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?

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.

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.

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.