Designers routinely create informal “thinking” sketches to explore a design space, “talking” sketches to communicate design ideas during the early phases of the design process, and “learning” prototypes to test potential concepts. This study presents two new tools to assess novice designers’ sketch attributes and prototyping reflections in the context of an introductory design course. First, it proposes a rubric for assessing the quality of early-stage design sketches including line smoothness, proportion, and understandability. Of particular note is the contribution of assessing understandability as a metric for sketches as communication tools. This study also presents a tool to capture designer reflections after each iteration of a prototype. Not only does this record what is learned about a design but also designers’ personal and emotional reactions to the process. Sketching-related results show a positive correlation between sketch quality and understandability, indicating the importance of sketch quality especially when designers use sketches to communicate. Results also indicate that early-stage sketch quantity, but not quality, is linked with design outcomes. This study also finds a link between the frequency of sketching and higher maximum sketch quality scores (i.e., at least one highly rated sketch) as well as a correlation between individuals’ maximum sketch quality scores and overall design outcomes. Preliminary results around prototyping indicate that reflection on both the technical and emotional aspects of prototyping may be a worthwhile area of further study. Finally, several results point to novice designers’ lack of consistent focus on users in their prototyping reflections and presentations.