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Have a look at "Software Estimation: Demystifying the Black Art" by Steve McConnell [0]

I really found this quote illuminating:

> When executives ask for an “estimate,” they’re often asking for a commitment or for a plan to meet a target. The distinctions between estimates, targets, and commitments are critical to understanding what an estimate is, what an estimate is not, and how to make your estimates better.

It's a pretty deep book that discusses everything around estimating:

- how to estimate and what things get missed during estimation

- why estimates gets missed

Really recommended.

[0]: https://www.amazon.com/Software-Estimation-Demystifying-Deve...




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