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This paper presents a qualitative case study of the ‘Leading Principals in Vulnerable Schools’ project, which aims to support a small group of newly appointed principals in disadvantaged Chilean schools, inquiring how does this project promotes school improvement and probing into the assumption that school leadership is key. Three topics emerged from the data analysis: (i) the leadership and effectiveness assumption; (ii) normalization, disciplining and innovation; and (iii) achieving and sustaining ‘success’. As a result the theory of change and improvement of this project is outlined, in order to critically analyze the current policy strategy of external support for school improvement in Chile, and to problematize the assumption that leadership is critical for school improvement.