Disclosed methods and systems determine levels of search sophistication for users of a customer self-help system to personalize a content search user experience provided to the users, to increase a likelihood of users' satisfaction with the search experience. The customer self-help system analyzes submitted search queries and provides an advanced content search user experience to users who are determined to have an advanced level of search sophistication and provides a simplified content search user experience to users who are determined to have a basic or less-experienced level of search sophistication. Providing users with personalized content search user experiences that are based on users' levels of search sophistication allows less-experienced users to feel comfortable searching and allows advanced users to search more quickly or precisely.