Leader development requires more than memorizing and regurgitating rote procedures. As a case in point, leaders must often navigate unfamiliar and ill-defined social situations where building and maintaining trust is paramount to success.  Honing the relevant attributes and competencies for such challenges is a central aspect of leader development as it would be impossible to develop procedures for an infinitely varied breadth of socially-dependent situations that impact trust. In the current research, we developed an approach to learner feedback to support the development of social interaction skills that support trust building in the context of the activities of military advisors. The novel feedback methods were based on established patterns of instructor-student interaction designed to uncover understanding, combined with methods drawn from the Social Autopsy process originally created for children with learning differences such as Autism Spectrum Disorder who may struggle with social interaction. Building on this foundation, we present a method for developing interaction skills via a modified, Advisor-centric Social Autopsy process, conceived as socially mediated problem solving. The method builds on an identification of common sources of difficulty for military advisors during deployment and provides guidance for learner feedback via discussion that progresses from what happened, to why, to implications, to strategies for the future. We review development of the process as well as supporting evidence from a formative evaluation conducted with instructors at a facility for training military advisors.  The outcome of this work is a set of findings to guide further refinement of the approach that can also be applied to leader development with respect to a broad set of social interaction skills that might similarly benefit from instructor-student collaboration to promote understanding and transfer to the operational environment.