With Watson was a project that involved using IBM's artificial intelligence to create a chat bot. This specific app's purpose was to help regulate a person's emotions and health through tracking their moods and activities. The intended audience is supposed to be able to talk with the bot through premade conversation options.
A problem that arised was that a user may have several different answers to a question, one that may not be covered by the options we provide. Trying to figure out a UI that allowed multiple chat options without cluttering the screen was difficult. Rather than limiting the amount of choices a user can make, it would make more sense to have the bot help narrow down an answer.
Another problem was figuring out an interesting way for users to track their progress on activities that help improve their mood and wellbeing. Such as eating well, excersizing, etc. Not only does the tracking UI need to be easy and simple to read and understand, users will probably need some sort of motivation such as achievements to keep them on track.