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How I Estimate Work as a Staff Software Engineer (Sean Goedecke)
tl;dr: Estimates don’t come from engineers, they come to engineers - your management chain already has a timeline in mind, and your job is to figure out what technical approaches fit within it. Instead of asking “how long will this take”, ask “what can we ship in the time we have?” Come back with a risk assessment and multiple options, not a single number.