Purpose: This study explores factors that influence the initiation of leadership coaching relationships that include externally employed coaches and school administrators. Design/methodology/approach: This qualitative research study includes semi-structured interviews, observations and documents collected across three academic years within the context of a university-based leadership coaching program. Participants included six leadership coaches and six school administrators who participated in the program. Findings: Qualitative analysis indicates that gender and race, prior professional experience, pre-existing professional relationships and the complexity of the district's organizational structure influence the initiation of the coaching relationship. Research limitations/implications: Confidentiality restrictions imposed by the program limit opportunities for member checking and other forms of triangulation. Additional data collection using more expansive research methods would help address this limitation. Originality/value: This study contributes to the sparse literature about leadership coaching with school administrators by describing how different factors influence initiation coaching relationships.