The implementation of the first iteration of a curriculum for an applied learning programme for police trainers received a hostile response from participants. It was perceived as irrelevant and supplanting, rather than augmenting, trainers' fixed and untested training practices. This paper presents the reflections on my journey as a non- police person straddling an outsider-insider position while challenging that which is taken-for-granted and introducing an educative intent, as opposed to a doctrinal, technical intent, to police training. On a daily basis I simultaneously work within and against the prevailing D/discourses and dominant subcultures, while establishing and nurturing relationships with police trainers: being teacher, coach and 'critical friend'. The response to the second and now third iterations of the learning programme has been increasingly positive, revealing shifts in trainers' thinking and practice.