Purpose: This article reports on a study designed to uncover the factors aspiring secondary school principals consider important when deciding whether to apply for a specific post. The aspiring principals involved in the study had all confirmed their desire to be a principal; about half were already vice-principals. Methods: Evidence for the study was provided by 164 aspiring principals in Hong Kong. Both exploratory and confirmatory factor analyses were used to establish the factor structure which, in turn, described the respondents' specific position attractors. ANOVA analyses were also conducted to see if the aspiring principals, due to their personal and school backgrounds, considered these attractors differently. Findings: The analysis confirmed a three-factor structure to describe the factors aspiring principals consider when deciding to apply for a specific position. The three factors, in order of importance were autonomy and innovation, convenience and fit and familiarity and status. Within each group, differences in terms of the school's academic standing were also identified. Implications: The findings emerging from this study may provide useful advice for enhancing the effectiveness of the principal recruitment process. Recruiters need to be aware of the factors aspiring principals take into account when deciding whether or not to apply for a specific post. Prominent among these is the opportunity to make a difference in the school. Considering what makes a certain position attractive to an aspiring principal may also give schools and systems valuable insights into what the next generation of principals sees as important for school in the future. Copyright © 2009 Taylor & Francis Group, LLC.