Abstract-Within the eclectic history of conflict research, subsuming number of theories and models of conflict resolution, the roles of mediators are often labeled based on cultural milieu. Using an in-depth semi-structured interview, this phenomenological study probed into the conflict mediation of 10 school administrators representing the Philippine Schools Overseas in the United Arab Emirates, the Sultanate of Oman and the State of Qatar with a view to understanding their unique roles as mediation persona. Transcribed field texts were read and reread for purposes of naï ve understanding after which a structural analysis was done via a dendogram. To emerge a collective and comprehensive understanding of the phenomenon, transcendental subjectivity was observed and was first subjected to the member-checking procedure. Themes were emerged following the inductive approach in theme development.Interestingly, results of cool and warm analyses paved the identification of trilogy of mediator's roles at Philippine Schools Overseas School administrators namely bracketing, balancing, and blending roles. The emerged mediator's trilogy of roles expands the overall capability of school leaders while viewing their role not only from the technical and managerial perspective but also from the humanistic point of view where conflict resolution is treated and interpreted in a way that it is less stressful yet humane and productive.