In today’s business environment, characterized by increasing uncertainty, unpredictability, complexity, instability, and ambiguity, practitioners must cultivate wise judgment through various decision-making processes and act based on actual situations while adhering to their values and morals. This chapter explores, through case studies, why existing companies are forced to withdraw from existing markets due to new products and business models created by “technology convergence (knowledge convergence)” encroaching on these markets. In promoting such exploratory research, field surveys have revealed that in response to changes in the environment (technological innovations and new business models), existing companies are unable to appropriately transform their high-quality tacit knowledge accumulated over the years and cannot drive the new knowledge creation spiral (SECI model). This chapter clarifies the reasons why existing companies cannot respond to technology convergence from the perspectives of existing research, such as knowledge creation theory and boundaries knowledge. Additionally, it discusses the core elements required of corporate organizations and individual practitioners to respond to diverse knowledge convergence, including technological innovation: holistic leadership, dynamic fractal organization, and collective phronesis.