This study determines and proves that impelementation of transformational leadership style and the character of the millennial generation development moderated by job enrichment can influence organizational performance optimally. The millennial is a unique generation characteristic and expected to become a successful leader who determines the future trend of leadership style and influences organization performance if they receive some approaches to build their capacity effectively. This study uses a random sampling technique with 160 junior and senior managers of the millennial generation. The data was analyzed with a quantitative approach, which classical assumption test and Moderated Regression Analysis (MRA) used SPSS. This study has found that job enrichment as the moderating variable does not strengthen the influence of transformational leadership on organizational performance and significantly influences millennial characters on organizational performance. It seems that organizations must overcome these challenges to create optimal leadership strategies for millennial employees and design job enrichment programs that suit the needs of millennial managers. Further research can be carried out with other case studies using more relevant approaches, analytical methods, and specific leadership theories.