In recent years, school leaders have recognised the need for developing emotional intelligence (EI) skills, such as self-awareness and emotion management, in students and educators. As they seek professional development (PD) to cultivate these skills in educators and their students, they may look to coaching, grounded in EI theory, as a feasible and effective PD option. This article describes findings from a case study conducted with 12 internal coaches in one school Federation in Kent, England from 2008 to 2010. This study explored the benefits and challenges of implementing a coaching programme delivered by educators for educators responsible for teaching EI skills to students. Twelve educators participated in a yearlong coach certification and delivery process grounded in EI theory and skills. Data collection included pre- and post- interviews and online reports from each of six coaching sessions. Findings revealed benefits for both coaches-in-training and clients, including: deeper commitment to teaching EI skills, increases in self-awareness and self-management, and improved relationships with others. While coaches and clients reported positive behavioural changes, lack of support at the leadership level was found to negatively impact successful implementation of the programme.