At the moment, Word’s grammar checker is a poor substitute for a seasoned writing instructor. However, a start-up company, WriteLab, is trying to perfect machine learning for programs that assess writing, not for just a few stylistic and grammatical errors, but “quality” of composition. Once a dogged critic of these programs, MIT research affiliate, Leslie Perelman, joined Writelab as Chief Research Scientist. A Boston Globe interview from last year documents the reasons behind his change of heart. I haven’t been able to discover evidence that he is still a member of the company team.