This chapter focuses on the mentors who wish to challenge good trainees to take risks in their pedagogic practice and professional development so as to become the best teachers they can be, and to inspire the highest levels of pupil and personal achievement. Having established classroom management procedures, extended and developed their subject knowledge and found a way that 'works for them', trainees are liable to continue to focus on themselves and their teaching, rather than the learning of their pupils. In the early stages of discussions, trainees and mentors need to articulate their 'risk appetite'. Barriers to risk taking vary depending on the risk, so it is difficult to isolate the 'primary' ones. The chapter looks at ideas loosely categorised using a model for (rather than against) behaviour change, based on incentives, role models, skills and positive reasons for doing it.