One of the Six Core Principles of Improvement is “Make the work problem-specific and user-centered.” Improving education requires looking at problems from the point of view of the “user” — usually students, teachers, or both — to build empathy for their challenges navigating education systems and to ensure that they’re participants in finding a solution. Shadowing is one way to focus on the users. Educators and researchers have long known that shadowing can lead to powerful observations and empathy insights to drive system improvements. We are intrigued by the Shadow a Student Challenge that offers methods, tools, and a network for educators who want to try this user-centered empathy approach.