Three hours of a recent call went into bargaining over estimates. The work behind those numbers stayed the same size.
I sat through one of these. A startup CEO joined a technical call and started bargaining over the engineers' estimates, one by one.
Three hours later, we had covered about 40% of the estimates. Working afterwards was hard; the feeling in the room was that we'd been had, the hours skimmed off us.
The CEO, as far as I could tell, was pleased with how far he had moved the numbers.
What shrank in that room was the buffer for being wrong — the one part of an estimate you actually miss when reality shows up.
And there's a second cost I think founders underweight. A team that watches its estimates get bargained learns, fairly quickly, that estimates here are opening positions.
So the next ones come in padded, and now the numbers you're negotiating are worse numbers.
The fair version of the other side: pushing back is sometimes right. Estimates can be padded, or built on scope nobody has questioned yet. If a number surprises you, asking why is your job.
But that's a question about the work. Three hours spent arguing a figure is not that question.
When a number genuinely needs to come down, I think the honest move is to cut scope. Remove work, and the estimate follows it down on its own. That's a real reduction.