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There's a book called "Dreaming in Code" which actually details how hard this problem was for a real project that ultimately failed. Good book for anyone who wants to read an account of a writer who followed an entire software team through the lifecycle of a product.


I'll second this recommendation. For a shorter take on it, Joel Spolsky's review of the book[^1] is a nice read.

[^1]: https://www.joelonsoftware.com/2007/01/21/the-big-picture/




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