I think the broadness is the problem. If it wasn't broad, you could hard code answers to all the questions. Examples of some basic questions that have no chance of working today: "Do you remember that discussion we were having last time?", "I've scanned the document you want, can I paste it straight into the chat window?", "Is PDF format OK?", "Can you look at page 2 in the PDF?".

I think just "No" would work as an answer to all of those questions. (Tongue only halfway in cheek...)

Haha. I guess that's what real people who work at my bank would say. But I'm not sure they possess general purpose intelligence either.