Hardcore Software by Steven Sinofsky

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085. The Memo (Part 1)

hardcoresoftware.learningbyshipping.com

085. The Memo (Part 1)

The state of affairs of the product development of Windows and Services is abysmal. —“Observations, Aspirations, and Directions for Windows and Windows Live” memo introduction

Steven Sinofsky
Jun 12, 2022
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085. The Memo (Part 1)

hardcoresoftware.learningbyshipping.com

Everyone in their career should have one memo that they think of as the most consequential. For me, it is a memo I wrote after a about six weeks on the Windows team. Under intense time pressure to figure out what comes next with Vista rapidly approaching final release (not formally, but it was going to soon be all but impossible for code changes to make their way into the product) I had to come up with next steps. Over the next four posts, I want to share not just the memo but more about what it is like to live through a major organizational crisis and work to set things up for building a new engineering culture and new team structure, all in a couple of months.

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Back to 084. How Many On the Team, Exactly?


Starfield background with 6 Star Trek original series movie posters. the top three are live long and prosper and the even numbered films, the bottom three are the thumbs down and the odd numbered films. Star Trek: The Motion Picture, Star Trek II: The Wrath of Khan, Star Trek III: The Search for Spock, Star Trek IV: The Voyage Home, Star Trek V: The Final Frontier, Star Trek VI: The Undiscovered Country
The Star Trek films (original series of course) easily fit the odd/even curse. 🖖Star Trek II: The Wrath of Khan, Star Trek IV: The Voyage Home, Star Trek VI: The Undiscovered Country 👎Star Trek: The Motion Picture, Star Trek III: The Search for Spock, Star Trek V: The Final Frontier (Source: personal viewpoint, images Paramount posters)

The history of Windows releases was cursed when it came to product and leadership. Like Star Trek movies, Windows releases alternated between good and bad, odd and even. Line up the OEM products by availability date, and you’ll see this is basically true—starting at Windows 3.0 and changing to the NT kernel with XP (3.0, 3.1, 95, 98, 98 SE, Me, XP, Vista.) Compounding this, the curse says, no leader seemed to last more than two major releases of Windows.

Series of Windows startup screens: Windows 3.0, Windows 3.1, Windows 3.11, Windows 95, Windows 98, Windows 98 SE, Windows Me, Windows 2000, Windows XP, Windows Vista
How do you define the odd-even curse of Windows releases? Conventional wisdom starts at Windows 3.0, counts Windows 3.1/3.11 as the same even though we marketed them quite differently, and then does not include Windows 2000 as it was not sold for consumer OEM PCs. Even then, does everyone agree? Incidentally, Windows 3.0 in beta is where this substack begins the PC journey. (Source: Windows startup screens via Archive)

My neighbor, a successful biotech entrepreneur, asked me about the curse the day he read the org announcement in The Wall Street Journal story saying that I was moving to Windows. He wished me luck.

After 140 scheduled 1:1s, 20 team Q&A sessions, over 30 hours of office hours, and countless hallway conversations in a dozen different buildings I had to do some thinking and organize what I observed, heard, and learned. That meant writing.

A dose of reality was needed with BillG, KevinJo, SteveB, and to some degree even the Board.

Movie still from overhead from scene in film "Jerry Maguire". Tom Cruise character sitting at a desk working at a laptop with papers all over the floor. He's working on his "Memo."
Everyone in their career should have one memo that they think of as the most consequential. A still from a scene in Jerry Maguire (1996) where the Cruise character is typing his memo that will cause great trouble but allow him to reinvent himself. (Source: Getty Images via Substack)

I did that with a 20-page memo titled Observations, Aspirations, and Directions for Windows and Windows Live. For me writing is thinking and I really had a lot to think about, hoping others would join in. I felt alone for long enough and I was certain SteveB was growing increasingly anxious for what would come next. I had been talking to KevinJo constantly over the past few weeks as he was doing a huge amount assuaging those that essentially rejected the idea of an Office person leading Windows.

The 20 pages were the most difficult I wrote in my entire career—to literally put these words down—I knew they would be impossibly difficult to read. I was deeply concerned that what I wrote would be viewed through the simple lens of setting expectations or painting as bleak a picture as possible so that I could be a hero later.

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