The original note, as written at the time
An app or tool that schedules and makes calls on my behalf to all my friends and family. It could accommodate situations where my direct input is required and where it isn’t.
Ongoing development
An app that schedules and makes calls on your behalf to friends and family — handling the situations where your direct input is required, and the ones where it is not.
The distinction in that last clause is the whole design, and it is subtle. Some calls need you on the line. Some need a decision made, or a fact conveyed, or an appointment arranged. An agent that can tell the difference is useful; one that cannot is an embarrassment.
The social risk is severe and should be named first. A machine that calls your mother is not the same as you calling your mother, and most people will feel the difference immediately. So the honest product is not an agent that impersonates you. It is an agent that does the arranging and leaves the relationship alone.
That means the work it takes is the logistics: the birthdays, the check-ins, the coordination of a visit, the chasing of a reply. The parts of family life that are administrative and that nobody does because they are tedious.
The interesting design problem is the handover. A call that starts with the agent and needs to become a conversation has to transfer without the other person feeling handled, which means the agent must announce itself and must be able to be asked for you directly.
And there should be a rule that the agent never pretends. Any system that speaks in your voice to your family is a system that will eventually be discovered, and the discovery will cost more than the calls saved.
Let it make the arrangements. Keep the conversations.