At Chicago, Hole studied under Robert Braidwood, who was investigating the origins of food production in Southwest Asia. In 1959, when political instability prevented him from returning to his excavations at Jarmo in Iraqi Kurdistan, Braidwood began working across the border in the Iranian part of the Zagros Mountains. Hole joined Braidwood's team, which in 1959 conducted the first systematic surveys of early prehistory in Iran, in the region of Kermanshah, and the following year conducted excavations at Asiab, Sarab, and Warwasi. After this Braidwood moved on to southeastern Turkey, but Hole and another of his students, Kent Flannery, returned to work in western Iran.