As millennial workers enter and dominate the global workforce by 2025, understanding their leadership styles is vital to bring about higher level of performance and productivity in the workplace. The Millennials, the next generation of leaders, are entering the workforce and assuming leadership positions in a relatively short period. More often, they found themselves leading employees that are older than themselves and yet their leadership traits and styles are not fully understood. The study explores factors affecting leadership styles of millennial managers and how they are manifested and applied in managing and resolving conflict involving older subordinates. Using a qualitative approach, it employs interviews, participant observation, and prolonged engagement with four millennial managers from the National Food Authority in the Philippines as they lead, manage, and interact with their older staff. Data collected were triangulated by document analysis and interview of the millennial managers’ subordinates themselves. The results of the study show that the participants’ leadership competencies are in the early stages of development. The participants consider building good impression and rapport highlighting the importance of soft skills in leadership, strong sense of respect, reverse mentoring, delegation of tasks, and the ability to handle expectations and performance as factors in managing older employees. This study draws the attention to examining the leadership attributes and potentials of Filipino millennial managers in the context of Philippine workplace culture using insights from Public Administration, Social Sciences, and Psychology.