Hiring preferences can often determine the amount and kind of consideration shown to candidates for teaching positions, and therefore can have a profound impact on school culture, but have been largely unexplored. This paper describes how one group of principals in Manitoba approach hiring decisions when assessing prospective teachers for "fit" both for the profession and for their schools. Based on a conceptual framework that examined the criteria used in hiring decisions along four sub-categories of person-environment (P-E) fit (Kristof-Brown, Zimmerman, & Johnson, 2005), the findings illustrate the critical role that principals can play in assessing applicants along various dimensions of fit even though they may have little formal preparation that would increase the reliability of such assessments. Additionally, these highly interpretive assessments constitute a significant part in decisions of who to hire, even though little is known about the relationship between assessments of fit and teacher effectiveness in the classroom. Finally, suggestions are offered that might improve the likelihood that those responsible for hiring teachers are aware of some of the biases that influence various decision-making phases of the hiring process. (Contains 2 tables.)