Cobalt N‐heterocyclic carbene (NHC) catalysts promote intramolecular olefin hydroarylation of indoles bearing an N ‐homoallyl or bis(homoallyl) tether and a C3 aldimine directing group to afford dihydropyrroloindoles and tetrahydropyridoindoles under mild conditions. The course of the cyclization is dependent on the tether, but can be controlled by the NHC ligand.