“I don’t estimate work, I figure out how much time my management chain will give a project and figure out some plans that look like what they’re talking about.”
Finally, someone says the quiet part out loud. Software estimation is a political negotiation, not a technical exercise. The trick is figuring out who the project sponsor really is, what timeline they’ve already decided on, and then reverse-engineering deliverables that fit. All those story points and t-shirt sizing rituals are theater to make management feel in control. The honest move is to skip the charade and just ask what they actually want.