As leaders, managers are expected to be proactive, self-confident, and independent, while as followers they must be willing to obey, conform and depend. Should middle managers roll the dice to choose which of the two roles they seek excellence in? The purpose of this chapter is threefold: first, to present some of the main internal factors and individual characteristics that define the work of middle managers as successful leaders or followers; second, to exhibit the main external factors that affect managers' opportunities to excel; and third, to analyze the potential impact of internal and external factors on the development of middle managers as better leaders or better followers. The analysis shows that to achieve excellence as leaders and followers, middle managers must be excellent influencers who correctly read situational factors and know how to take advantage of them.