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The challenges in 21st century has expanded as leaders need to adjust their leadership approach to suit with the diverse workforce coordination. With such a pressing demand on skilled worker. They were expected to deliver their task effectively neglecting that some may have difficulties. With so many issues in turnover and early retirement, Malaysia seems to face with major withdrawal of their talented, and experience employees in labour force. Prior to this, job satisfaction was said as the antecedent in early retirement and turnover. In today‘s workforce orientation, the workforce was composed by these four generational cohorts from Baby Boomers to generation Y. They coloured the environment in their own way. Each generational cohort have different characteristic that represent them. It is best to understand that their distinctive characteristic was shape by demographics trends, cultural phenomena, and many more. Technical competency is far more common place for a gen Y and Z. This is certainly a reality of technical deficit to gen X. With knowing about the challenges, issues and their characteristic, it is best to help us understand how they work and lead to promote job satisfaction.