In my opinion, there aren’t enough diverse users telling Microsoft what they really need to hear about Windows 10. I’ll get into plenty of painstaking detail below, but the gist of it is this: despite some fantastic new hardware, extremely compelling touch and pen capabilities, excellent gaming support, a fairly nimble pivot away from the Windows 8 debacle, and a marked improvement in branding, Windows 10 still does not appeal to Mac users en masse.

If you already buy the premise that Mac users aren’t all that impressed by Windows 10 yet, and that Microsoft probably doesn’t really know why, feel free to skip the next section and scroll right down to the good stuff (lots of pretty pictures await!). But if you’re interested in more context around why I wrote this article, and why I think it’s critical that Microsoft learn to see Windows 10 through the eyes of Mac users, the following Q&A is for you.

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.)

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.

~ 1 ~ There’s no simple, fluid way to input common accented characters in Windows 10.

Mac power users know that they can hold down certain keys in order to have the option to input an accented version of that character. If you want to enter an “é” character, for instance, just hold down the “e” key and wait for the pop-up. I use this feature surprisingly often, and I believe it makes the OS feel not just modern, but somehow sophisticated and inclusive.

Here’s a mockup I did of easy accented character input in Outlook:

The best way to do this on Windows is to use the virtual touch keyboard — a workflow which I feel was inspired by the Windows 8, tablet-first mentality. For keyboard-optimized typing experiences (desktops, non-convertibles, and convertible laptops with keyboards attached), the approach Apple took with macOS feels much more fluid. (That said, the Windows 10 touch keyboard is great for entering emoji.)

~ 2 ~ The Windows 10 app switching paradigm feels inferior to macOS.

Note that I said it feels inferior — not that it actually is inferior. I don’t think either the macOS or the Windows app switching paradigm is inherently better than the other, but I do know that most Mac users prefer the way it works on macOS. (“Command + tab” switches between applications and “command + `” switches between the current applications’ windows; Windows, on the other hand, doesn’t group windows by application, so “alt + tab” switches between all open application windows.)

Rather than dogmatically adhering to one position or the other, I think Windows should be the type of OS that lets users choose how they want to work. Here’s a mockup I made of the “Multitasking” configuration I’d like to see:

Unfortunately, Microsoft is already using tabs in the File Explorer and across the Office suite as a way of organizing and grouping features, so from a design perspective, there’s no easy and elegant way to graft new tabs on top of existing ones. My guess is that we’ll have to wait for UWP (Universal Windows Platform) versions of these apps before we have the same level of convenience that Mac users have been enjoying for many years now.

~ 4 ~ The File Explorer context menu is basically a mess.

If you have access to both a fully configured Mac and a fully configured Windows 10 machine, try right-clicking on any file in the Finder and File Explorer respectively and note the difference (by “fully configured,” I mean two computers that are used as “daily drivers” meaning they have things like Dropbox and other third-party utilities installed). I’m willing to admit that this is as much personal preference as objective fact, but I find the File Explorer context menu to be far more convoluted. Here’s a study I did suggesting how much better organized the Windows 10 File Explorer context menu could be:

Admittedly, there are more subtleties around this issue than I have time to explore here. For example, if Photoshop is the default application for JPGs, right-clicking on them and choosing either “open” or “edit” will open them in Photoshop. And in file properties, you can change the “Opens with” property for any file at which point “open” and “edit” will do the right thing for all files of that same file type. But the original point still stands: if you want to have the option of opening multiple files — even files of the same MIME type — in different applications depending on your specific task, you’re using the wrong operating system.

If you’re accustomed to Windows, you’ve probably internalized workarounds to the point where you may never even noticed this issue. But if you’re a designer accustomed to using macOS, you will almost certainly run into this, and you will wonder why so many rough edges still remain in an operating system that time really should have done a better job at smoothed out by now.

~ 7 ~ Windows needs a universal “Paste Plain Text” or “Paste and Match Style” clipboard option.

I maintain that both Apple and Microsoft got copy and paste fundamentally wrong in the context of text. I haven’t done an exhaustive user study, but I’m almost certain that the majority of users in the majority of cases don’t want to copy text styles along with the text itself. Yet, inexplicably, that’s the way it works by default.

I know Microsoft isn’t responsible for stagnant third-party ecosystems, but as I’m fond of saying while wearing my Product Manager hat, while it may not be their fault, it is their problem.

Update: An altruistic reader pointed out to me that there is now a version of Divvy for Windows. My day has officially been made. I have it installed, configured identically to my Mac, and it’s working great. He also mentioned that the built-in Windows 10 Snap Assist works fine for him which I agree is sufficient for most users (and better than built-in window management support on macOS).

~ 9 ~ Windows 10 doesn’t have a built-in pixel ruler.

Both macOS and Windows 10 provide various ways of capturing what’s on your screen and saving it as an image. Between “PrtScr,” “Alt + PrtScr,” and the Windows Snipping Tool, I feel like Windows 10 does screen captures as well, if not slightly better, than macOS. But designers (and even a few devs) have a little trick they use on macOS that doesn’t work on Windows.

On Macs, “Shift + command + 4” turns the mouse pointer into crosshairs that you can use to drag out an arbitrary rectangle, and subsequently screenshot whatever is behind it (it’s the same thing as a “rectangular snip” on Windows). But what makes the macOS implementation better than the Windows implementation is that the crosshairs initially show the screen’s coordinates, and then once you start dragging, they switch to the width and height of the rectangle being drawn. Pressing “esc” before releasing the mouse aborts the screen capture which means designers and developers can use this built-in utility to quickly and easily measure the dimensions of anything on the screen.

Since there are no dimensions beside the crosshairs on Windows, the alternative is to install a third-party “pixel ruler” application — almost all of which look like they were written over a decade ago and are probably bursting with Russian malware by now. (The one I use is so uninspiring that I’m not even going to dignify it by linking to it here.)

Here’s a mockup I did of what I’d like to see on Windows:

It’s also worth pointing out that QuickTime on Mac has gotten to the point where it does very good video screen captures, as well — something Windows users have to install, and possibly buy, yet another third-party app to do. (I use Icecream Screen Recorder.)

Update: It has been pointed out to me that you can use the built-in Windows 10 Game Bar to capture video of your screen. I tested it (it worked!), but I haven’t used it enough to know how it compares to QuickTime’s screen capture capabilities.

~ 10 ~ Windows 10 doesn’t have a built-in dictionary (or thesaurus).

Dictionaries and thesauruses are to writers as pixel rules are to designers. Just as designers might not really think about having an easily accessible pixel ruler constantly at their fingertips until such time as they don’t, those who do a lot of writing on Macs will not realize how much they rely on the built-in dictionary — and specifically, the convenient global keyboard shortcut to access it in-line — until they’re typing away on Windows, and suddenly trying to remember the difference between “imminent,” “immanent,” and “eminent.” Of course, you can break your train of thought and use a horrendously ad-riddled online dictionary, or you can install a third-party utility like WordWeb, but this is just one more detail that Apple took the time to get right and Microsoft, as of yet, has not.

Update: It has been pointed out to me that you can use Cortana to look up words, and while that works fine, a virtual assistant is not the experience I’m after here. Friction matters a great deal in these types of workflows. A global keyboard shortcut that instantly shows me an inline definition (see above) is very different from stopping what I’m doing, opening Cortana, and typing “What does imminent mean?” (I know I can also ask Cortana verbally, but again, that’s much more disruptive than it needs to be.)

~ 11 ~ Windows 10 doesn’t have a built-in color utility.

Hey Mac users, I hope you aren’t tired of downloading anachronistic, third-party utilities just yet because you have one more to go: a color utility. Apple has shipped Digital Color Meter with macOS for as long as I can remember, and for as long as I can remember, most of the designers and developers I know use it on a regular basis to “eyedrop” colors across apps. On Windows, I use a tool called Instant Eyedropper which I like, but it’s just one more utility I have to keep up to date, install on new Windows machines, and hope hasn’t become an unwitting vector for ransomware since the last version.

These are the types of very basic omissions I was hoping to see addressed in Windows updates that Microsoft claim to be focused on creators. Headlining features are obviously important, but if you ask longtime Mac users about the best release of macOS (or OS X) in Apple’s history, most will claim that Snow Leopard was the pinnacle of the Mac experience — a $29 update that focused almost entirely an refinements and optimizations rather than bold new features.

Microsoft also has Windows 10 S to consider — a managed version of Windows designed primarily for education. By “managed,” I mean that Windows 10 S users can only install applications from the Windows Store, guaranteeing them to be as secure as possible. I know Microsoft is hoping that Windows 10 S will incentivize developers to put more of their apps in the Windows Store, but until that happens (if that happens), Windows 10 S users will simply have no way to access some very basic utilities Mac users have been taking for granted for years. Microsoft either needs to make absolutely certain that these types of apps make it into the Windows Store (preferably yesterday), or better yet, bundle them in with Windows 10 in order to save users the time, trouble, and risk of hunting them down. In the process, they will also make the Windows platform feel more modern and more approachable to inquisitive Mac users.

~ 12 ~ Three more things about Windows Mac users love to hate.

I. Installing and uninstalling applications.

Mac users love that they can drag and drop .app files into their application directories, and uninstall them just by deleting the application bundle. Most users don’t know (or really care) that files are often left behind in their “~/Library” directories. Those who do care might go to the trouble of deleting them by hand, or they might use a utility like AppCleaner. The point is, despite some disadvantages of manual application management, they like knowing exactly where their apps are installed. It helps to demystify the operating system, and gives them an increased sense of control. In contrast, it feels to them like Windows buries applications’ true locations, leaving behind a convoluted trail of shortcuts and requiring an opaque “wizard” intermediary which, let’s be honest, sometimes works and sometimes doesn’t.

Because I have some sense of how this came to be (a combination of legacy workflows, evolutionary dead ends, and a long-term vision far too ambitious to be rolled out in a single release), I don’t mind the dust and the construction noise all that much. But loyal Mac users do. They’re accustomed to an operating system that had the luxury of essentially starting from scratch as recently as 2001 (though its predecessor was in development since 1997), and only has to support a relative handful of hardware configurations. Windows has both the blessing and the curse of being the platform that more or less ran the majority of the computerized world for the overwhelming majority of the PC’s existence. I think it’s fair to say that Microsoft is now a victim of its own success, and while that’s definitely the best kind of victim to be, it doesn’t make resolving your problems any less necessary.

Epilogue: I’m not a hater. Seriously.

As I wrap up, I think it bears repeating that I am a big fan of Windows 10. Although I could easily do my job without it (with the exception of cross-platform testing), I choose to split my time between Windows and macOS because there are aspects of Windows I really love. I enjoy building my own PCs, and exploring the diversity of third-party hardware, peripherals, and accessories available to Windows users. Additionally, the Surface product line has set a new standard for the Windows experience which, in my opinion, is better now than it has ever been.