Reinvention (Premium)

Microsoft, the Oldsmobile of personal technology, has jumped back into the public consciousness thanks to AI. But AI is only an ingredient, a back-end service, in Microsoft’s direct offerings to individuals. And while AI can breathe some new life into tired, legacy product lines like Windows and Office, it’s not enough. These products need to be reinvented as well.

And there, we see good news and bad news: Microsoft has spent decades trying to reinvent both Windows and Office. But it has rarely been successful.

Given my fixation on Windows, that story has been told many times. Indeed, I wrote an entire book about it, called Windows Everywhere. But Microsoft Office is even more widely used than Windows, and it’s gone through its own ups and downs over the years as Microsoft wrestled with the same problems that bedeviled Windows, most obviously the rise of web and mobile.

That said, Office better lends itself to a heterogeneous world in which Microsoft customers are using some variety of devices, and not just PCs. As such, it made a much quicker and more seamless transition into the cloud-focused Microsoft of today, starting with Business Online Productivity Services (BPOS), which, over time, expanded and evolved into such things as Office Online, Office 365, and now Microsoft 365.

But for better or worse, most people think “Microsoft Office” when they think of this now-expansive family of offerings, and they very specifically think of the Windows-based desktop application suite. Office and Windows are so synonymous in people’s minds that many still believe that Office is part of Windows. And Microsoft has done nothing to shake this belief by enticing PC makers to bundle the (Microsoft 365-based) Office suite on most of their new PCs. I can’t recall the last time I turned on a PC and didn’t find Office preinstalled.

The negative side-effect of this perception is that it’s hard for Microsoft to introduce successful new Office apps and services. In fact, it’s possible that the only truly successful new Office app of the past two decades is Microsoft Teams. And that one is such an outlier that many likely don’t even associate it with Office per se as it’s a full-featured platform of its own, complete with its own extensible app infrastructure.

This is problematic in the productivity space because Windows is no longer at the center of personal computing but is, depending on how you measure things, only the third most-used personal computing platform, behind Android and iPhone/iPad. And so, yes, it was big news when Microsoft brought Office to mobile, starting with the iPhone, just as it was big news when it did so previously on the web. But these lesser Office versions have done little to drive new revenues because they’re basically perks for Microsoft 365 subscriptions and not standalone offerings. People just aren’t buying standalone Office products anymore, and, again, the classic desktop offerings are seen as part of Windows. Which is essentially free to individuals now.

I’ve written in the past about the need to respect Microsoft’s desire to monetize a user base of 1.4 or whatever billion Windows users in a world in which none of them are paying for upgrades anymore and PCs last longer than ever. And I’ve railed against the choices they made to do so: forced tracking with no way to disable it, the resulting selling of your private information to advertisers, an ever-escalating number of advertisements in the product, and bundled crapware chief among them. This is what happens when a product line can’t make a seamless transition into the cloud-focus Microsoft of today.

But Office has a different problem, albeit it one that was triggered by the same market conditions. Office, like Windows, is largely legacy software and, as noted, few of the “new” Office-branded products and services that Microsoft has released over the past 20 years have achieved any meaningful level of success. Instead, customers expect—demand, even—the Office suite on Windows. And they expect to be able to read their documents and maybe do some light editing on mobile. And they are proven themselves uninterested in anything new or different.

And, boy, has Microsoft tried.

There have been three major efforts to modernize Office in the past two decades. The first was the Office Ribbon, a still-controversial user interface that tried to solve the problem of command density, where there were simply too many features in Office to present them adequately using a toolbars and menus-based UI that had debuted over 20 years earlier. The second was a later aborted attempt to bring Office to the Metro/universal Windows platform that debuted in Windows 8, an effort that would have required basically rewriting the entire application family from scratch and was quickly shown to be technologically impossible. And the third was a compromise by which Office would continue forward with the existing legacy base but it would evolve to use a web-based extensibility model that would work across all of the products across Windows, Mac, web, Android, and iPhone/iPad.

The net result there amounts to a retreat: the classic Office suite—again, what most people think of as “Office”—will never be upgraded in a meaningful way. Like Windows 11, it will be given the occasional spit-shine to accommodate what people think looks modern in any given era. But it will mostly just soldier forward because the codebase is too old, too big, and too messy to do otherwise. A combination of entrenched customer expectations and technological reality has made these products the Walking Dead Apps.

This problem has been obvious to Microsoft for a long time, of course. And so there have been related attempts, over the years, to expand Office to include unique mobile and web experiences—both apps and services—that perhaps could co-exist alongside the classic Office apps and then one day form the foundation of a new generation more modern Office solutions.

I’m guessing you’ve forgotten about these efforts if you remember them at all. But the two key entries that stick in my mind are Office Sway and Office Mix. Office Sway came about because old-timers were using PowerPoint to share photos (which I’ve actually experienced, my father used to do this). And Office Mix, which was literally an add-in for PowerPoint, aimed to turn unidirectional presentations into interactive online lessons that you could share with others.

Both were good ideas: some still mourn the passing of Sway, while the functionality from Office Mix is basically just part of PowerPoint now. But more to the point, both represented new thinking. New thinking at a time in which Microsoft wasn’t ready to replace what worked (the traditional Office suite) because of fears about its short-term revenues. Everyone knows that change is hard. But change can also be expensive.

The underlying issue here has never been solved. Personal computing has evolved dramatically in the past 20 years, while Office has not. Microsoft’s user base expects traditional Office. They are not interested in anything new. Left unsaid, those legacy tools are so overbuilt with features and commands that they’re almost too hard to use. Unless you’re an expert in Word, PowerPoint, or Excel, opening up one of those apps today feels like stepping into the cockpit of an airliner. It’s hard to know where to start, let alone find the one switch you need.

This is something I’ve always felt keenly, and it’s likely you recall me expressing at one point or another that I should gravitate to Microsoft Word because I write professionally, and yet I find this tool to be too complex and too full of features I will never use. You will also probably recall Microsoft saying at different times, and with regards to different products, that its goal is to “get out of the way” so that the user can focus on the work they’re doing and not be distracted by the application chrome.

But we’ve also seen how hard that is, especially when the tool in question is bristling with functionality and the removal of even an esoteric, rarely used feature will result in howls of protest from the user base. We’ve seen this problem with Windows 11, where we should give Microsoft credit for finally trying to overcome the complexity of the Windows user interface, which has built up an enormous amount of cruft over the years, and yet all we do is complain when the one feature that was removed in the name of simplicity is the one we cannot live without.

We’ve also seen this again and again with Xbox. For example, when Brad and I discussed yet another Xbox Dashboard redesign recently, I opined that Microsoft was overthinking this and that what most users need most frequently is to turn on the console, click the game they want, and just start playing. (I compared it to a FedEx website idea I came up with several years back when I couldn’t easily find a link for tracking a package.) But everyone likes and expects different things, and one of the key complaints about this change was that it hid too much of the Dashboard wallpaper they hand-selected. Who the frick is looking at the wallpaper on an Xbox?

Getting back to Office, complaints about the Ribbon have led Microsoft to develop, over time, something called the Simplified Ribbon, which only makes sense on the web app versions of the traditional Office apps because those apps have fewer commands. (And on Outlook for Windows desktop, interestingly, but probably for the same reason.) The firm then spent years trying to bring the Simplified Ribbon to its desktop apps but failed for the same reason that the original Ribbon was required: there are just too many commands. And so the solution, the compromise, was to use something now called the Personalized Toolbar. This is a Simplified Ribbon-like interface that doesn’t replace the Ribbon. Instead, it hides the Ribbon and you can still access it at any time.

And in case it wasn’t obvious how entitled Office users are, Microsoft also had to revert its decision to hide by default the Office Quick Access Toolbar (QAT), a vestigial user interface that occurred because so many people complained about the original Ribbon. This isn’t UI design by committee, it’s UI design by insanity. The Office user base doesn’t just refuse to use any non-standard apps, it refuses to use any changes to the legacy apps they do use.

What’s fascinating to me is that Microsoft, finally, might have found a solution to its Office problems. And that this solution arose in the wake of Microsoft Teams and is clearly inspired by that product is not coincidental.

That solution is Microsoft Loop.

Like the classic SNL skit Shimmer Floor Wax, which was both a floor wax and a dessert topping, Microsoft Loop is both a platform and a new collaborative creation application. The platform bit is what was inspired by Teams, I think, but it’s also what will enable Microsoft’s user base to transition from the legacy Office apps to a more modern experience over time. And the ability to use Loop as a standalone app speaks to Microsoft finally addressing a new generation of lightweight notetaking and writing apps that are viable alternatives to the complex and feature-heavy traditional Office apps.

A few years back, I had breakfast with the person in charge of OneNote at Microsoft and they asked me whether I’d be interested in a simpler new OneNote client. I was begging for such a thing: I had been using OneNote since the first beta and initially loved the product, but it grew big and unwieldy over time and, like Word, was full of features I didn’t want. I’m not sure that this person was referring to what became Loop, but I can say that nothing that’s happened with OneNote since then is anything like what we discussed. It is not coincidental that my frustrations with OneNote—the worst being that it’s real-time collaboration functionality never worked correctly—led to me, an early adopter, abandoning the product for Notion in early 2022.

And it is likewise not coincidental that the Loop standalone app is an obvious (and frankly embarrassing) rip-off of the Notion user experience. Of course, Notion isn’t the only such app, there are many. But in a market in which the original OneNote alternative, Evernote, feels old-fashioned and passe, apps like Notion feel fresh and modern because they are. They’re not complex but they are full-featured. They’re everything that traditional Office is not.

So, great, Loop achieves that goal (and there are some nice nods to the expectations of traditional Office users, too, like familiar keyboard shortcuts). But the brilliance of Loop is that it lays the groundwork for the future while respecting the past, a needle that Microsoft threaded to great success with Teams. That is, when Teams first debuted as a Slack-like message-based collaboration solution, it wasn’t enough to pry Outlook away from the old-timers that still gravitate to that mess. But as Teams evolved quickly over the years, it attracted more and more users. And that started to include Outlook users, people who had, for decades, organized their workdays through that one app. Over time, those people will move on. And Teams will be left standing.

Loop seeks to do this for the traditional workflows that users now perform in Word, Excel, and PowerPoint. It’s not enough today to get long-time Office users to just switch apps, but it will attract the younger folk. And more importantly, its platform features— its use of components—are what bridges the past with today. You can host Loop components bidirectionally, meaning that an Excel user can work their magic in their favorite app and then link the relevant part of a worksheet into a friendlier collaborative Loop document that their coworkers will better understand. And that worksheet will always stay up to date. This will work across all the key Office apps and solutions.

This interaction is key to what I see as the future success of Loop. And a future in which Loop and Teams, together, become Office (or Microsoft 365, or whatever we call this thing in the future). Where Outlook, Word, Excel, and PowerPoint define the Office of the past, Loop and Teams define the Office of the future.

Yes, this is speculative and there’s no guarantee that Loop will succeed. But I think Microsoft has found a template in Teams for moving the world forward and that Loop can succeed where past attempts to modernize Office have failed. It’s a new era, and the reinvention that Office—and, more important, its users—deserve.