In coaching there is a lack of research that focuses specifically on progress, despite increasing global debate on what progress means for individuals and societies. This study uses the coach’s experience to explore some of the dilemmas and controversies that the coach may face when dealing with the phenomenon of progress. The heuristic inquiry, used metaphors to draw upon the experience of the researcher and ten other coaches from executive, life and community coaching. Three main themes arose; who determines what progress means in the coaching relationship, identifying indicators of progress, and the coach’s experience. The findings suggest that the coaching profession has both a duty of care towards its membership and an important role to play in contributing to the global debate on progress. Moreover, indicators of progress are paradoxical in nature and open to misinterpretation by different stakeholders but adopting a new mindset may help increase organisational effectiveness.