Communicating is hard. Words are crude tools that mean different things to different people. Unless they are words created, or understood, together through shared experience. In knowledge work, many people spend most of their time trying to explain what they have done, or plan to do. Rather than doing. We don't understand why we understand most of what we understand. One way Artificial Intelligence may help us is as a communication coach. Instead of bashing out an email, an AI may pull together our thoughts: listening carefully, clarifying, fact checking, pointing out holes, adding research and getting feedback from the AI of the person we would like to talk to - first. Translating from how we understand to how they understand. Establishing the common ground, new knowledge, and points of disagreement. A lot of our misunderstanding is not dissimilar to frustrated toddlers - we just don't have the right words.