Conversational Recommender Systems are recommender systems that utilize multi-turn interactions in order to help users find items of interest. Their advantage over traditional, one-shot recommender systems lies in their ability to elicit and adapt to the changing user preference in real time.Common approaches to eliciting user preferences include asking about items and item attributes. This strategies can fail, if the user does not have the prerequisite knowledge about the item or item attributes but they know what they plan to use the item for. In this thesis we propose a novel approach to eliciting preferences by asking implicit questions based on item usage.We identify the sentences form a large corpora of user reviews that contain information about item usage. Based on those sentences and by utilizing crowd workers, we generate questions that could be used in an preference elicitation setting. Lastly, based on the labelled dataset, we train a large neural model to automatically generate question for any viable sentence in the corpus.Using standard metrics for automatic evaluations of generated questions and manual evaluation, we demonstrate the potential viability of such a system in a production setting.Finally, we identify clusters of questions where the system fails. i Thank you to the University of Stavanger for the great years of studying, for giving me the opportunity to do this research and for the access to essential hardware.Thank you Krisztian Balog for being my mentor and a great teacher. Thank you for your contribution in bringing forward this idea and for continuous invaluable guidance throughout the project. Our weekly meetings gave me inspiration and motivation to keep working and expanding the scope of the research.Thank you Filip Radlinski also for being my mentor, supporting the idea and providing great insights and new ideas.Thank you to my girlfriend Kirsti for unwavering support through my years of study, and especially these last couple of months while working with this thesis.Thank you to my daughter Matilde, born just after we started this project. While giving me some sleepless nights and countless of distractions, you bring joy to my every day, even when I am stressed or tired.