Broad community-scale, collaborative planning processes can help stakeholders develop trust. However, planners should also consider ways to develop trust before embarking on larger community processes. When relationships are fostered between community organizations through smaller planning exercises, those relationships can lead to unexpected and innovative outcomes. Such partnerships lead to independent projects as well as to more effective participation in formalized, broad-based planning. The central components of small working sessions and of their process include allowing relationships to develop over time, creating alternative narratives in the context of community conflict, and validating local knowledge in formal planning discourse. What our experience tells us is that although trust can be built in large, formalized processes, when community members learn to work together beforehand, that earlier groundwork facilitates more effective participation in later projects. Planning as discussed here is iterative and supported by local NGOs in Monteverde, Costa Rica.