If I had a nickel for every time I saw a potential client's eyes glaze over, as I kept asking questions about why they had already chosen a particular solution when they hadn't actually identified their problem...

Talking myself out of work, regrettably, seems to be one of my core competencies. I keep asking "but how are we going to measure if we've succeeded?" "What is the goal?" "Can you describe the problem that we're trying to solve?"

I'm generally known as an annoying little bastard.