I think the fundamental problem with Siri is that it’s still kind of the flat file system of AI. Remember MFS? The original floppy format of the Mac? Lord, I’m old. At any rate, it was a system where everything was laid out before you in one big mess and you had to hope you could locate what you wanted.
With a hierarchical system, you start at a general level and drill down to what you want. Siri can’t seem to do this. She doesn’t know how to hold onto context. If she doesn’t understand your question, perhaps because it is a little too vague, you want to help her by offering clarification. Showing her which “subfolder” you want. But she takes you back to the root level every time and you have to start all over. Like in the current implementation, Siri would have no hope of playing a game like 20 questions with you, because that would require the kind of skill set I’m talking about.
I am looking forward to the Shortcuts feature, though. At least you might have the ability to teach Siri a few little tricks which could be useful. We’ll see I guess…