Here's a really good article on closing the gap between project predictions and realization. Jenner covers the well-known sources of error and misrepresentation. Unlike other writers on this topic, he doesn't just wring his hands but responds with well-thought-out prescriptions.
His prescriptions include effective planning (start with benefits and requirements, design the solution later), Science (seek disconfirming evidence), Reference Class Analysis, Probability Management (distributions rather than point forecasts).
In short, this is an article I wish I had written.