Review: Hardcore Software by Steven Sinofsky

Hardcore Software: Inside the Rise and Fall of the PC Revolution by Steven Sinofsky is an insider’s account of the events that drove Windows and the PC first to prominence and then to their inevitable downward slide. If you care about this history as much as I do, you should read it immediately.

Yes, Hardcore Software can be a bit of a slog. The book is overly long and riddled with grammatical issues, and would benefit from a professional editor. But Sinofsky was either in the room for, or a key player in, many of the events he describes in the book. And his analysis of these events in the context of history is what makes the book so rewarding, even when I disagree with him.

Indeed, it’s so rewarding that I’ve already re-read several sections of Hardcore Software repeatedly. This is rare. The last book to have this effect on me was Walter Isaacson’s Steve Jobs, and for the same reasons. Both books describe major milestones in a personal computing history that I’m heavily invested in and am quite knowledgeable about, and yet both also provide unique views and information about those events, deepening and expanding my understanding of them. I feel like I learn something new each time.

Hardcore Software is also a complementary companion of sorts to my own book, Windows Everywhere, with Sinofsky on the inside explaining the why of certain decisions and me on the outside describing the impact of those decisions. And like my book, Hardcore Software was originally written as a long series of blog posts, in this case on Substack, and then self-published. These parallels fascinate me, and while the two of us often had an adversarial relationship, Sinofsky’s book helps to humanize him, despite its almost complete lack of personal information. A decision I understand and respect.

The story told in Hardcore Software spans decades. Sinofsky joined Microsoft in the late 1980s straight out of college, and while his tenure at the company started humbly in developer tools and languages, a right time/right place stint as the technical assistant to Bill Gates set the stage for his future successes by amplifying Sinofsky’s presence and stature within Microsoft far beyond his pay scale or responsibilities.

That perch next to Microsoft’s leader also gave him a unique view of the entirety of the company at the time, and of the different cultures that defined its constituent parts. From the outside, Windows was where all the action was in the 1990s, as Microsoft rode its success to dominance. But from inside the company, Sinofsky saw only chaos and missed deadlines, and when his time with Gates came to a close, he chose the steadier, more professional and polished Office side of the house.

He flies through this part of the story with uncharacteristic brevity, but Sinofsky was promoted repeatedly in rapid succession, and he eventually led the Office team. During this tenure, the team evolved Office from a bundle into an integrated suite and managed a focus shift from individuals to businesses, a key factor in the success of Microsoft’s broader transition of this era. And after delivering several versions of Microsoft’s most important product in increasingly reliable fashion, he presided over a wholesale reimagining of the product that was controversial at the time but incredibly successful. He had seemingly done the impossible.

The contrast between the stable and predictable output of Sinofsky’s team and the chaotic mess over in Windows wasn’t lost on Microsoft’s leadership. Windows had finally delivered on the transition to the NT codebase, but it happened several years later than expected. And it failed to further reimagine Windows through two projects, Cairo and Longhorn, that overreached and failed, wasting even more time. And so Sinofsky was tasked with bringing his particular set of skills to Windows. Perhaps he could achieve the impossible there as well.

The culture clash was immediate, with Sinofsky and a core team of trusted lieutenants upending Windows and making it work more like Office had, more rigorously and structured. The results are well understood: Windows 7 was delivered on time and as promised, the problems of its predecessor and setting up the platform for the next decade. And Windows 8. Well, Windows 8 was another story.

This is, of course, the era I was most eager to revisit. So much so that I read the book in reverse order on the first pass, starting with its last section—which covers Windows 8 and Surface—and then moving on to the second to last section, about Windows 7, and so on, back to the beginning. I was looking for closure. It was during this time that Sinofsky and I clashed, and I was looking for answers. Why was Windows 8 such a disaster? Was this avoidable?

Microsoft and the outside world celebrated Windows 7 as an unqualified success. But Sinofsky had identified a nexus of challenges that would prove that success to be temporary. The web had decimated native Windows app development. The iPhone had refocused personal computing on mobile devices, diminishing the role of the PC. And new competitors like Amazon, Google, and Facebook were pulling more and more consumers away from Windows and the PC.

Surveying this new world, Sinofsky had a decision to make. He could have delivered another Windows 7, a stable but boring evolution of the time-worn desktop paradigm. Or he could disrupt Windows from within with a bold reimagining of the product that embraced the outside forces sweeping the industry. Either way, he would need to deliver the resulting product, Windows 8, in the same three-year timeframe he had achieved with the less far-reaching Windows 7.

Sinofsky dismissed the first option, correctly understanding that such a release would do nothing to change the dynamic, undermining the relevance or influence of Windows. He chose to reimagine Windows instead, and boldly.

It was the right decision. As he explains in Hardcore Software, Windows 8 would embrace the web and mobile paradigms that threatened the platform. But the product was doomed from the start: In addition to some coincidences of timing—for example, the inability of the Windows and Phone teams to work in concert on a single apps platform, shared code base, and release schedule—and its newly emboldened and competent competitors, Sinofsky also contributed to the coming defeat via a series of radical decisions, some of which still confuse me today.

He admits to his contribution in the book, but without apology. He knew that Windows 8 was too much, too soon, but he doesn’t acknowledge that it was also wrong, an all-or-nothing touch-first release that customers understandably rejected. Likewise, he also knew that Windows 8 was incomplete, and he was relying on subsequent revisions to the product to fully realize his reinvention of the product. But then he undermined that future by abruptly leaving Microsoft just as Windows 8 limped to market, leaving his team behind, confused and directionless. For that, he does apologize.

Sinofsky’s controversial departure from Microsoft is still endlessly debated—did he jump or was he pushed?—but his explanation of this crucial event in Hardcore Software feels purposefully incomplete. He repeatedly states only that “it was time,” and he acknowledges that the split was mutual. “I was spent,” he writes. “The company was spent too.”

I may never get the closure I want, but the final chapter of Hardcore Software comes close in thoroughly documenting the many forces, inside and outside of Microsoft, that contributed to the failure of Window 8. This may be the most interesting part of the book, and Sinofsky makes a compelling case that this defeat was inevitable and unavoidable. The challenges were just too many.

In the 12 years since Sinofsky’s departure, Microsoft has released two major new versions of Windows, the first of which reversed his most radical changes, in effect delivering what he would not, yet another familiar evolution of the desktop computing paradigm that would do nothing to change the competitive landscape. There have also been three leadership changes and a dramatic drop in quality, reliability, and predictability.

Hardcore Software doesn’t address these changes beyond decrying the risk-averse nature of post-Sinofsky Windows teams. But I would love to know what he really thinks about the creeping enshittification of Windows 11, in particular, and how he might have handled demands from Satya Nadella that Windows be contorted to make sense within Microsoft’s broader focus on the cloud and then AI.

Sinofsky certainly has his opinions, many of which I disagree with. And his Apple envy and self-aggrandizing nature can get in the way. In his view, for example, Windows 7 was “peak Windows” and Office 2007 was “peak Office,” the important takeaway being that he was responsible for both. And yet, the more I read—and re-read—this book, the more I found myself agreeing with him and appreciating the insights throughout.

Hardcore Software: Inside the Rise and Fall of the PC Revolution by Steven Sinofsky is available on Amazon Kindle and Apple iBooks for $9.99. It’s highly recommended.