How I Estimate Work as a Staff Software Engineer

Summary

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 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 add 20%“. This is basically the same as giving up and saying “just estimate everything at a month”. Should tech companies just stop estimating? One of my guiding principles is that when a tech company is doing something silly, they’re probably doing it for a good reason. In other words, practices that appear to not make sense are often serving some more basic, illegible role in the organization. So what is the actual purpose of estimation, and how can you do it well as a software engineer? Why estimation is impossible Before I get into that, I should justify my core assumption a little more. People have written a lot about this already, so I’ll keep it brief. I’m also going to concede that sometimes you can accurately estimate software work, when that work is very well-understood and very small in scope. For instance, if I know it takes half an hour to deploy a service, and I’m being as...