While design and designing are core elements in computer science and software engineering, conventional curricular structures do not adequately support design learning. Current methods tend to isolate the study of design within specific subject matter and lack a strong emphasis on reflection. This paper reports on insights and lessons learned from a user study in the context of ongoing work on developing an educational intervention that better supports design learning with a particular emphasis on learner-driven reflection. Insights drawn from this study relate to general aspects of design learning, such as the importance of collaborative reflection and the impact of learner perceptions regarding their abilities, as well as to specific improvements to our approach.