Especially on the non-IT side in the corporate world, it seems like a lot of people have an irrational fear of making a decision on anything in case that decision ends up being wrong. Instead you end up with either a watered down solution that doesn't really solve the problem or the decision to delay the problem entirely.
It is also important to create a culture that doesn't punish mistakes excessively. You want smart, creative people taking some measure of risk. If they perceive they will be punished for small mistakes, they'll stop making mistakes (which means start doing only mundane boring things) or will just leave.
Unfortunate but I suspect that wisdom cannot be taught, only learned from experience.
