Alex Chekholko

The amount of Microsoft energy that went into trying out this theory—a database running locally as a file system—would be hard to calculate across Windows, Office, email. It is one of those ideas that seems interesting on paper. In practice it is never good enough for everything you want to do and the constraints do not help you to think of better or more clever ways to get things done. The constraints just got in the way of getting anything done. There's significant utility in having a local database available for use in the platform, but that too carries with it challenges in backup/restore/upgrade/security/privacy/etc. In hardcoresoftware.substack.co… I think I wrote about this adventure in four times (working on strategy for Bill, Outlook, SharePoint, Longhorn.) I don't know if there is another example of a technology aspiration that endured so long and lacked a solution that worked. And also caused so much division and consternation inside Microsoft. Perhaps more than anything it is the lesson of a big company thinking it can invent the future in isolation—all sorts of isolation or tunnel vision. Big companies, it turns out have a surplus of two things: 1. Hubris. There was no shortage of people starting at the top who become "obsessed" with delivering on an idea and believed the success Microsoft had recently achieved was a license to know how to build it. 2. Doubt. There was also no shortage of people who thought from the first days that the idea made no sense and believed the defined solution in no way benefitted the products that are being made, loved by customers, and pay the bills. This 1-2 punch is fascinating because it sets up a divisive dynamic where you are either an "innovator" who is "on board" with the future OR you are a "obstacle" who does not see the value in "big bold bets" on the future of the company. Along comes a book like "Innovator's Dilemma" [1998] and suddenly resisting the next big corporate strategy makes one throw out common sense engineering because you don't want to get disrupted. It is the other side of the disruption coin no one talks about—sometimes the new thing does not in fact work very well nor will it in any finite time. The lesson applies to the product and technology leadership of a company. Part of what happens in a big company as well is the ability for the company to speak broadly and enroll their ecosystem in their own excitement for the future. Microsoft described WinFS as early as 1992 and over the course of more than a decade it polluted our ability to talk about new products. The email product (Exchange, today the mail for 365) was famously the most important product to be launched and for the first decade of its life was always about to become strategic even while it was in fact the most strategic product the company made. The strategy nearly wrecked Outlook the face of the email strategy. It did in fact derail an entire generation of Windows. There was fallout across a range of products never released. All the while Microsoft was talking about the grand future of this product while customers were investing and buying into products built an entirely different way. A dynamic few are willing to speak about is another 1-2 punch: • Customers and the press talk all about waiting and seeing if the current product will adopt the all important strategy. The first signs of this are the sales force freaking out and escalating their concerns. • Customers actually ignore the strategy because "product market fit" dynamics take over and they can't buy and adopt the actual product soon enough. The first signs of this are visible to those in the real world who never get asked about the strategy because customer have a million feature requests. This is the second way the whole dynamic divides the company. The "obstacle" people start to look like they are focused on the past to the "innovators" who are clearly focused on the "future." You can find many examples of this near computing technology and broadly in other industries: • Intel Itanium (which Dave below knows well) was a chipset architecture that just never panned out. Itanium occupied Intel for more than two decades. • Copeland OS pursued by Apple muddled their decaying ecosystem and divided the company, cancelling it set the stage for Jobs return with NeXT becoming the future OS. • IBM "Stretch AND "Future Systems." IBM was such a defining company it had two generations of this dynamic in an effort to reinvent (or invent!) mainframes. Stretch was much like Microsoft Longhorn in that there were portions that went on to greatness in the 1960s. FS just got cancelled. • IBM also had the Micro Channel Architecture (MCA) which divided the hardware side of PCs at just the wrong moment. It just went away. Also IBM had OS/2 which I think still runs some bank ATMs :-) [There's a theme that maybe IBM invented this whole level of hubris which would follow from second-system-syndrome in "Mythical Man Month"] • Hydrogen Fuel cars have been surpassed by improved gas and now EV yet you can still see them being pushed in Japan though at last Detroit moved on. This one has been going on since I was a kid. • GE Predix was a broad SAP-like industrial information technology bet that was the technical undoing of GE IMO, though the 2008 financial crisis really did the work. Predix was Immelt's bet (his book details this) while cleaning up was left to a successor as often happens. There's a difference between a failed product and a failed all-consuming strategy. All companies have failed products essentially all the time. Technology companies seem unique at hubris required to broadly pursue—in public—a direction that doesn't work. They do so under the guise of preventing the decline of the company that makes it all the more painful. Likewise there is a difference between a successful product line that can't escape its own success gravity and failed attempts to reinvent it. The most common thread is the inability of a successful company to find a new strategy for an existing product. We are living in this moment now with AI as we see Intel which could not transform its chip architecture into something different while at the same time Nvidia's long term architectural bet ended up as the foundation of the the AI era. Had we found ourselves in some other chip architecture from a third company it might very well be that we'd be talking about Nvidia's GPU bet as a strategy initiative they just would not give up on. One of the things that happens over time is this corporate hubris can get rewritten into "we had the right idea but were just early." The problem with this is it separates the broad concept at 30,000 feet from the actual technology and implementation. I've watched this happen with everything from Clippy to TabletPC to Windows Phone. There's a huge difference between a concept and an implementation that makes the claims of being right. I love Clippy but there was no path where it went from what we did in 1995 to today's AI agents, any more than the clipboard Captain Kirk used was a product precursor to an iPad. And of course as always with product development, no matter what happens...someone always said it would. Which makes me sharing all the times I thought WInFS would fail all the less satisfying for me. Here are the places in Hardcore Software where WInFS was part of key decision making and controversy. 024. Discovering “Cornell is WIRED!” [1994] hardcoresoftware.learningbys… 053. Strategy Tax: Outlook Storage, First Attempt hardcoresoftware.learningbys… 065. SharePoint: Office Builds Our Own Server hardcoresoftware.learningbys… 069. Mega-Scale, Mega-Complexity hardcoresoftware.learningbys… 074. Outlook Pride, Finally hardcoresoftware.learningbys… 085. The Memo (Part 1) hardcoresoftware.learningbys… 091. Cleaning Up Longhorn and Vista [2006] hardcoresoftware.learningbys…