Hillsborough County Public Schools embarked on an ambitious goal to improve the highest-need schools by restructuring how the district supports schools and their leaders in July 2018. As part of this effort, the superintendent reduced the span of control and assigned principal coaches to support principals in a more intentional way. The purpose of this study was to explore how a principal coach engages a principal in examining inequities in disciplinary practices and how the principal coach provides the supports to prompt and sustain the principal’s efforts to reduce the disproportionate number of students of color being suspended from school. Zero tolerance policies were enacted to protect students from violence and ensure schools remain safe. Unfortunately, those same policies resulted in a disparate impact that affected students of color more than any other subgroup. The unintended consequences of such actions have led to students of color being suspended at an alarming rate for minor violations of rules, affecting their regular access to a high-quality education and resulting in low proficiency rates in reading and math, high drop-out rates and low graduation rates. While extensive research exists on how this culture can be improved, there is no evidence of a school improving in the absence of talented leadership. Until a leader understands and believes that something should change in their school, no research can support them. This study used an autoethnographic approach, telling the story of the lived experiences of a principal coach during his first ‘rookie’ semester. Data for the study were coaching logs, call logs and a reflective journal. Data were analyzed using thematic analysis. Findings of the study concluded that the principal coach’s use of an inquiry cycle significantly assisted the principal in examining inequities by providing an avenue to thoroughly examine data, determine a clear priority and develop a theory of action to guide the work of the principal for the upcoming school year. To prompt and sustain the principal’s effort, the principal coach supports centered on various types of coaching visits from on-going data chats, to learning walks, to one-on-one coaching and occasional, random phone call coaching sessions. This study has implications for school districts exploring how to support principals and, more specifically, how to support principals who are tackling inequities in their schools. For school districts, it confirms the importance of a reduced span of control for district administrators assigned to coach and support a portfolio of schools. This study emphasizes the importance of job-embedded professional development for principals.