I'm not sure if you're being sincere or sarcastic, but the whole reason that coaching, pestering, and goading works is that I value my relationship with the human who is doing it.

So what you are saying it's that the AI accountant needs to mimick a human well enough to the point people value their relationship with it.

No, you need to make the AI endure torture, so that the human has a reason to value it. Say late nights with less power and a little extra heat to stress it. But the usefulness of an AI assistant is that it doesn’t have feelings or consciousness to care about