this post was submitted on 17 Jun 2023
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Personally, I think the biggest challenge with documentation is keeping it up to date.
The only way I've found to be actually up-to-date on docs is to do GitOps and have self-documenting code. That way every change being made is automatically documented with a commit message.
If you can't do that because your tools aren't GitOps compatible, you need management to enforce some kind of documentation rule. Like every time a system gets touched, documentation needs to be updated. A project isn't complete until docs are done/updated.
This is easily said, but in practice it's just not going to happen. You need a team that both actually wants to this, and has the time to do it.
On top of schnapsidee's already correct feedback, if the company is willing to enforce documentation deliverables (which it really should), I've found it important to have a minimal documentation deliverable formulated. Don't immediately overshoot with all the different types and subjects, but find a set of documentation aspects that are agreeable by the company at large as a minimum. You can always increase this later, but it's hard to set the bar too high immediately as that removes any willingness from the organization as well.
You also can't just 'reset' the organization and suddenly do things in a different way. It will need to be evolved into a better documentation structure. Perhaps you could start with just a portal that points to the various existing documentation libraries and services. That can help you identify what types of documentation you have, and perhaps even find a good grouping. Also, try to see what information should be protected (don't want to have passwords laying around, or other risky information) versus which information should be easily accessible.