Ex-Microsoftie Explains How the Firm Lost Windows (Premium)

James Whittaker has left Microsoft, and my does he have stories to tell. And when it comes to Windows, he gets it right.

Whittaker’s tell-all, available on Medium, hits on a number of topics, some of which will be familiar to readers of my Programming Windows series, which hits on just how terrible Bill Gates and his company were in the 1990s, in particular.

I’ll touch on some of that in a bit. But what I’m more interested in is his hot take on Windows. Some may recall that I was asked in a recent Ask Paul about me describing today’s Windows team as “b-teamers.”

“Windows phone … started out with some of the best minds at the company, folks who had worked on Windows for many years in many cases,” I wrote. “But as the platform stalled, all the good people left. The only people still working directly on Windows phone at the end were, largely, the B-teamers I refer to. Terry Myerson, as you may know, replaced the ultimate B-teamer, Andy Lees, when he took over that team; Lees didn’t know his own product particularly well, and I recall being astonished by this at the Windows Phone 8 launch in New York. Just a total bozo. When Terry took over Windows, he did what Sinofsky had done by replacing key people with his own people; over time, virtually everyone who had previously relied on Sinofsky for their career successes, deserved or not, was out. (The one major exception? Panos Panay.) But by that point, all the key players from the old Windows days were gone. What Terry had was … B-teamers. And that’s what came to Windows. You can think of it as multiple levels of sifting, where less and less good is left by the end.”

Here is what Whittaker says to this topic. It’s part of a broader discussion around the new culture at Microsoft under Satya Nadella, who quite obviously doesn’t care all that much about Windows, which is tied to the old Microsoft (Gates’ Microsoft), and will never be part of his legacy.

“It’s worth noting that cultural transformation didn’t happen in places, like Windows, where Nadella simply rearranged the made-men deck chairs,” he writes. “Instead of following his culture-change playbook, he simply swapped Windows’ made-men with Windows Phone’s made-men. The same people unable, over the course of a decade, to craft a winning strategy for mobile were suddenly tasked with crafting a winning strategy for the desktop. The unsurprising result is that Windows continues its tradition of boring, buggy software and consistently fumbled updates. [The emphasis there is mine. –Paul] Made-men aren’t fixable, and the real talent in Windows, and the diversity of ideas it possesses, remains anonymously buried under layers of made-men above it.”

Made men is an interesting term, and it’s obviously supposed to evoke the Mafia. But what he’s really describing is b-teamers, guys who are lifers who have jobs because they have jobs and can’t be touched. He’s describing b-teamers.

“If Windows was the only refuge for recycled failures — the wannabe leaders who energetically and emphatically backed Gates’ and Ballmer’s strategy that whiffed on the web, cloud, and mobile — Microsoft might be ok,” he continues. “But the residue of the past is thick in enough places that it is suffocating the culture of tomorrow.”

The Windows part is the most interesting to me. But his broader point—that Microsoft “can’t leave an outdated culture behind while continuing to worship its icons”—is an issue I’ve certainly raised too. There is something going on right now, with the horrible Netflix documentary about Bill Gates in particular, but elsewhere too, where Microsoft and Gates are trying to salvage his reputation when, in fact, he’s always been a terrible human being. And the toxic, bro-tastic culture he created held back Microsoft for many, many years.

Whittaker also touches on the “lost decade” that hampered Microsoft and led to the rise of Amazon, Apple, Facebook, and Google.

“The Microsoft of the 2000s, under Steve Ballmer, was … bruised and battered by the consent decree handed down by the DoJ for the very same ambition that brought it to dominance,” he writes. “Ballmer’s Microsoft was sales-forward and cautious. It was either gazing at its own Windows-shaped navel or nervously clutching its pearls at the approach of Google in its rearview mirror. This inattention to anything resembling the imaginative or innovative caused it to hemorrhage talent, flatline its stock, bore its customers and miss (or at least be very late to) the next three technology megatrends — web, cloud, and mobile — on the trot. It was an era of hand-wringing and coming to grips with a profitable but uninspired slide into irrelevance.”

I’ve been saying all this for years. But this is fascinating specifically because it comes from someone who experienced it all from within the company. I highly recommend you read his whole piece. And while you may come away a bit overwhelmed by his ego, Whittaker is right about Microsoft pretty much across the board.