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How I estimate work as a staff software engineer

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Estimating how long software projects will take is very hard, but not impossible. A skilled engineering team can, with time and effort, learn how long it will take for them to deliver work, which will in turn allow their organization to make good business plans. This is, of course, false. As every experienced software engineer knows, it is not possible to accurately estimate software projects. The tension between this polite fiction and its well-understood falseness causes a lot of strange activity in tech companies. For instance, many engineering teams estimate work in t-shirt sizes instead of time, because it just feels too obviously silly to the engineers in question to give direct time estimates. Naturally, these t-shirt sizes are immediately translated into hours and days when the estimates make their way up the management chain. Alternatively, software engineers who are genuinely trying to give good time estimates have ridiculous heuristics like “double your initial estimate and

There’s a kind of polite fiction at the heart of the software industry. It goes something like this: Estimating how long software projects will take is very hard, but not impossible. A skilled engineering team can, with time and effort, learn how long it will take for them to deliver work, which will in turn allow their organization to make good business plans. This is, of course, false. As every experienced software engineer knows, it is not possible to accurately estimate software projects . The tension between this polite fiction and its well-understood falseness causes a lot of strange act

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