This dissertation in practice employed a multiple case study design to better understand how two executive directors within a national network of arts and technology educational organizations defined, nurtured, and measured empathy with in their students. Empathy can connect diverse people and improve relationships, and it has been proven to positively impact academic success. Many schools and educational organizations working with adolescents measure success through outcomes such as graduation rates, attendance, grades, and more. Therefore, since research has shown that empathy correlates positively with these outcomes, many educational programs now articulate the development of empathy as an organizational strategy or value. While many educators now understand its importance, there is little consensus as to what empathy actually is, how one can develop it in adolescents, and its impacts. This study uncovered four key themes that emerged throughout interviews with the two executive directors: value and respect, collective discovery, challenging of assumptions, and satisfaction of basic needs. Within these four themes, two gaps emerged: the absence of tangible measures and intentional training and programming that supports the four key themes. This informed the recommendations, which are broken into two sections, the co-development of a network-wide theory of change logic model and intentional professional development that focuses on Human Centered Design and cultural competency. [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.]