Abstract For the past 3 years work has been done on the development of a systemic thinking methodology to help decision makers in complex social systems make better decisions. This methodology, titled the ¨Complexity Funnel,¨ takes the form of a series of social transformation workshops (STW) that seek to map the current state of the social complex system, with emphasis placed on the identification of actors , the interrelations between the actors and the resulting impact of the relationship on various variables. The goal is then to reduce the complexity within the system. These workshops have previously been tested and refined based on implementations in private, public and mixed companies, however their application to community related projects is still emerging. This paper specifically shares the use of the first workshop in the Complexity Funnel methodology called “The Web of Life” and its implementation in an engineering capstone design project where students worked alongside various transnationals community partners (i.e., a national estuary research reserve, a local canyon community, and a non-profit organization that focuses on youth development) to support the creation of a community-based waste business that applies a ‘waste is a resource’ approach. The Web of Life workshop invited the participation of a wide variety of stakeholders to co-create a common systemic model of the community system. The resulting artifact was in turn used to help the students and their community partners begin to understand the breadth of the community needs and challenges and identify key criteria for defining, evaluating and monitoring potential solutions. This paper presents the structure and execution of the Web of Life workshop and the resulting artifact created by participating stakeholders. It will also discuss the implications for further work within the context of the capstone design project and more broadly for communities-engineering partnerships.