This article reports on a case study of a school that had ongoing coaching for up to six years. The study focused on coachees’ perspectives, in particular what factors allowed them to achieve their set coaching goals. The investigation into longitudinal coaching (one to six years) indicated how coaches positioned themselves or peers, when reflecting on and seeking to establish why some coaching goals were more achievable than others. A key finding was that coaching goals were deemed attainable when they aligned with coachees’ specific focus, which was reflected by the six core themes that emerged: Pragmatic I, Pragmatic We, Student Driven, Team Driven, Data Driven, Research Driven. The seventh theme (temporality) indicated that over time coachees’ dominant concerns shifted to become less of a focus with other overriding needs emerging.