For some time, both practitioners and scholars have been arguing that coaching should play a stronger and more central role to achieve successful business outcomes. However, when looking to inspire leaders to gain competence in the skills of coaching, ill-founded assumptions are made. Including, but not limited to, the very definition of leadership and the very nature of coaching when embedded into leadership (termed in this chapter, leaders-who-coach). The research described in this chapter looks into these practices to proffer 15 dimensions of leaders-who-coach, drawing on multiple sources which seek to ameliorate the shortfalls of previous research in this area. Finally, the chapter includes a discussion on the less than perfect nature of the approach taken due to the philosophical misalignments between the described realities of leadership and coaching and the ontological and epistemological challenges of research. The primary aim of this chapter is to respond to the growing organizational calls for more leaders to have the skills of coaching.