The purpose of this qualitative case study was to understand how coaching support structures enabled and sustained leadership practices of urban principals. The study investigated how the intervention of coaching for academic leaders can serve as evidence-based professional development for building leadership capacity. The central focus was on principals' perceptions of coaching engagements over time to identify recurring themes and essential elements of the coach-to-client relationship. With a goal of meeting 21st century school accountability requirements of standards and assessments, the urban district in this study implemented coaching for academic leaders who were selected to participate in the coaching intervention as job-embedded professional development. The district assigned a cadre of trained coach leaders to building principals with the primary goal of coaching academic leaders to attain desired goals. The district's director of professional development was a certified coach leader and had the responsibility of screening applications from principals and assigning coaches. The data collection process included in-depth interviews, direct observations, and review of archival documents. Holistic analysis captured recurring themes and assertions. Essentials of participants' perceptions of coaching were collected through semi-structured interviews, analysis of textual content, coding, and categorizing by themes. The significant themes revealed the perceptions of coaching as: (1) Supportive Environment, (2) Relationship Built on Trust, (3) Confidential Conversations, (4) Leadership Support, (5) Significance of Reflection, (6) Benefits of Coaching Language in Communication, (7) Co-Constructor, (8) Thinking Partner, and (9) Trust.