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This study attempts to understand how professional coaching, offered to five school principals, helped to strengthen their entrepreneurial skills, encouraging change in a context marked by familiarity and religious diversity. It approaches everyday school life through the eyes of the actors and is based on content analysis, using data from semi-structured interviews, focus groups, and diaries. These data were collected and provided by a professional coach to three researchers from the Faculty of Educational Sciences at Saint Joseph University (USJ) in Beirut. They conducted an ex-post study in the research laboratory to understand the change process initiated by the professional coaching of school principals. The results showed the development of entrepreneurial skills including creativity, agility, and initiative, based on a “servant leadership” model and embedded in an institutional structure.