Oh god, that is the worst. I have seen this plenty of times. Boss won't give direction because either he is intimidated or, he is the "idea man" who shouldn't have to be bothered by implementation. It's fine if you want the dev to just wing it, but you have to align expectations constantly. I ping senior management at least every couple days with screen shots or questions asking for input, even if they never read my emails, I want to be able to say that I informed them of exactly what direction we were taking and that they had input.I keep my PM looped in on almost every email I send just incase someone pops into his office he won't have to say "I don't know" if someone asks him where the project is.

Even then, we still run into "misfeatures". I have no idea how you could tell a dev to wing it, let him work for months with no oversight and then be shocked when he came back with something unexpected.