All software engineering and management practices are based on cultural and social assumptions. When adopting new practices, leaders often find mismatches between those assumptions and the realities within their organizations. The SEI has an analysis method called Readiness & Fit Analysis (RFA) that allows the profiling of a set of practices to understand their cultural assumptions and then to use the profile to support an organization in understanding its fit with the practices' cultural assumptions. RFA has been used for multiple technologies and sets of practices, most notably for adoption of Capability Maturity Model Integration® practices. This paper summarizes the principles of RFA and describes the SEI's work in extending RFA to support profiling and adoption risk identification for the Department of Defense and other highly regulated organizations that are considering or are in the middle of adopting agile methods.