In this Chapter’s beginning, we introduce the degree to which emerging information technologies have changed both the organizational context and the traditional leader-follower power relationship, and the significant challenges that have arisen from this evolution. In addition, we examine the emergence of leadership substitutes, such as teams, that are common to many information technology work groups and discuss the kind of leader influence that appears to be warranted. Most importantly, however, we present a leader behavior model tied closely to the situational leadership paradigm. In this model, we seek to show that unique actions and behaviors are associated with four specific leadership styles. Further, the model shows leaders’ behavioral differences based upon whether they do or do not possess rational legal authority, commonly referred to as “position power.” Most leadership discussions are limited to the descriptive nature of leadership and fail to offer specific guidance in identifying which leadership style is situational appropriate. We seek to remedy that shortcoming and take the critical next step of identifying leader behaviors that are appropriate for enhancing followers’ effort toward successful goal-directed behavior.