Millennials, who by 2024 will make up approximately 34% of the U.S. workforce, will play a critical role in organizational strategies and productivity, as will the supervisors who manage them. The purpose of this multiple case study was to explore the intergenerational communication strategies that Generation X supervisors used to motivate and engage high performing millennials in the workplace. The framework for this study was Mannheim's generation theory and the 2-factor theory of motivation by Herzberg, Mausner, and Snyderman. Data were collected from parks and recreation employees in the southeastern region of the United States, including 4 Generation X supervisors who completed semistructured interviews and 2 millennial cohort focus groups. Data were transcribed, coded, and validated through member checking and methodological triangulation. The 4 themes identified were culture and socialization, relationship building and intergenerational connectedness, employee growth and development, and rewards and recognition. The findings of this research may benefit millennials, frontline supervisors, parks and recreation agencies, and leaders in other organizations by providing an understanding of generational needs. The data presented in this study may support positive social change by showing that supervisors and millennial employees can build high quality relationships within their organizations, enabling those organizations to support the communities they serve.