This article details a large-scale study of vice-principals in Hong Kong secondary schools. The study aimed to examine the core competency areas that pertain to the work of vice-principals and the way in which vice-principals perceive these areas to relate to school success. It also examined the factors that affect their level of job satisfaction, and differentiated these factors according to whether they did or did not aspire to principalship. The findings indicate that competency gaps, if large enough, can affect the level of job satisfaction of vice-principals and that the impact of these gaps varies according to career orientation. The results show that vice-principals who aspire to be a principal are more satisfied in their jobs than their less ambitious colleagues; and that the effect of these gaps on job satisfaction differs between the two groups. The implications of the findings for the future supply of principals and leader development are expounded. (Contains 6 tables and 2 notes.)