Links in the original are dead but I think this is the Microsoft doc on “what could Windows do better” - https://web.itu.edu.tr/~dalyanda/mssecrets/hotmail.html
The tone and content of this document is shockingly candid and frank. I think it did a ton to make Windows Server a better product. I have a lot of respect for the people at MSFT who reviewed the company's own product in such a critical light.