**Abstract**

Leadership, especially that associated with collaborative endeavors, is important for addressing emerging, increasingly complex challenges. That development is relevant to liberal arts colleges that are dedicated to educating generalists rather than specialists. The author maintains that such an education helps young people cultivate three sets of individual characteristics: values, capabilities, and aspirations. As well, it provides young people opportunities to become involved in a six-part iterative process intended to promote positive change. In spring of 2019, the author's home institution Dickinson College launched a call for proposals from faculty, staff, and alumni that were consistent with the College's mission and strategic priorities; and would strengthen its competitive position and deepen its relationships with stakeholders. Over a two-year period, the author played a central role in (1) helping shape a proposal originated by two alumni and (2) with several Dickinson community members, translating the proposal to an implementation plan. The efforts fell short; but the author learned lessons about such an endeavor. A well-conceived plan must find the areas of intersection among the interests of key stakeholders. A plan must be of scale that enables organizational practicality and financial feasibility. Successful implementation hinges on the components of good collaborative leadership highlighted above. Explanation and launch of a plan must create excitement among sponsors and potential beneficiaries.

**Keywords:** Leadership Development, Liberal Arts Education, Relational Leadership, Case Study, Personal Stories, Personal Leadership Characteristics, Systems Insights
