Under the present invention, a distribution list of message recipients within an organization undergoing the IT migration is generated by analyzing the infrastructure of the organization. Once the message recipients are known, they can be grouped into a set of mailing groups. Thereafter, specific message templates can be assigned to each group, and a schedule for sending messages to the message recipients can be set. Messages will then be generated and sent to the message recipients using the message templates assigned to their respective mailing group(s) and the schedule. Responses to the messages will be tracked and processed, and records associated with the message recipients will be updated based thereon. Follow-up messages containing additional questions and/or instructions can be generated and sent using any data that is contained in the responses. Also, “non-responses” can be tracked so that reminder messages can be sent.