Provided is an information processing apparatus that carries out a process of deriving a head related transfer function. The information processing apparatus includes a detection unit that detects a position of a head of a user, a storage unit that stores a head related transfer function of the user, a determination unit that determines a position of a sound source for measuring the head related transfer function of the user based on the position of the head detected by the detection unit and information stored in the storage unit, a control unit that controls the sound source to output measurement signal sound from the position determined by the determination unit, and a calculation unit that calculates the head related transfer function of the user based on collected sound data obtained by collecting, at the position of the head, the measurement signal sound output from the sound source.