This study aimed to improve the implementation of school self-evaluation in our school and how I, as principal, in collaboration with staff, could create the optimal conditions necessary. The study investigated school self-evaluation in practice. From this perspective it describes the characteristics which promote good quality implementation. The research used an action research design, putting school staff at the centre of all efforts to improve the school self- evaluation process. I worked through two cycles of action research, based on Elliot’s (1991) action research for educational change model using a range of predominantly qualitative tools including surveys, interviews, a reflective journal, field notes and interaction with a critical friend. The data was analysed using thematic analysis techniques. The constructs of complexity theory and school improvement theory were used as the basis for coding the data and examining the generated themes for key findings. From a school evaluation perspective, the work provides the reader with a deeper understanding of school self-evaluation in practice. The study also examines the impact of values and reflective practice on a school principal’s ability to lead the school self-evaluation process successfully. The study concluded that when school leaders resource school self-evaluation, in terms of professional and personal supports, the process can be implemented successfully. The study showed a positive change in staff members’ attitudes, commitment and capacity to implement school self-evaluation when the school leadership itself was reflexive and positive towards the process and provided opportunities for staff members to take ownership of the process in a spirit of collegiality and collaboration.