Some initial thoughts. I think it'll require slightly different strategies for more user-focused documentation versus more developer-focused documentation. In both cases:
- Concentrated effort to reduce the backlog. There are 116 open issues on the docs repository right now. I haven't looked through and seen what I might be able to help close. I should. I'm sure there are others who could just use a little encouragement or a reminder about the docs.
- Some sort of workflow so that, for example, releases on Github are linked in a checklist for "add to documentation". Consolidate in one place a running list of software updates and changes so that it's easier to keep track of what needs to be added to the documentation.
- Possibly adding "coming soon" sections to the docs when things are added to the roadmap. These could serve as a visible flag of a needed update. It also might be easier to think about integration into the docs right when you are also thinking about integration of a change into the software of the project.
For user-focused:
- More guidance on contributing to the documentation. This has already been flagged, see issue 825.
- Social engagement campaign to encourage people to contribute or at least highlight problems/short-coming. A friend started #ValidationFriday on Twitter to encourage people to help check existing OpenStreetMap data (that may have been created by new mappers), and not just trace new features. He does a great job coming up with puns and light-hearted references to current events that helps draw attention to the task.
For developer-focused:
- I haven't needed to use these, so would need to talk with people about it.