ABSTRACT Purpose Guided by situated learning theory, this study explores the influence of a professional development program on the evolving perceptions of middle leaders as entrepreneurial leaders. It investigates which elements of situated learning design foster the growth of middle leaders’ entrepreneurial behavior. Design Using a narrative case inquiry approach, 20 participants from five primary and seven secondary schools in Hong Kong. These participants engaged in a situated middle leader development programme designed to enhance teacher entrepreneurialism in authentic, job-related contexts. Findings This study uncovers the incremental learning growth of middle leaders across three phases: initial struggle with authority constraints; reflection on the role of entrepreneurial middle leaders; and eventual advocacy of innovative opportunities to colleagues. It underscores the importance of authenticity and guided reflection in the situated learning program design, which fosters a social environment stimulating reflective dialogue and enables middle leaders to reflect on their leadership behavior. Originality This study broadens the application of situated learning theory by demonstrating how the interplay of contextual, social, and individual-level environments can enhance the professional development of middle leaders, particularly in fostering entrepreneurial behaviours.