There has been a growing emphasis among education policymakers on coaching as an important aspect of professional learning for school leaders. This paper describes a qualitative study of long-term leadership coaching for school principals. The study aims to fill the gap in the literature on coaching for experienced leaders and, reflecting the 2019 conference theme, offers systematically collected stories from the field that can inform policy and practice. Data included interviews with veteran principals who had chosen to engage in leadership coaching for more than five years, and their coaches. The study identified areas of principal practice consistently emphasized throughout the coaching work, and found that the leaders in the study had longer than average principal tenure in their school.