Technical leadership is a difficult proposition even when there is an agreed and welcome mandate for it. The moving pieces are complex and relate in difficult ways. The challenge is significantly bigger if that leadership needs to happen from the sidelines or from a support position - for example, Security Engineering - and the person providing it is not a formal member of the team. In this talk we use the experience of a Security Engineer tasked with helping a development team raise their security posture, without being part of it. We will look at what works and what failed, propose tactic and techniques to best position the outsider in, and what observed results were achieved.