The Canvas LMS Ask Your Data feature is meant to help educators turn complex institutional data into clear, actionable insights. As lead UX designers and art directors, we partnered with the Intelligent Insights team to reimagine how instructors pin, search, and return to the insights that matter most. We simplified the pinning workflow, introduced more intuitive patterns for chat search and history, and designed clearer waiting states that keep users oriented instead of stalled. The result is a calmer, more predictable experience that lets educators focus on making data-informed decisions—not wrestling with the interface.