If the goal of teaching is to help students understand a subject, teaching cannot begin until student difficulties with a subject are understood. In order to create a guide for assessing student difficulties with chemistry material, students were asked to rate exam questions on three factors: problem difficulty, familiarity, and self-confidence. These surveys were then compared to difficulty ratings of the same questions as determined by chemistry professors. Students' ratings of problem difficulty, problem familiarity, and self-confidence correlated, as expected, with their success on exam problems. There was also some agreement between students and faculty on the difficulty of exam problems, though students were much more accurate of judging problem difficulty than were chemistry professors. Students were surveyed in two separate cohorts to test year-to-year reliability.