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There little agreement regarding what constitutes an exemplary design problem or case analysis problem for modeling undergraduate engineering instruction and less agreement regarding the best way to measure students improvement toward being better problem solvers. We describe the development of a research method toward accessing how students think about design is described, what constitutes a measurable response, how to measure undergraduates' appropriation of typology frameworks, and how to compare through qualitative research methods pre and post student performance. The discussion draws from Jonassen’s (2000) framework for problem typology, as well as cognitive learning frameworks of design thinking, and metacognition as a theoretical basis that informs the problem formulation and planned approach for analysis.