Coaching is a growing industry focusing on helping individuals perform better at work and in their lives. Coaches specialize in facilitating a conversational, relationship-based process that assists individuals in attaining meaningful personal and professional goals. As clients work side by side with coaches, they may experience varying degrees of internal psychological, and emotional barriers. As a result, courage for the client has often been discussed in popular coaching literature (Kimsey-House, Kimsey-House, Sandahl, & Whitworth, 2011), and is considered an important aspect of the client’s success much of the time. However, during a review of the psychological literature on courage it was determined that, compared with the client, courage of the coach is something that has been explored much less, or not at all. More precisely, the internal psychological or emotional barriers coaches often face, and whether or not courage is seen as an important aspect of a coach’s ability to deliver high quality coaching are concepts that appear to have no empirical foundation. The objective of this study is to better understand the experience of leading coaches. Specifically, the following qualitative interview-based research aims to explore opinions and attitudes regarding common professional obstacles, primarily centered on the emotion of fear. This series of structured interviews asked participants to report on their own professional experiences and to articulate steps they have taken in facing and overcoming fear within their professional role, and throughout the course of their coaching development. Additionally, the interviewers inquired as to whether or not participant coaches perceived the construct of courage as an important factor in the professional development of coaches, in delivering high quality coaching, and ultimately in achieving mastery as a coach.