Your most experienced writer just left the company. A week later, the new hire asks: “Where do I even start?” Half your content structure existed only in one person’s head. The other half? Scattered across Google Docs in three different shared drives, a wiki that hasn’t been updated since 2022, Slack threads that are now impossible to search, and someone’s personal Notion workspace that you didn’t even know existed.
Welcome to documentation debt
Your team ships features faster than you can document them. Writers leave without transferring knowledge. “We’ll update the docs later” becomes “we never updated the docs.”
Take Sarah. She’s your go-to person for the API — not because she’s the only one who understands it, but because she can actually explain it. She knows which endpoints are deprecated but still in use, which parameters have undocumented quirks, why the authentication flow works differently for legacy customers.
She’s translated all that complexity into answers that support can use. None of this is written down. Sarah’s got it figured out, and everyone’s learned it’s faster to just ask her. When she goes on vacation, support’s response time doubles. When she leaves for a better offer, that knowledge walks out with her.
But even if Sarah had documented everything perfectly, you’d still have a problem. Documentation doesn’t just need to exist — it needs to stay accurate.
Say, you open a three-year-old article to update it. Ten minutes in, you’re still figuring out why it references features that don’t exist, uses screenshots from a UI redesigned twice, and links to 404 pages. The article was accurate when written. The product evolved. The docs didn’t. Users find one outdated article, then another, then a third that contradicts the first two. They stop reading documentation and just open support tickets.
The product evolved. The docs didn’t.
Meanwhile, two writers just spent a week documenting the same feature. Neither knew the other was working on it. No process for coordinating, no shared view of what’s covered.
And somewhere, a critical security update from three months ago fell through the cracks and still isn’t documented because everyone assumed someone else was handling it.
Why you don’t see it coming
You don’t see documentation debt accumulating. Your product keeps shipping, features keep launching, everything looks fine from the outside. But underneath, the cracks are spreading.
I’ve watched this pattern play out across teams of different sizes. At five people, everyone knows where everything is. At fifteen, new hires spend weeks asking “where do I find…?” questions instead of writing. At thirty, you’re paying senior writers to be tour guides. Onboarding that should take a month now takes three because nobody documented how things actually work here.
At thirty, you’re paying senior writers to be tour guides.
Or when someone leaves. The writer who set up your entire content structure gives two weeks’ notice. You realize that critical decisions — why things are organized this way, what the naming conventions mean, which templates to use when — lived only in her head. About 42% of job expertise is unique to each person. When they walk out, so does that knowledge.
Sometimes it hits when you’re trying to move fast. A competitor launches a feature you’ve had for six months, but nobody knows because it’s not documented. You scramble to publish something, anything. A month later, support is drowning because the rushed docs missed three critical edge cases and now users are confused.
The damage compounds. Your support team becomes a human knowledge base, answering the same questions repeatedly — questions that should have been handled by documentation people no longer trust.
The real cost
Documentation debt doesn’t just slow you down. It actively damages your business in ways that are hard to see until you add them up.
People leave. I’ve watched tech writers burn out not because the work was hard, but because they spent their days fighting knowledge chaos instead of actually writing. Every person who leaves frustrated takes their expertise with them. Replacing them costs 1.5 to 2 times their annual salary, and that’s before you account for the lost knowledge.
If losing one person means critical knowledge disappears — what they call a “bus factor of one” — you’re in trouble. You might not know who that person in your team is until they give notice. Is it the writer who set up your content architecture? The engineer who documented your API three years ago? The support lead who knows why certain processes exist?
Productivity drains away gradually. When people can’t find information, they waste time searching. Or they give up and recreate work that already exists somewhere. McKinsey found employees spend 19% of their workweek just looking for information. For a 50-person team, that’s nearly 2,000 lost hours every month — hours you’re paying for but not getting value from.
New hires ramp up slowly. Without clear documentation, onboarding becomes an oral tradition. What should take a month takes three because everything has to be explained person-to-person. Your senior writers spend their time teaching instead of writing. Your new hires spend their time confused instead of productive.
In 2022, Southwest Airlines canceled almost 17,000 flights when its crew scheduling system buckled under holiday chaos. It wasn’t just a tech failure — it was documentation debt coming due. Years of tacit knowledge, half-documented systems, and invisible dependencies made recovery slow and painful.
The bill: over $700 million and a massive hit to trust.
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The solution exists — structure, processes, tools built for those processes. Professional documentation platforms like ClickHelp are designed around workflows that prevent this kind of drift: version control, review processes, content reuse. But knowing what you need and actually implementing it are different problems.
A couple months back, we built an experimental AI tool to help teams stay on top of documentation updates. It flopped. Not because it didn’t work — it did exactly what we designed. It flopped because we’d misunderstood what the actual barrier was.
Want to hear what we learned? Join our webinar on October 28: System over symptoms: What a failed AI experiment taught us about fixing tech docs.
Webinar
System over symptoms
What a failed AI experiment taught us about fixing tech docs.
October 28th, 2025, 11:00 EST / 17:00 CET
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Ian Avilov
Product Manager at ClickHelp
