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This paper examines the role of school leadership in creating the organisational conditions that impact mentors’ job satisfaction, well-being, and retention decisions. The conceptual framework of the study reflects a longstanding line of research on successful leadership and empirical evidence is drawn from the mentor survey component of a four-year study on teacher retention in England. Results of the structural equation modelling analysis show the paths of influence connecting school leadership to mentors’ retention decisions through a number of key in-school conditions and personal disposition. The vision and quality of school leadership to improve mentors’ capacities and capabilities – individually and collectively – and enhance their sense of belonging in their places of work holds the key to achieving these outcomes successfully.