Self-esteem is generally perceived as fundamental to performance and research highlights its central role in our psychological well-being. Yet there is little coaching literature to help us understand this phenomenon. This article reports on a phenomenological study to understand the real-life experiences of six executive coaches who had clients with issues of self-esteem. As a result, four key findings emerged: in ‘contracting’ meetings, self-esteem is rarely the presenting issue; coaches find themselves operating somewhere between coaching and therapy; the process of coaching self-esteem requires the client to embark on a courageous journey of transition; the coach’s ‘unconditional positive regard’ creates an environment that allows their clients to generate their own self-esteem.