This chapter asks: how does a young, British woman succeed in leading a group of patriarchal, hierarchically organized, tribal head hunters? In Burma during World War II, Ursula Graham Bower recruited, trained and led a group of Naga head hunters successfully against the Japanese. She was the only woman to hold a de facto combat command in the British Army during WWII. This chapter distinguishes between transactional and transformational models of leadership, discusses some of findings on the role of gender in transformational leadership and then examines the literature on cross-cultural leadership, which indicates that roles and norms of leadership depend on the cultural context. If desirable leadership traits are culturally dependent, then it seems likely that the Naga would not have accepted Bower as a leader under any circumstances. Yet, in a society where leadership was hereditary, male, and based on the collective, Ursula Graham Bower was able to lead the Naga successfully against the Japanese. This chapter considers the topics of cultural difference, cultural congruence, rapport and cultural adjustment in cross-culture in extremis military leadership.