This study employed a phenomenological approach of qualitative inquiry. It aimed at exploring and understanding the lived experiences of head teachers as program owners in implementing the school 's annual improvement plan. It also highlighted the challenges they encountered in the implementation of the school annual improvement plan as well as the coping mechanisms and insights in addressing the challenges. Participants were chosen through purposive sampling based on the relevant experiences and alignment with the criteria of the study. The study was conducted in two schools of New Corella District, Division of Davao del Norte. There was a total of 10 participants; three underwent in-depth interviews and seven participants in focus group discussion. The data gathered were analyzed through thematic analysis, and results revealed five major themes in their experiences namely: making consideration of educational priorities; difficulty in budget management; fulfillment of the program implementation; experiencing delays and cancellations of the proposed program and projects; and establishment of collaboration among internal and external stakeholders. In addition, in addressing the challenges, head teachers employed various coping mechanisms that underscored their resilience and leadership capacity. Five key themes were identified: establishing supportive leadership; planning and preparing strategically; allocating resources; facilitating task management; and cultivating interpersonal qualities. Moreover, this study also highlighted critical insights gained from the head teachers regarding strategies for overcoming implementation challenges. These include the value of data-driven planning; leadership resilience; supportive leadership; funding strategies; and inclusive stakeholder collaboration. Emphasis was placed on the importance of transparent communication, visionary leadership, and strategic flexibility in navigating systemic constraints.