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INTRODUCTION Effective continuing professional development (CPD) is critical for safe and effective health care. Recent shifts have called for a move away from didactic CPD, which often fails to affect practice, toward workplace learning such as clinical coaching. Unfortunately, coaching programs are complex, and adoption does not guarantee effectiveness. To resolve this problem, thus ensuring resources are well spent, there is a critical need to understand what physicians try to achieve and how they engage. Therefore, we examined the types of change physicians pursue through clinical coaching and the impact of context on their desired changes. METHODS In the context of two clinical coaching programs for rural physicians, we applied a generic qualitative approach. Coachees (N = 15) participated in semistructured interviews. Analysis involved iterative cycles of initial, focused, and theoretical coding. RESULTS Coachees articulated desired practice changes along a spectrum, ranging from honing their current practice to making larger changes that involved new skills outside their current practice; changes also ranged from those focused on individual physicians to those focused on the practice system. Desired changes were affected by factors in the learning/practice environment, including those related to the individual coachee, coach, and learning/practice context. DISCUSSION These results suggest that the current focus on acquiring new knowledge through CPD may miss important learning that involves subtle shifts in practice as well as learning that focusses on systems change. Moreover, an appreciation of the contextual nature of CPD can ensure that contextual affordances are leveraged and barriers are acknowledged.