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Software development ONLY misses its deadlines when the programming team is absolutely INCOMPETENT. The most crucial step in development happens before a computer is even powered up; that is, the team's leader MUST figure out EXACTLY what the customer wants.
This process SHOULD take longer than you think it will (as the customer). It's a sign of competence.
Then, when new stuff is added to the specification, as happens inevitably, the deadline can be pushed back. "Software always misses deadlines" is NOT true, it's just that good, competent programmers -- capable of accurately assessing time/money requirements -- are difficult to find.
Especially on the web: "I knoe teh PHP" does not mean "I am a competent programmer." It usually means "I can show teh today's date" or "I can make teh feedback form."
Your programmer should push you to the point of INSANITY with his seemingly inane questions about the task at hand. Programmers who DO NOT do this are only setting you up for bad news in the future.
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