The improvements of technical documents quality influence the popularity of its relevant product; as the customers do not like to waste their time in the help desk’s queue, they will be more satisfied if they can independently solve their problems through the technical manuals in an acceptable time. Moreover, the cost of support issues will decrease for the product providers. In addition, the help desk team members could have more time to support the rest of unresolved issues in a better-qualified way. To afford the mentioned benefits, we have done the current thesis to estimate the usability of the documents before publishing them. As the result of such prediction, the technical documentation writers could have a goal-driven approach to improve the quality of their products or services’ manuals. Furthermore, as different structural metrics have been observed in this research, the result of the thesis could create an opportunity to have multi-discipline improvement in Information Quality (IQ) process management.