As the pace of innovation in process automation continues to accelerate, the challenges of operationalizing these advances are of increasing interest. Reducing loss incidents in the process industry requires increasingly knowledgeable operators to access multiple sources of current and historic data through industrial informatics. To evaluate the effectiveness of new designs and design features, clear criteria for performance and performance improvements must be developed. The situational design model was developed to assess and develop problem solving skills, the higher cognitive processes necessary for high performing operators to employ in abnormal situations. The situational design model recognizes learner readiness and the disambiguation of “recurrent’ and “non-recurrent” skills. In this paper, the situational design model is demonstrated in a workplace-analogous study to evaluate the effectiveness of Distributed Control System interface adaptation. This type of structured assessment can be used to tie design features more directly to the specific skills of interest and improve the value propositions for new features and designs. The demonstration in this study shows the possibilities for structured assessment and suggests next steps toward aligning business and operations objectives with design evaluation techniques.