A system and method for providing customized content recommendations to a user based on extrapolated data is described. The system may receive an answer to a question from a user and determine a second unanswered question having a threshold relationship level with the question. The system may compute a predicted probability that the user would answer the second question correctly, calculate a first comparative skill level of the user among a cohort of similar users, and rank the first comparative skill level of the user against a second comparative skill level of the cohort to determine a skill gap of the user. Further, in some implementations, the system may generate a search query based on the skill gap of the user, and determine recommended content customized to the skill gap of the user.