Thinking of practical ways forward, how about we experiment a bit, and see what sticks? There’s two things in particular I’d love to try to organize if people are up for it:
““Roadmap”” workshop
This would involve brainstorming and voting on ideas for things to happen in the Django universe (core, community, packages). Similar in some ways to Django feature vote spreadsheets of the past, but more community-driven / non-binding, in the spirit of Jeff Triplett’s DjangoCon US Talks I’d Like to See.
I think this would help contributors have a sense of where other people’s interests are in broad strokes. If time allows we could even go beyond the voting; classify the ideas on an impact/effort matrix, discuss timeframes and ways to take things forward (“is this a good GSoC project”, “does this need a DEP”, “should we look for another MOSS-style grant”, etc). Perhaps even discuss risks / gaps (shifting expectations on static typing, deployment, bus factor on a specific module, etc).
Who knows, we might even identify some quick wins for new contributors like Djangonaut Space to take through!
““Sprint”” retrospective
Agile-style, we’d record our different pain points on working together as contributors, and also note things that work well. Spot any commonalities. Have people vote on the ones they relate to the most / think are the most common / worth discussing further.
Then we’d devise solutions on the spot. Or re-assess suggestions like the ones from Jacob at the start of this thread based on how likely they are to help with common pain points.
In essence, I’d really recommend an action-oriented attitude here. We can find meaningful improvements without having to figure out the best process ever!