This paper attempts to address the principal shortage issue from the concept of fit perceived by job applicants. It links vice-principals' perception of suitability for principalship to their conception of how well they can match with the selection criteria set out by school hiring bodies. Based on evidence collected from aspiring principals in Hong Kong, the study found that the respondents believed their suitability for a principal position was generally measured against four criteria by school hiring bodies; namely generic managerial skills, communication and presentation skills, knowledge and experience, and religious value orientation. Respondents were confident about their capability in the first three attributes, but were less assured about the last one. The results further showed that respondents' perceived deficiency in the religious related attribute affected their confidence in being considered a suitable candidate. Implications of the findings for policy makers and practitioners are discussed.