The purpose of the present study was to examine the effect of regulatory factors on the level of aspiration of school teachers to become school administrators focusing on the difference of their gender.A web survey was conducted for 205 male teachers and 105 female teachers working in public elementary and junior high schools across nation. For male teachers, the results of a multiple regression analysis suggested that experience in school management indirectly influences their aspiration to become school administrators through “organizational contribution efficacy”and, the encounter with the school manager who becomes the role model directly influences their aspiration to become school administrators and indirectly through two variables “organizational contribution efficacy” and “positive attitude toward school principals”. With regard to female teachers,the years of experience indirectly influences their aspiration to become school administrators through two variables, “school management effectiveness” and “approval from school manager”. Experience in school management and the encounter with the school manager who becomes the role model indirectly influences their aspiration to become school administrators through approval from school manager”. These findings suggest the necessities to use different strategies when training men and women school managers.