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This paper explores how a situated professional development (PD) program influenced novice middle leaders’ (MLs) perceptions of their roles as entrepreneurial leaders in Hong Kong schools. Drawing on Situated Learning Theory (SLT), the study used a narrative case inquiry to examine the incremental development of Teacher Entrepreneurial Behaviour (TEB) among 20 newly appointed MLs across 12 schools. Findings suggest that guided reflection, authenticity, and social support within a situated learning environment enabled MLs to reflect deeply on their leadership practices. The study contributes to understanding the contextual, social, and individual dimensions of leadership learning and offers insights for designing effective PD for novice MLs.