Nonprofit organizations are typically comprised of staff from different backgrounds and education, and with varying degrees of leadership experience. In many cases, underequipped staff members are thrust into senior roles without mentorship or development that would prepare them for increased responsibility, leading to operational challenges, depleted morale, and staff burnout. Furthermore, without developing future leaders, issues of succession planning become evident both at the organizational level, and at the sector level. These concerns, in part, can be remedied by embedding strategic and intentional leadership development into the organizational culture of small nonprofit human service organizations. The problem of practice (PoP) in Kehillah Care Alliance (Kehillah) is the lack of intentional leadership development, and the organizational improvement plan (OIP) is focused on analyzing Kehillah through multiple lenses and frameworks in order to identify solutions to the PoP. This OIP examines Kehillah’s organizational context through Bolman and Deal’s four frames, Quinn’s competing values framework, and Nadler and Tushman’s organizational congruence model. It is determined that the best solution for the PoP is a collaborative leadership development program with customized options. Through use of a hybrid authentic-servant leadership approach, and in consideration of Kehillah’s systems theory framework, Lewin’s three-step model is used as the guiding change tool supported by plan-do-study-act (PDSA) iterative monitoring and improvement cycles. The desired state of Kehillah is one of high performance, caring culture, and growth opportunities. The OIP is mapped out to achieve this state, and can be modified, applied, and scaled for nonprofit organizations of any size.