Some of the caboose (cabin in prr talk) crew would be tasked with watching the train, and would face forward watching for dragging equipment, hotboxes, derailments, or other problems with the train. This would most likely be the rear end brakeman and the flagman.
the conductor most likely, especially on a local, might be sitting at the desk inside the caboose doing paper work to figure out his next switching move and documenting cars dropped and picked up.
Remember the conductor is the "captain" or boss of the train. He gives signals to the engineer telling when to move and stop etc. They work together obvisously, but the conductor is officially in charge of the train.
