This is a qualitative research study, seeking an explanation on conditions surrounding the low number of Pacific Islanders (PIs) working towards principalship positions and the impact these conditions have on their decision making. I investigated PIs in Deputy and Assistant Principals roles, and the factors and barriers impacting them in gaining a principalship. The study concluded that the very low number of PI DP/APs progressing towards principalship will continue unless they are assisted and supported to overcome two overwhelming sets of conditions that act as barriers towards their aspirations for higher roles. These are personal and systemic conditions. Systemic conditions include a lack of support; institutional racism, discrimination; lack of motivation during socialisation experience; a lack of career professional development; PI role models. Personal conditions include a lack of confidence and professional network; impact of gender and ethnicity; silent voice. To counter personal factors PIs working as DP/AP's should engage in ongoing studies in leadership development. To counter systemic factors it's recommended a PI-specific programme for PI DP/APs be developed.