Purpose: This study examines the human resource challenges associated with managing a multi-generational workforce in the information technology sector of Coimbatore, Tamil Nadu. Methodology: A qualitative research design was employed, utilizing semi-structured interviews with 25 HR professionals and team leaders from 15 IT companies in the Coimbatore region. Thematic analysis was applied to identify recurring patterns in generational dynamics, conflict points, and management strategies. Findings: Results revealed four primary challenge domains: communication style differences, varying work expectations and commitment definitions, divergent career progression aspirations, and knowledge transfer gaps between generations. Baby Boomers and Generation X employees emphasized hierarchical respect and institutional loyalty, while Millennials and Generation Z prioritized flexibility, purpose-driven work, and continuous skill development. Practical Implications: The study recommends implementing reverse mentoring programs, developing flexible policy frameworks that accommodate life-stage needs, creating cross-generational project teams, and training managers in generational intelligence. Originality: This research contributes to the limited literature on multi-generational workforce management in South Indian IT contexts, providing region-specific insights for HR practitioners in Coimbatore's growing technology sector.