late 15c., "a guide," from Anglo-French directour, French directeur, agent noun from Latin dirigere "set straight, arrange; give a particular direction to," from dis- "apart" (see dis-) + regere "to direct, to guide, keep straight" (from PIE root *reg- "move in a straight line").
Corporate sense of "one of a number of persons having authority to manage the affairs of a company" is from 1630s; theatrical sense of "the leader of a company of performers" is from 1911.
word-forming element meaning "quality, condition; act, power, skill; office, position; relation between," Middle English -schipe, from Old English -sciepe, Anglian -scip "state, condition of being," from Proto-Germanic *-skepi- (cognates: Old Norse -skapr, Danish -skab, Old Frisian -skip, Dutch -schap, German -schaft), from *skap- "to create, ordain, appoint," from PIE root *(s)kep-, forming words meaning "to cut, scrape, hack" (see shape (v.)). It often forms abstracts to go with corresponding concretes (friend/friendship, etc.).