The purpose of our multi-case study was to understand the experiences of non-novice New York City and Washington, DC public charter school principals who had participated in leadership coaching as a component of their leadership development. Eight New York City and Washington DC public charter school principal cases were selected through purposeful sampling. Data were collected through semi-structured interviews, documents, and artifacts, which were analyzed, coded and grouped into three broader themes: the coaching process, the impact of coaching, and principal leader identity construction. The findings supported the following conclusions: (a) Participants' experiences of coaching were inconsistent with the coaching literature; (b) The impact of coaching was shaped by perceived competencies of the coach and the structure of the coaching session; and (c) Participants' leader identity construction was supported through the process of coaching.