The problem in your story is a non technical boss making time estimates/demands. If that's gonna happen, the developers shouldn't bother with estimates at all b

The problem in your story is a non technical boss making time estimates/demands. If that's gonna happen, the developers shouldn't bother with estimates at all because no one is listening. They can just go on missing the boss's fantasyland deadlines and save themselves the trouble. If the boss wants to know how long things will take, they have to ask the engineering teams. And the most accurate way for an engineering team to answer is with a track record of abstracted unit estimations and how long they took, to predict how long the abstracted unit estimation in question will take. And when the PHB says "make it two", the engineers can only reply "ok, tell us what features or standards to cut." No different than wiring a house: we can finish faster if you choose some rooms to skip, or some safety standards to skip. But those are the boss's decisions, not the engineers. BTW I agree with the responder who says quit from those environments ASAP. I don't know how engineers can overcome a dysfunctional business lead like that... and that kind of business lead is often an expert at making sure the repercussions land on someone else. Case in point, by asking you to finish faster he is tacitly asking you to skip capabilities or safety checks... and that way you're responsible for the fallout.