Hardcore Software is a professional memoir of former Microsoft executive Steve Sinofsky, who began working at Microsoft as a software engineer and eventually led the Office and Windows groups. It is the greatest professional autobiography I have ever read. It is deeper on disruption than Lou Gerstner’s book about IBM, more on organizational politics than Gil Amelio’s book on Apple, more reflective than Sid Meier’s book on his career in game design, and with a keener eye on business risks and opportunities than Ken Williams’ work on Sierra On-Line.
But first, a disclaimer. I once (multiple levels of management removed) worked under Steve Sinofsky. Further, a visualization I prepared from that time is linked to from the online site for Hardcore Software.
I made this!
Hardcore Software is also – at least for me – even more nostalgic than Wozniak’s book on Apple. Many chapters overlap with the period covered in Douglas Coupland’s fictionalized Microserfs. You can read these chapters as a companion to that book. Sinofsky started his professional career earlier than I did, but I still loved the shared memories we somehow still have:
I walked over to building 5 to find the private, interior office in which I’d begin my career. It had no exterior window but had one to the hallway. As I searched for my office, I passed the kitchen and saw the giant glass-door refrigerators filled with cans of every variety of Coke and Pepsi products like a convenience store.
It would be decades before I paid for a beverage.
Just across from the kitchen was the mail and copy room. This room had everything one could imagine needing for work. It was like a CompUSA and Office Depot all in one. Along with a big laser printer (and a copy machine), there were 5.25-inch and 3.5-inch floppy disks by the case, notebooks of every size writing paper (not computers which hardly existed in portable form at this time), printer paper, pens, tape (transparent and masking), thumb tacks, and more. There were boxes of colored pencils (legend had it that BillG used those to annotate code with different colors, but I later learned that was a myth). There were rulers for scanning across lines of code in landscape. Best of all were the staplers with the Microsoft logo on them. This was like a gift shop, and anyone visiting left with a box of floppies and one of those staplers.
Chapter 2, “SteveSi”
Except for the floppies, I remember all of this!
These touches of daily life and the company’s high (and low) lights were very special to me. Even events that I did not attend were so similar to the pattern of events there. I recognized the happiness people in the stories and pictures often felt:
Happy times at work
Hardcore Software is a historical chronicle of much of Microsoft’s first few decades. Chapters focus on the technical foundations of Windows 95, Microsoft Office first as a marketing and then a technical reality, the discovery of the internet tidlewave, an incredible amount on web-first Office development, and so on. As far as I know, the scope and depth of the history is unparalleled about a major American software developer. It’s incredible.
Left Me Wanting More
Ironically, the section I was most looking forward to is the least described. Microsoft Surface was a truly innovative project, and I previously reviewed Brad Sam’s history of the project. It’s probably unfair to expect the most comprehensive story of a career, told through major projects, to be any longer – but there I go. The chapter “Click in With Surface” (chapter 107!) is great. It left me wanting more.
Windows 8, RT, and Microsoft’s Organizational Landscape
Hardcore Software ends shortly after the release of Windows 8, with Sinofsky’s departure from Microsoft, so it’s not surprising that the most controversial passages relate to that (either in the chapter dedicated to post-release, “The End of the PC Revolution,” or in foreshadowing leading up to it). As Sinofsky begins that chapter:
Windows 8 was a failure.
Hubris. Arrogance. Lunacy. Egomaniacal. Pick any word to describe the product; it was likely used somewhere. No one knew, or felt, the weight of the product failure more than I did. Chapter 108, “The End of the PC Revolution”
Sinofsky’s greatest weakness in the book is occasionally falling into habits of communication that are more common inside of Microsoft. Microsoft is traditionall run as semi-automonaous organizations, or “Orgs” (such as Windows, Office, and so on) whose executives are primarily evaluated on their own Org’s success.
Windows 8 vision. Note Start Menu, links to (classic) Office apps, Metro apps as desktop-facing widgets
Office’s Refusal to Assist in Windows RT
An extended passage on the Office group’s unwillingness to asst Windows RT begins with this paragraph:
Surface RT was designed to be the epitome of productivity for mobile information work. We wanted Surface to be people’s primary work computer, the way they used a laptop (PC or Mac), but with all the reliability, security, battery life, and mobility of an iPad. To accomplish that we needed Office: Word, Excel, PowerPoint, and (some would say) Outlook. The problem: I was not successful at evangelizing the new platform opportunity to the Office team. Let that sink in.
Chapter 108, “The End of the PC Revolution”
and later, within another paragraph:
The biggest irony was that the entire time the Mac Office team was busy building Office for the iPad, which is why it was ready to release on the heels of Windows 8.
The reason from Office’s perspective is clear: iPad is immediately a potentially large market, Surface RT is starts at 0. Why invest in a risk when you can invest in a sure thing? It may not be (or may be) in the best interests of Microsoft, but Office’s leadership was rewarded for the success of Office in a near-term sense more than Microsoft in a medium- or long-term sense.
Windows Refusal to Leverage Windows Phone
A painful example of this is Sinofsky’s decision to not support Windows Phone 7 (“Silverlight”) apps on Windows 8. This was a critical decision as it led to Microsoft taking the fourth and fifth position (behind Apple, Google, and Valve) in US-based app stores. Sinofsky nearly begins his book with a discussion on the importance of Apps for an ecosystem:
The early and successful Microsoft strategy of developing applications that ran on multiple platforms, remained the cornerstone of the Apps strategy. Only now Apps was busy enough just developing for Microsoft’s own platforms consisting of the mature MS-DOS where Apps never gained a lead, the nascent Windows that few were buying (yet), the non-existent, mostly non-functional but strategically critical OS/2, and the monster money-maker Macintosh that competing with all of those. As crazy as the strategy (or lack thereof) seemed to the press and Wall Street, it was even more taxing for us developers in Apps.
Chapter 4, “Everything is Buggy”
And later describes Windows Phone’s use of Silverlight in nearly identical terms:
Recall that Silverlight, in the 2010 timeframe, had originally been Microsoft’s answer to compete with Flash but had been repurposed to be the API for Windows Phone 7 and, subsequently, Windows Phone 8. Silverlight was related to the whole .NET umbrella term but came with its own set of constraints. It had little to do with our Windows platform. Silverlight was non-apologetic about running on not just old versions of Windows but also Mac and soon smartphones. Microsoft’s evangelism kicked into high gear for Silverlight. Many Microsofties fondly remember Netflix using Silverlight in the browser in the early days of Netflix.
Chapter 103, “The End of Windows Software”
and again:
The hallmark of Microsoft’s strategy had always been apps and platform, platform and apps, and if necessary, by force. Early on the apps were forced to work on Windows against their judgment, and then later Windows was forced to be good for the apps even when it thought Office was not the focus, and this see-saw continued for the benefit of the industry. It was like we had reached a point where both businesses were so entrenched that their own worldviews precluded a bigger, all Microsoft bet. Perhaps we reached a level of fatigue in cross-company bets after the Longhorn and .NET eras.
Chapter 108, “The End of the PC Revolution”
From a business standpoint, the decision makes sense. The Windows Phone app store was under the control of the Windows Phone team. Adopting Windows Phone on Windows apps would provide leadership and leverage to one group (Windows Phone) at the short-term expense of another group (Windows). Windows’ refusal to allow Windows Phone apps to run on public builds on Windows contrasted with another decision, where Windows group copied and reimplemented the Windows Phone design language.
Taking From Partners
First, a quick word on my aesthetic competence. So take this example with a grain of salt:
As mentioned, I made this. That disqualifies me from being considered an expert on anything aesthetic
For instance, consider the “Metro” or “Modern” design language used by Windows Phone. For instance, consider this line that references a critical review but explicitly praises the design aesthetic of Windows Phone.
By the time it released, with its stark Metro tiles and hubs rather than apps, Windows Phone felt unique and differentiated, despite the potential limitations. The Windows community would develop a wildly enthusiastic following for WP7, despite the paucity of apps relative to iPhone. Walt Mossberg wrote a review with the headline, “Microsoft’s New Windows Phone 7: Novel But Lacking.” He concluded “…Microsoft has used its years in the smartphone wilderness to come up with a user interface that is novel and attractive, that stands out from the Apple and Google approaches, and that works pretty well.” Ultimately, he did not recommend it and said it was neither as good nor as versatile as iPhone or Android.
Chapter 100, “A Daring and Bold Vision”
This is remarkable, as Windows design aesthetic was borrowed from Windows Phone…
We chose to significantly expand this capability with Live tiles. The easy to press launching and switching buttons could come to life with useful information available at a glance. We went a step further and made it easy for developers to add additional tiles for users of an application to pin additional information to the Start screen, called secondary tiles. This was a feature initially on Windows Phone 7 and enabled pinning a single contact or stock quote to the home screen. This capability made further customization of the Start screen possible, again something not possible with the combination of Start menu, taskbar, and notification area in any system-wide manner.
Chapter 102, “The Experience”
… but without the art of the style. It is not for nothing that Windows 8/RT’s design aesthetic for called childish or child-like.
Windows 8 nearer release
I do not think it is fair to say Windows was designed to be “authentically digital,” and Windows Phone was not. Instead Windows copied and modified – badly – a better received aesthetic developed within Windows Phone group. Doing this was a gamble and a mistake.
The basement had a visceral reaction to the design language of Metro-style—the rectangles, solid and bright colors, and use of text. This would be surprising because the basement, specifically the basement committed to Microsoft, were huge fans of Windows Phone. The phone was monochrome and we defaulted Windows 8 to more colors by virtue of our authentically digital experience. The basement quickly dubbed the look of the Start screen as “Fisher-Price” aligning with the view that tablets were for kids to use in the back seat, not for real work.
Ch. 106, “The Missing Start Menu”
I say this not because I’m a designer or could have done it better. But because in another section, Sinofsky found himself in precisely the opposite situation and reacted in the opposite manner:
Not Sharing with Partners
Just as Windows borrowed without supervision the design aesthetic of Windows Phone, Windows Phone borrowed without supervision program code from Windows. In this case, Sinofsky correctly saw the costs of Windows Phone grabbing wanted to and moving independently:
The Windows and Windows Phone teams would eventually go through a challenging period where in the middle of Windows 8, we on the Windows team learned that the Phone team had been taking snapshots of various subsystems of Windows 8 for use in the phone OS. This got the product to market but did not give us a chance to align on quality, security, reliability, and code maintenance. This wasn’t done in any coordinated or even transparent manner. Had we, Jon DeVaan and Grant George specifically, not intervened the company would have been set up for significant issues with security and reliability given we were not finished with the code and there was no process in place to manage “copies” of the code. Jon worked through a better process once the team got ahead of the issue. I had a super tense meeting with SteveB and the co-leaders of the Phone team about this lack of transparency and process and why it showed a lack of leadership, or even competence, on our part. In the new world of security, viruses, vulnerabilities, and more the company could not afford to be cavalier with source code like this seemed to demonstrate. This was all in addition to the lack of alignment on the developer platform as the Phone team made their early bet on Silverlight as previously discussed.
Chapter 104, “//build it and they will come”
But not the benefits: Windows Phone shipped the Modern/Metro design language first and was iterating more quickly than windows. And would continue doing so. While Windows Phone 7 debuted on the aging Windows CE kernel in October 2010, the kernel was upgraded to a Windows kernel with Windows Phone 8 in 2012.
Microsoft’s answer to iPhone and Android 1.0 was still being developed. Windows Phone 7, originally codenamed Photon, would be released a year after Windows 7. The mobile team was heads down trying to get that release done, which had been in the works since Windows Mobile 6.0 shipped in early 2007. By the time Windows Phone 7 shipped, the Windows 8 team would have completed the first of three milestones. The next full chapter will detail the challenges this lack of synchronization created. We had Windows Phone 7 on a mission to get to market and compete and in doing so was pre-booking the next release; Windows 8 attempted to plan a major release that in theory would lend support to the mission of modernizing the codebase which was desperately needed by Windows Phone 7 competing with the modern Linux kernel and OS X.
Chapter 97, A Plan for a Changing World“
These actions are all typical of Microsoft’s internal structure. There are probably good lessons here for others navigating similar organizational structures. I wish Sinofsky had spent more time reflecting on these patterns, as he reflected on other temporary circumstances throughout the book.
Conclusion
Hardcore Software was published over a two year period on Substack, from January 2021 to December 2022. Early chapters were published similarly to blog posts, and Sinofsky simultaneously released the most recent chapters as podcast episodes. I loved the experience of reading Hardcore Software in the Substack edition.
