What’s the biggest challenge you face in keeping documentation up-to-date as your product evolves?
Whether you're a solo builder or part of a fast-moving product team, documentation always seems to lag just behind reality.
Is it the speed of product changes?
Getting engineers or PMs to consistently update docs?
Lack of ownership?
Tooling limitations?
Or is it something else entirely?
Would love to hear your thoughts on this.
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X-Design
It's definitely the "Lack of ownership," but specifically the lack of incentive. I’ve never seen a dev get promoted for having pristine documentation, but I’ve seen plenty get promoted for shipping half-baked features fast. Until docs are a hard gatekeeper for merging PRs (and actually enforced by culture, not just a checkbox), tooling doesn't matter. How do you solve the "boring work" problem without just hiring a technical writer to clean up the mess later?
IXORD
Updating documentation after a product update is a common challenge for many companies :(
Documentation slips because no one feels the pain until a user does. The toughest part is making accuracy everyone’s job, not a last-minute chore.
Honestly the hardest part is the product change faster than anyone can document it. By the time I finish updating one section, there’s already a new feature or tweak waiting. It feels like chasing a moving target, and it’s easy for things to fall out of sync.
Documentation.AI
@shiv_kumar_sharma4 What if, after every push, the agent reviews your code changes and PRDs, then suggests improvements you could review, ask follow-up questions about, or tweak? Will it be helpful?
Continuous updates from a PM would be ideal, but realistically there’s only so much one person can do.
I’m starting to think AI is pretty much necessary , just curious to hear your thoughts!
Documentation.AI
@hee323 We’re running an internal PoC on our own updates. While AI isn’t magic, we’re clearly seeing it can improve things by 60–70% here
Triforce Todos
It’s never the speed of shipping. It’s the speed of forgetting to update things. 😂