Most teams spend hours documenting everything.
Notion workspaces. Confluence pages. GitHub wikis. You name it.
But here’s what happens:
☑️New hires still get stuck. ☑️Devs still ask questions that are, “Somewhere in the docs” and crucial context gets lost.
This is the Documentation Paradox: The more you write, the harder it gets to find, trust, and maintain what actually matters.
Conventional wisdom says, “Async teams need tons of docs!”
But I’ll say: More docs often mean less clarity.
Here’s why:
First, there's the maintenance burden.
Every line of documentation is a liability that needs updating as your codebase evolves.
How many teams actually do that?
Second, comprehensive documentation creates a false sense of security.
Teams believe they're covered because it's in the docs somewhere.
What you should do is treat documentation as a conversation, not an artifact.
Use tools that make updating docs as easy as sending a message.
Encourage annotations and questions directly in the documentation.
And remember the 20/80 rule: 20% of your features generate 80% of questions. Focus your efforts there.
The goal isn't to have everything documented – it's to have the right documentation that actually helps your team move faster.
This is why every Rally session lives forever inside Jira
No more sorting through old Slack threads.
Every discussion stays tied to the task, so your team’s knowledge grows with the work—not in a dusty folder.
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