Thanks for writing this up, I agree entirely.
We’ve had a few years now to convert to an “all online, all the time” mode of operation, but ultimately there are some kinds of discussions that really do require a room full of people. What we’ve been doing in these threads is sometimes called “level-setting,” where a group of diverse experiences have all identified a single problem but need to reach a common understanding of it before any unified forward movement can begin.[1] So far, I think we’ve handled it incredibly well for an online discussion.
What seems to be the ideal (for most people) for these kinds of discussions is to be physically co-located for an extended period (~days to weeks, depending on the scale - I’d expect days for this one) and producing some concrete artifact at the end of it. Less ideal is to have regularly scheduled meetings in amongst other distractions, and at the bottom end is to have an online-only, text-only, open-invite discussion without a specific goal (sound familiar? 
)
Since we haven’t even agreed upon a suitable goal (I give examples below), it’s going to feel like we’re making no progress at all. Especially since we’re all in such different places on the whole issue, so there’s a lot of level-setting required. And also because people arrive late to the discussion, sometimes don’t read everything preceding their arrival, and so we have to restart all the context for them.[2] It’s very hard to do this without sounding (or becoming!) exasperated, and unfortunately that affects the tone for everyone else in the discussion even when they are up to speed.
In terms of deliverable or a goal, it’s fairly typical to produce a document or two of some kind. For example, when I participated in Microsoft’s response to dependency confusion, our goal was an internal policy document and an external guidance whitepaper. But it took six months of regular 2-3hr meetings between 20+ stakeholders to establish what needed to be in those, let alone what was accurate or useful to put in them. A lot of that time looked very much like our packaging discussions have been, so I’m also not concerned about how we’re doing
The pypackaging-native site is another great example of a possible goal (well, not now that it’s been done 
). A survey of the problem, summarised and presented in a way that lets anyone discover the context without having to have been part of the days of discussions to get all the information out. I hope that one of the results from our discussions will be like this, and we definitely made progress toward agreeing on what we recognise as the fundamentals of the problem.[3]
So yes, I’m feeling positive about the discussions. I’m a bit sad that I’m likely to miss all the in-person chats that will happen at various US-based conferences this year (though hopefully I can make some of the Europe ones), because those will be very beneficial. However, I would like to see us at least agree on a goal, which I assume will be some kind of document for us to refer to as the discussions move from level-setting into brainstorming, design and planning.
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Get everyone “up to the same level” while also collaboratively figuring out what that level is - hence, level-setting. ↩︎
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One of the biggest advantages of online-only, text-only is that literally all the past discussion is available for people to catch up with. If you miss the first day of in-person talks, you’ll be lucky to get a formal summary. ↩︎
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Because the complaints aren’t the fundamental problem. Complaints are typically [best to treat as] cries for help because of the fundamental problem, and so while we can and should respond directly to the complaint to treat the symptom, we also are the ones who need to dig deeper and find and fix the root causes. ↩︎