Microsoft May Not Recover From Losing Our Trust

Windows 10 and the failure of trust

Our relationship with technology is built on trust.

Self-inflicted errors are causing Microsoft to lose our trust.

A series of bugs has emerged in updates to Windows 10. Chances are none of them have affected you directly. But the indirect effect is longer lasting and arguably more damaging: each one chips away at your belief that Microsoft should be trusted as your technology provider.

Microsoft is already greatly diminished in the eyes of consumers and small businesses. There have been several high-profile failures that tarnished Microsoft’s brand: the failure of Windows 8; the complete collapse of Windows Phone, leaving Microsoft on the sidelines of the growing market for mobile devices; and lower than expected sales for Xbox One, which lost much of the Xbox momentum and allowed Playstation to take the lead in sales and gamers’ perceptions of coolness.

Microsoft says it’s trying to improve computer reliability and ease of use, but we don’t believe the promises any more. That’s part of the reason that upgrades to Windows 10 happened at a far lower rate than even the most pessimistic of Microsoft internal projections. (I’m not a journalist and I don’t have any inside sources but this has been the consistent tone of comments by Microsoft insiders and journalists in the last few months.) An important reason that people held back is that we didn’t trust Microsoft to make the upgrade go smoothly.

Now we get bugs and crashes that affect large numbers of people: attaching a Kindle to a Windows 10 computer might cause a blue screen, an upgraded computer with an SSD might freeze, video doesn’t work with a popular type of webcam, and more. As Peter Bright says on Ars Technica: “None of this is excusable. I wrote last Friday that issues like the webcam problem would “inevitably recur” due to the problems of Microsoft’s current testing regime: lack of internal testing (the people who did this were laid off); Insiders not testing on real systems (because they’re advised not to use it on their primary PCs); and Insiders tending to give poor feedback (they’re not professional testers, and Microsoft’s very weak release notes give no indication of what things have been changed and hence need testing in the first place).”

There are four things that determine whether we trust a technology company.

•  We trust that our technology will continue to be basically the same as it was when it was purchased. If new features are introduced by updates, the new features will add value.

•  We trust that the technology will work as promised, whether it’s a device, an operating system, a program, or an online service – that it is represented fairly and does what is promised with a reasonable design that makes it comprehensible.

•  We trust that things that work today will also work tomorrow.

•  We trust that our important choices (especially for business) will be around for a reasonably long time – that the company making them won’t go bankrupt and won’t abandon them.

No technology company gets a perfect score. Updates are as likely to change things around onscreen in iOS and Android as in Windows. Google is famous for launching online services, then abandoning them when it loses interest a few years later.

But Microsoft is lagging behind the others, and seems to be losing ground. The new features in Windows 10 are not catching fire, in part because declining trust creates a vicious circle: our lack of trust makes us suspicious of and resistant to changes; instead of believing they add value, we resent them. We don’t start using Cortana, for example, because we don’t trust Microsoft to make it compelling. The new Start menu in Windows 10 hits many people as a step backward, not forward; it might theoretically have advantages but all we see is the intrusion.

And the trust that things that work today will also work tomorrow – I deal every day with Microsoft’s violations of that trust. I said recently that computers are just too hard to use, and it’s not your fault. Let’s not beat around the bush: all too frequently, it’s Microsoft’s fault.

Last year I noted two things that Microsoft needed to do for Windows 10 to earn our trust.

(1) Make the upgrade process smooth and uneventful.

(2) Create the first impression that Windows 10 is both familiar and slightly improved over your previous version of Windows.

Neither of those went very well. There were enough upgrade problems that I dissuaded Windows 7 business users from upgrading their computers to avoid the risk of a failed upgrade. What should have been good first impressions were compromised by poor Microsoft choices – arbitrary changes in default programs, pushing an unfinished web browser, and more.

Now there’s a third element that will be required for Windows 10 to keep our trust.

(3) Since Microsoft has complete control over updates, the updates have to keep us safe and add value without breaking anything.

Maybe that’s impossible. Windows may have become such a diverse, unruly mess on the 1.5 billion computers running it that Microsoft simply cannot keep it running everywhere.

Another possibility: maybe Microsoft just isn’t good enough. Its days are past. Windows will spiral downhill, increasingly unreliable and resented. Frankly, this seems to be the path we’re on.

Or perhaps Microsoft can declare that reliability is going to be the single-minded company focus until it gets Windows back under control, as it did back in 2002 when it addressed security problems in Windows XP with a widely publicized Trustworthy Computing Initiative. Paul Thurrott is leading the call for something like that now. It’s not too late – but it’s close.

Microsoft hoped that Windows 10 would be an unparalleled success that would invigorate the market for Windows PCs and inspire developers to return to the platform. By some measures Windows 10 is successful. But it absolutely did not live up to Microsoft’s hopes and dreams. Today Microsoft looks like a slumping giant, not quite a punchline but certainly several steps behind the technology companies that dominate our thoughts and our devices – Google, Apple, Amazon, Facebook, and others that we trust more readily.

It’s worth noting that much of this criticism is irrelevant to Microsoft’s enterprise and cloud computing divisions, which represent the true future of the company. Microsoft does not want to give up the consumer and small business space, of course; quite the contrary. But the future of Microsoft is with enterprise and cloud computing and if Windows continues its steady decline, well, Microsoft will be just fine.

Nonetheless, the long, slow decline of Windows makes me sad. I’ve spent 35 years believing in Microsoft, promoting its products, selling its services, following its vision. Today I wince when the phone rings. Things have deteriorated to the point that I’m fixing the kind of problems that I thought we had left behind – printers that don’t work, monitors that won’t come to life, things we should have outgrown. While I was writing this, I had to figure out why OneDrive wasn’t syncing files on my desktop, and why a client’s copy of Outlook had stopped sending messages – messages that were then irretrievably lost from the Outbox when Outlook was restarted. I spent half an hour today troubleshooting my Powershell connection to Office 365, only to discover that I was a victim of the update bug mentioned in my last article that I thought didn’t apply to me.

There was no good answer to any of those problems except that Microsoft’s programs don’t always work. And that’s the point.

It ought to tell you something that the devices I’m most looking forward to are the touchscreen Chromebooks that might give the laptop industry a shot in the arm.

Come on, Microsoft! Step up.