A headman is the leading man in a village or tribal group — the man people look to as the most important, the one who speaks for the place. You meet it in older books and in talk about traditional village life, not in the name of a modern city mayor. It points to a man; a woman leader is not a headman. The word feels old-fashioned in today’s English. Though actually, it can also mean a man in charge of a small work group, but the village-leader sense is the one this entry is for. Do not mix it with headsman, which is a different word: the man who used to cut off heads.