A critiquing-based recommender system acts like an artificial salesperson. It engages users in a conversational dialog where users can provide feedback in the form of critiques to the sample items that were shown to them. The feedback, in turn, enables the system to refine its understanding of the user’s preferences and prediction of what the user truly wants. The system is then able to recommend products that may better stimulate the user’s interest in the next interaction cycle. In this paper, we report our extensive investigation of comparing various approaches in devising critiquing opportunities designed in these recommender systems. More specifically, we have investigated two major design elements which are necessary for a critiquing-based recommender system: