Artificial Intelligence, UX & The Future of Findability

I'm completely obsessed with the idea of using artificial intelligence, search patterns and information architecture to improve the findability of content. 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. 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?