Conversational recommender systems powered by generative AI can enhance personalization by facilitating information elicitation through follow-up questions. However, engaging in these conversations imposes a communication cost on users. As platforms with different objectives and monetization models deploy these systems, a central question is: how does the platform’s objective and sellers’ strategic response shape the design of these systems in terms of their elicitation strategy? We develop a parsimonious model of conversational elicitation in which interaction generates noisy preference information and imposes a communication cost borne by the user. A user-welfare-maximizing platform elicits more information when accurate niche matching yields large gains, even when niche users are rare. In contrast, under a conversion objective, for the same setting, the optimal strategy is to immediately recommend the same mainstream option to all users with no or minimal preference elicitation because the incremental conversion benefit from improved matching is bounded, while communication costs are borne by all users. When prices are endogenous and the platform earns a commission, increased elicitation is again optimal because improved screening raises equilibrium prices and platform revenue; however, these price responses can counteract consumer benefits and reduce user welfare. The model also highlights that the optimal elicitation intensity increases with preference heterogeneity, helping explain why conversational systems ask more in highly differentiated categories than in low-heterogeneity ones. We complement the theory with a dataset of long-form product queries that vary in length and informational content. Using our dataset and LLM-based user simulation, we quantify how additional information impacts user decisions and demonstrate that the magnitude of this impact depends on the degree of preference heterogeneity. Additionally, this dataset provides a testbed for measuring the (incremental) value of preference elicitation and may be of independent interest.