Mechanisms for training a human user to perform an operation and provided. The mechanisms generate a domain specific knowledge base comprising a set of entities and corresponding domain specific attributes and expand the domain specific knowledge base to include values for the domain specific attributes through an automated bootstrap learning process that performs natural language processing and analysis of natural language content using a set of pre-condition annotated action terms, thereby generating an expanded domain specific knowledge base. The mechanisms evaluate an input from another device identifying an action associated with an entity in the set of entities, based on a retrieved domain specific attribute value and the retrieved pre-condition annotation from the expanded domain specific knowledge base. The mechanisms output a notification to a user computing device indicating whether the input is correct or incorrect to thereby train a user associated with the user computing device.