Twelve things Microsoft should know about Windows 10 (that Windows users won’t tell them)

Want to see Windows 10 through the eyes of a Mac user? Strap in.

Windows 10 has a built-in application called Feedback Hub which allows anyone to submit and up-vote feedback about the Windows 10 experience. Microsoft has come to rely heavily on Feedback Hub for bug and feature prioritization, which is obviously sensible, except for the fact that it has one fundamental flaw: only Windows users use it. That means Feedback Hub is susceptible to the same self-selection biases as our current political discourse. Mac users who poke around Windows 10 to see what all the hype is about, but who end up shrugging and walking away dismayed, don’t stop to leave feedback on their way out the door. And even if they did, Microsoft probably wouldn’t see it since staunch Windows users are unlikely to vote it up to the level of prominence.

The “trending” section of the Windows 10 Feedback Hub.

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.)

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.


~ 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:

This will probably look familiar to many Mac users, but remember what has often been said of great artists.

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:

And while I’m on the topic, I’d really like to see the edges of windows become slightly “magnetic” like they are on macOS Sierra, greatly simplifying window alignment and arrangement. Here’s another mockup:


~ 3.0 ~ Windows File Explorer: It needs a “Quick Look” feature.

In the macOS Finder, if you select a file, then press the spacebar, you activate “Quick Look” which gives you a preview of the selected file. I loved this feature the moment it appeared in 10.5 Leopard, and I still use it all the time (in fact, it’s gotten noticeably better over the years).

On Windows, I use a third-party application called Seer which is slightly better than nothing, but not nearly as polished or useful as Quick Look.

Update: It has been pointed out to me that the File Explorer Preview Pane is the Windows equivalent of “Quick Look.” I do use the File Explorer Preview Pane, but I always thought of it as analogous to the macOS Finder’s preview pane (while in column view) with Quick Look being an additional, more robust feature. Also, the File Explorer preview pane doesn’t support audio, video, or animated GIFs (in my world, GIFs aren’t just for memes; I create animated GIFs all the time to attach to things like bug reports). But I fully admit that I might be approaching my File Explorer critique with some amount of Mac bias.

Preview panes (background) are great, but there’s no substitute for tapping the spacebar and activating Quick Look (foreground).

~ 3.1 ~ Windows File Explorer: It doesn’t render SVG thumbnails.

This one is so blatant that it skirts the line between unimplemented feature and bug. There was a time when you could argue that SVG wasn’t a very relevant file format, but that time has long since passed. As its name implies, Scalable Vector Graphics are a perfect alternative to JPGs and PNGs for rendering visuals such as icons, graphs, and diagrams across any screen size without losing any fidelity whatsoever (and they’re easily animated). Now that SVG enjoys widespread browser support — and now that Flash, the only other vector-based option, is dead — SVG is a critical tool in both the web developer’s, and the designer’s, toolbox.

~ 3.2 ~ Windows File Explorer: It needs a column view.

The Windows File Explorer has a multitude of layout configuration options, but one it doesn’t have is the one most Mac users seem to prefer: column view. This is purely anecdotal, so I could be wrong, but I bare witness to a lot of shared screens, and I peer over a lot of Mac users’ shoulders, and I believe column view to be the layout option of choice (at least among users sophisticated enough to know that the layout configuration can be changed).

Column view in the macOS Finder — in my experience, the most popular layout option, and the one view Window’s File Explorer doesn’t support.

~ 3.3 ~ Windows File Explorer: It needs multiple tabs.

We’re all in violent agreement here, right? Probably no need to launch into a lengthy thesis on this one. The reality is that the utility and convenience of browser and document tabs is well understood if not proven at this point, and should be brought to applications like File Explorer and even the Windows command prompt (especially now that we have such great Linux support).

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:

To be fair, Microsoft is working on a UWP version of the File Explorer which, if it’s anything like Mail and Calendar, will be much cleaner. But the reality is that the standard Windows File Explorer will probably be in service for many more years to come, if not forever, so I maintain that it deserves a little love, as well. For example, it would be nice if something as basic as context menu icons looked like they were implemented properly:

Note the difference in context menu icon rendering on Mac vs. Windows. On Windows, it looks like the Dropbox icon hasn’t been watered in several weeks and is starting to shrivel up. This lack of polish is the kind of thing that makes many Mac users cringe. (I realize this may be the fault of Dropbox, but users don’t distinguish; someone at Microsoft needs to reach out to them to make sure it gets fixed.)

~ 5 ~ For all its complexity, the File Explorer context menu is missing a “Duplicate” option.

I realize that saying the File Explorer context menu is too complex, and that it doesn’t do enough, is a little like saying that a restaurant has terrible food, and that the portions are too small (thank you, Woody Allen), but the reality is that taming complexity is what design is all about. Therefore, I feel perfectly justified in complaining that duplicating a file using the context menu on Windows is a two-step process: first you copy it, then you paste it. Power users will know that if you drag and drop a file in the same folder while holding down the “ctrl” key, you can create a fairly quick duplicate in a single step, but I don’t consider that a particularly discoverable gesture. The answer is to simply add “Duplicate” to the context menu, probably grouped with “Create Shortcut,” “Delete,” and “Rename,” like this:

(Note that in the context menu simplification study I did above, I snuck a “Duplicate” option in there, as well.)


~ 6 ~ “Open with” mysteriously disappears from the File Explorer Context menu when you have multiple files selected.

If you’re on a Windows machine, or you have access to one, humor me by trying the following:

  1. Open File Explorer (remember: you can use “Windows + e”).
  2. Find an image (JPG or PNG — doesn’t matter).
  3. Right-click on it.
  4. Note the “Open with” option. If I have multiple applications installed capable of viewing or editing images, I’m happy.

But don’t get too happy. Now try this:

  1. Select two or more image files.
  2. Right-click.
  3. Note that the “Open with” option has miraculously vanished.

Wait, what? So if I have multiple files that I want to work on in Photoshop, and I’m staring at them right in front of me in the File Explorer, I have to open Photoshop first, then navigate to the same list of files I was just looking at in File Explorer?

Yes. Yes, you do.

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.

It’s probably way too late to change the default copy/paste behavior, but it’s not too late for Windows to support a universal “Paste Plain Text” or “Paste and Match Style” option. For some bizarre reason, the ability to paste text without destroying your document in the process is something that is left up to individual applications on Windows. On the other hand, macOS provides a global keyboard shortcut meaning that once you learn it, you can use it everywhere. I can’t tell you off the top of my head what the keyboard shortcut is on macOS (actually, it’s “Command + Option + Shift + V” — I just looked it up), but my fingers know it every bit as well as they know how to tie my shoes because, for me, that’s the default. And on macOS, I know it works as-expected in every single application I use.

Once again, on Windows, I’ve had to install a third-party app (in this case, PureText) to get simple, straightforward, and obvious behavior that should be built right into the OS.


~ 8 ~ Window Management is good on Windows 10, but power users have nowhere to go.

The default window management functionality on Windows 10 is pretty good, but power users need more. And unfortunately, unlike with macOS, there aren’t very many good options.

On macOS, I used to use an application called Spectacle, but eventually switched to Divvy with a smattering of BetterSnapTool, depending on what I’m doing. I haven’t come across anything nearly as good for Windows. I’m getting by with a tool called MaxTo which is sufficient, but not nearly as feature-rich, polished, or robust as its macOS counterparts.

macOS applications like Divvy give you powerful, flexible, and modern window management. I haven’t found anything remotely this good for Windows.

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:

(“Colorless” image by Harc Lee.)

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.

Not only does macOS have a very good built-in dictionary (and thesaurus), but it’s integrated into the OS in such a way that you can invoke it in-line to look up words in just about any application.

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.

The Digital Color Meter utility built into macOS is a staple of the design and development communities.

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.

Not exactly what you’re hoping to see after attempting to uninstall an application.

II. Mac users think font rendering on Windows is rubbish.

By no means am I a font expert, but I’ve worked with them enough to know that font formats and font rendering heuristics are crazy complicated — especially with the proliferation of high-DPI display technologies. Personally, I don’t hate font rendering on Windows (though I’m more of a product and engineering manager than a designer), but I would count myself among the non-vocal minority; many hardcore Mac users, after only hours of Windows exposure, are prone to using all kinds of colorful language to characterize Microsoft’s multiple approaches to font rendering.

When font rendering is at its best, both Windows 10 and macOS do a good job. But if you use both operating systems enough, you will probably find the quality of font rendering across Mac apps and experiences to be both higher, and more consistent. (See various Windows screenshots above.)

III. Windows doesn’t have a coherent design language.

If you hadn’t been keeping up with Windows, and you were to walk into a Microsoft store to play around with the latest and greatest in Windows hardware and software, you would almost certainly be blown away by how modern and polished the experience has become. In some respects, it might even make macOS look a tiny bit dated. But buy a Windows computer, take it home, and start using it as your daily driver, and very soon you’ll begin to encounter vestiges of versions past. You will encounter multiple ways of accomplishing the same things, seemingly different configuration options which actually compete with one another, other similar configuration options which aren’t associated with one another at all, and sometimes even more than one version of the same application. You’ll see fonts rendered differently, menus stashed in different places, and wildly different UI conventions. With the new and emergent Fluent Design System, we might even be about to get yet another design language woven into the Windows 10 experience before discrepancies in the old ones have been fully reconciled or eliminated.

In the background, an example of what was known as “Metro” or “Modern UI,” but is now “Microsoft Design Language 2,” and soon to be consolidated under the brand “Fluent Design System.” In the foreground, the legacy Control Panel. Your brand new Windows 10 computer will come with both apps installed, and both apps affect the same OS-level configuration.

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.

The Surface Studio is one of the most innovative new PC form-factors since the iMac. (Personally, I love the Surface Book, but it’s slightly less photogenic.)

I should also point out that, thanks to Windows Story Remix, I didn’t need to rant about a lack of decent, non-professional video editing software in this article. That is to say, it’s clear that Microsoft is well aware of some of the major holes in their ecosystem, and that they’re taking steps to not just plug them, but to innovate in the process.

But sometimes I wonder if Microsoft is so focused on potentially game-changing, tectonic shifts like mixed reality, and conspicuously demo-able features like Cloud Clipboard and Windows Timeline, that the little things get dropped on the floor and forgotten like so many Lego pieces just waiting to bore into the heels of cautiously approaching Mac users. All it takes is one or two sharp edges to make them swear, turn, and hop right back to safety.

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