Windows 8: Microsoft Isn’t Going to Make This Easy. Or Is It?

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Michael Mace is a former executive at Palm and Apple, and the CEO of a bootstrapped startup named Zekira. He also blogs at Mobile Opportunity, and his latest item, about Windows 8’s prospects, is the best thing I’ve read about Microsoft’s upcoming upgrade. It’s a great read, chock-full of well-expressed, perceptive comments.

Mace doesn’t declare that Windows 8 is going to be a blockbuster or a flop. But he does say that the more he ponders Microsoft’s plans, the more nervous he is about its chances:

My conclusion is that Windows 8 in its current form is very different; attractive in some ways, and disturbing in others.  It combines an interesting new interface with baffling changes to Windows compatibility, and amateur mistakes in customer messaging.  Add up all the changes, and I am very worried that Microsoft may be about to shoot itself in the foot spectacularly.  Even the plain colorful graphics in Windows 8 that looked so cool when I first saw them are starting to look ominous to me, like the hotel decor in The Shining.

He also outlines three Windows 8 scenarios:

  1. Windows users adopt Windows 8 enthusiastically. (“Wall Street analysts short Apple’s stock, declaring the era of iEverything over.”)
  2. Windows users cling to Windows 7 tenaciously. (“Windows 8 becomes the new Vista.”)
  3. Windows collapses. (“Microsoft survives as a fragment selling Office and some server software.”)

There’s another possibility which he doesn’t quite address. It’s a modified version of scenario #2 , and it involves most Windows users deciding that Windows 8 isn’t for them. But in this scenario, Microsoft isn’t fazed. It releases Windows 9, which is a bit better than Windows 8. And then it releases Windows 10, which is downright good — and a success.

If that happens, it’ll be reminiscent of the earliest days of Windows. 1985’s version 1.0 wasn’t popular. 1987’s version 2.0 wasn’t popular. And then, in 1990, version 3.0 came along — and boom.

Before that boom happened, many people were deeply skeptical about Windows. As Charles Petzold wrote in the June 9, 1987 issue of PC Magazine, back when the current edition of Windows was version 1.03:

Some people refer to the program as “Broken Windows” or “Microsoft Widows.” Others refuse on general principle to use a PC program that uses a mouse or otherwise reminds them of the Apple Macintosh.

Nor does Windows have a good reputation among users who have purchased and installed the program. You’ve heard the complaints: Windows is slow. Windows takes up too much hard disk space. Windows is a memory hog. Windows doesn’t allow many existing RAM-resident programs to work under it. Windows can’t adequately run existing applications.

For a $99 package, Windows comes with an impressive array of applications (a word processor, a monochrome painting program, a communications program, a notepad, calculator, calendar, clock and print spooler), but none of them come anywhere close to the functionality of popular programs written for the normal MS-DOS environment. Although Windows can run existing MS-DOS programs, it doesn’t do so very well.

Thus for many users, Windows ends up as “shelfware” — the program that almost everybody owns but nobody uses.

(Petzold goes on to explain why Windows is the future of PC software despite its seemingly shaky state. Several years passed before it was absolutely clear that he was right.)

I keep saying that the Windows-7-to-Windows-8 transition is a whole lot closer to the move from DOS to Windows than it is to any past upgrade from one version of Windows to another version of Windows. In terms of sheer radical change, it is. But as Mace’s post makes clear, there are also some striking differences in Microsoft’s approach this time around.

Here’s the big one: Microsoft isn’t going to let Windows users dip their toes into the Windows 8 pool. Instead, it wants them to shut their eyes, hold their breath and jump right in.

When Microsoft shipped Windows 1.0 back in 1985, it didn’t force it on all those millions of DOS users. DOS just kept on being DOS, so you could get Windows, install it, and then acclimate yourself at your own pace. That was hugely important, because Windows 1.0 and Windows 2.0 were rough drafts at best.

Even when Windows 3.0 came along, it changed nothing about DOS, and didn’t load automatically. But over the next few years, most DOS people became Windows people — not because Microsoft gave them no other viable option, but because the advantages of Windows were clear.

The Windows 7/Windows 8 shift won’t be like that. With Windows 8, the all-new Metro interface is the default, and you can’t get into the familiar old Windows interface without a detour through Metro. And the familiar old Windows interface is no longer quite as familiar: Microsoft is doing away with its signature element, the Start button.

Some folks will be willing to race ahead to where Microsoft is trying to lead them. Maybe most people, over time. But if you’re doubtful about Windows 8 and don’t want to adopt it until it’s proven itself — which isn’t an unreasonable attitude with any new operating system — there’s only one way to guarantee that it won’t complicate your life. That’s to refuse to install it, clinging instead to whatever version of Windows you’re currently running.

We already knew that Microsoft can’t force its customers to make upgrades which they don’t believe are in their own best interest. (Exhibit A: The still-wildly-popular Microsoft product known as Windows XP.) By giving Windows 8 only a secondary, modified version of the old Windows experience, it’s betting (almost) everything on the appeal of Metro. For people who are reasonably comfy with Windows the way it is, it’s making the choice harder, not easier.

It’s rare to see Microsoft be so decisive. If you were rating its strategy in terms of sheer boldness, you’d have to give it a 9 or a 10. If nothing else, I’m glad it’s axing the Aero look and feel.

Pragmatically, though, if the goal is to get lots of people to give Windows 8 a try, it seems clear to me that it would be better off letting them ease their way into Metroland. It could allow them to boot directly into the old desktop and then flip into Metro, rather than the other way around. It could retain the Start button. If it made these two moves, much of Windows 8’s fear factor would fade away.

Mace addresses the question of keeping the Start button, and says that he can’t see Microsoft backtracking on its decision to terminate it. I’m not so sure.

As he notes, the people who buy Windows are in charge here — not Microsoft, not PC makers, not tech journalists. If Windows users find Windows 8 foreboding rather than inviting, it’s not hard to envision Microsoft feeling like it has no option but to release a Windows 8.1 that tries harder to make them feel welcome. And nothing would make them feel more welcome than an experience that isn’t quite so aggressively new.

If Microsoft does end up undoing a bit of Windows 8’s sweeping change — well, you read it here first. If it doesn’t? Let me be the first to congratulate the company for sticking to its guns.