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Fundamentally, Wikipedia has always had a "people-ware" problem: the distribution of the expertise that is freely donated to the right places. It has been and always will remain its greatest challenge. The amazing thing about Wikipedia is that it managed to do this for so long, such that a valuable knowledge repository can be built up as a result. At first, people simply came because it was the place to be. Now, we have to work a little harder.
We spent a lot of time talking about the best way to model this people-ware problem, either using biological metaphors (evolutionary systems with various forces), or economic models (see last post here). However, one thing to be aware of is the danger of "analysis paralysis", where you spend so much time analyzing the problem, and forget that there are already many ideas that have been generated for moving the great experiment forward.
For example, there are many places in Wikipedia that are not well populated. It's well-known that many scientific and math concept articles, for example, could use an expert-eye to catch the errors and explain the concepts better. How can we build an expertise finder that would actually invite people to fix problems that we know exists in Wikipedia?
Another idea might be to have the whole system be more social. Chris Grams blogs about a part of this idea here. We suggested some time ago to have a system like WikiDashboard, where you actually show the readers what the social dynamics have been for a particular article.
Wikipedia was created in 2001, when social web was still in its infancy. During the ensuing 9 years, it has changed very little, and I would argue Wikipedia have not kept up with the times. Lots of "Social Web" systems and new cultural norms have been built up already. For example, I suspect that many of us would not mind at all to reveal our identities on Wikipedia, and we might like to login with our OpenIDs and even have verified email addresses so that the system can send me verification/clarification/notification messages. The system perhaps should connect with Facebook, so that my activities (editing an article on "Windburn") is automatically sent to my stream there. My friends, upon seeing that I have been editing that article, might even join in.
I think that Wikipedia is about to change, and it is going to become a much more socially-aware place. I certainly hope that they will tackle the People-Ware (instead of the Tool-Ware) problems, and we will see it become an exciting place again.