A system displays a representation of an original equipment remote control device for a target device to be controlled using a macro button of a configurable controlling device. The displayed representation of the original equipment remote control device includes representations of buttons that would be used on the original equipment remote control device to control controllable functions of the target device. The system accepts input by which one or more of the displayed representations of buttons are selected. The macro button is then configured whereby an activation of the macro button will cause a transmission of commands from the configurable controlling device to control those controllable functions of the target devices that correspond to the one or more of the displayed representations of buttons that were selected.