disciplines—philosophy, ethics, feminist theory, positive psychology, and the organizational sciences. In addition, the analysis and model draws on literature of human-service occupations—health care, social services, and the ministry—that consider caring and caring leadership at both interpersonal and organizational levels. The synthesis of this literature results in a multidisciplinary and cross-occupational model that extends and deepens current understanding and theory about caring school leadership.