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This paper meta-analyzed 83 case studies conducted in 17 countries derived from the International Successful School Principalship Project (ISSPP). Employing a qualitative-meta-analysis approach and meta-ethnography techniques, we investigate the context classification, how principals react to contexts, and how principals achieve success over time. By using Bronfenbrenner’s Ecological Systems framework (1979), we find that each sub-system influences principal practices, and principal reaction to contexts varies among education systems. Through our research, we delineate three key stages of principal practices— the "beginning stage," "middle stage," and "final stage"—each with distinct priorities and objectives. The findings enhance our understanding of the contextual antecedents of successful principalship and inform leadership preparation in a global educational context.