Q1. If Microsoft is still the dominant desktop operating system by such a wide margin, doesn’t that mean they’re winning? Shouldn’t they care more about keeping existing Windows users happy than catering to snobbish Mac users?

When I started working for Macromedia (now Adobe), Macs were unconventional enough that I had to make sure a new MacBook was part of my employment agreement. Almost fifteen years later, it’s rare to see a Windows computer among my coworkers unless it’s being used for testing, or it was purchased out of curiosity with extra hardware budget. Although the ratios might differ, the same overall trends hold true for conferences I attend, partners I visit, and even friends and family members. While Apple has certainly made missteps with respect to “pro” users over the last several years, they have recently course-corrected, and are already well on their way to recapturing the interests of the professional market. (Just wait: Apple is going to sell the hell out of that sleek new iMac Pro, and it’s just a stopgap measure until they can rebuild their real professional machine.)

Mac users can complain all they want about the new iMac Pro, but come December, I believe these machines will sell.

In other words, I’m less concerned with statistical snapshots and more concerned with momentum. It’s also important to keep in mind that operating systems haven’t existed in isolation for at least a decade. Rather, they are components of broader ecosystems, and Apple’s ecosystem is arguably the richest. There are well over one billion active iOS devices in customers’ hands (or on their wrists) which is enough for one in seven people on the planet, the overwhelming majority of which run the latest version of iOS. While OS updates aren’t exactly Android’s strong suit, Google recently announced over two billion monthly active devices scattered across the globe, and in terms of internet usage, may now be the dominant operating system. In contrast, while still growing steadily, Windows 10 has an install base of around 500 million — less than half that of iOS and about a quarter that of Android.

Q2. How dare you presume to know what Mac users like or don’t like about Windows!

That wasn’t actually a question, but I’ll answer it anyway. I switch off between macOS and Windows 10 (and iOS and Android, for that matter) more than anyone else I know. My workstation is configured such that I can move from one to the other in a matter of seconds, and I switch back and forth often in order to take advantage of each environment’s strengths. In short, I know both operating systems intimately.

Additionally, in my role as a Senior Experience Development Manager, I interact daily with dozens of professionals (engineers, designers, product managers, marketing managers, program managers, researchers, etc.), and I pay close attention to their technology preferences. That doesn’t mean the list below qualifies as exhaustive, objective, rock-solid user research, but it does mean that I have a high level of confidence in its accuracy.

Q3. Are you a Windows hater? A Mac hater? You must hate something.

I’m the opposite of any kind of hater. I love all kinds of devices, environments, and platforms. I like Apple’s vertically integrated product line, and I like that I can build and upgrade my own PC exactly to my personal specifications. I’m writing this article for no other reason than to express patterns and observations around barriers that I strongly believe are preventing Mac users from switching to Windows — things that are unlikely to even appear inside the Feedback Hub, much less get voted up.

Microsoft has piqued professional Mac users’ curiosity with the Surface line of products, highly responsive touch and pen capabilities, and an architecture that has traditionally been much more friendly to GPUs than Apple’s (though Apple is now desperately trying to change that perception). But even when these potential new Windows customers approach Windows 10 with a completely open mind, it’s usually only a matter of hours or days before they’re rushing back to the comfort and safety of their MacBooks. I believe Microsoft deserves to know why.

Enough preamble. Let’s dig in.