In this article, we describe a project in which philosophy, in combination with methods drawn from mental modeling, was used to structure dialogue among stakeholders in a region-scale climate adaptation process. The case study we discuss synthesizes the Toolbox dialogue method, a philosophically grounded approach to enhancing communication and collaboration in complex research and practice, with a mental modeling approach rooted in risk analysis, assessment, and communication to structure conversations among non-academic stakeholders who have a common interest in planning for a sustainable future. We begin by describing the background of this project, including details about climate resiliency efforts in West Michigan and the Toolbox dialogue method, which was extended in this project from academic research into community organization involving the West Michigan Climate Resiliency Framework Initiative. This extension involved application of several methods, which are the focus of the Methods section. We then present and discuss preliminary results that suggest the potential for philosophical dialogue to enhance mutual understanding in complex community initiatives that focus on sustainable responses to climate change. Overall, the article supplies a detailed, instructive example of how philosophy can support policy-relevant decision-making processes at the community level.