Background: Rapid technological advancements have modified the nature of employment, presenting both opportunities as well as difficulties for all generations. The often use of automation and digital tools by organizations has further raised concerns with regards to various aspects of work life among employees, especially Generation X and Millennials. Therefore, it is essential to comprehend and compare how these elements affect both the generations differently whilst managing a multigenerational workforce. Objectives: The study compares Gen X and Millennials on five core dimensions: de-skilling, reskilling, redundancy, tech-driven changes, and job loss anxiety, to investigate notable generational disparities. Methodology: Data collection took place via an online google form to gather information from working individuals of Indian nationalities, belonging to the Generation X (n = 50) and Millennial (n = 50) generations. Independent sample t-test was used for data analysis. Results: The findings depicted a significant difference in dimensions of de-skilling, redundancy and job loss anxiety among the two generations, with Generation X having higher scores than Millennials. On the other hand, there was no statistically significant difference between Generation X and Millennials with regards to tech-driven changes and reskilling. Conclusion: The results of this study will be helpful in developing organizational strategies and interventions meant to assist various generations in adjusting to changes in their workplaces brought about by technological advancements.