In one aspect, a computerized method for assessing and managing information security risks in a computer system includes the step of receiving a customer security assessment. The method includes the step of obtaining a set of already-answered security assessment questions. The method includes the step of applying one or more machine learning methods to generate a strength of one or more similarities scores. The method includes the step of automatically populating one or more direct mappings between the set of already-answered security assessment questions with the other set of questions in a customer security assessment. The method includes the step of setting a baseline score for the one or more direct mappings to already-answered security assessment questions to a set of answered questions in the customer security assessment by using the strength of one or more similarities scores.