A document creation assistance apparatus includes a tree structure generation unit configured to analyze a learning document for system development and generate a tree structure representing separate sections of the learning document, a frequency calculation unit configured to calculate, per leaf node of the tree structure, a frequency vector of a word that appears, a question extraction unit configured to extract, according to the frequency vector, a word about which a user is to be questioned, a question presentation unit configured to present a question about the extracted word to the user and receive an answer, and a document generation unit configured to generate a document with the extracted word and the answer set in a section of the separate sections of the leaf node according to the separate sections of the tree structure.