You cannot teach a man anything. You can only help him discover it within himself.

This article sheds light on the challenges facing coaches when undertaking the journey to becoming a group coach. It begins with observations on the state of the art of group and team coaching and continues with a description of the various conundrums faced by coaches interested in pursuing this kind of activity. Subsequently, it describes a coach’s reflections on leadership group coaching and shares his inner journey toward becoming a group coach. The second part of the article reflects on what makes group coaching an effective intervention, discussing the dynamic processes applicable to individual participants and the ‘cloud issues ’ or themes that the group-as-a-whole brings to the table. It describes seven premises that characterize the clinical paradigm, a psychodynamic lens that can be turned on our inner theatre. The article also highlights a number of other psychodynamic processes that take place during the group coaching process, creating tipping points for change. Key Words: group coaching; clinical paradigm; Plato’s cave; tipping points; transitional space