A system and method for gathering information from an operator of an asset is provided. The system interfaces with a management computer to provide a list of questions for response by the operator. A wireless infrastructure operates to distribute the list of questions from the management computer to the operator. The wireless infrastructure includes an asset communicator having a wireless communication device for communicating the questions, a processing unit, a storage unit for storing the questions and responses thereto, a display unit for displaying the questions, and input unit for the operator to input such responses. The processing unit is operable to prompt the operator with a first question, receive a response from the operator to the first question, select another question based on the response, and prompt the operator with yet another question.