These were literally a digital version of the book with a search box and hyperlinks between entries. To find what I was looking for, it helped to have a general idea of what was in there. Every team had someone who memorized the entry titles and numbers as a service to the rest of us. Also to show off.

My interest grew in the experience of using style guides, how search worked, the classification and tagging of guidelines. We needed to think of the guidelines themselves as content and as part of our scope.

Copy-paste all over the place

Next came web sites known as “auto checkers.” They offered a growing variety of features like keyword extraction for tagging. Though, a whole website was dedicated to one feature alone. I had to leave Google Docs and bounce between a bunch of browser tabs to catch everything.

Screenshot of readability-score.com
My favorite for readability checks by Added Bytes, 2013. I had an opinion on the selected background.

During those days, I managed a “very affordable” content marketing agency’s work. It required a heavy editing process. This involved taking their draft from Google Docs and pasting it into a plagiarism checker. Then pasting it into another site for reading level, making edits until it hit the target. Then to another for proofing and comments. By pure luck, I checked plagiarism first. Had I edited their content first, I would have missed that section they lifted from The New York Times. (I know!)

Knowing where to go and in what order was part of the job. We exchanged and recommended links to these checkers like insiders.

AI writing assistants

The next generation style guide is here now. Grammarly and Writer, formerly Qordoba, have the best of everything that came before in one place, plus AI. AI improves the quality of automated language checks in the context of what the content means. The suggestions are delivered out to teams as they write, where teams write.

Screenshot of writing style settings
Writer, 2020

My team manages Writer for Intuit. In return, it extends the expertise of our style council and its decisions to folks all over the company who create content, especially to non-writers who shouldn’t be making those decisions. With its help, our style council doesn’t have to spend tons of time promoting the style guide, communicating updates, providing training, and pleading for adoption.

What’s the same

Fussy writers define the style. A lot of history sticks with us as content creators: having the luxury to debate, caring about tiny elements, knowing a preferred answer, thoughtfully diverging. We still accept or reject what the assistant suggests.

The interaction hasn’t wildly changed. Comparing the first software checkers and today’s writing assistant, you could time travel in either direction and comfortably use any.

I wouldn’t hate it if the assistant also had a bit of a chatbot feature. Or even a Slackbot into our style guide. As part of my writing process, style questions come to mind. Tangential thoughts, but help me get it done all the same. My hack , for now, typing those questions into the document to get my answer roundabout.

Screenshot of Writer with a question typed
Even now, I haven’t completely adapted to Writer

What’s different

Language models are new and better. The machine learning is semantic. Writer learns how writers write as we feed it more content and interact with corrections. It outperforms other checkers.

Style decisions scale automatically. In the past, there was a rush to add almost anything writers discussed as if the style guide were a notepad. Now decisions go out to anyone creating content as an automated check. Are you comfortable with them making the call in any fringe context that challenges your custom guideline? Deciding what stays out of the writing assistant is as important as what goes in.

The style guide is a thing we do rather than a thing we deliver. Today our responsibilities include managing users, tweaking settings, creating feedback loops, troubleshooting, and reporting.

The style guide site as we know it today will change. Publishing a site for style isn’t needed. They may morph to richer, descriptive frameworks, knowledge sharing, and community. Instead, we think about the relationship between it and the writing assistant.

You don’t have to know guidelines or remember where to look for them. If the writing assistant provides just about everything proactively, how much do we really need to know? You can debate whether basic competency is required as a user. With technology, is style falling the way of spelling and handwriting? Don’t freak out.

What do we leave behind?

When tools evolve, the old mentalities and behaviors get exposed. Older technologies make them easy to spot. For example, how does the fountain pen or typewriter define me as a content person, the problems I take on, or how I do the work? The same should be asked of style guides.

AI writing assistants free us up for more creative, strategic, and critical thinking.

This article was originally published by Jennifer Schmich on UX Collective, a publication sharing curated stories on UX, visual & product design. You can read the original piece here.