In this article, the author describes how an Oregon district redefines coaching roles to find a balance between school and district goals. As director of improvement for North Clackamas School District in Milwaukie, Oregon, near Portland, the author's role of coaching the coach was new, and the coaches welcomed the immediate feedback. Through the four years of redefining the roles of site-based coach, principal, and central office staff, Oregon district achieved a balance between district initiatives--the goal was to implement writing workshops--and site-based professional learning. This redefinition of roles and collaboration during instruction penetrated the "core technology" of teaching--what happens between teachers and students in the classroom. School and district administrators learn in practice with teachers and coaches to improve literacy learning for students.