The attractiveness of the principalship is a variable that may help explain why candidates do and do not pursue principal positions. This study sought to determine if a discrepancy exists between what potential principal candidates desire and what they believe to be true about the attributes of the job of principal, and if that discrepancy can predict the attractiveness of the principalship to prospective candidates. A researcher-developed instrument was administered to teachers who are currently enrolled in four principal preparation programs in Virginia. Survey items were related to the domains that explain the attractiveness of the principalship. An overall attractiveness score was measured using a Thurstone Scale of Equal Appearing Intervals. A demographic section was included to collect background information. Overall, respondents rated the principalship as somewhat attractive. The regression found that there were five predictors of the attractiveness of the principalship. School location and number of years in education, both demographic factors, were the most significant predictors. Discrepancies in what candidates desired and believed to be provided regarding recognition of achievement, the ability to form relationships, and opportunities for professional growth followed as significant predictors of job attractiveness. / Ed. D.