One of the factors that influence software marketability is software interfaces. In this marketing rat race, Microsoft created a revolution in its Office software. In year 2007, they replaced menus and toolbars with a new structure called it Ribbon interface. Although the new interface has many advantages, usability researchers are criticizing MS Office interface from different aspects. They believe, it still has serious usability issues that hinder usage of MS Office for users with less computer literacy. Since middle-aged and elder users with less computer literacy are a large group of users who need to work with MS Office, this study aims to increase the learnability level among them by proposing an interface design solutions for MS Office. This research utilized in-person usability testing to evaluate the usability issues of MS Office in terms of both visual and cognitive issues. In order to ensure the validity of the data, it was tried to triangulate the data collection process by collecting data from different sources, namely, quantitative measurement of users’ improvement, direct observation, and interview. The results of data collection has led to design a prototype for MS Office. Based on the usability test on the prototype and finding the factors that has led to users’ improvement, a number of solutions are extracted for MS Office interface as a contribution to the body of knowledge. Putting these solutions into action, self-learning would be promoted and learning issues of middle-aged and elder users with less computer literacy would be decreased.