The healthy functioning of a school system depends upon many factors. The internal micro factors require a leader to take into account the heart and human conditions that coexist within the lived environment. The external macro factors are the events that occur in unexpected ways. When these internal micro factors are not functioning well, and a macro external event occurs unexpectedly, the system can struggle. While leaders may equip themselves with dynamic leadership skills to assist in navigating through the uncharted macro events, there is no disputing the fact that the pandemic of COVID-19 caught all leaders off guard. Many leaders just wanted to get through it. Many yearned to get their organizations back to normal. This qualitative case study examined the leadership's responses from Ulster BOCES (Board of Cooperative Education), during and after the COVID-19 pandemic. Ulster BOCES-Educator Edge leadership attended to the hearts and minds of staff in human ways throughout each stage of the pandemic. This qualitative case study used the adaptive resilient frameworks from (Heifetz, 1994; Scharmer, 2009; Schein & Schein, 2017) as an inquiry into three research questions: 1) What kind of environment nurtures human development and promotes learning? 2) How did leaders attend to the human elements in virtual and hybrid spaces? and, 3) How did inclusive contexts highlight the need for varied approaches to nurturing and developing learning for both the leader and the learner?