Recent research largely focuses on measuring the outcomes of strengths-based coaching but fails to consider coachees’ individual experience of the process. This study aims to deepen the understanding of the experience of coachees when they explore their strengths and to examine what insights this provides for the application of strengths-based approaches in coaching. Interpretative Phenomenological Analysis was used to analyse data from semi-structured interviews and coaching sessions with six female participants. The findings suggest that strengths-based coaching could be improved by taking account of several key factors that appeared to influence how participants responded to exploring their strengths. These were: the relationship between strengths and key life experiences; the level of comfort when talking about strengths and weaknesses; and the timing and perceived relevance of strengths to the participant’s situation. The study concludes that an understanding of the coachee’s experience has implications for many aspects of the coaching process including the coaching relationship; structuring coaching interventions; the skills and role of the coach and the issues for which strengths-based coaching may be appropriate.