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You and I act like weathermen in this situation.

But plenty of engineers do estimate based on what they think they can get away with or other negotiable ways.

I used to be a non-technical manager “managing” a team of developers. I later (through circumstances) became a developer. Looking back at the games my team played with me I can see why many managers are cynical about the estimates they are given and attempt to negotiate.

I always overestimated because it was the only way that I could ever devote anytime at all to technical debt reduction.

I'd say you're including necessary maintenance in your estimates, not overestimating!

Not claiming it applies to you, but a lot of managers don't understand the difference between an estimate and a deadline. It comes back in all kinds of weird ways.

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