Documentation Isn't Broken — It's Just Not How Teams Actually Work

Most teams believe documentation is the solution.

If something goes wrong, the answer is usually:

"We need to document this."

So they do.

They write a page. They put it in Notion. They drop the link in Slack.

Problem solved.

Except it isn't.

A few weeks later, the same questions come back.

"Is this still accurate?" "Did this change?" "Which doc should we trust?"

The problem isn't effort. It's that documentation doesn't match how teams actually work.

1. Documentation Assumes People Will Search

Documentation is built on a quiet assumption: that people will stop what they're doing and go look for answers.

In reality, work doesn't pause.

When someone needs information, they're usually:

• In the middle of a task
• Under time pressure
• Already in Slack or Teams

So instead of searching, they ask.

Search loses to chat every time.

2. Finding a Document Isn't the Same as Getting an Answer

Even when people do search, they don't get what they need.

They get:

• Multiple versions
• Long pages
• Partial context

Now they have a new problem:

"Is this the right answer?"

Documentation gives information. Teams need certainty.

When certainty is missing, people fall back to asking someone they trust.

3. Documentation Doesn't Age Gracefully

Docs don't fail all at once. They decay slowly.

A sentence changes here. A policy updates there. A decision gets reversed—but never reflected.

Soon:

• The doc looks legitimate
• But no one is confident it's correct
• And trust quietly disappears

Outdated documentation isn't harmless. It creates confident mistakes.

4. Work Happens in Chat — Documentation Doesn't

Modern teams run on conversation.

Decisions happen in Slack threads. Clarifications happen in DMs. Updates happen in passing messages.

Documentation lives outside that flow.

Every time a tool requires people to leave their workflow, it loses relevance.

If knowledge isn't accessible where work happens, it might as well not exist.

5. Documentation Doesn't Learn From Questions

Teams ask the same questions repeatedly.

That's a signal.

But traditional documentation systems don't listen.

They don't tell you:

• What people are confused about
• Which answers are unclear
• Where knowledge is breaking down

So teams keep documenting— without fixing the real gaps.

The Bottom Line

Documentation isn't broken.

It's just built for reading, not for execution.

Teams don't struggle because information is missing. They struggle because answers aren't accessible, trustworthy, and available at the moment they're needed.

That gap—between written knowledge and real work— is what modern teams need to solve.

And it can't be fixed by writing more pages.