July 10, 2016

I first learned about puzzle interviews in my freshman year discrete math class. When Microsoft interviewed potential software developers, our class was told, interviewers would ask more abstract problem-solving questions such as “How many golf balls would fit in a 747?” or “Why are manhole covers round?”

“Why do you think Microsoft asks these kinds of questions?” asked Steven Rudich, my professor. “Why don’t they ask if you can write good software?”

“Because Microsoft doesn’t make good software,” I replied to my friends sitting nearby. My joke was a little too loud and a little too good; the class laughed at my wiseass response.

I grew up during a chaotic time for home computing. As a child in the ’80s I read BASIC programming books and magazines that covered as many as 10 different personal computer types because editors didn’t know which of them would win the market share war. (In the end, none of them did.) Thanks to some dubious business deals, Microsoft emerged as a dominant operating system provider with MS-DOS and Windows. In the ’90s I latched onto OS/2, the stable but unpopular operating system made by IBM. I saw IBM as the rebellious underdog that could defy the odds and defeat Microsoft’s evil empire. At the time I had no idea that IBM had earned a reputation as a competition-crushing juggernaut that nobody ever got fired for choosing.

All through college, I only ever noticed Microsoft as a source of high-quality branded trinkets and lots of free food at recruiting events. I still didn’t think much of Microsoft in 2006 when I moved to Seattle to work at Amazon. Amazon was and still is a Linux shop; an engineer can get their work done without touching Windows. Through friends and coworkers, though, I met a lot of people who had worked for the Redmond software giant. The local papers gave Microsoft heavy attention: when Bill Gates announced he would step down as chief software architect, for example, the Seattle Times printed the news as a banner headline on page 1. I started seeing Zune billboards a few months after moving here. When I saw an employee at my local gym using one of the ill-fated music players, I asked her how she liked it and she gave me an ebullient sales pitch. I definitely felt like I was in a different place.

Microsoft’s reputation worsened during the years when Steve Ballmer was running the show without Gates. I personally lamented the company’s lack of trust in its paying customers when in 2009 I had to beg Microsoft to activate the Windows 7 upgrade I bought. Under Satya Nadella the company has been courting users aggressively with free dev tools and Office apps at the short-term expense of software sales. Microsoft, which for so long had been the default choice, is now trying to get long-time Apple users to consider an alternative. There are now Microsoft fanboys — I’ve met and worked with a few — for whom Microsoft is now the underappreciated challenger that is chosen as an act of defiance. The lone Windows laptop owner in a room full of MacBooks is now like the woman who threw the sledgehammer in the Macintosh “1984” commercial.

As I spent time in Seattle I’ve met many current and former Microsoft employees who lament that the company’s internally-competitive culture and bewildering marketing had stymied ideas that could have changed industries in ways that competitors later did. Microsoft introduced Tablet PCs for the masses and sold them to the few. Windows Media Center had a flexible, powerful, and useful Digital Video Recorder (DVR) that ran rings around the DVRs offered by cable companies; Media Center is now dead. Xbox, which now sells more home game consoles than Nintendo does, caused major infighting prior to its launch in 2001. At a party in 2012 I found myself defending Windows Phone to a bitter drunk ex-Microsoftie who had worked on it and who bitterly sulked that only 4 million Windows Phone devices had been sold.

Personally I’ve changed from a dogmatic Microsoft hater to an occasional Microsoft sympathizer. I’m typing this on my first-generation Surface Pro, a remarkably capable 10-inch laptop with a comfortable keyboard. Earlier this month I folded my old Evernote notes into OneNote, which is excellent and free for everyone. At both Amazon and Tableau I’ve used Microsoft Office Web Apps, which are basically Google Docs with more features and native clients for Windows, Mac, iOS, and Android. I owned an Xbox 360 for about 8 years and, although I now use a PlayStation 4 for gaming, I still appreciate the thoughtful gamer-friendly touches that Microsoft brought to the industry. For example, every Xbox game has a free demo, but on my PS4 I have to buy a game based on YouTube demo videos.

Now that I work for a company that is both a Microsoft partner and a Microsoft competitor, whose staff includes scores of ex-Microsoft developers, I’m learning more and more about the Microsoft universe. I write some of my code in Visual Studio, the only integrated development environment I’ve enjoyed using since Borland Turbo C++. I work from home using Remote Desktop, the Microsoft protocol that still works better than VNC or remote X servers do. I’ve become a “use the right tool for the job” person, and sometimes, that tool comes from Redmond.

This is part 6 of 10 Years, 10 Things to Love, a yearlong series commemorating my 10th anniversary of moving to Seattle.