When I was working in Corporate America managing multi-million dollar development projects, I always used to try to figure out how deadlines got set. Unless there was some government regulation that was changing how we did business, the deadlines were almost always random guesses. They might be the manager's wedding anniversary or his mother's birthday or the date of the last blue moon of next year.
I always tried my best to spend at least a couple of weeks for a project that was expected to take 3 people more than a year to at least layout a preliminary design plan and estimate the parts. Projects always took longer in the early days of computing, not because there was more work but because, the process was much slower. Getting three compiles and tests in a single day was HUGE. Typos were disastrously expensive and slowed everything down so you had to actually do a serious amount of desk checking. Today, with a tool like Access, I could easily get a dozen in an hour so I can work on smaller pieces and build them together. A compile with Access is almost instantaneous and typos are immediately fixed or even prevented with Intellisense.