> It is human nature that when talking to your boss you put things in the most optimistic way that fits your understanding, and your boss hears it even more optimistically. After a few steps up the chain this results in a complete disconnect from reality.
I learned this the hard way, maybe 3 months into my first real job. I was testing safety critical systems, but it was still being developed so the tests procedures were also being developed and executed. I was asked for my status, I said: I've tested about 60% of the system (this one was small enough that that sort of statement was actually valid), everything has passed so far. My boss heard: Everything passed. He released the build to the customer, who found a failure almost immediately (about the same time I did, but I had no idea it had been released). I was taken into a conference room and chewed out for making us look like amateurs (we were, when it came to software). I learned several things: 1) I needed a new job; 2) Never use the words "done", "everything", "all" until everything is actually all done, managers only hear those words and nothing else.
> Now, you say, reality eventually intrudes. Yes, but it is normal for upper management to not realize that deadlines will slip until about 2 weeks before they do. And will continue to think it is about 2 weeks off indefinitely.
A manager, fortunately not mine I was his peer though he got promoted for his "successes", would always say that his products never shipped late. "How can you say that? I know your last release was 3 months late." "We updated the schedule and we hit the new schedule." "But you didn't update it until the last month. It was 2 months late by then already." "But we hit the final scheduled release date." He just got lucky that the customers weren't loud enough for his boss to realize the spectacular, repeated failure until after he got promoted. The new manager got hit with it instead.