Several years ago, Clay Shirky gave an excellent talk titled "A Group Is Its Own Worst Enemy." (Link is to lightly edited text version of talk.) I just noticed that I had never linked to it from this blog.
I've liked pretty much everything I've read of Shirky's. But I particularly like this piece.
Some tidbits to whet your appetite:
[W. R. Bion] said that humans are fundamentally individual, and also fundamentally social.
[...G]roups often gravitate towards members who are the most paranoid and make them leaders, because those are the people who are best at identifying external enemies.
Now you could ask whether [this problem a BBS encountered] was a technical or a social problem. [...] But in a way, it doesn't matter, because technical and social issues are deeply intertwined. There's no way to completely separate them.
As a group [...] begins to think that the group is good or important, the chance that they will begin to call for additional structure, in order to defend themselves from themselves, gets very, very high.
The informal part is the sense of "how we do it around here." And no matter how [the rules are] substantiated in code or written in charter, whatever, there will always be an informal part as well. You can't separate the two.
The world's best reputation management system is right here, in the brain. [...] Almost all the work being done on reputation systems today is either trivial or useless or both, because reputations aren't linearizable, and they're not portable.
If you want a good reputation system, just let me remember who you are. And if you do me a favor, [...] I'll just get a good feeling next time I get email from you; I won't even remember why. And if you do me a disservice and I get email from you, my temples will start to throb, and I won't even remember why. If you give users a way of remembering one another, reputation will happen[....]
There's lots more good stuff in the full talk; the above isn't a summary, just some of the lines I particularly liked.
Sure, I have a few nitpicks. He might've mentioned APAs in that opening section, for example, and I think the analysis of party dynamics is a little oversimplified, and there are plenty of very small Yahoo groups that are not at all failures, and I disagree with him about anonymity and the lessons of the Kaycee Nicole incident; and although some bits of his discussion are dead-on descriptions of mailing lists I've been on, there are some bits that he says are essential/inevitable that haven't actually happened on some long-lived mailing lists I've seen. And I'm not convinced that his solutions are the right ones. And so on. But setting those small points aside, there's a lot of fascinating food for thought in this piece.