During their school years, students encounter difficulties of various types from both content-related and emotional aspects. Often, when asked directly about their learning difficulties, students struggle to express these difficulties explicitly and clearly; as a result, teachers find it a challenge to provide them with a suitable and satisfactory response. In order to help students express their scholastic difficulties, particularly cognitive and emotional ones, and foster their ability to chart out courses of action for coping with these difficulties, we have developed a tool we call “Corresponding with the Professor”.