That can often be a good plan = force people to explain to you their crazy rules,
Plus you get the fun of watching the clouds roll away as the person discovers 'all by themselves' that they have a great idea that will solve this problem, and it happens to be the great idea you've had in you mind all along.
I'm always looking for the question to ask that will help a person break the logjam of unreality in their mind and be free to jump to the next stepping stone on the path. I've read that you can't talk anyone into anything, but you can listen them into quite a bit.
Full Disclosure - as amazing as I've been over the years, sometimes I've gotten good results and sometimes I've been 'taken out' by the higher ups who see that I've 'softened the locals.' Just because we Advocate spectacularly, doesn't mean we will always win. A lot depends on finding an advocate on the inside who is powerful and agrees with you - luck. But it's still worth trying even if the outcome isn't completely effort-dependent.