In recent years, rapid and continuous innovation has occurred across fields of information technology (IT) and information and communications technology (ICT). Digital transformation (DX) initiatives are also accelerating. In this context, our research question is “how will our careers change?” This paper reviews previous research on careers, technological innovation, and employment through the lens of diversity to explore how careers are changing in the Internet of Things (IoT) and artificial intelligence (AI) era, focusing on both workforce and working style diversity. Prior studies have confirmed that background diversity and other factors positively influence performance. Additionally, from a technological innovation perspective, a high level of education is known to have a favorable impact. In the IoT/AI era, the importance of skill development is expected to grow, yet only a limited number of companies have implemented reskilling initiatives for diverse workers. Adapting older workers to emerging technologies remains a significant challenge. From a career development standpoint, there is a growing emphasis on diversity and values that transcend demographic attributes. As diverse working styles continue to expand, the number of individuals able to participate in the workforce is expected to rise. Hence, companies must now confront the challenge of integrating diversity into management and identifying concrete strategies to realize its benefits.

This paper examines the factors necessary for Japanese companies to achieve organizational transformation through reskilling. It begins by reviewing the global context wherein reskilling has gained attention; subsequently, it provides an overview of two prominent success stories of organizational transformation using reskilling, which are studied even in overseas business schools. Finally, it discusses the applicability of these insights to Japanese companies and identifies the challenges that Japanese companies must overcome during implementation. Addressing reskilling, which has become a buzzword, is not merely a transient issue but an ongoing challenge for companies in an ever-evolving business environment. For the future development of Japanese companies, it is necessary to foster employees’ awareness of career autonomy and habit of skill learning, and most importantly, to cultivate Dynamic Managerial Capabilities among management.