Purpose: In times of reform and consequential changes, school superintendents act as mediators between government policies and those who implement them in the field. This article explores the perceptions of school superintendents in Israel concerning their professional development (PD) process, especially during the implementation of Israeli educational reforms. Methodology: Research employed in-depth, semi-structured interviews with 34 superintendents to elicit their views on their role and their preferred PD processes. Findings: Analysis of their responses indicated that their views of their role and of current reforms shape their preferences for training and PD. They suggested various strategies to enhance their professional training: (1) regular learning programs throughout the year, (2) a focus on development programs in small homogeneous groups, (3) practice-based learning building on dilemmas from the field, (4) the construction of a professional community of practice as a participatory model for PD and project promotion, (5) updating relevant theoretical knowledge with potential to enhance their role performance, (6) structuring active experiential learning including practical learning in the field, and (7) adaptation of learning institutions' programs for life-long learning over the superintendents' professional life. Recommendations: It is suggested that superintendents' PD should be adapted to the different types of superintendents' specific needs and a supportive institute should be established where they can reflect on issues arising from the field.