Thank you to everyone who has replied! I have uploaded the resulting responses:
Some of my take aways:
Respondents
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Most of the respondents are people already participating to the sprints: 13 out of the 17 responses (76%) submitted a response during the last check-in.
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We thus didn’t have a lot of responses from core contributors who don’t submit check-ins, whom we were especially interested in, to understand how to make them more useful to everyone – but we still get some insights on the topic. If you’re one of these core contributors, don’t hesitate to comment on this, to get your insight and confirm/amend conclusions about this.
Sprint & check-ins rating
Among the ones who did participate, the average rating for the experience on a scale of 0 to 5 is 3.75, or 75% – which is not bad for an initial iteration, but could still use some improvements. It has the following distribution of answers:
Missing check-ins - lack of time for contributions?
The most common reason invoked for not posting the check-ins is the lack of time to make contributions, which would make the check-in useless (note: it isn’t useless - it helps us to know that already). It is the reason invoked for 2 of the 4 responses without a check-in, and came up a few times in response to individual emails I’ve sent to some of the core contributors who weren’t posting check-ins.
So it looks like the lack of time of core contributors is at least one of the main issues at play, when considering the proportion of check-ins that aren’t submitted – and can probably act as a proxy to measure it, as well as the impact of changes made to address it.
Missing check-ins - too much metawork?
Drawbacks to sprints are also pointed out, one of the answers without a check-in remarks that it adds some additional metawork for core contributors: “Sprints are useful, but right now they’re simply one sprint too many in terms of metawork.”
He also points to the duplication of information that’s already on boards: “since most of what I do now can be considered community work, there would be a whole lot of duplication involved in reporting it to yet-another-board”. It’s a fair point that technically since we work in the open, the information about “what has been done” and “what will be done in the next sprint / 2 weeks” should be somewhere already. Though in practice there I don’t think we have tickets scheduled in sprints for all the core contributor work planned, currently? It could be a good goal to have that for everyone.
Though I suspect that even then it would remain useful to sum up and present the work done?
Another direction on this could be to make updates more useful, to be worth the metawork for more people. Ideas are welcome on this. For example, we could do video updates instead of a list of bugs - it could be nice to see/hear it directly from the person, which is more personable and nicer? We do our own async sprint checks with videos at OpenCraft, and it’s a nice way to keep seeing regularly others, even when they are on another timezone. That might increase the interest of the what did you do / what will you do sections of the check-ins, making it likelier that others will read/watch them?
We don’t work together much
The other comment mentioned another issue with sprints, and core contributor work, at the moment: “It’s just seems that everyone is posting about their progress and no one works is related to one another” – which is sadly largely true. Making the work and needs of other core contributors more visible is a step to help, as it should provide more opportunities for collaboration. But those collaborations largely haven’t happened often so far – why not?
Maybe it would make sense to be more deliberate about assigning ourselves as core contributors to the various projects from the roadmap, keeping the number of projects small enough to have multiple core contributors on each?
Check-ins improvements suggestions
I’m not sure when we’re supposed to submit them? I start receiving pings in the middle of the sprint, at which point I haven’t worked on anything.
Yes, there has been some erroneous notifications sent, which have been confusing. They are now hopefully disabled. The real notifications are sent on Tuesday the 2nd week, with until Thursday evening to submit them. It’s not done at the very end of the sprint because we need time to discuss the blockers ahead of the following sprint and the contributors meetup, but you can submit an update for the previous 2 weeks on the day you make that report?
I’m also not sure were’s the documentation for CC processes (when and where should I check in, meetings, other processes)
That is true, currently this is only documented in the current forum thread - it makes sense to document it somewhere more appropriate, I have created a task about this and assigned it to myself: Document Core Contributors Sprints processes · Issue #61 · openedx/wg-governance · GitHub @sarina Where do you think it would be best to put this documentation?
Emphasize collaboration and coordination in the questions. The most useful thing to come out of the check-ins so far for me was learning what Jill was working on, and trying to coordinate with her.
Maybe providing that responsibility to the working groups for a “divide and conquer” approach? So the working groups are their own cells. But during the contributor’s meetup or the core contributors sprints, the purpose of one of the meetings can be repurposed to coordinate between the working groups instead, depending on their needs/availability?
+1 on working on helping collaboration. How would it work with the workgroups exactly, though? We would have each workgroup submit an update for all its members, similar to what we have in the contributors meetup? Why not, and having them all async in the first place could be an improvement over the current purely synchronous working groups updates, where the right people with the information can be missing.
But how would the working groups collect that information from its members reliably? The advantage of the check-ins is that they are in place for everyone, there isn’t the need for each working group to put in place its own async check-ins, which take time to coordinate – instead, working groups can use the information from the check-ins, to build a summary?
Idea: organizations should nominate representatives, instead of having each CC do the reporting. This should reduce the overall burden.
Organizations or working groups? Having one person per organization reporting for them could help in some cases, but the core contributor work is meant to be a personal status and commitment, with hours provided by the employing organization. Though since these hours are the organizations commitments, it could be a way to keep them accountable to hold their promise?
I can only post a check-in when I receive an email reminder – there doesn’t seem to be a place in the UI to post them early.
True, I wish there was one – it makes the experience confusing, especially when notifications aren’t received, or bogus ones are sent. I don’t know of a way to do this with Friday currently, unfortunately.
If anyone has an idea, let me know.
I think if we want this to be more effetive, then it would be better if the sprint check-ins would be involved with CCs from the begging, for example if a CC doesn’t have much to do, whos job is to recommend or assign them a task…
You mean if some core contributors don’t report work for the following sprint, or don’t do enough hours, we suggest tickets or projects to them? That sounds like a good idea 
Also a few comments approving the current check-ins 
I feel they are fine
Having more people filling them
They work well for me as they are. I can’t think of anything that could improve check-ins.
Not sure – they are very useful and take 2 min to fill out.
I think sprint check-ins are fine as they are now.
They seem fine to me.
Synchronous planning/retro meeting
The sycnhronous planning meeting had barely the average rating for usefulness, at 2.5/5 or 50%, and a majority of responses preferred to do everything async (9 out of 16, or 56%). The meeting time was also problematic, as it doesn’t work for 9 respondents (59%). The move to a full async process has already been implemented, and the synchronous meeting replaced by an async discussion of blockers, plus a synchronous discussion of any outstanding point at the contributors meetup.
Keeping the sprints?
At the question “Should we continue doing sprints for core contributors?”, we get 13 out of 17 yes (76%). It’s good to confirm that it’s useful for many! 
It would have been interesting to get this answer from more of the people who haven’t submitted their check-ins. The rating might have been lower – or some the others might have been happy to report contribution work if they had had time available for it?