Purpose: The purpose of this research study was to examine the role perceptions of superintendents and their supervisors in Palestine regarding the roles and training needs of superintendents. It was part of a larger study conducted by the Department of Administration and Educational Leadership at Teachers College, Columbia University. Design/methodology/approach: A grounded theory approach was used in this study. Data were collected by interviewing 16 superintendents and four general directors using guided qualitative interviews, in addition to examining Ministry of Education documents and archival data. Findings: The grounded theory approach analysis revealed that superintendents and general directors held variant perceptions regarding the roles and training needs of superintendents. Most superintendents felt they were ill prepared for the job and had to rely on the Ministry of Education for support and direction. They perceived their role as a combination of educational managers and educational leaders. Their supervisors, however, perceived them as keepers of the status quo. The findings showed that superintendents in countries similar to Palestine (newly emerging) appear to experience problems similar to their counterparts in other transitional societies. Originality/value: The findings of this research are important to new educational systems. It shows clearly the difficulties experienced by superintendents in a newly emerging system. Furthermore, superintendents in such systems may require training needs different than their counterparts in developed systems. The findings are discussed in terms of their relevancy and contributions to educational leadership theory.