With exponentially exploding technology, individuals prolonging retirement, and the melding of generations, leaders today face a variety of challenges. Differences in cultures, values, genders, and educational experiences form a wide divergence between traditionalists and Generation Y. A majority of traditionalists have retired or are in the process of retiring; Baby Boomers are continuing to work; and Generation Y is entering the workforce. Due to these various factors, leaders are facing challenges that have never been faced. Skills vary from the top-level management throughout the organization’s structure and to the customer.