The Iron Lion Design Challenge is a design-build-test event held annually at the Penn State University Park campus. In addition to providing hands-on experiences for students, it is an opportunity for faculty to pilot new strategies for teaching design practice to students. Over the last six years two important lessons have emerged: 1) prototyping very early in the process improves subjective outcomes as does 2) evolving these prototypes through iteration. This was observed across skill-level, time available to participants, background, and the nature of the project.