[Insanity]

YMMV indeed, I have not encountered that yet, and have definitely missed initial deadlines.

But some things help - when giving estimates or timelines, I go through my usual charade of "they are guestimates, usually you should double or triple them, the further out they go the less likely they are accurate etc".

Also, I promise I will monitor progress, keep them up to date, and let them know as soon as possible when plans deviate. I also discuss backup plans early (cutting features or pushing back, starting with pilots and tests, etc..)

It has worked pretty well for me so far. Not to say it's _just_ about how you handle the situation, you can have a shitty manager, that part is out of your control unfortunately.. :)