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Sep 19, 2022Liked by Steven Sinofsky

This is the probably the best writing on "Innovator's dilemma" from a lived experience I have ever read. The impossible tradeoffs, the challenges, and the gravity of the future implications couldn't be more higher for MSFT. Eagerly looking forward to read the next few chapters.

You probably would be touching these future chapters, but I am very curious on how you would you thought about the following: 1/ Best case scenario playing out looking back from 2022

& 2/ The risks you deemed to be dire which fizzled out.

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Now we're firmly in my era, and I remember all this well. The memos were both inspirational and pragmatic. A question: Were you having fun during all this?

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Interesting post Steven. This similar set of planning would have occurred for Windows 7 also correct? (perhaps less ‘future focused’). I do remember reading several of your Engineering 7 blog posts that likely filtered from the initial planning. Curious to know, and this might sound cynical, if the focus on the Windows 8 planning and discussion here on the Substack is to set the scene / cushion the fall regarding the eventual flop? Or it was a genuinely different ‘betting the company’ existential crisis scenario on doing something very different (although it didn’t really work out)? Something of a side note, but I remember Steve Ballmer in an interview at the time being asked a quick fire round of questions that included ‘riskiest product?’ to which he said ‘next version of Windows’ (being Windows 8).

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