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I've been using the Rumsfeld Matrix to classify software estimations into 4 categories:

Known knowns: familiar tasks that can be reliably estimated from past experience. You can improve these estimates by better knowledge sharing (internal wiki, adding comments).

Unknown knowns: tasks that can be increasingly better estimated the more time you spend on estimating (for example creating Draft PRs with pseudo code).

Known unknowns: tasks that haven’t been done before, so estimations need a decent buffer (30-50%) to account for research and potential blockers. You can improve these estimates by benchmarking your previous efforts combined with the team's skill levels (aka sprint story point velocity).

Unknown unknowns: the unforeseen blockers that come out of nowhere, can't really be estimated, and can really disrupt a project's schedule. Improving these estimates is really hard. The key to improving these is by improving team/company communication and building agile feedback loops so you can identify these issues early and reprioritize as needed.



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