@polotek@social.polotek.net I think I learned the theory of different models of software development in college (early 90s, so pre-agile) and estimation was probably part of those. My first job out of college was for an educational/games company (CD-ROM releases!) and they definitely put a lot of effort into generating estimates and deriving deadlines from those. I can’t put a finger on how I learned to do it or how well I did it, but as I got promoted to team lead on a project it was certainly part of what I did. There was an expectation that we would get better at it individually and organizationally, but also an understanding that it was hard.