This paper identifies four models of educational administration--the rational, mechanistic, organic, and bargaining models--and argues that a fifth model of leadership--a caring model--is needed. The ethic of caring (Nodding, 1986) is reciprocal, natural, and ethical and emphasizes connection, responsibilities, and relationships. Creating a model of caring involved secondary analysis of data originally collected to describe career assistant principals (CAPs). These data were derived from participant observation, interviews with 10 CAPs, focus group interviews with 14 award-winning assistant principals, and a mailed survey of 26 award-winners in other states. Three interrelated patterns of leadership emerged from the data: (1) CAPs derived the strongest satisfaction from knowing that their actions helped students and teachers; (2) their career adjustments have been affected by their desire to retain flexibility and discretion; and (3) their value of caring extended into the community. It is recommended that professional association, university, and district policies incorporate the alternative career motivations of CAPs, and that caring should be modelled as a valuable function. In conclusion, caring is a necessary condition for transforming schools into successful living and learning environments. (LMI)