It's more Machiavellian than that. What the middleman wants is a heads I win, tails you lose deal. He wants to present a low number, to encourage whoever he's dealing with on his end to do what he wants, gaining the benefit from that. So he'll use every technique under the sun to encourage devs to give him a number he likes more, while never making it look like an order or coercion (which would make it his number - s…
Sometimes, but not always. I've been on both sides of this situation. As an engineer I'm always adamant - yep, no way this could be done any faster and please stop pressuring me to just get the number you want to hear. It'll be done when it's done, and it'll be robust and good. Now please go away and let me cook. But when I've been the manager pushing for smaller estimates, it's been because the business realities we…
You don't say "hey, how long do you need to do X, Y, and Z? Oh, no, that's too much time, how can you shorten it?"