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The story of Windows 10 from inside Microsoft

Tom Warren a senior editor covering Microsoft, PC gaming, console, and tech. He founded WinRumors, a site dedicated to Microsoft news, before joining The Verge in 2012.

Windows 10 has a lot to live up to. Microsoft has made a lot of promises about it. And oddly enough, we’ve heard most of them before, with Windows 8. Both were designed to acknowledge and embrace mobile and mobile apps, work well on touchscreens as well as laptops, and form the basis of a new phone platform. But there’s a big difference between them: Windows 10 actually does all those things.

Windows 10

The story of Windows 10 from inside Microsoft

The company's latest trick: listening to its users

By Tom Warren

Windows 10 has a lot to live up to. Microsoft has made a lot of promises about it. And oddly enough, we’ve heard most of them before, with Windows 8. Both were designed to acknowledge and embrace mobile and mobile apps, work well on touchscreens as well as laptops, and form the basis of a new phone platform. But there’s a big difference between them: Windows 10 actually does all those things.

Three years ago, tablets like the iPad looked like they might be a serious threat to Windows. In response, Steve Ballmer, Steven Sinofsky, and the rest of Microsoft took a big bet on a forward-thinking interface that asked its users to forget their old point-and-click ways and embrace a tiled future. Windows 8 and Windows Phone 8 were related pieces in a bold strategy to move the company into a future of touchscreens and connected apps.

That strategy flopped. Users roundly rejected the confusing new version of Windows, and without them, developers balked. But the iPad hasn’t killed off laptops, and consumers haven’t shown a big interest in touchscreen PCs yet. Another version, 8.1, attempted to stem the bleeding, but it was too late. The market had spoken. Like Vista before it and Windows ME before that, Windows 8 was the version of Windows you skipped.

Now, a new leadership team for Windows under CEO Satya Nadella and executive vice president Terry Myerson are trying it all again. But this time around, the goal is much more ambitious: if they succeed, Windows 10 will be the final iteration of Windows: The one that will be updated like a service, continuously, in perpetuity. The one that finally makes good on all the promises of a synergistic ecosystem of like-minded devices designed to work together.

In a series of exclusive interviews with The Verge, the team behind Windows 10 revealed how they’re doing it, why they think it will succeed, and what they’re working on next. This is the story of Windows 10 from inside Microsoft.

Terry Myerson

Developing in the open

Terry Myerson never imagined he’d last at Microsoft. "I thought I was going to stay here a couple of weeks, but found that I really loved the people."

It’s now 18 years since Myerson sold his small company to Microsoft, during which time he worked on Exchange, Windows Mobile, and Windows Phone. Now, he’s sitting in front of me as the head of Windows, just days before the software maker launches Windows 10. It’s been two years since Myerson was promoted to the top job, and the release is important to him and the company. Microsoft needs customers to love and want Windows enough to upgrade to it, thereby creating a massive install base to attract developers. The pressure is on.

Myerson is confident without being arrogant — he’s more than happy to tease me about my MacBook. His forthright manner is mirrored in how he chose to release Windows 10: out in the open, bugs and all, even before the company had finished thinking through what it should be.

Microsoft now solicits feedback directly from users in a very public way: over the past nine months, the company has been testing Windows 10 with 5 million "Windows Insiders." Anyone can sign up to test, and the results of Microsoft’s work will go on display today as Windows 10 launches to millions of people around the world.

"It has sometimes been daunting," says Myerson. "You're putting it out there when it's not done, then you're getting all kinds of feedback and stuff that you know is broken." That feedback has been constant and varied over the last nine months, and it will continue over the months and years ahead.

Initially, "there was a lot of hand-wringing around what was that going to be like and were people going to form opinions too early," explains Gabe Aul, engineering general manager for Microsoft’s operating systems group. "I think we just decided to go for it."

Aul launched his Microsoft career in product support 23 years ago. He went on to help build Dr. Watson, a debugger that gathers error data when your PC crashes, into basically every product at Microsoft.

Today Aul is the face of Microsoft’s Windows 10 testing. He receives Microsoft feedback, praise, and abuse on Twitter daily, but he remains perfectly cool. Even before we start our interview, I start moaning about some Windows 10 bugs I have, and he’s keen to listen, even emailing me a fix for a problem within seconds.

He admits he’s "passionate about quality" after working in product support for years, and it’s clear he genuinely cares. While many will joke IT support is simply a help desk asking a user to reboot their PC, Microsoft has built a whole system to process the feedback it receives for Windows 10. It all gets collected in a database where Microsoft engineers can use tools to analyze it visually. If Cortana starts breaking in France, Microsoft will hear about it, and engineers can detect trends and issues based on pop-ups that appear for testers.

Feedback doesn’t always come from within the operating system, though. The Continuum feature, which lets you switch between desktop and tablet modes in Windows 10, generated a wave of negative responses from social media. That’s probably because Microsoft initially ripped out all of Windows 8’s good touch work, a move that surprised testers, before slowly building it back in. "The trash can icon — the feedback we got on that thing..." He cuts short to laugh because Windows Insiders (myself included) were really vocal in comments and online forums about the how ugly the first version was.

Sometimes, Windows customers reached out to Myerson directly, including one during the time when the Windows chief misspoke and the result was that everybody thought Windows 10 would be free. "There's this kid in Bangladesh who somehow got my email address, he runs pirated Windows," Myerson says. "It was a great dialogue. It was more for me a learning experience about how did he pirate Windows, and why did he pirate Windows." The conversation hasn’t changed Microsoft’s stance, though. Windows 10 still isn’t free for pirates.

Xbox app Windows 10 Photo by Chris Welch / The Verge

The new Xbox One app on Windows 10

Taking feedback

To handle feedback, the Windows build team hosts daily "flight ops" meetings to decide which prerelease versions of Windows 10 get released. A "flight commander" takes control of the team, for that day. "He has a red hat that says ‘phone’ on it, and he has a black hat that says ‘PC’ on it," Aul says. "When it’s time to talk about phone, he will take the PC hat off and put the phone hat on. That’s how we keep the room in check."

There’s also a red outfit hanging on the wall, a symbol of a time when one employee came to the ship room wearing embarrassing matching red shorts and a T-shirt (he’s an Ohio State supporter). It became a running joke. Now, if a Microsoft engineer enters the meeting with a bug that’s equally embarrassing, they have to wear something red.

To continue with the red theme, Aul has a 3D-printed red button that’s become something of a Microsoft meme among Windows fans. Aul hits it when a build is ready to be released to the public. "It’s mostly ceremonial, but it actually does send a trigger to the flighting system," explains Aul. "The other thing it does, that most people don’t know, is it says something inappropriate in a Stephen Hawking voice because it’s got a voice synthesizer in there." Aul wouldn’t give me any examples, but quotes are sourced from the team or jokes about his tweets.

Microsoft’s willingness to solicit user feedback on early versions is a big change from the past. During the days of Vista, Microsoft’s lawyers ended up at my doorstep because I dared to write about prerelease versions of Windows. And while Windows 8 had a few public previews, it was largely developed with little consideration to feedback. Windows 8 shipped despite user concerns about fullscreen apps and a lack of attention to keyboard and mouse users. Microsoft’s management seemed to spend more time explaining every new feature in sprawling, technical blog posts instead of understanding why users hated the changes.

Myerson has a different philosophy: "It isn't one guy comes down from a mountain with a tablet [saying] what the right product is," he explains. "We just believe the customer feedback shaping the product is how we're going to build clarity and confidence that we have a great product."

Joe Belfiore

From apps to phones

Microsoft may have been confident about Windows 8, but the ambitions to push touch computing didn’t work out. Microsoft has been forced to admit several times that it’s aware customer satisfaction rates for mouse and keyboard users are low. Microsoft’s new Start menu isn’t as domineering, it’s just designed to get them to move to Windows 10. "Our strategic belief is, if we have a big audience of people… then developers will put apps in that store because there will be demand," explains Microsoft’s Joe Belfiore.

Belfiore looks after the customization of Windows for PCs, tablets, and phones. He spent years building Windows Phone, alongside Myerson. To many fans, he’s the face of Microsoft’s mobile efforts. Microsoft has been constantly resetting and rebuilding its Windows Phone OS. Windows Phone 7 users couldn’t upgrade to Windows Phone 8, and it took far too long for Windows Phone 8.1 to arrive with features that should have been there from the beginning. It’s knocked developer confidence, to say nothing of crippling its chances at gaining significant marketshare.

Part of Windows 10’s big promise is that the same apps can run across PCs, tablets, phones, and even the Xbox One console. As a result, the next phones will have an expansive set of apps from Windows 10 to jumpstart the ecosystem. "We have one common operating system for all the device types that we are making," explains Belfiore. He’s also surprisingly blunt when he characterizes Windows Phone 7 and Windows Phone 8, products he was intimately involved in developing. "We've had a couple of, sort of, practice runs with phone and PC," Belfiore says, before pivoting to the presumably brighter future with Windows 10, "We now have all the devices lined up. I don't expect to see the platform change again, in the same way it has before."

That’s encouraging to hear, but it doesn’t help Windows Phone right now. Microsoft CEO Satya Nadella revealed recently that the company is restructuring its phone business, scaling it back massively as part of a $7.6 billion write-off from the Nokia phone business acquisition. Around 7,800 jobs are being cut, and Microsoft is planning to make fewer models. "We are going to focus on a few great devices and the most notable being that premium consumer category," explains Myerson, adding, "The direction we will head is the premium-branded lineup." I push him on whether that’s a similar approach to Surface, and he claims "the goal is to have one Microsoft device family that plays this role in the Windows ecosystem." I’m not sure if that means a Surface Phone is in the cards, but it sure sounds like it.

The first example of that one Microsoft device family will arrive later this year. "One's coming. Maybe two are coming, but at least one is coming," teases Myerson, as he hides an unreleased Lumia phone in his pocket. Microsoft is rumored to be working on two high-end devices that will include a new Continuum feature from Windows 10. Continuum on phones lets you use the phone as kind of a PC. You can connect up a keyboard, mouse, and monitor and start using Windows 10 apps. "I think it is the future of the phone," says Myerson.

Belfiore is equally bullish about Continuum, but the phone version of Windows 10 doesn’t ship until later this year. "The phone is significantly feature complete, but we'll continue to polish and tweak and iterate the things that still need to work," explains Belfiore. "We'll put features in right up near the end. But in general, the broad feature set is set."

Phil Spencer

Windows 10 and the Xbox One

Windows 10 is also coming to the Xbox in a big way. A new Xbox app for Windows 10 is a significant addition, and it’s one of the best built-in apps available right now. You can stream Xbox One games to a Windows 10 PC and use the Xbox controller, and you can chat freely from a PC to an Xbox One with or without a headset. It’s a great addition for Xbox gamers after a rough couple of years. Sales have been second to Sony’s PlayStation 4, but it feels like Microsoft is recovering from the original unveiling of the Xbox One two years ago. "The launch of Xbox One, it was from a brand and a customer pride standpoint… a tough time," says Phil Spencer, Microsoft’s head of Xbox. "A lot of the original ideas around Xbox One didn't meet the expectations that Xbox fans have of what we should do with our product."

Spencer, who has worked on products like Encarta at Microsoft, has spent the last year or so getting the Xbox team re-centered on its fans and gaming. It’s an approach that Myerson says inspired the Windows Insider program. "Xbox had this passionate focus on their fans and engaging with their fans and listening to their fans," says Myerson. "Something that Phil Spencer just has at his core is his caring. He lives for those Xbox fans."

Spencer sees Windows 10 as a "massive opportunity" to bring Xbox Live and a single store to people. Today, the Xbox store is separate from the Windows store, but Microsoft is unifying them this fall. That doesn’t mean apps will be immediately available on the Xbox One, though. "Getting to one store where all the content is there will happen a little bit later," says Spencer, meaning we’ll be waiting until next year until we finally see Windows 10 apps on Xbox One. Microsoft’s store isn’t designed to kill off Steam, either. "Five years from now, I want Steam to be incredibly popular and successful. I look at the health of Steam as a harbinger of the health of Windows gaming."

What is coming this year is a Windows 10 update for Xbox One that brings a refreshed UI, speed, and Microsoft’s Cortana digital assistant. "You can imagine scenarios of ‘Hey Cortana, what are most of my friends playing? What are most people watching?’" says Spencer. "The next step is being able to help you in-game, of really thinking about scenarios like ‘Hey Cortana, how do I get past this boss?’" Further out, Spencer says that streaming PC games to Xbox One is something he wants to enable. "We understand if you're going to go PC to Xbox, we need to get keyboard and mouse working completely so you could play those games. In terms of where we want to go with our platform, those are absolutely in the scope of things that we want to do."

Terry Myerson

The last Windows

Myerson and his team have shifted Windows 10 to a "Windows as a service" model, meaning regular updates instead of a major release every few years. It doesn’t feel like Microsoft really knows exactly how this is going to play out, but the Windows 10 release marks a milestone.

But it’s not the kind of milestone we’re used to. Windows 10, even at release, is not done. Right now, it’s all about updates that fix issues and bugs. If you upgrade from Windows 7 and Windows 8 this week, then you’ll start to see those regular updates, and they’ll install automatically to keep everyone up to date. Myerson is confident in the quality of Windows 10. "We look at these quantitative metrics and we think the quality's great, and we're continuing to fix more," he says. "We're going to keep fixing. We're committed to listen and respond. Every day we're shipping out new updates with 30 more fixes."

That listening and responding sums up Windows 10. If there’s something wrong this time, then Myerson and his team will be listening. This can’t (and likely won’t) be another Windows 8 or Windows Vista mess for Microsoft. The company simply can’t afford to make those mistakes again. "Our goal is to roll out Windows 10 and build a base of millions of happy and engaged Windows 10 users," says Myerson.

"Happy and engaged" is one of those talking points you hear a lot from Microsoft. Myerson used it nine times in our hour together. But behind the PR-approved phrasing is a simple truth: it’s been a long time since Windows users have been either, and Microsoft needs to fix that. It’s as good a North Star as any, especially when your product development cycle is founded on taking user feedback seriously. If Microsoft can make people love Windows again, then the rest — developers and apps — is easy.

If I’ve learned anything from speaking to the team building Windows 10, it’s that Microsoft is taking user feedback very, very seriously. Everything Microsoft is making — from the Xbox to phones to HoloLens — is based on Windows 10. It’s not just the foundation of this operating system, it’s the future foundation of the company. Microsoft doesn’t have a Plan B for Windows, and it’s proud of the fact: "There's no one working on a Windows 11," Myerson says, "but there's a group of people working on some really cool updates to Windows 10." When Windows Insiders see those updates, you can be sure Microsoft will want to know exactly what they think.

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Photography by David Ryder

Edited by Dieter Bohn and Michael Zelenko