Recent advances in deep learning based methods for language processing, especially using self-supervised learning methods resulted in new excitement towards building more sophisticated Conversational AI systems. While this is partially true for social chatbots or retrieval based applications, the underlying skeleton of the goal oriented systems has remained unchanged: Still most language understanding models rely on supervised methods with manually annotated datasets even though the resulting performances are significantly better with much less data. In this talk I will cover two directions we are exploring to break from this: The first approach is aiming to incorporate multimodal information for better understanding and semantic grounding. The second part introduces an interactive self-supervision method to gather immediate actionable user feedback converting frictional moments into learning opportunities for interactive learning.​