This report aimed to understand the reasoning that leads cities to undertake efforts to move towards sustainability. Interviews and surveys were undertaken with cities that are following the Framework for Strategic Sustainable Development and other models in moving towards sustainability to understand the motivators and drivers, the barriers and challenges, and the benefits that these cities have encountered and realized through the move to sustainability. The motivators and drivers, barriers and challenges, and benefits were categorized within seven forms of community capital – natural, economic/financial, physical/built, social, cultural, human, and political. Returns on investment were categorized, and those that were pronounced were highlighted. A guidebook has been developed to assist sustainability practitioners and sustainability leaders in cities to engage senior-level decision-makers with language that would encourage them to move towards sustainability.