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This chapter aims to identify differences in the perception of transformational leadership (TL) of three generations – Baby Boomers, Generation X, and Generation Y or Millennials – for an in-depth understanding of the immediate role and challenges facing leaders in organizations. Current days is an excellent time to question what is known and what should be known about leadership and leaders. Latin American leadership characteristics can have a direct effect on the success of business ventures in the region. Leadership can be understood in diverse ways: as an attribute of a position in the organization; as a trait, according to the characteristic of the person; as a behavior, according to the way in which the person acts (Mallma-Vivanco & Córdova-Marcelo, 2015). Several studies carried out in Mexico, Colombia, and Chile show that the Latin American leaders believe that having good working relationships with low conflict is essential to their satisfaction and high performance, and they are usually authoritarian and prefer aggressiveness and assertiveness (Romero, 2004). This study reviews the literature across different generations and related best organizational practices to identify key definitions and empirical results. We compared and contrasted the data from different generations. The findings show that Baby Boomers have a better perception of TL of their leaders than Millennials and even those from Generation X. Thus, the empirical results allow business leaders to understand the differences in perceptions and the unique characteristics of the three generations of workforce in organizations: Baby Boomers, Generation X, and Millennials.