Techniques that facilitate generating and executing an optimal dialogue strategy are provided. In one example, a system includes an information gain component and a question selector component. The information gain component estimates information gain data associated with first dialogue data of an information system. The information gain data is indicative of an amount of change in entropy associated with the first dialogue data. The question selector component selects between second dialogue data associated with a first question strategy and third dialogue data associated with a second question strategy based on the information gain data.