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This paper explores the use of a mentored model of gradual release within one Canadian teacher organization to support teachers as they become leaders of professional learning. Sources included observations of teacher workshops and interviews with twelve teachers. The findings suggest that becoming a leader of professional learning is a complex process of gaining confidence, building capacity, and transitioning into a new professional identity. This process was markedly supported through an intentional system of modelling and peer-mentorship that promoted leadership development across the group. The paper provides important insights into both the process of becoming a teacher leader as well as the manner in which teacher organizations can support the continued development of teachers as leaders of professional learning.