This chapter explores the nature of positive and transformative leadership, as well as problematic leadership related to constructs such as Social Dominance Orientation, dark triad leadership and elements of power use and misuse by leaders. It demonstrates how the dark triad might correlate and interact with other dimensions of power, leadership, compassion, individual and organizational well-being. The chapter also explores leadership through the lens of social mentalities starting with self-focused, competitive ones. High social dominance orientations (SDOs) prefer to be dominant in normal relationships, are immoral, lacking in empathy and benevolence, scoring high in Machiavellianism and psychoticism. The chapter suggests a need for intervention programs that facilitate an increase of compassion for others or a reduction in fears of compassion from others, for others and for self. A mediational role was found between fear of compassion from others and for self in the relationship between SDO and positive leadership.