While design research can be useful for designing effective technology integrations within complex social settings, it currently fails to provide concrete methodological guidelines for gathering and organizing information about the research context, or for determining how such analyses ought to guide the iterative design and innovation process. A case is described, in which the author explores one way that researchers might go about systematizing the analysis of contextual influences within a design research study. It borrows a method from engineering called "Cognitive Work Analysis" (CWA) (Vicente 1999), to methodically study the impact of political, organizational, team, psychological, and physical factors within an initial teacher education setting. The study illustrates how a modified CWA was helpful in making contextual information more explicit and organized. Important information in the form of human factors "constraints" were identified through the CWA, providing valuable details about context that might otherwise be overlooked during design research cycles or within the reporting process.