A descriptive case study approach is employed using a content analysis of the blogs of 36 school leaders who took part in the 2016-2017 Shadow a Student Challenge project and follow up interviews of five of the school leaders. This research was used to explore and describe how an empathetic design approach provided a greater vantage point for school leaders. By viewing school through the eyes of students, school leaders gain a deeper insight into the school experience. School leaders play a key role in establishing the culture, climate, and educational outcomes within their school environments. An empathetic design approach to school reform provides a stronger point for initiating change than an atmosphere focused on evaluation and accountability. Taking a school-based approach, encouraging school leaders to immerse themselves in the school experience, provides an opportunity for school leaders to gain empathy and insights foundational in generating meaningful and innovative change leading to sustainable education. Three major themes emerged from the findings: 1) pace and structure of the school day, 2) student learning experience, and 3) reflective and innovative insights.