Microsoft 365 and the Future of Windows (Premium)

What happens when you integrate three previously separate product offerings into a single solution? For Microsoft, the answer is simple: The future.

Or as I might think of it, the future of Windows.

My very career exists because of this product, and like many of you, I’ve spent much of the past few years wringing my hands nervously as this once-proud center of the Microsoft empire has been reduced, seemingly, to a bit player. But I spoke last week with Microsoft corporate vice president Brad Anderson about this future. And I’m starting to feel better about the strategy.

First up, if you haven’t done so, I recommend watching Mr. Anderson’s keynote from Microsoft Ignite 2018. Like everything else at Ignite, this talk is very much focused on the enterprise and IT. But it also neatly frames how Windows fits into Microsoft’s broader strategy and product lineup. And as is so often the case, there are interesting bits here that will impact consumers and other individuals as well.

I went into my meeting with Anderson a bit unprepared, as I hadn’t seen his keynote. I wasn’t worried about that: I was ready to talk about Microsoft 365, Windows Virtual Desktop and the other highlights from his talk as it was.

We did so, of course. But Anderson was ready to take on the concerns I’ve raised about Windows on this site without any prompting from me. This discussion, and some of the other related conversations I had with various folks from Microsoft, inspired my earlier Integrity (Premium) article.

Before getting to that, let me briefly explain who Anderson is, and how we ended up in this meeting together.

And we do go way back. Since arriving at Microsoft in the early 2000’s, Anderson has always been very closely associated with Microsoft’s management solutions, dating back to Systems Management Server. That product has since morphed into Microsoft System Center Configuration Manager, or ConfigMgr. And on a parallel path, Microsoft has brought its management services to the cloud with Intune.

Microsoft talks a lot about “digital transformation,” but if one were to look back on its management strategy and how it evolved over time, two things would stand out. One, it has absolutely transformed over time to become cloud-powered. And two, there were some strategy shifts over time.

And on that note, I was a fan of what was originally called Windows Intune right from the beginning, in 2011, when it was focused solely on PC management and was the lightweight, cloud-based alternative to ConfigMgr. You have to remember the era: Windows 7 was still the most recent version of Microsoft’s core OS, Microsoft Azure was still called Windows Azure, and the cloud was still pretty scary to IT.

But things changed. Aside from renaming Intune, Microsoft evolved the product to include Mobile Device Management (MDM) capabilities for phones and tablets. Thanks to ConfigMgr integration, it formed the basis for Microsoft’s so-called hybrid MDM offering for several years. Today, Microsoft still supports co-management, with both ConfigMgr and Intune. But most enterprises are now comfortable managing PCs and devices from the cloud.

This evolution should sound familiar as similar changes occurred with both Office and Windows 10. Office has evolved into Office 365. And Windows has evolved into what Microsoft calls “Windows as a Service.” (I don’t like that phrase, but whatever: Windows is literally serviced like a service.) And it is not coincidental that all three of these things—Microsoft’s management offerings, Office 365, and Windows 10—together constitute Microsoft 365.

And Microsoft 365 has changed Microsoft a lot.

Anderson had previously spent his entire career at the company working for the part of the company that owned management. But 18 months ago, just ahead of the Microsoft 365 announcement, Microsoft CEO Satya Nadella asked him to join Terry Myerson’s business.

“Satya wanted more enterprise DNA and experience in Windows,” he told me. “He wanted me to help them better understand the enterprise, and how fast we were able to make progress.”

Anderson didn’t speak to the politics of this move, though he notes that this seemed like an odd move to him at the time, as it did for those like me on the outside. But the results kind of speak for themselves: After releasing two nonsense-laden “Creators Updates,” Microsoft has shifted Windows 10 to a more mature path over the ensuing year. Terry Myerson played a role in this change, to be sure. (In fact, my other sources tell me that the Spring 2019 Windows 10 release will be the last that was directly impacted by Myerson.) But one has to think that this shift was largely a result of Nadella’s desire to make Windows more compelling for Microsoft’s biggest customer base. And of Anderson’s direct involvement.

Today, Myerson is out and Windows core development is under Azure. Anderson is responsible for Windows for businesses, with Joe Belfiore responsible for consumer experiences. And they are both under the Microsoft 365 group, which combines Windows with Office 365 and the management solutions, from both scheduling/planning and functionality perspectives.

“The company feels like a smaller place to me now,” Anderson told me. “With Satya betting big on Microsoft 365, all those teams and leaders meet once a week in one place. We have common metrics and goals. The culture has really evolved, and there is such agility and alignment. And we’re starting to realize that in end-to-end scenarios that span the products.”

I had had this minor insight before speaking to Anderson: That Microsoft 365 allowed Microsoft to do with Windows 10, Office 365, and management what Office 365 years ago had done for the Office servers. Now, the firm could assume that its customers had all the solutions, not just some of them. And that means that they can be updated together, and made more compelling and full-featured as a result.

Then again, this change is part of what drove my fear that Windows was being deemphasized. That by being part of something else, it was diminished.

That’s not the case, Anderson assured me.

“Windows is a priority,” he said. “It’s the largest installed base we have at Microsoft. That it’s important is well-understood.”

The last two Windows 10 feature updates (versions 1803 and 1809) have been positive changes from the past. But I had to bridge my final major worry: That Windows 10 could still be undermined by the Windows Insider Program. This is a painful topic I had first expressed in full form back in July, in Windows 10 at 3: The Good, the Bad, and the Ugly.

“The Insider program was started for all the right reasons,” I wrote at the time. “In this case, a desire to reverse the hyper-secretive policies of Steven Sinofsky. But the Insider program has failed us: It gives too strong of a voice to the enthusiasts that would be attracted to this kind of program, thus skewing the focus of the product horribly. And this needs to change: Windows should be designed for its most numerous users, not its loudest users. (To be fair to Microsoft, it did start an Insiders program for business. But we don’t hear much about this, and I suspect that engagement is low.)”

I was surprised when Anderson agreed with me. And he noted that Microsoft has programs in place to ensure that the enterprise has a bigger say in Windows 10. And that Windows 10 must be acceptable to the broader audience of users.

Fast Track for Microsoft 365 and its Desktop App Assure service is part of this effort. And a key part of this solution is its application compatibility assessments that run across millions of PCs.

“We’ve worked with customers to identify over 60,000 applications in use across our enterprise customers,” Anderson said. “We identified 57 that have compatibility issues with Windows 10, a tiny percentage. So now, customers can file a Fast Track help ticket, which goes right to the engineering team. If the problem is Windows, we’ll fix it. If it is the application, the team will write a shim to fix it.”

To date, Microsoft has fixed 6 bugs in Windows thanks to this system. And this should result in a “huge confidence in Windows 10 application compatibility,” Anderson notes.

Best of all, this means that the whole ecosystem system got better: Those fixes impact all customers, not just the enterprise.

For me, that’s not just good news. It’s the entire point of all this. So we’ll see what the future brings. How co-development of Windows 10, Office 365, and Microsoft’s management solutions makes each better, and not just for businesses. For now, I’ll take a welcome break from my normal worrying posture. And embrace the fact that responsible adults who actually care about Windows are driving the train now.