I used to believe (deeply, earnestly, and with the kind of conviction usually reserved for people who alphabetize their spice racks) that if we just wrote better documentation, the questions from customers would stop.
Not all of them. I’m not unreasonable. Just… most of them.
Our Users Will Always Have Questions
It’s a nice idea. Clean. Optimistic. And…completely detached from reality.
Because our users don’t stop having questions. They don’t wake up one morning, stretch, and think, “You know what? Today I’ll rely entirely on the doc team’s careful prose and never bother another human again.”
No. They click around for a bit, get mildly annoyed, and then — frustrated — they go looking for an answer the fastest way possible. This usually involves asking someone. Anyone.
And that’s the moment where most of our documentation strategies (assuming we had them) quietly fall apart.
What eCommerce Already Figured Out
Somewhere else on the internet, far from our lovingly maintained knowledge bases and documentation portals, eCommerce companies solved this problem without holding a single panel discussion about it.
They didn’t try to eliminate questions. They assumed questions were inevitable (like software updates that arrive at the worst possible time) and built systems to deal with them.
Most customer questions? Handled automatically. Instantly, if possible. Order status, return policies, “where is my stuff?,” “why is my stuff late?,” “can I return this thing I bought at 2 a.m. after a glass of wine or three?” — all of it gets answered without a human lifting a finger.
The rest? The strange, the emotional, the oddly specific? Those get routed to a person mostly likely to be able to handle the query.
That’s it. No drama. No philosophical crisis about whether the FAQ is “complete.”
We Built Libraries, Not Answer Systems
Meanwhile, over in technical documentation-land, we built… a library. A very respectable library, indeed. Shelves neatly arranged. Topics carefully labeled. Maybe even a search bar that works (most times). And then we sat back and thought, “There. That should do it.”
What we didn’t build was a system that handles questions and delivers reliable answers.
We built a place where answers live, but we left it up to users to connect the dots…meaning that we left them to their own devices to translate their problem into the right search terms, to recognize the correct answer when it appears in front of them wearing slightly different terminology than the one they used in their head. It’s a lot to ask from someone who just wants the stupid thing to work.
The Same Questions Keep Showing Up
If you peek behind the curtain of almost any customer support organization, you’ll notice something mildly embarrassing. The same questions show up again and again.
Not metaphorically. Literally. The same handful of questions, slightly rephrased, endlessly repeated by different people who all believe they are the first to ever encounter this particular inconvenience.
That’s your 80 percent.
The predictable questions; the ones you’ve already answered — maybe, probably, certainly — multiple times, in multiple places.
Related reading: Why Your Customers Hate Repeating Themselves, and What It’s Really Costing You
Save Humans For The Weird Stuff
And then there’s the other 20 percent. The oddball edge cases. The “this shouldn’t be happening but here we are” scenarios, and the ones that require a human to squint at the situation and say, “Huh. That’s new.”
Those questions should absolutely be routed to a human. But often, everything goes to a person. Which is a bit like calling a surgeon every time you need a Band-Aid.
Users Don’t Want To Browse; They Want Answers
This is where things start to shift. Our users aren’t looking for docs anymore. They’re looking for answers.
They don’t want to browse our site, filter our categories, or figure out what we’re trying to say. They just want to ask a question and receive an answer — the right one.
This is why conversational interfaces keep showing up.
The Chatbot Isn’t The Point
The instinct, in tech docs circles, is to treat these as shiny add-ons. Another channel — another thing-a-ma-bob to manage.
But that’s not what they are.
They’re an admission that our old model (publish and hope) was never really aligned with how our users behave. The interesting part isn’t the interface. It’s what sits behind it.
Structure Is What Makes The Conversation Work
If our content is well-structured, consistent, and governed (a word that tends to make people nervous) then a system can do something useful with it. It can retrieve the right pieces, assemble a coherent answer, and deliver it to those who need it in a way that feels immediate.
If our content is a bit… freestyle? Then the system will still produce answers. They’ll just be confidently wrong, which is somehow worse than being obviously incorrect.
The Writer’s Job Quietly Changes
At some point, if we follow this thread long enough, we must eventually come to realize that our job’s changed. Because now we’re not just writing docs. We’re deciding what deserves an immediate answer and what requires human conversation.
Today, we’re shaping how questions flow through our system., while also working to identify which gaps matter enough to fix and which ones can wait for later.
We’re not just producing content. We’re designing how knowledge gets used. This, if we’re being honest, is a much more interesting job than updating the same troubleshooting topic for the fifth time because someone noticed an Oxford comma was out of place.
If We Don’t Design It, Someone Else Will
Of course, there’s a catch. If we don’t quickly step into this role, someone else will. It’s only a matter of time. And these others won’t wait for perfectly structured content or a carefully governed taxonomy. They’ll take whatever exists, pour it into an AI system (PDFs included), and declare victory.
Yes, our users will get answers. Some of them might even be correct. Others will be… imaginative.
Without a clear sense of what should be handled automatically versus what should be escalated, our system will start to wobble. Simple questions get overcomplicated. Complex questions get oversimplified. Trust erodes, slowly and politely.
The First Step Isn’t Magic, It’s Triage
So maybe the goal isn’t better docs. Maybe it’s figuring out which questions we can answer instantly, reliably, and at scale. Then do that. On purpose.
And for everything else…bring in humans who know what they’re doing.
eCommerce figured that out a long time ago. We’re just now catching up. 🤠