This paper presents a factor-analysis based questionnaire categorization method to improve the reliability of the evaluation of working conditions without influencing the completeness of the questionnaire both in Taiwanese and Chinese construction enterprises for structural engineering applications. The proposed approach springs from the AI application and expert systems in structural engineering. Questions with a similar response pattern are grouped into or categorized as one factor. Questions that form a single factor usually have higher reliability than the entire questionnaire, especially in the case when the questionnaire is complex and inconsistent. By classifying questions based on the meanings of the words used in them and the responded scores, reliability could be increased. The principle for classification was that 90% of the questions in the same classified group must satisfy the proposed classification rule and consequently the lowest one was 92%. The results show that the question classification method could improve the reliability of the questionnaires for at least 0.7. Compared to the question deletion method using SPSS, 75% of the questions left were verified the same as the results obtained by applying the classification method.