This study examines the extent to which male and female principal candidates use language to signal their perceived values specific to open positions in the field. We analyzed Wisconsin school-leader application data by gender, seeking to understand whether or not men and women present themselves differently through language in the initial application phase. Using an electronic linguistic analysis tool (Docuscope), we identified patterns in the writing samples from 2,061 applicants and applied critical discourse analysis to determine the role gender plays in candidates' portrayals of themselves. This mixed-methods approach revealed that language use differs significantly between male and female applicants. Notably, linguistic variables common in female candidates' writing tend to focus on elaborating ideas and using compare/contrast techniques to describe beliefs. Male applicants' language is often more formal and relies heavily on passive voice. Our findings raise questions as to whether candidates may be selected because of an unconscious preference for language patterns commonly used by females or males.