From the Editor’s Desk: For Write or Wrong (Premium)

As a writer, I have a long and complex history with Microsoft Word, the greatest word processor the world has ever known. And with Word turning 40 last week, I reflected on my personal history with the app, which oddly predates my switch to Windows in the early 1990s by several years. And in comparing that history to my current experiences, I realized I have a few stories to share. It starts off good but goes downhill suddenly.

As you may know, I was an Amiga user in the early 1990s and I was not at all fond of Microsoft because of the shoddy nature of its software. This was a different era: MS-DOS and the PC had come to dominate the personal computer industry by that point, and Windows, despite its glaring issues, was just taking off. I couldn’t understand why. Here was this computer, the Amiga, that had sported a native GUI with real multitasking for several years, and yet most of the world was falling in lockstep behind one of the most technically inelegant platforms imaginable.

But even then, there were little flowers growing out of the dung heap that was the Microsoft of that era. As a budding software developer, I looked enviously at the simple elegance of Visual Basic (which is a description that could only be used by someone who had not actually experienced the language). But Microsoft’s productivity software, first released as individual apps over time and then organized into a bundle, or suite, had an even more profound impact on young Paul. Especially the word processor, Microsoft Word.

For all its strengths, the Amiga had multiple failings that Commodore either didn’t address or addressed too slowly. One of those, ironically, was tied to the system’s graphics display: Sure, the Amiga could display 4,096 colors and was particularly good at 2D and sideways scrolling games. But those capabilities were locked to specific low-resolution modes and were never improved in meaningful ways. And as the PC world moved into rock-steady high-resolution VGA and SVGA display resolutions, the Amiga did not. These resolutions were ideal for productivity software, like Word and the rest of Microsoft Office. And we had nothing like it on the Amiga.

We had WordPerfect, all too briefly. And a host of word processors and similar software that few would remember today. Excellence! (yes, with that exclamation point in the name). ProWrite. Final Writer. And others, I’m sure. It’s all lost in my brain to time. But what I remember all too well was that feeling of inferiority, of being stuck with less capable tools and longing for something better. Something that was already out there in the world. Just not for me.

By this time, I was already plotting my return to school so that I could study software development. And I knew that this would involve Windows and the PC, not the Amiga. In preparation for this inevitability, I started reading up on Windows software development, starting with Charles Petzold’s classic Programming Windows, which at that time would have covered Windows 3.0. This book, like the topic it covered, was technical and obtuse, and because I had come up in the world first with Pascal (most recently on the Apple IIGS) and then C (on the Amiga), both of which were comparatively elegant, I was shocked—but given my stance on Microsoft, not surprised—how terrible this was.

I researched other approaches and came across a book by Woody Leonhard that taught WordBASIC for Windows. This book was approachable and even entertaining, but it also gave me my first experience with a Microsoft BASIC and, go figure, Microsoft Word. Which I used, slowly, on my wife’s underpowered IBM PS/1. And just like the PC game Castle Wolfenstein 3D, it was a revelation. The Amiga was doomed, and the PC was the future.

And it was all because of Microsoft Word.

Word was elegant and capable in ways that Windows, the platform on which it ran, was not. And I suspect it was the combination of the two, and not Windows alone, that drove the PC buying boom of the early 1990s: Many people put up with Windows so that they could use Word and other applications that shone best there. I couldn’t wait to get started with Windows, but it was because of Word. It was the first chink in my anti-Microsoft armor.

Sadly, I had to wait. We moved to Phoenix in 1993 and, jobless and unable to get in-state tuition, struggled for a year before we found our footing. I went to school part-time and got a job, and before my wife landed the job that would kick off her still-current career in writing, she worked briefly as an editor for a local software documentation company that was creating, among other things, a user’s manual for Microsoft Word 6.0. And she brought home some of this work—on paper, remember this was the early 1990s—and so I got my first look at that.

And this, too, was a revelation. Word 6.0 was notable for many reasons, and it introduced what then felt like futuristic features that had been handed down by benevolent alien visitors, like AutoCorrect and AutoFormat, features that today would be described, incorrectly, as AI. The UI was tightened up and made consistent across the Office applications. And it was released in 32-bit form for Windows NT, a then-mysterious OS that maybe, just maybe, would bring the technical elegance I saw in Word to Windows itself.

Finally, I had to switch. Not just for Word, but because school was spinning up and I was exceeding what was possible on my lowly Amiga. And so I did switch, and in a “right time, right place” coincidence I’ve never been able to rationalize or explain, I quickly moved into my current career in writing. And Word, this tool I had wanted so badly for so long, became the center of my universe. I would use this product to write dozens of books over the years, and I would learn some of its more esoteric features so I could interact with the edits made by others and shipped to me on floppies. I would go on to chart its progress across Windows 95 and Office 95 and into the 21st century.

Have I written millions of words in Word? Of course I have. And I now know Microsoft Word as intimately as I do any software, including Windows. I can and do configure this application exactly the way I want it—and yes, I have a very specific configuration—and could probably do so blindfolded.  I know that I use only a tiny percentage of its feature set on most days. And that I could easily get by with a much simpler version of this product, something akin to the web version perhaps, or the blink-and-you-missed-it mobile version that was going to take over in the touch-first Windows 8 years.

I obsess over Word. I love it and I hate it now in ways that are as confusing as any human relationship. I see its strengths and its flaws, and it is the poster child for what’s wrong with the AI era into which we are being thrown with abandon and, it seems, little thought of the consequences. When I argue against AI, when I insist it’s time to put on the brakes, it is Word I am thinking of. Maybe we should fix today’s software before piling on the AI.

Here’s what I mean.

If you consider a basic word processing document, like one I might create for any web article, the very first line will be the title. I wrote this article in Word, for example, and the first line in the document I created was originally written as “Microsoft Word, a Love Story” (with no quotes). And so I typed that and then auto-typed “CTRL + S,” the keyboard shortcut that is hard-wired in my brain as securely as is the need to type that shortcut continuously as I write, and out-of-date habit dating back to the less days of the past. You get religion when things go wrong, and I compulsively save everything I write repeatedly because I lost data once. That’s how this works.

Anyway, when I typed CTRL + S, a Save As dialog appeared. This is tied, in part, to that specific configuration I mentioned: Today, Word wants to save to OneDrive by default, and it will auto-save for you, a safety mechanism designed to overcome that data loss issue I mentioned. And in that Save As dialog, the title I wrote appears as the default name for the document that Word will create. That’s smart and obvious: In my case, I always want the title to be the name of the document.

Except this part of Word is not smart. The name that appears in the Save As dialog is not “Microsoft Word, a Love Story.” It’s “Microsoft Word.” Because Word, all these years later, still truncates that name if it hits punctuation or any characters that once, in the distant past, couldn’t be used in a filename. It’s that dumb.

This, to me, is obvious: Word should use the entire first line of a new document as the default name. If there is a character that cannot be used in a filename today in 2023, it should auto-replace it with an obvious alternative (and give you the option to configure that character). For example, a document titled “Microsoft Word: A Love Story” would be named “Microsoft Word- A Love Story.”

That’s just one example of a failing in Word that has persisted for decades and for no good reason I can imagine. But it is also an example of my argument against AI: If we can’t solve this simple problem, why on earth would we trust AI to work correctly in Word or anywhere else? Why would we trust Microsoft, which has ignored this simple problem forever, to do the right thing with AI?

These questions are not rhetorical. And there are more specific examples of AI-type functionality today in Word that fail spectacularly every single day. And these failures cut to the heart of the AI value proposition.

The most obvious is tied to grammar checking. I don’t recall when Word added grammar-checking capabilities, but this, too, must have seemed like an alien gift at the time. After all, spell checking started out humbly, with rote dictionaries of words that the word processor would compare your writing to, first manually and then automatically as you wrote. In time, spell-checking got more sophisticated, as these things do, but grammar-checking was far more complex, even at the beginning. It needs to understand context. And as the tool itself evolved, we got things like squiggles under words that were misspelled and under grammatically incorrect terms.

As a writer, I rely on grammar checking and other corrections. But I have also watched over the years as Word’s prowess in this area became its Achilles Heel. My contemporary workflow involves writing in Word and publishing to the web, and that latter step includes a spelling and grammar pass by Grammarly via a web browser plug-in. And that tool has, for years, consistently found many, many spelling and grammar mistakes that Word missed. This is a sobering about-face to my initial reaction to Word thirty years ago. It’s troubling: How can a tiny start-up do a better job at a task that is central to what I earlier described as the greatest word processor in the world?

I can’t answer that question. I can only observe that Word’s correction features have gotten worse with each passing month in recent years. And it doesn’t just miss things: The corrections it offers now are often wrong too. This happens so much that my wife and I routinely call out these correction mistakes to each other as we write in our respective offices as if trying to outdo each other. I have done so several times while writing this very article. And to document this issue, I’ve started taking screenshots. Here’s a typical example, and it’s from this very article.

The pertinent part of the sentence in question is:

Most of the world was falling in lockstep behind one of the most technically inelegant platforms imaginable.

And Word wanted to rewrite that as:

Most of the world was falling in the lockstep behind one of the most technically inelegant platforms imaginable.

No. That is grammatically incorrect. As noted earlier, grammar checking relies on context, and this is a sadly typical example of Word failing in that. This happens to me all day, every day. It’s like Word has some kind of digital disease, eating away at its good bits from the inside.

This is dangerous. Grammar checking and the other corrective features in Word are what Microsoft would today describe as AI. Tools like Grammarly are AI. As is the Microsoft Editor, a utility that ostensibly competes with Grammarly but is literally based on the terrible underpinnings of, wait for it, Microsoft Word. We know that AI hallucinates, a cute way of saying “makes mistakes.” And we know that the value of AI is that it allows people to accomplish tasks in which they are not necessarily proficient. Non-artists can now create art. Non-professionals can now create beautiful PowerPoint presentations.

Can non-writers now write?

Sort of. The reality of AI is that there needs to be a human with real skills between the AI creation and its output. We all know this. But we also all know that this will rarely happen.

In this case, I am in fact a professional writer. And I know that what Word often suggests to me is wrong. But most people are not professional writers. They will accept the AI creation, or suggestion, and just run with it. We are on the cusp of a generation of horribly written content that was generated by AI and not properly vetted by people. This problem I see today in Word is only going to be worse. Much worse.

When Adobe launched the digital desktop publishing market in the late 1980s, users were so excited by the ability to mix and match fonts and layouts that were inundated with documents that looked like ransom notes. This AI era will be worse and, I think, longer lasting. Worse, the impact will be far greater. Think of all the incorrectly written legal filings and rulings, health documentation, financial advice, personal and professional correspondence, treaties, and documents of all kinds that will be written in the coming years and the potential fallout of each. Wars might start. Criminals will be let out of jail. People will be killed because an AI-written travel guide sends them to the wrong neighborhood in some city. On and on it goes.

And all I can think is that we have this tool that works so well in so many ways, one that was, in fact, my gateway drug into the Microsoft ecosystem. And yet all these years later, it cannot get the basics right. And Microsoft is about to flood it and the other Office apps with iffy AI functionality that most people will accept as definitive and correct when it is not.

To be clear, Word is only part of this emerging problem. But from my perspective, with my hands on the keyboard, it is very much at the center of my hopes and fears. And the real change we deserve, not just as Microsoft customers and users, but as humans, is to get this right. Now. Not later. Let’s nail the basics before we step forward.

Otherwise, Word’s legacy could be quite a bit more negative than the celebration Microsoft threw last week to mark its 40th anniversary. Unless it somehow gets this one right.