The project and risk management literature have plentiful examples of this sort of thinking, including performing post mortems now, before starting anything: "Assume we are 2 years out and everything failed: What went wrong? How did we fail? Why?"
One of the things I like best about my current position is that the colleague I work most closely with (he's head of development, I'm a senior technical contributor sort of thing (it varies by project/week/day/need)) do this all the time, pretty much whenever one of us proposes a change or a new feature.
We listen to the other, make sure we understand, then we critique, find flaws, consider gotchas, but reasonably, not pathologically.
It's at the point where we will each sometimes start critiquing our own ideas, with the other defending.
It helps our work immensely.