Steve Ballmer and the Albatross Known as Windows

How Microsoft's phenomenal success led the company astray.

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Steve Ballmer in 1994, surrounded by the software that made Microsoft into Microsoft

For years now, Microsoft watchers have wondered about the timing and other specifics of Steve Ballmer’s departure. Now we know them — or a lot more than we did yesterday, anyway. After 33 years at the company, the executive who started at Microsoft in 1980 and has been its CEO since 2000 has announced that he’ll retire within the next 12 months, once a successor has been named.

For folks interested primarily in the stock market, Ballmer’s time as Microsoft’s head honcho is defined by the fact that its shares have largely flat-lined during his tenure. Here, courtesy of Wolfram Alpha, is a chart comparing how MSFT has compared to AAPL during that time period:

Microsoft and Apple stock prices

Wolfram Alpha

If you — like me — don’t care much about Microsoft’s stock price, Ballmer’s legacy is far more complicated. It can’t be summed up in a chart or a tweet or even in one blog post.

I am not among the man’s harshest critics, in part because I believe that all tech-company hegemonies are destined to decline, sooner or later. The dustbin of tech-company history is littered with outfits which were once market-defining behemoths: Lotus, WordPerfect, Netscape, Palm and oh, so many more. Microsoft in 2013 is not a company on the verge of joining them: It’s still making vast amounts of money and managing to be highly competitive in everything from mundane business software to blockbuster videogames.

Bill Gates and Steve Ballmer

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Bill Gates and Steve Ballmer pose together upon Ballmer’s appointment as Microsoft CEO in January 2000

Bottom line: I’m pretty sure that there are alternate universes in which the company was run by someone else in recent years — maybe even Bill Gates himself — and fared considerably worse than it has under Ballmer.

Still, I can’t imagine that there’s anyone out there who believes that it’s a given that Microsoft will be anywhere near as important to the future of personal computing as it has been to its the first four decades. Including Steve Ballmer: Last month, he instigated a massive reorg, with the aim of turning Microsoft into a “devices and services” company. Those moves acknowledge that the Microsoft of the future, assuming it’s successful, won’t be the Microsoft we’ve known.

Like the reorg, many of the most notable Microsoft moments of the past few years involve sudden, epoch-shifting change. Ballmer’s company has done things you wouldn’t have expected Microsoft to do, from giving Windows 8 an entirely new primary interface to making its own PC hardware. It’s been a lot for the company’s customers to process all at once, particularly since so many of them value comfortable familiarity over great leaps forward. (Exhibit A: Windows XP, the 12-year-old operating system Microsoft can’t kill.)

If Microsoft is behaving like it’s trying to make up for lost time, it’s because…well, it’s because it needs to make up for lost time. And it’s lagging behind Apple and Google in the race to define the future of personal computing mostly for one simple reason: For too many years, Windows was too damn successful. At some point along the way, Microsoft’s golden goose became an albatross.

The Windows era — which began with Windows 3.0 in 1990 and continues on, at least if you’re talking about laptops and desktops — made billions for Microsoft and its investors. But it also gave the company a number of bad habits it’s still trying to overcome.

Such as:

  • Windows’ success led to hubris. From its very earliest days, Microsoft was never a company afflicted by a crippling lack of self-confidence. In the years when it was crushing the competition in categories such as PC operating systems and productivity software, being unimaginably headstrong helped. But after that competition was crushed, Microsoft lost its ability to take the most serious threats to its dominance of personal computing seriously. (I’m still not sure whether Ballmer’s famous blustery dismissal of the iPhone was sincere or not — but either way, it was unfortunate.) The company also treated paying customers shabbily in some instances — like with the dismal copy-protection scheme it insultingly named Windows Genuine Advantage — in a way that couldn’t have been less humble or less lovable.
  • It gave Microsoft tunnel vision. Microsoft has a remarkable track record for identifying important trends early on and diving right in — from pocket-sized computers to tablets to smartwatches. But it nearly always saw them as offshoots of its Windows empire, an outlook which led to misbegotten product-design decisions, such as giving Windows Mobile a microscopic Start button. Only after Apple released the iPhone — a new device that didn’t look or work like a tiny Mac — did Microsoft come around to the notion that new stuff shouldn’t necessarily be very much like old stuff, a philosophy that led to the Metro interface used by Windows 8 and Windows Phone.
  • It encouraged sloth. Microsoft’s nadir came back in the middle of last decade, when Bill Gates was still involved on a day-to-day basis as Chief Software Architect. That’s when the company released Windows Vista, a product which fixed very few of the many things about Windows that needed fixing. It’s also when it let Internet Explorer 6 calcify into an unusable, archaic wreck. A Microsoft which was running scared would have released much better products on a far faster schedule.
  • It provided Microsoft with too much money to play with. Microsoft has long been a famously patient company, willing to plug away at markets for years before making much headway or turning a profit. That’s sometimes paid off spectacularly, as in the case of Microsoft Office. But by being able to afford to try almost anything, Microsoft hasn’t had to face the character-building challenge of picking its battles. For instance, as much as I’m glad that Bing exists and provides Google with its only real search-engine competition, it’s hard to figure out how Microsoft has benefited from being in the search business. Mostly, it’s been a money pit and a distraction.
Steve Ballmer at BUILD

Justin Sullivan / Getty Images News

Ballmer delivering the keynote at Microsoft’s BUILD conference in San Francisco on June 29, 2013

Ballmer, of course, has been partially or entirely responsible for every strategic decision Microsoft has made in this century. So I’m not blaming Microsoft’s woes on Windows’ inordinate success as a way of getting him off the hook. But I do think that most of the other people who might have been running the joint would have made many of the same mistakes — and that some of them would not have been as willing to make as many big, scary bets on change as he has over the last few years.

And if you want to helpfully give Microsoft advice on what it should have done but didn’t — hey, it’s easy when you can do it retroactively — the road not taken seems obvious to me. The company would have been better off if it had spent less time defending and extending Windows’ turf, and more time acting like a company that wanted to kill off Windows with the next bright, shiny, useful thing. It should have assaulted its own monopoly with the same belligerent gusto it once applied to attacking Lotus and WordPerfect and Netscape. Ballmer didn’t do that when it would have made the most difference, and it’s awfully late in the game for his successor to try.