This study explores the coaching experiences of educational administrators in an attempt to gain greater understanding of how they develop the necessary skills to implement, lead, and support technology rich professional learning communities (PLCs). Participants came from a mix of urban, rural, and suburban school districts. Using semi-structured interviews and qualitative thematic analysis, the researcher examined what these administrators perceive as the most important factors in developing skills to lead technology rich PLCs from the perspectives of the participants and the cluster coaches who mentor them. Three primary themes emerged from the data; the strength of network learning, the utilization of technology as a form of communication in a professional learning community, and the constructivism of leadership.