This original research examined the intersection of school leadership and teacher to parent communication. The analysis used hierarchical linear modeling (HLM) to determine how principal actions and school level factors were related to teacher actions and the focus of communication. Secondary educators in four district school boards were surveyed about their communication with parents. HLM was used to analyze the survey data with individual teacher responses as the first level, nested within principal responses and school data at the second level. This research was designed to identify how teacher level and school level factors were related to the focus of individual teacher to parent communication and how secondary school principals could leverage these factors.