This study examines the effectiveness of upskilling and reskilling initiatives in enhancing workforce agility and adaptability in a rapidly changing employment landscape. A quantitative methodology is employed to collect data by surveying 250 employees from 45 prominent companies in Bangladesh. The Study employed Partial Least Squares Structural Equation Modeling (PLS-SEM) to examine the relationships between Strategies for Upskilling and Reskilling (SUR), Workforce Agility and Adaptability (WAA), and the Organizational Support Environment (OSE). The findings suggest that a positive organizational climate significantly influences the effectiveness of upskilling and reskilling initiatives, leading to improved employee capabilities and higher organizational performance. The report also emphasizes barriers such as insufficient financial resources and resistance to change, emphasizing the significance of tailored training programs, a culture that encourages continuous learning, and integrating modern educational materials. These insights give organizations practical advice on establishing effective strategies for maintaining a flexible and adaptable workforce in a dynamic job market. The Study emphasizes the need for strong leadership and organizational support in fostering a culture that highly values ongoing learning and innovation.