A system and method are provided that transforms the typical voicemail interaction into one in which the client does not feel that their voice messages could be easily ignored. Instead of being prompted in the traditional manner to simply leave a message, the client is asked to choose from a list of available times, each representing a potential time for the service provider to call the client back. The system is aware of both the service provider's calendar appointments and the times that they have made available for client appointments. Once the client chooses a time slot, the service provider's calendar will be updated with the new appointment details. When that time arrives, the provider's calendar system will alert them of their impending appointment and they will be reminded to telephone back their client at the scheduled time.