Guess you're not the CEO of the Fortune 500 I used to work for. I see this frequently the time in corporate structure as well - the bigger the structure, the worse it is.

Underling: "That's impossible. We might get it done in N days, and C isn't actually possible without a complete rewrite."
Low-Boss: "Great. The time frame is tight but we can do it with some extra elbow grease! Let's meet about the specs."
Mid-Boss: "Timeline is great and we'll iron out the details."
Upper-Boss: "It's all on track."
BIG Boss: "Great job."

The developer has to do the work, and is the most accurate about time constraints and difficulty of the project. At each level of reporting, though, the prognosis get's a little better because nobody wants to deliver bad news. Low management says it will be tough and there are some problems. Middle management says things are looking good and they're working out the kinks. Upper management says everything is great. The Boss has no idea. The more levels there are, the more dilute the bad news becomes.

Seriously as soon as I read "Mickey can interact by using paint thinner" I thought Disney had finally broke down and sold mickey out...