The use of coaching as a developmental methodology has been instituted as a way to develop leadership in schools in Scotland as elsewhere in the UK. While there are studies that examine the skills and impact of coaching, there is only limited discussion of the process of coaching and the role and experiences of the coaches. This article examines the role of coach in a development programme for aspirant headteachers, "The Flexible Routes to Headship" (FRH), piloted in Scotland, UK in 2007-2009. Coaching was as the core learning process and consequently the quality of coaching is a major consideration in the success of this programme. This development programme is intended to enable candidates to demonstrate their achievement of a professional standard, The Standard for Headship and, as a consequence, the coaches have to undertake a number of different tasks including coaching, mentoring, facilitating, tutoring and assessing. This article draws from the data gathered from coaches and candidates in the evaluation of the FRH Pilot Project which suggests that while there are potential benefits for the coach as well as for candidates, there are some inherent tensions. The question of a model of leadership development based predominantly on coaching is explored. (Contains 2 tables and 3 notes.)