Artificial Intelligence, UX and the Future of Findability

It seems like we're on the cusp of doing amazing things with chatbots and data mining, which can augment manual information architecture work and result in a better user experience overall. Automated information processing can help us identify search patterns and recommend information structures, to improve the findability of content. Let's say you have a service that includes a search component. Right now, your users might be running searches and using manual filters to sort through the results, as search users are wont to do. How do you know if they are finding what they need?