Over the months of a graduate course in literacy education, the authors engaged in many conversations about their leadership roles in the district in which they both work. Their schools are actively engaged in school improvement with a focus on enhancing student achievement. The district and the provincial Department of Education have given priority to literacy and numeracy through curriculum initiatives, teacher professional development, and student assessment. They both have a responsibility to support teacher change. The authors play different roles, Alayne supports elementary teachers as a literacy coach in two schools; as a principal of an elementary school, Amy guides and supervises the work of teachers. They shared many of the same questions and issues as they grappled with how best to foster teacher learning. In their conversation, similar themes surfaced such as resistance to change, trust and relationship building, and the need to build capacity and leadership in the school.