This study, based on a sociological viewpoint concerning everyday school reality, explores the relationship between cultural and symbolic specificities of the school organization and its processes of management and leadership. Inscribed in a specific cultural and identity matrix, school leadership profiles are simultaneously built as a reproductive outcome of culture and as a creative element of new cultural manifestations. From this perspective, the processes of school leadership are seen as agencies of cultural regulation, a sort of cultural trading point, a point where cultures of diverse origin meet, that require ongoing adjustments to the cultural specificities of the modern day school. To illustrate the importance of this theoretical approach, we debate some of the information obtained regarding a case study, where one sought to reconstruct the practices and profiles of management and leadership of two school principals that held their respective mandates in the same secondary school for a period of more than ten consecutive years.