This is the number one problem facing Microsoft today

The Microsoft logo on the outside of a building.
Credit: REUTERS/Bogdan Cristel

Microsoft is a gargantuan company.

They have 114,000 employees. They make a popular gaming console, the only viable operating system used by more people than anyone by far, and have their toes dipped in every conceivable market segment, from consumer chatbots to social media for business. There’s no question the company competes easily with Apple and Google for the top crown of all technology, assuming you can forgive them for Windows 8.

Yet, they have a major problem in the age of immediate access from anywhere. Bowing out of the smartphone market is not as troubling as a much more serious issue related to usability: Microsoft has a crisis of confusion.

Here’s a good example. Let’s say you want to play the game Gears of War 4 on your PC. Anyone who pre-ordered the game for Xbox One can play starting today, and Play Anywhere means you can download the game on Windows for free. But where do you find it? You can search using the Xbox app, but that doesn’t work. You can try going to or and checking there, but that doesn’t work, either. In fact, the only way to find the game is through a rat’s nest. You have to go to the Windows store app, login with your Xbox account (not your Windows account), and then click a tiny avatar icon. (By the way, this icon is for Windows, not for Xbox.) There’s an option called My Library in that menu, but it’s not a tab on the main screen. Then, you have to select all apps, because only a few are listed. Finally, you find the game.

I decided to test this out with a  few colleagues who have used Windows forever. I asked them to find the My Library option in the Windows Store app. Three friends didn’t know anything about it. When they want to find an app, they looked under the Start menu. They didn’t even know they could click the icon in the Store.

What would make this much easier? For starters, having the download option shown in your online accounts would help (even if it explained how to go to the Windows Store), but it would be even better if there was an app called Play Anywhere that listed the supported games with a download option. (There is a Play Anywhere site, but it’s an online brochure.) Maybe Cortana could help here as well. “Cortana, where do I find my Gears of War 4 game for Xbox to play on Windows” does a web search for the game. Not helpful. None of the tech support info for Play Anywhere mentions how to find the game.

This maze of confusion is just as startling if you try to figure out how to use a new app like Microsoft MyAnalytics, which is designed for personal productivity data. Hashtag irony. It doesn’t help at all that the name used to be Delve Analytics. How do you get the app? Don’t ask me, I have no idea. It’s included for free in something called the Office 365 E5 plan and in the Office 365 enterprise suite. I’m pretty sure Office 365 is an estimate on the number of days you need to allocate to figuring this all out.

This is one reason I like the Microsoft Sway app. Do you know how to access it? You type S-W-A-Y with a .com into your browser. It’s fast, the app works, and it has some cool A.I. that can create an online brochure automatically when you type in a few keywords.

It makes me wonder if anyone at Microsoft ever thinks about making the ecosystem work better. In other words, more like the one for Apple and Google. If I own Gears of War 4, and if the price includes dual platform support on Windows and Xbox, I shouldn’t have to figure out which icons to click. For a massive, iconic company like Microsoft to stay massive and iconic in the coming age of immediate mobile access, they will have to figure out how to make this work smoother. On a desktop, you click around until you find the right option. On a mobile device while you’re waiting for an Uber to show up, you don’t have time. Things either work right away or you move on.

Microsoft, are you listening?

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