This chapter examines methods for evaluating the return on investment (ROI) of reskilling and upskilling programs within organizations. It highlights the critical role of strategic alignment and the use of meaningful metrics (both hard and soft) to measure learning impact. Despite the growing adoption of data-driven strategies, many companies continue to face challenges in effective evaluation. Building on established models such as the Kirkpatrick Model and the Phillips ROI Model, the chapter explores their practical applications in corporate settings. It advocates for a blended approach that integrates qualitative and quantitative analyses to create a comprehensive evaluation framework. The chapter concludes with actionable recommendations, offering strategies to maximize the value of training programs. By presenting a structured framework for strategic decision-making, it aims to support sustainable organizational success.