Assistant Benchmark

I have been trying to build an assistant for a year+ at this point. I have still yet to come up with a model, harness, and set of instructions that get it to reliably not contact me just to regurgitate things I already know like text messages, emails, or calendar events. I want it to have those things so it can alert me to 2nd order situations.

For instance, lets say I have a meeting with Bob, but look Bob emailed me 30 minutes ago saying to bring XYZ to the meeting - that's worth notifying me. But pinging me to say "Nothing in the next 3 hours, good time to work on <overdue reminder from 3 months ago to take garbage out". Boggles my mind they can solve novel math problems but can't figure out what is worth my attention and what is not.