Process modeling is useful during the analysis and design of systems. Prior research acknowledges both impediments to process modeling that limits its use as well as customizations that can be employed to help improve the creation of process models. However, no research to date has provided a rich examination of the linkages between perceived process modeling impediments and process modeling customizations. In order to help address this gap, we first conceptualized perceived impediments to using process models as a “lack of fit” between process modeling and another factor: 1) the role the process model is intended for; and 2) the task at hand. We conducted a case study at two large health insurance carriers to understand why the lack of fit existed and then show different types of process modeling customizations used to address the lack of fit and found a variety of “physical” and “process” customizations employed to overcome the lack of fits. We generalize our findings into propositions for future research that examinethe dynamic interaction between process models and their need to be understood by individuals during systems analysis and design.