What idea(s) do you have for what the new structure for the U.S. and Canada Wikipedia Education Programs could look like?
Wikimedia ambassadors will come to academics, schools, and other institutions with prepared curricula: suggested activities, data showing the efficacy of previous initiatives, help documentation for students, etc. In the case of colleges and universities, on-sight ambassadors (students, employees, alumni) will already be lined up and trained to give presentations to professors and the administration of educational institutions.
Projects should emphasis collaboration and access to open knowledge. In my experience as a Campus Ambassador, there is no continuity across semesters and projects have only involved one class of students. Future projects should encourage contribution across semesters, universities, public institutions (libraries, museums, etc.), and different Wikimedia Foundation sister projects rather than exclusively Wikipedia. For instance, a project about the U.S. Old West can involve photography students taking high-quality photos from a local museum to upload to Commons, library science students archiving documents to Wikisource, and history students generating articles on Wikipedia. Contemporary topics can include journalism students writing on Wikinews as well. Collaborators don't have to be at the same university or in the same course--all collaboration is done real-time across several Wikimedia projects throughout a semester.
To this end, there should be a more permanent structure of academics, administrators, and Wikimedia volunteers who are on-going members of a structure to administer projects. The precise number and ratios aside, a board of something like 12 members (e.g. four academics, three administrators from galleries/libraries/museums, and seven Wikimedia-associated personnel: WMF staff, trusted editors, developers) will serve for one-year periods. At the end of their tenure, they can decide to run again or nominate new members to replace themselves. This more-or-less approximates stewards with the exception that there would have to be members from the academic as well as the Wikimedia communities and that the number of members does not have to be fixed. This organization should be mostly self-propagating with members taking it upon themselves to find replacements and police themselves in creating projects or proposing new members. In terms of legal and tax structure, I can't speak to whether this should be a part of the WMF or some independent structure that collaborates with them.
How would you ensure this new structure involves all key stakeholders, including academics and the Wikipedia community?
Any project should be tailored to the strengths and interests of the institution or academic being courted: a successful project could be useful for a CV or innovative use of technology could secure grant money. In my experience, several educators are willing or interested in using Wikipedia as a resource, but they simply don't know how: if high-quality curricula were presented in the first place, it would make more academics interested in long-term commitments to using Wikimedia Foundation projects in the classroom or for their own research.
Projects that have a widely-distributed network of collaborators are more likely to sustain themselves as they don't rely on the interests of one class of students or professor.
Archives of past projects can be saved on Wikiversity and Wikibooks. High-quality content can be amalgamated at Wikibooks for use in future projects and these textbooks can be used as actual instructional material. Furthermore, the quality and success of such projects can be hosted at Wikiversity--fulfilling the scope and promise of several Wikimedia projects simultaneously.
What are potential pitfalls of this approach?
The burden falls upon Wikimedia volunteers to create the presentational material in the first place and they are the ones with the least material incentive to do high-quality work. As with all collaborators on Wikimedia projects, volunteers have to be interested in free knowledge and be willing to give their time and expertise.
Metrics and studies for what constitutes effective projects will require long-term study on the part of academics themselves. Who will determine what constitutes an effective project and how that will be measured will itself require courting academics to investigate this data. (The incentive may be that they can get their graduate degrees or write publications of their own.)
Any other comments about your proposal?
The emphasis on collaborating across time, space, and sister projects is the real strength of this proposal. Individual contributors will be more likely to keep on contributing after their semester is done if they have a deeper connection to the Wikimedia community. Instead of having a series four-month assignments experimenting in isolation, I believe that creating continuity between different projects will enhance quality and quantity of experiments using wiki collaboration in the classroom.
