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The Windows Shutdown crapfest
I worked at Microsoft for about 7 years total, from 1994 to 1998, and from 2002 to 2006. The most frustrating year of those seven was the year I spent working on Windows Vista, which was called Longhorn at the time. I spent a full year working on a feature which should've been designed, implemented and tested in a week.
Each team of 8 was separated by 6 layers of management from the leads, giving us 43 total people with a voice in this feature. Twenty-four of them were connected sorta closely to the code, and of those twenty four there were exactly zero with final say in how the feature worked.
By the way "feature" is much too strong a word; a better description would be "menu". Really. By the time I left the team the total code that I'd written for this "feature" was a couple hundred lines, tops.
From: Moblog