We focus on the long-term impacts of service-learning pedagogy on an oft-overlooked assessment group: graduate instructors. We describe the civic engagement program we participated in as graduate student teachers, the Chicago Civic Leadership Certificate Program, and we illustrate how our early experiences with community-based pedagogies led to formative and long-term impacts on our approaches to research, teaching, and service and on our professional and personal work and identities. Based on our experiences, we offer a set of best practices that can serve as a foundation for the intentional design and assessment—both formative and summative—of forward-thinking graduate instructor objectives and outcomes.