Conversations that facilitate and enable learning are an essential part of education. Skilled teachers engage in frequent conversations with their learners. These interactions take time but intelligent software assistants and robots can help. These machines set new expectations for what can be achieved. For example, they can help a learner understand something by providing a partner for conversation who is always available. They can assist teachers by responding quickly to frequent queries or by helping them with assessment. This can free teachers to redirect their energy towards essentially human tasks, such as exercising judgement and providing emotional support. Robots are also becoming capable of learning through interaction and conversation with a human tutor. Once they understand humans sufficiently well, this approach could be used for skill-based assessments.