Over the past 20 years the concept of school turnaround and how to achieve it has been at the forefront of educational research. Although a quality teacher is the most important factor in changing outcomes for students, to positively change the culture and learning outcomes of a school, a transformational leader is the second most important factor (Waters and Marzano, 2006). The purpose of this qualitative study was to understand the role of the district level supervisor in supporting the building principal to accomplish increased student achievement through turnaround. This qualitative study acquaints the reader with the concept of school turnaround and how the district must provide support and accountability to the building principal to successfully carry out systemic change. In addition to the creation of a model of district support, the resulting implications were threefold: 1) A vision, specific to the school turnaround, must be collaboratively created that defines the scope of the principal’s autonomy; 2) Strong relationships are created through support, conducting acts of collaboration and acts of accountability to create a balanced support structure; and 3) Leadership agility must be developed in a district supervisor by understanding from which side of the continuum the supervisor is most comfortable leading from, and then developing their skills on the side that is less comfortable. The role of the district supervisor is vital to principal development and as a result, essential for successful turnaround.