An information processing device stores difference information indicating a difference, for each of a plurality of users, between a first schedule time point and an execution time point, the first schedule time point indicating a time point at which each of the plurality of users was to execute an operation, and the execution time point indicating a time point at which each of the plurality of users executed the operation, and when it is detected that a first terminal device carried by a first user included in the plurality of users enters a first region, specifies the difference corresponding to the first user, specifies a timing at which content data used for the operation is to be transmitted to the first terminal device, based on the difference corresponding to the first user and a second schedule time point at which the operation is to be executed by the first user.