What Microsoft needs to do to convince a generation to adopt Windows 9

I guess I’ll come right out and say it: I’m a millennial, and Windows(s msft) confuses me.

Not from a technology standpoint — after a few minutes on a modern computer running Windows 8, I can navigate around and work with it happily — but from a strategic standpoint. It’s clear that Microsoft wants to embrace the future with Windows 8 and 8.1, I’m just not exactly sure what that future is supposed to look like. And that’s not a particularly encouraging thing to say, especially because — with all apologies to those who have come before us, but you had your day too — young people are in the driver’s seat when influencing buying habits in the 21st century.

2014 is a new year, and it could be a big one for Microsoft: According to a tip-off from noted Microsoft watcher Paul Thurrott, the company will release a new OS with the codename “Threshold” sometime in 2015, which he suspects will arrive as Windows 9. It’s another chance to prove that Windows can attract a young, digital-savvy, tech-loving clientele.

Surface 6

Or, it’s another year for the company — which is still trying to find someone to replace lame-duck CEO Steve Ballmer — to scramble while trying to marry the Windows of yore, which still maintains a presence on many PCs, with the cutting-edge Windows that Microsoft needs to compete with Apple(s aapl) in the hearts and minds of those too young to remember the days when people actually got excited about Microsoft OS releases.

Cutting edge? Not so much…

If I’m going to be completely honest, Windows 8, billed as a “No Compromise Experience,” was certainly a compromise, and one that didn’t satisfy . Although it tried to take a step forward in merging the traditional desktop experience with Surface RT, it proved too confusing for desktop users and not deft enough for mobile users. This disconnect led to fixes (or concessions) in Windows 8.1, such as bringing back the “Start” button and changing some of the gestures.

Microsoft’s good intentions were clear, but morphing Windows into a lean, mean, unified platform while keeping the enterprise IT customers it worships happy is proving to be a difficult task. It needs to figure this problem out now more than ever, especially as Apple’s iOS and Mac devices are expected to reach usage parity with Windows by next year, according to Asymco.

Speaking as a person in the (often admittedly annoying) Millennial age bracket that all tech companies (and heck, all companies in general) want in their corner, I’ve compiled a list of expectations for the upcoming Windows 9. Since very little is known about the actual product, much of this is wishful thinking. But there are some common-sense items that I hope Microsoft has kept in mind in its latest OS development period.

Keep Windows simple

Keeping Windows simple has been easier said than done. Windows 9 doesn’t just have to juggle the carryover from Windows 8.1 — it has to be seamless with the Windows Phone interface, provide a similar experience to Windows RT (if not eclipsing it entirely), and look like a proper cousin to the Xbox One interface. Windows 9 has to work for desktops, tablets, conversions and all-in-ones, handling both touch screens and the keyboard/mouse combo to boot.

But most importantly, it still has to evoke nearly every OS Microsoft has ever made, so not to completely disorient late-comers. Microsoft has backed itself into a corner by trying to satisfy different factions of its audience while still remaining very, well, Windows-like.

windows 8.1

The result is a complicated system that never quite commits to one thing: The traditional desktop mixes in with the slightly edgier Start Screen and Live Tiles from Windows Phone 7’s acclaimed Metro design, conflating signals about which screen is the true “home.” Even worse, Windows 8.1’s reintroduction of the Start button may have pleased some users, but it works nothing like the way it used to on previous OS iterations. Given how fragmented the Windows environment currently is, Windows 8.1 is unintuitive for a casual computer user of any generation — everything that is familiar now works differently.

Windows 9 needs to address the needless complexity head on, and can start by fully committing to one idea: Make the Start Screen more capable of handling non-Microsoft programs and nix the traditional desktop, or relegate the Start Screen to a widget add-on that amplifies (but not competes with) the desktop. A single decision like that could not only separate the new OS from the old, but also make everything much clearer.

Don’t make a full experience inaccessible

Speaking of all-in-one computers, I will not lie: my personal frustration with Windows stems from the fact that its best experience is saved for a small number of devices (pricier “Full Windows 8” tablets or giant all-in-ones). In fact, I’ve never actually felt like I’ve gotten a “true” Windows 8 experience, because I’ve only spent time with it on a traditional laptop or more wallet-friendly RT tablets like the lower-end Surface. The truth — both for me and many members of my generation — is that when it comes down to spending $900 for a Surface Pro that runs full Windows 8.1 or spending $499 on an iPad (or even $999 on a comparable lightweight netbook) why bother?

surface pro 2

For example, Windows 8 focuses heavily on touch capabilities, but those capabilities do not translate to traditional computers. In an effort to make navigating with a traditional mouse “accessible” and the touch screen “cutting edge,” Microsoft missed out on an opportunity to create universal, simple gestures in Windows 8 to use on both a tablet and a laptop — a glaring oversight considering that the PC laptop market is still moving a lot of units and the Mac has had universal gestures for a long time.

Windows 8.1 alleviated this problem to some extent with new touchpad gestures, but they were minimal at best and complicated. It’s most prominent when you consider Microsoft’s dream of a user who owns multiple Windows products: A single user has a completely different set of inputs on a Windows tablet versus a traditional Windows computer, even though it’s (nearly) technically the same OS. Why can’t the Start screen have a universal gesture, like a three-finger swipe upwards?

My colleague Kevin Tofel believes that Windows 9 may do its part in killing Windows RT, and that would be the right step forward: if Microsoft is determined to put mobile-like features on something intended to behave as a desktop OS first, then it should show up as-is on as many tablets as possible. But the “full” Windows experience is too bloated to run on a lower-cost, modern piece of hardware. How can you unify an experience with an OS so large that it disqualifies most mobile users?

In the meantime, gestures and behaviors need to be as unified as possible, across multiple platforms, to give consistent usability across all devices. In short, if Windows 9 is expected to serve the needs of multiple platforms, and take cues from multiple device structures, then it needs to present a simple, bold statement that is easy to understand, reliable to use, and relatively inexpensive.

Commit to apps

But if Microsoft really wants to create a more minimal experience on Windows, now is the time to follow through: Windows Store Apps should be expanded on with Windows 9. Introduced with Windows 8, these apps are perhaps the most dynamic part of what the system offers: they offer smart experiences that actually do a good job of bringing that “mobile” feel — and they transition smoothly onto the desktop, snapped alongside programs.

Right now, there is a distinct difference between Windows apps and programs — apps have the benefit of flexibility and minimalism, while programs are desktop-only software. Microsoft should not only consider expanding the number of apps available for the PC, it should also eliminate the idea of separate “programs.”

HTC Windows Phone 8X

First, the apps available in Windows 9 should behave more like modern apps — available from the Start Screen and easy to access at all times, not hidden away in a separate place unless pinned for priority. In turn, independent software developers should be encouraged to do more mobile-like things, like more sophisticated push notifications or smarter always-on interactivity that mimics the way that Windows uses Skype. Right now, “apps” are separate from traditional software in a way that makes it too confusing. Even if more traditional software doesn’t have an “app,” per se, the Windows 9 experience should go out of its way to not separate the two.

The important thing here is that Windows is, by and large, fixable. In my lifetime (near as I can remember back to, well, Windows 95), Windows’ progression has always been a sort of “one step forward, two steps back” dance that often leaves my generation exasperated. Rather than stick with an awkward blend of familiarity and cutting edge, Windows 9 could benefit greatly from a modern, simpler experience.

I fully recognize that with with a generation of business computing developed around its older operating systems, Microsoft cannot please everybody. But the relevance of the PC relies on the company to pare down its iconic product to produce usable, functional software.

Microsoft needs to make a clear decision about which group of users — stodgy CIOs, aging baby boomers or the generation born after Chairman Bill Gates’ famous 1995 internet memo — it wants to court in 2014 and beyond.