Technologies are described for an insight framework for suggesting shared calendar events based on detected usage patterns and behaviors. An insight service or module acting in conjunction with calendar applications (or calendar services) of different users may collect calendar information, usage pattern, behavior, and other relevant information such as exchanged communication, shared documents, etc. The insight service or module may make an inference to determine a need to schedule a meeting for a user with another user. A deadline for the meeting and user availability may be determined, and a shared calendar with available meeting times may be suggested to the other user. Upon selection of one of the available meeting times, the selected meeting time may be incorporated to the user's calendar.