Earlier quoted context omitted.
> I won’t be mad about a long estimate So... my experience with this mindset is that you won't be mad , but you'll just say "that's too long/expensive" and cancel the project entirely. Then the same project will come up again in two months with different wording, again and again, until I give you the estimate you think you can afford. And then the thing will end up taking longer than the original "too expensive" esti…
I've seen this, but I don't think it was a problem or a bad thing. Let's say the project was first proposed in January 2021. Got estimated as taking a year. Didn't get scheduled, since that was seen as too long, and there was other stuff people wanted done in 2021. It's pitched again in June 2021. Same story. Come Feburary 2022, it's pitched again. Now it's estimated as 15 months - there's more to do since more code…
Repeat that until the problem gets a singularly misleading wording, or some key person is away, and the project gets a 6 weeks estimation. It will take 19 months anyway, because nothing changed, but for 17 of those you will be late.
(Anyway, I have never seen a problem statement to be well defined enough for this to be the problem.)