This study explored the experiences and insights of principal’s test non-passers in their leadership management. Employing descriptive phenomenology, a qualitative research method as the research approach, the participants were 7 school heads from public elementary and secondary institutions in Davao Region. These participants were purposively identified for focused-group discussion and in-depth interviews and met the set inclusion criteria. The participants experienced administrative leadership and management as school heads who are principal’s test non-passers. Research findings show significant leadership challenges and struggle as principal’s test non-passers. School heads adopt leadership approaches in overcoming leadership challenges including adaptive leadership and resourcefulness, Transformational and Shared Leadership, Cultural Sensitivity and Inclusion in Leadership; and Feedback Utilization and Responsive Leadership which are very helpful in their leadership management. Professional development and Self-improvement, Relational and Collaborative Leadership, Adaptive and Reflective to Change and Awareness of Systemic Responsibilities are also necessary on continuous improvement, especially in areas such as leadership competency, teacher development, and decision-making of the school heads.