When asked to draw, most people are hesitant because they believe themselves unable to draw well. A human instructor can teach students how to draw by encouraging them to practice established drawing techniques and by providing personal and directed feedback to foster their artistic intuition and perception. This thesis describes the first methodology for a computer application to mimic a human instructor by providing direction and feedback to assist a student in drawing a human face from a photograph. Nine design principles were discovered and developed for providing such instruction, presenting reference media, giving corrective feedback, and receiving actions from the student. Face recognition is used to model the human face in a photograph so that sketch recognition can map a drawing to the model and evaluate it. New sketch recognition techniques and algorithms were created in order to perform sketch understanding on such subjective content. After two iterations of development and user studies for this methodology, the result is a computer application that can guide a person toward producing his/her own sketch of a human model in a reference photograph with step-bystep instruction and computer generated feedback.