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Contra my optimism on software estimates, some realism: I gather as much political context as possible before I even look at the code. How much pressure is on this project? Is it a casual ask, or do we have to find a way to do this? What kind of estimate is my management chain looking for? There’s a huge difference between “the CTO really wants this in one week” and “we were looking for work for your team and this seemed like it could fit”.

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