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.