Sustainable development for cities and communities presents challenges planning for economic and environmental resiliency. Workshops can bring stakeholders’ local knowledge in combination with planning experts’ professional knowledge. This paper proposes a system model for workshops operating as transdisciplinary problem-solving systems of functions, processes, and roles. The identified mechanisms link to three steps: first, stakeholders define the relevant problems; second, stakeholders and planning experts contribute to exploring a range of possible decisions. Finally, decision methods illuminate and prioritize options for selecting concepts of desired solutions. An approach to examine and test the workshop system model for a site-specific example focuses on land-use at transit stations. The research aims to improve human capacity to address the growing complexity in cities increasing social equity with economic and environmental resilience.