The purpose of this study was to determine the factors that are associated with qualified teachers' decisions not to apply for the role of school principal. Recent research has shown that schools in North America are currently facing a shortage of principals and this shortage is expected to continue. In this study, three teachers, who are qualified for the principal's position but are not interested, answered semi-structured interview questions.Their responses were taped, transcribed and analyzed to identify common themes.Findings suggest all of these individuals value the relationships with their students and other teachers. They enjoy teaching and the flexibility that it provides. They perceive the magnitude of the relationships that a principal has to maintain with parents, school board, and senior administration as undesirable. It was concluded that efforts could be made to nurture teachers' interest and knowledge of the principal's role. Support for local courses, job shadowing, and mentorship programs are suggestions that are discussed. If continued effort is made, appropriate solutions can be found to help remedy this shortage.ii