Empathy plays a vital role in improving student engagement and supporting organizational change in schools. In fact, empathy is widely recognized as an essential skill for integration during such efforts. In collaboration with Battelle for Kids, the Cumberland Valley School District in Mechanicsburg, Pennsylvania, launched a vision for school improvement with its Portrait of an Eagle initiative. Utilizing Leader Learning Walks and Studio Classroom instructional strategies, empathy-driven approaches in support of the Portrait of an Eagle rollout were launched in the inaugural year of the initiative. This action research study sought to determine the impact of empathetic strategies in supporting the Portrait of an Eagle strategic initiative implementation at Cumberland Valley School District. Through investigation of the impact of empathy, with emphasis on the perspective taking domain of empathy, qualitative methods focused specifically on empathetic strategies employed by district leaders and teachers. The study highlighted empathy in collaborative leadership and instructional design to support the district initiative. The study further analyzed qualitative data from district leaders and teachers in the form of surveys and interviews. The action research methods determined the effectiveness of empathy-driven strategies during the initiative rollout. Recommendations also disclosed how to further support district progress in efforts to best incorporate Portrait of an Eagle competency adoption in both leadership and teaching practices at Cumberland Valley School District to best support student engagement. The study added to the research on the value of empathy in initiative launch efforts and offered a model of implementation for other districts to follow. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]