Many psychological studies have shown that facial appearance matters in the people we select as leaders. An evolutionary-psychology approach suggests that facial cues serve as inputs into an adaptive, context-sensitive followership psychology. That is, leadership suitability may be contingent upon the match between facial cues (indicating, e.g., dominance, trust, competence, and attractiveness) and follower needs. There is much support for this evolutionary-contingency hypothesis in the psychological literature. People prefer leaders with dominant, masculine-looking faces in times of war and conflict, yet they prefer leaders with more trustworthy, feminine faces in peacetime. In addition, leaders with older-looking faces are preferred in traditional knowledge domains, whereas younger-looking leaders are preferred for new challenges. We speculate about whether such followership heuristics are evolved or culturally learned, currently adaptive or mismatched, and, finally, we address the implications of the evolutionary-contingency hypothesis for leadership theory and practice.