Purpose: This study attempts to link four groups of contextual factors to vice principals' desire for principalship using regression analysis. Relevant items representing context are grouped under professional, school, demographic, and motivational factors. The findings aim to provide greater understanding of the desire, or lack thereof, of vice principals to become principals. Research Design: A questionnaire was sent to all secondary school vice principals in Hong Kong. Respondents were asked to indicate on a 4-point Likert-type scale their degree of involvement in a set of professional work dimensions and to rate their agreement with motivational items to describe their needs. They were also asked to provide information about their school and demographic background. Of the 803 questionnaires distributed, 331 were returned, giving a response rate of 41.2%. Findings: A number of professional, demographic, and motivational factors appeared to link to vice principals' desire for principal positions. These included involvement in professional development in school, a personal desire to keep learning, the applicants' age, and their predisposition to disregard relational factors. Conclusions: Vice principals who have a stronger desire for personal growth and who are more actively involved in professional development opportunities in their schools have a greater desire to become principals. On the other hand, vice principals who value harmonious working relationships are less inclined to apply for principalships. Further professional development is necessary to increase both the quality and the quantity of principal aspirants. This should recognize the power of ingrained beliefs and norms and be built around human resource issues. (Contains 4 tables and 2 notes.)