A recent Forbes article stated that “Mindfulness is hot right now – Hollywood hot, Davos hot, Main Street hot … For business leaders, encouraging mindfulness is more than just being tuned in; it's a strategy to improve person and company-wide performance and productivity” (Bruce 2014). Leadership is a perennially trendy topic, and its fusion with mindfulness creates a combination of potential über-trendiness. But is this hype justified? Our endeavour in this chapter is to elaborate on the connections between mindfulness and leadership. A related goal is to take a critical look: generally both mindfulness and leadership are viewed in a positive light. Although “leadership” evokes ideas of strengths and charisma, transformation, and achievement. Yet at the same time, a “dark side” of leadership and leaders also surfaces in the form of leader arrogance, hubris, cronyism, abusive supervision, and outright dictatorships.