014. Executing on the Expansive Vision of Bill Gates [Ch. III]

014. Executing on the Expansive Vision of Bill Gates [Ch. III]

Author: Steven Sinofsky March 20, 2021 Duration: 11:06

At the start of Chapter III towards the end of 1992, I thought I was about to start on the next release of Visual C++. Instead, a surprise email has me discussing a new job working for BillG as his “technical assistant”. I begin think about what the company is like to the outside world. Inside the company, we’re just working (and working, and working some more) trying fix the bugs, to ship, and get PCs to actually work. Microsoft was growing up. I was growing up. I didn’t even know Bill yet, having only met him at the new hire party.

This chapter and the following chapter (about 15 posts) describe the next two years. These years were probably the craziest time for the company, for Bill, and even to date for the technology industry.

Just a gentle reminder, this post is free to all those that signed up for the substack. Shortly I might do some posts that are subscriber only. Everyone will receive an excerpt though.

Back to 013. End of the Beginning

I blew off Bill Gates the first time I was supposed to meet with him—well, at least the first 20-plus minutes of our meeting in the fall of 1992.

I had been in AFX group leader Jeff’s office talking about some last-minute ship details for VC++ when I realized, “Oh crap, I am supposed to be meeting with BillG.”

Days earlier, Natalie Yount (NatalieY), at the urging of Jeff, spoke to me about taking a job that I knew nothing about, working for a person I had never really met, doing . . . I had no idea what. It was called technical assistant.

NatalieY represented a rarity at Microsoft. She was a core torch-carrier of the company culture, but not a technical person. She came from the famed Xerox PARC where she worked as a research librarian in the labs during some of the most innovative years at one of the most innovative places in technology (or anywhere). At Microsoft, she quickly captured Microsoft’s culture and became the leader that bridged fresh-out-of-college technologists and the real world.

During our meeting, she and I talked for a bit about me, my least favorite subject, but our conversation did not feel like an interview. Then she described the job. There had only been one other formal technical assistant and that was Aaron Getz (AaronG), another college hire who had worked with DougK on Microsoft Money as the only program manager. Carl Stork (CarlS), a college classmate of BillG’s, had previously unofficially held the job very early on where he worked with Bill on the organization of commands for Multitools apps. Richard Brodie, the original Word for DOS developer and former Xerox PARC engineer held the job for a year. Jabe Blumenthal (JabeB) had as well. JabeB had joined Microsoft as a college hire in the early 1980s. JabeB was the original program manager at Microsoft and had led the design of Microsoft Excel before leading efforts in the newly formed Consumer Software Division, where multimedia CD-ROM products and other home software was being developed.

It sounded like the job was “assist BillG with technical stuff” I thought to myself. In other words, there was no real job description. Jeff later described it as BillG’s “eyes and ears” on a deep technology level so he could continue to be engaged in a way he wanted to. That helped slightly. One thing was clear: The previous holders of this job were Apps program managers, while I was more of a Tools software design engineer. A concern (BillG had, I was told) was that as an SDE I lacked a big picture view and was too focused on the code, but that was not how I had been trained. (JeffH told me not to worry.)

Natalie later sent me a note and copied BillG’s assistant to schedule a meeting.

In thinking about what this sort of meeting would be like and how to prepare, the realities of Microsoft began to sink in. Not the product realities, those I understood well, but the realities of the company and that it, and BillG, were changing.

Jeff, my mentor who clearly arranged for this meeting to happen, offered me some of his insights. First and foremost, he confided in me that the company was now at a scale that Bill can’t keep track at the level of detail that he wants to. This was not to take away from his IQ or anything, but just simply that Microsoft had a lot of stuff going on. Jeff talked about how he could not put a finger on it, but Bill was “different” during the formation and shipping of AFX products—different in the sense that his input was more abstract, strategic for sure, but not at the level of detail he engaged on the evolution of Word or the first versions of Windows. Bill wanted to and believed he could continue to engage at a deep technical level, but Jeff felt he needed tools, or a person, to scale that effort. That’s how he came to suggest me to Bill.

The first few years after Microsoft’s IPO had been kind to Microsoft. Whether before the IPO on the cover of Time Magazine in 1984 or the cover of Fortune Magazine in 1986 just after the IPO, the image of the youthful and brainy nerd cemented Bill as a leading innovator of our age. Heck, it seemed like the whole country was embracing khakis and button-down shirts. It was like the ten-year old film Revenge of the Nerds had become reality.

Then came the book Hard Drive: Bill Gates and the Making of the Microsoft Empire by two reporters for the local Seattle Post-Intelligencer who had covered Microsoft for some time. The book had just come out, Spring 1992. Everyone at the company knew Bill (and allies and employees) did not cooperate. It was clearly intended to portray events in a negative light and was trying to be the first to do so (and succeeded). Writing today, I’ve learned that books like this are written too soon and amplify (or even get incorrect) events that are still happening and still unclear, the fog of war. Even today reading the book’s stories of hidden bugs designed to disadvantage customers or third-party developers seem as patently absurd, and false, as they did back then, even if the book spun a yarn saying otherwise. The arrival of the book began to color interactions with the press that to this point had been even-handed or even celebratory. Microsoft and Bill seemed to be entering the bad part of the cycle of build you up, then tear you down.

The real difficulty was the cloud of regulatory oversight that was just starting to form. While there were one-off stories, there began to be a critical mass of what might be called business practices that were claimed to be at the root of the success Microsoft was achieving. In other words, with the success, people were looking for the cause. Microsoft’s aggressive business practices were starting to be viewed as crossing some line. There had to be a way to explain the success that was not rooted in building great products, or so it seemed.

The way that employees could see this were through stories in trade press most often with quotes from who we viewed as competitors, or perhaps even bitter competitors that had lost. The primary dynamic going on that we talked about at lunch endlessly was how the success of Windows even caught Microsoft off guard compared to the determination to make OS/2 and the IBM partnership work. What Microsoft did was not pull back or even sacrifice that partnership to bolster Windows, but rather was just quick to recognize the product was not working and to find a different path. Unfortunately, most of the leaders in the industry chose to stick with IBM even longer than Microsoft did. That caused a lot of bitterness among the software leaders of the first era of the IBM PC, all of whom were under increasing pressure to have similar success on Windows. My old friend from drinks at the Software Development Conference, Philippe Kahn the founder and CEO of Borland, was one of those who led the charge, even advocating for IBM.

What was so weird was that in the lunchroom we were mostly relieved. It was not a master plan, but a master pivot.

There were then the constant stream of opinion pieces in the trade press criticizing Microsoft for products that were late or buggy. Every product was late and buggy and while we might argue at the very least our products were less buggy given the financial success the industry and customers were expecting better.

Across the industry trading barbs in the press nearly continuously for the past year or more over the future operating system platform was now routine. Analysts and executives on all sides would say the others are spreading “fear, uncertainty, and doubt” or FUD. FUD is a tactic, or theory about a tactic, designed to prevent customers from buying rival products by sowing negative views. In an ironic twist that really gnawed at Microsofties, often it would be said that Microsoft was employing a FUD strategy just as IBM had done before and perhaps even Microsoft, in the early 1990s, had become the new IBM—a recognition of the declining influence of IBM in the personal computer industry and Microsoft’s rising influence, or even dominance. NT was viewed as the center of claims of FUD because it was shipping real soon now, and at the same time Microsoft was indeed putting forth a pretty grand vision for the product that would take years to materialize.

Internally both now and for quite some time, Microsoft felt and acted like the insurgent. The computer companies we knew growing up were being left behind and many companies we knew from just a few years ago were struggling with the transition to PCs from mainframes and minicomputers. It was not difficult to imagine that fate for us if we just missed a few beats, executed slowly, or failed to deliver. At the same time, we were just struggling to keep the wheels on trying to deliver products, fix all the bugs, and make things work.

The narrative outside of power and influence simply didn’t match our day-to-day experience of fragility and challenges. We’d read about power and did not feel it or even understand what it felt like. Certainly, no team returning from a BillG review felt power. They felt the same pressure to achieve technically.

It was all super weird.

These were all really big issues, the subject of lunch time gossip. I could never hope to have an intelligent conversation with BillG about them.

I was more worried about Bill asking me questions about technology I would not know the answer to. Or pushing me on flaws in our products that I had been part of creating. Maybe even saying something that was “the stupidest thing” he had ever heard. I wanted to be “high IQ” even though it was still unclear if I was interviewing for a job or just doing some sort of informational meeting. I had no idea what it was like to change jobs inside of Microsoft and almost no one I know had even done that yet, save for OS/2 people moving as the project started winding down.

I set up a time to meet with BillG.

On to 015. Every Group Is Screwed Up



This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit hardcoresoftware.learningbyshipping.com

There’s a story behind every line of code, every product launch, and every industry shift, but rarely do we hear it from someone who was in the room for decades of defining moments. Hardcore Software by Steven Sinofsky (Audio Edition) offers exactly that: a firsthand narrative from the trenches of the PC revolution’s peak and its complex evolution. Host Steven Sinofsky doesn’t just recount history; he unpacks the visceral realities of building software at scale, the management dilemmas faced under immense pressure, and the human decisions that propelled successes or led to stumbles. Having joined Microsoft in 1989 as a software design engineer on C++, his 23-year journey weaves through critical projects like Visual C++, six major releases of Office as its Senior Vice President, and the era-defining development of Windows 7 and Windows 8, culminating in his role as President of Windows overseeing internet services. Each episode of this podcast feels like a detailed retrospective, blending personal anecdote with hard-won lessons on technology, leadership, and strategy. It’s for anyone curious about the intersection of business, engineering, and history, told with a level of specificity and reflection that only an insider can provide. You’ll hear not just what happened, but how it felt to make those calls and what those experiences mean for building things today.
Author: Language: English Episodes: 100

Hardcore Software by Steven Sinofsky (Audio Edition)
Podcast Episodes
058. Synergy [not-audio_url] [/not-audio_url]

Duration: 32:43
Welcome to planning Office10 and going inside the strategy, synergy, unification engine that characterized the early 2000s Microsoft (beginning in late 1998). This is a beefy post (too long for email) and even includes a…
057. Enterprise Agreements [Ch. IX] [not-audio_url] [/not-audio_url]

Duration: 21:41
Welcome to Chapter IX, taking place 1999 to 2001 where the world realized just how dependent it had become on email and the PC when viruses became a mainstream part of the technology vernacular. In the halls of Microsoft…
056. Going Global . . . Mother Tree [not-audio_url] [/not-audio_url]

Duration: 22:31
Launching a product in a local market, natively so to speak, is an extraordinarily special experience. It is so special that for nearly every product I worked on I chose to be outside the US and participate in some aspec…
055. Office 2000 is Good to Go! [not-audio_url] [/not-audio_url]

Duration: 15:54
Office9 (aka Office 2000) was the very first release of Microsoft Office built by a team that began the project and ended the project as one. Well, almost as there was that pesky Outlook challenge. That said, the project…
054. Steve and Steven Get New Jobs [not-audio_url] [/not-audio_url]

Duration: 16:42
Steve Ballmer was named Microsoft president in July 1998. There was not much fanfare because it seemed an entirely natural progression of his role at the company, partnership with Bill, and recognition of the incredible…
053. Strategy Tax: Outlook Storage, First Attempt [not-audio_url] [/not-audio_url]

Duration: 24:33
Most tend to think of Microsoft strategy as the march from BASIC to DOS to Windows to Azure. While that is a robust external narrative, the more interesting view is how the company changed strategically and organizationa…
052. Alleviating Bloatware, First Attempt [not-audio_url] [/not-audio_url]

Duration: 19:44
What happens when your biggest strength and greatest asset as a product development organization becomes your biggest weakness? Perhaps that is inevitable. With so many potential disruptive forces, at least that’s what w…
051. HTML: Opportunity, Disruption, or Wedge [not-audio_url] [/not-audio_url]

Duration: 25:55
While we knew the time was wrong to build a whole new Office out of one of the new disruptive technologies, we did need to arrive at a strategy for HTML. After the debacle of the file format changes for Office 97, the al…
050. The Team's Plan in the Face of Disruption [not-audio_url] [/not-audio_url]

Duration: 23:29
With the looming threat of disruption, at least according to everyone at the company and the desire to get moving on adding new features to the apps, there was a need to have a strategy in place. Putting together a plan…
049. Go Get This Rock [not-audio_url] [/not-audio_url]

Duration: 32:24
The most difficult thing to do in a big company is change a core belief. Microsoft was going through a late 1990s change, and rather unevenly. We were moving from a company primarily or almost exclusively selling product…