This phenomenological study explored the lived experiences of elementary school heads who were transferred to secondary integrated schools in the Municipality of Glan, Division of Sarangani. Utilizing in-depth interviews and thematic analysis guided by Braun and Clarke’s (2006) approach, the study examined the challenges, coping strategies, and leadership transformations experienced by five purposively selected participants. Grounded in Transformational Leadership Theory and Role Transition Theory, the findings revealed three major challenges during the transition: establishing leadership identity and credibility, adapting to a more complex secondary curriculum, and managing adolescent behavior. To navigate these, participants relied on peer mentorship, continuous professional development, and personal coping practices such as reflection and spiritual grounding. The transition also reshaped their leadership approaches, shifted their pedagogical perspectives, and contributed significantly to their professional and personal growth. The study underscores the need for structured support systems and targeted leadership training programs for school heads undergoing similar transitions. These insights offer valuable implications for educational policymakers and leaders aiming to strengthen leadership continuity and school effectiveness across academic levels.