The first contraption the Wright Brothers built didn’t fly. And they knew it wasn’t going to fly when they built it.
But they didn’t know why it wouldn’t fly – not yet. That took experimentation. Sometimes you have to break something, failing again and again, to figure out the weak points. To improve on the design.
When you’ve done that enough, you get a keen sense of structural weak points. Someone might pull you in to observe something and ask “Do you think this will work?” They want you to say “yes,” of course. But if that isn’t true, a far more valuable answer is: “No, but I can tell you exactly why.”
When responsibility is deferred enough, people would rather charge blindly ahead than see the weak points. Pointing out problems doesn’t make you popular, and if there’s almost no chance that you’ll be blamed personally for the resultant disaster, a prudent strategy can just be to keep your head down and not rock the boat.
If you see an organization where that does seem to be the default strategy – run. When no one is responsible, then… well, no one is responsible.
You want to be the kind of person who can explain the miss. But once you are, you want to make sure you’re in a room where they’re happy you did it.
The Opportunity Machine 