In this study, we address the relative lack of rigorous research on instructional design (ID) practice via an exploratory study in which pairs of researchers observed design judgments made by eight practicing instructional designers in two consulting environments as they went about their normal work activities. In our analysis, we sought to characterize their practice on its own terms, rather than through superimposition of existing ID models or frameworks. A nonprescriptive, philosophical framework of design judgment by Nelson and Stolterman (2012) was operationalized and used to frame two phases of analysis: identifying and coding design judgments and creating holistic summaries of the observed practice. We found that design judgments occur quite frequently throughout design, often in clustered or layered ways, rather than in "pure" forms. These judgments appeared to be shaped by factors unique to the firm, the role or position of the designer, and project, client, or other external factors.