The role of personal and contextual factors in predicting principals' age, gender, experience, self-concept, and personal incentives is examined in this exploratory study. Contextual factors include characteristics of the school, staff, and community, and the district's psychological environment. In a sample of 160 Illinois principals, multiple regression was used to identify significant predictors of two leadership behaviors and three management behaviors. Findings indicate that the most influential personal characteristics are individual goals and incentives, and the most influential contextual factors are district psychological environment. Staff characteristics are associated with four of the five administrative behaviors, and community characteristics are unrelated to either management or leadership functions. Four tables are included. (25 references) (LMI)