In human-machine systems, a user gets abstracted information of a machine via an interface and operates it referring to a manual. If a manual has an erroneous description leading to automation surprises, the user may be lost in his/her operations so that he/she may make a serious human error. In this paper, we propose an algorithm for generating a manual by which automation surprises never occur. We model the machine and the interface as a discrete event system and a mapping from machine's state to a display of the interface, respectively. First, we represent a manual as a finite language and model behavior of the system operated by the user with the manual as a tree called an operational tree. Next, we characterize three automation surprises using the tree. Finally, we propose an algorithm for generating an operational tree by which the machine reaches a target state.