Previous studies have researched how developer experience affects code quality, but difficulty was ignored although experienced developers are more likely to work on more complex parts of a project. We examine work difficulty by focusing on revised files. Using product metrics, we evaluate file complexity for each type of file origin. Specifically, we analyze three large commercial projects (each with about 250,000 LOC) executed by the same organization to analyze the relationship between previous project experience and developer's work. Although experienced developers do not necessarily work on more complicated files, they introduce fewer defects, especially if the difference in work difficulty is not significant.