Global fragility and conflict have challenged business to identify solutions to some of the world’s most “wicked problems.” Yet corporate practitioners struggle to analyze the relationship between the firm and society in conflict-affected and fragile spaces. Systems analysis, emergent in peacebuilding, offers a compelling approach for management practitioners and scholars to better understand the role of business in complex social environments. This participatory, qualitative approach applies collaborative inquiry and causal-loop diagraming to analyze the complex dynamics that create the operational conditions and to trace the impact of the firm on those conditions. This article outlines the application of this approach and argues that it fills a gap in the current tools used to understand the private sector’s role and agency in contributing positively to society. What emerges is a pathway to enhancing theoretical development and practical understanding of the risks and impacts of corporate operations in the most challenging of contexts.