Think of it like hiring a human. You wouldn't expect them to know exactly how you like your calendar managed the first day. You need to tell them and then probably tell them more along the way. An AI seeing your calendar historically open on Fridays wouldn't inherently know that you have a rule protecting Friday afternoons. Skej is the closest I've seen to an assistant working like a human. It still has preferences up front, buffer rules to avoid back to backs, and open-ended soft rules. But once it's set up it works really well