A digital radio communications transceiver programming apparatus and method are used to load personality defining information in a non-volatile EEPROM memory within a portable or mobile digital radio transceiver. A user interface defines display formats organized in a hierarchial tree structure with more general tasks nearer the "root" of the structure and more specific tasks existing at the "leaf" portions of the structure. The tasks are organized in a hierarchial fashion to simplify operation. Pop-up display formats filling only a portion of the display are used to display help text and for specific user selection tasks. Help text is provided on a field level and on a display format level. Error and range checking are also provided on a field-by-field basis. A changing prompt is displayed on a field-by-field basis to guide the user in filling in input fields, and different operative function key assignments are made on a display format basis.