In case OP reads this. I tried it again with a harder task with my friend's company. It got into a good conversation about materials and permits, but then my friend asked if they had a survey done. At that point the AI abruptly hung up and asked me in the chat if I had a survey. Obviously this wasn't ideal. It was doing great until that point, though. It should have just said that it didn't know and it would have to get back to the person with that information, and tried to see how much further it could get without that info.