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What the company seemed to lack was a vision. COLOR FINESSE CRASHES WHEN GOING INTO FULL INTERFACE WINDOWSThen we had Windows Vista, another train wreck, followed by Windows 7, which was pretty decent again, followed by Windows 8, another train wreck. Windows Millennium Edition was a train wreck in conflict with Windows 2000, but Windows XT, which blended the two, seemed pretty decent. The 2000s were a transition period for Microsoft when almost every other OS was a disaster. It was the first and only time I’ve ever seen a market get so frustrated with the dominant vendor and lack of competition that it birthed a competing offering. ![]() For the first time, the industry revolted with its own product: Linux. In the 90s, Microsoft also went from being one of the most well-regarded companies in the industry to one of the least well-regarded due to this behavior. COLOR FINESSE CRASHES WHEN GOING INTO FULL INTERFACE PCCustomers wanted the flexibility and control the PC promised but hadn’t agreed to give up the mainframe’s reliability and security. The entire PC industry was like that, though, which seemed odd given the intense focus on reliability and uptime the preceding mainframe companies, led by IBM, had. It was a fun company, but it was killing its reputation with almost a decade of overly buggy products and failed launches. Like many young companies, Microsoft had a bit of an identity crisis, and its power structure was fluid, creating an increasing number of execution issues. By the end of the keynote, there were many Bob boxes tied to those balloons floating against the venue’s ceiling. COLOR FINESSE CRASHES WHEN GOING INTO FULL INTERFACE SOFTWAREI still remember a Microsoft event filled with software engineers who were not fans of Bob and were given free copies and a helium balloon. Yet, Bob failed when Microsoft tried to position it as the next UI for everyone. Microsoft made one of its biggest user mistakes with Microsoft Bob, which worked well with its initial target audience of older people who didn’t understand technology. Even Microsoft Office became surprisingly unreliable. It’s hard to believe we tolerated just how unreliable everything was in the 90s. Back then, Microsoft didn’t think that was its problem any more than security was. So getting those customers to replace their PCs in a timely manner eventually hit a hard wall. The industry was living on churn and rapid hardware replacement, and that process was so painful customers hated it. ![]() The entire industry seemed a little out of whack because customers wanted an appliance-like experience, something they had with terminals, and they weren’t even getting that from IBM. The company cared a great deal about the product but hadn’t grown to care that much about its customers, which was strangely far from unique at the time. ![]() I’m fascinated by how much Windows reflects Microsoft over the years.īack in the 1990s, when Windows 95 was born, Microsoft was a model of proprietary software and near-rabid competitiveness. Let’s talk about Windows 11 this week and we’ll close with my product of the week, the Microsoft Surface Laptop Studio, which is arguably the most Apple-focused product that Microsoft has ever released. I have been running the final version of Windows 11 since the launch last week, and while there is a bit of a learning curve, it is nothing like the weeks it used to take to get an existing PC on a new OS back when this all started. ![]() Microsoft has learned a great deal and changed its personality and focus since Windows 95 debuted, and Windows 11 showcases those changes. Pre-launch Windows 95 was one of the most powerful efforts I’ve ever seen it was a disaster post-launch. COLOR FINESSE CRASHES WHEN GOING INTO FULL INTERFACE DRIVERSIn 1995, Microsoft spent a mint on demand generation for the platform but didn’t spend enough on support and realized too late how vital drivers and hardware compatibility would be. Windows 11 launched last week, and since my career as an external analyst started at the same time Windows 95 did, I feel deeply connected to this platform. ![]()
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