A method of providing reminders to facilitate a business transaction can include first identifying a personal representative of a business entity, wherein the personal representative is associated with the transaction, second determining a current availability of the personal representative according to context information for the personal representative, monitoring the transaction involving a customer and the business entity and determining whether the transaction is complete. If the transaction is not complete within a predetermined amount of time, the method can include automatically notifying the customer on behalf of the personal representative. If the transaction is not complete within an additional amount of time, the method can include automatically notifying the personal representative over a selected communication channel to contact the customer. Determining a current availability can include accessing a calendar system corresponding to the personal representative to determine whether a scheduling conflict exists.