Problems in the world are classified into two classes; the ones that people can foresee to the details beforehand (to such an extent that making computer programs for solving them is possible) and the others. Because of very the nature of current information technology computers are used only for the former class problems but the latter problems are left to human without exception. Only possible method to deal with unforeseen problems in the latter class is to take trial-and- error approach. When an unforeseen problem comes arise, human tries to make a hypothetical solution and evaluate it. When the scale of problem gets large however, it becomes a very difficult task even for human. Recently, the number and the scale of the latter class problems are increasing. It is anticipated that in near future they go beyond human capability. Then no one can deal with these problems satisfactory and it is expected that many troubles happen to be. An innovative technology is required to deal with these problems in order to avoid the troubles. It is expected that computers have potential to contribute in this process by undertaking evaluation of the hypothesis. Since however the problems are not foreseen beforehand, it is not possible to provide any specific method suited for evaluating the hypothesis in advance. Automatic and dynamic generation of evaluation system in real time is necessary as an innovative information technology. The major objective of this paper is therefore to discuss such an information technology that can aid human trial-and-error approach. An analysis of the process of solving unforeseen problems and a method of generating automatically information systems for evaluation are discussed.