Terry (Premium)

I want to address today’s news about Terry Myerson in a way that is unique, personal, and respectful. So I’m going to tell you a few stories.

The first regard Terry’s two most recent predecessors.

In late May 2011, I headed down to the southern end of Manhattan to attend the launch of Windows Phone 7.5. And I witnessed something I’d never seen before. As Andy Lees discussed whatever advances were coming in this new generation of phone software, it suddenly dawned on me that this guy had no idea what he was talking about. He didn’t know the product, certainly not at the level of detail one should expect.

Lees didn’t last too much longer in this position, and his replacement, Terry Myerson, was someone I had never heard of. But it seemed like anyone would be an improvement. And the subsequent release of Windows Phone, version 8, was perhaps not coincidentally the first truly excellent version of the software, and a major rearchitecture.

I now measure every Microsoftie on what I think of as the “Lees” scale. This scale goes from One Lees to One Elop. And Myerson is far more Elop than Lees: He knows what he’s talking about.

Concurrent to all that, a madman named Steven Sinofsky had taken over Windows, stolen the best ideas from Windows Phone, and then created Windows 8 and, worse, Windows RT. The result was the worst disaster in the history of Windows and Microsoft ousted Sinofsky—who had been plotting to replace Steve Ballmer as CEO—ahead of the product’s launch. Imagine having to launch Windows 8 knowing that it was a train wreck. That’s what Microsoft faced in 2012.

Myerson wasn’t immediately chosen to lead Windows. There was a brief and weird period in which two unqualified Sinofsky underlings were for some reason given responsibility for this product. But after a series of purges, the Sinofsky era finally ended for real, and Myerson was tasked with fixing the Windows 8 disaster.

The irony here is thick, though many outside of Microsoft are probably unaware of why. When Sinofsky took over Windows in the wake of Windows Vista, he got rid of most of the key people from the previous regime, and many of them ended up on Windows Phone. So the reason Sinofsky stole from Windows Phone and then stopped collaborating with that team is that he considered them the B team. And the B team wasn’t going to impact “big” Windows. They were just the quickest way to get moving on mobile. And then they could be dropped.

With Myerson leading big Windows, however, the B-teamers got their revenge. Now they would chart the course forward. Would fix all the terrible problems that Sinofsky created. Would make Windows great again.

Given this history, I was quite happy about Myerson’s new role at Microsoft. And the initial vision for Windows 10, which Myerson and Joe Belfiore unveiled in late 2014 confirmed my hopes. Everything was going to be fine.

The intervening years saw some ups and downs. Microsoft, of course, purchased the only parts of Nokia that mattered, but that business still cratered. Satya Nadella replaced Steve Ballmer as CEO, a move I initially applauded because he was an engineer and it seemed like an engineer was right for Microsoft.

And during this time, I got to know Terry pretty well. Not, “we hang out on weekends well.” But we’ve spoken many times, on record and off. And while there are conversations we’ve had that will remain private for the duration, I will say that I think I’ve come to understand him.

He’s a good guy. But he’s also a good man, if that makes sense. He seems real to me. He’s pushed back at me when he disagrees with things I’ve written, and I’ve done the same when I disagree with his decisions. He’s taken some things personally, which bothered me because I like him. But that shows me that he cares, too, which is great. And we’ve laughed about it at times, which is even better.

Flash forward to 2018.

You have undoubtedly seen me express frustration in recent months about the direction in which Windows is headed. And I can understand why one might transpose this frustration with Windows into frustration with Terry. But that is not the case. Far from it.

I’ve heard from multiple sources that Terry was basically given an ultimatum to get in line with Nadella’s corporate vision for Microsoft. And that Windows would need to take a back-seat to the initiatives that Nadella wanted to drive forward. Key among them cloud and AI.

Myerson took this to heart. Outside of Microsoft, we can see one physical manifestation of the change by just looking at Terry: He’s lost an astronomical amount of weight, and this guy wasn’t exactly overweight to begin with. I’d have called him normal.

But it was more than just that, of course.

As I see it, as my sources have described it, Terry has only wanted the best for Windows. But he has been forced to oversee a massive decline in the things that make Windows great in order to push Nadella’s broader vision for the company.

The problem for Terry—and it’s the problem for anyone who cares about Windows—is that Nadella’s strategy has resonated with Wall Street. Microsoft’s big new bets are generating news and driving the stock price to new heights. Windows? It’s old news. Windows is the old Microsoft. Windows has no place in the new Microsoft. Microsoft, we’re told, has “hit refresh.”

And I think that’s why Terry is out. It was only a matter of time. And all you have to do to understand Nadella’s position on Windows is to look at how he describes its fate in the post-Myerson Microsoft.

Windows is being split into three parts. Is literally being scattered to separate parts of the company.

Core Windows development is moving under Azure. That’s an incredible turn of fate, given that Azure came out of Windows Server, which itself came out of Windows. Nothing says “has-been” more than this.

The “experiences” stuff, which amounts to all the new nonsense that Microsoft has been adding to Windows 10 for the past several releases, is falling under Joe Belfiore. A moment of silence for Joe, please. I have to believe he’s as unexcited by the ad-funded, AI-fueled, Cortana-scatting future of Windows 10 as Terry no doubt was. Maybe he’ll fight for what’s right. Or maybe he’ll give up when the weight of the new reality becomes more obvious.

And then there’s the enterprise: Brad Anderson, one of my favorite people at Microsoft, will continue to lead the Windows enterprise, deployment, and management efforts. I thought it was weird when Anderson was moved under Myerson last year. Now it makes sense. He’s perfect for this role.

As for Terry, he was given a shit job. And he made the best of it, and lasted as long as he could. What comes of Windows now is a subject for the future. Right now, my thoughts are only with Terry.

So, thanks Terry. I hope it’s obvious that I was pulling for you the whole time. Regardless, I suspect I’m about to learn that we agreed a lot more than we disagreed.

Note: Please forgive me if this is disjointed in any way. The timing of this event couldn’t have been worse for me, as we traveled last night to Colorado to visit potential schools for my daughter, had to get going on only six hours of sleep, and are literally busy all day today. But I couldn’t let this pass without commenting on what happened. I have much more to say. Hopefully, I’ll have time in the next few days to do so. Thanks for understanding. — Paul