In this short article, we share our work as part of a partnership to study and promote community-based leadership in San José, California. Our objectives are to contribute to applied anthropological work on community-based leadership and to relay how our project evolved from a standard applied “contract” partnership to a more equitable collaboration. We employed focus groups, pile-sort exercises, and follow-up interviews with established and emerging community leaders and residents in their communities in order to inventory leadership attributes, skills, and relations and social networks. Our results point to the need to think beyond the idea of one-way transfers of skills and resources from established to emerging leaders—“the bucket theory”—and instead support a more collaborative and multidirectional approach. We conclude by discussing how this project developed—initially unexpectedly—into a participatory action initiative.