To empower users of wearable medical devices, it is important to enable methods that facilitate reflection on previous care to improve future outcomes. In this work, we conducted a two-phase user-study involving patients, caregivers, and clinicians to understand gaps in current approaches that support reflection and user needs for new solutions. Our results show that users desire to have specific summarization metrics, solutions that minimize cognitive effort and solutions that enable data integration to support meaningful reflection on diabetes management. In addition, we developed and evaluated a visualization called PixelGrid that presents key metrics in a matrix-based plot. Majority of users (84%) found the matrix-based approach to be useful for identifying salient patterns related to certain times and days in blood glucose data. Through our evaluation we identified that users desire data visualization solutions with complementary textual descriptors, concise and flexible presentation, contextually-fitting content, and informative and actionable insights. Directions for future research on tools that automate pattern discovery, detect abnormalities, and provide recommendations to improve care were also identified.