As we prepare for the next round of strategy planning, it is important for everyone who has cared about the previous incarnations of this process to share their reflections on what we have accomplished, where we are going, and what parts of the grand mission we've been ignoring for too long.
Slices of plans, 2010-2012 
- global, gender
- Tech rollouts
- Notifications (enwp)
- Discussion of sorting projects by awe, pushing out capacity to run with them.
- Gather links to docs/templates. (from mail: , ?)
Quick thoughts 
- Wikimedia's strongest opportunity today is to define what access to knowledge means in practice, and choose parts of the implied problem space to tackle first. No other group on the planet can speak to this with as much impact, even though we don't use that phrase.
- My own priorities for advancing the WMF's goals are to make the foundation less fragile, to expand the types of knowledge the projects organize and illuminate, and to expand the types of audiences helped/engaged (readers, contributors, and reusers).
- Less fragile here means four things : support by a network of independent friends and collaborators; more diverse long-term funding sources; broader support from skilled volunteers in most areas of organization; and a more modular structure, so that core operations improve even as peripheral initiatives come and go.
- The current foundation goals are deceptively broad. It is worth separating strategy for the current WMF as an entity (which some will say can take on a limited number of initiatives at a time), from strategy for the world's inhabitants to most effectively further its goals.
- Wikipedia's greatest strength lies in its empowered community of contributors. We have only begun to tap into what this means, or what it could enable in the future. Clear guidance, good community standards, and a sense of shared ownership of their work and goals are important.
- The Foundation both focuses in part and dissipates in part this strength. Focuses for instance by facilitating clarity, predictability and sustainability, and communication. Dissipates for instance by taking ownership of things the community is implicitly unable to do. [Although one can imagine replacing "is unable to do" with "requires certain measurable skills and capacities and commitment to do"]
Concerns with the current process 
- setting the right initial balance of community ownership/engagement and structure in this process,
- including recognition of all the work, in various places and languages, that has gone into strategizing in the past
- including a core group? focus? to discuss/review/interpret mission and vision guidelines.
- Slight changes in vision and interpretation can open up (or close off) channels of millions of new contributors and billions of new readers.
- Interpretations of shared vision help people to feel identity and become part of a larger movement; to associate our work with empowerment to contribute and not just a useful website; and to find and direct endowment efforts.
Some specific questions 
that I don't have answers to (and have only recently formulated as such)
Frontload an outreach and motivation phase 
I want to explicitly request an additional phase (2 months? starting now) be added at the front of the strategic planning process. What's a general way to make such meta-requests of WMF plans? see the point below about more public drafts of currently internal work and plans (when the result is meant to be a community discussion). Spend this beating the bushes for active strategy efforts on the 10 largest wikis, outreach to non-wikipedians who care about the topic, and developing community buy-in to the idea that centrally organized planning will add value, before defining how it will work.
- Ask for input without providing a template, before laying out a draft which might be taken as fixed.
- This captures the spirit of open collaborative planning, which would be lost if there is unclear process ownership
- Encourage input that leads to ideas which can't be covered in a 5-year planning session. Identify ways in which such ideas are different (timeframe, audience, novelty, lack of specificity?) and create a space to develop them. The capital Planning Process will certainly not cover all of the strategizing that already takes place on the many projects; it needs to define its own boundaries to help clarify its purpose (the scope of its final documents).
- Specifically distinguishing time-bounded strategic commitments from more organic work is one boundary; timeframe may be another... others may emerge over the course of the year if not at once.
* NB: The whole process of defining and sharing plans is a bit opaque, since it starts in an office of staff mott of whom are not active wiki editors (and may not be very comfortable with plotting out where to put things, how to deal with responses on-wiki, &c)... and at some point switches over to being posted and discussed publicly with little active input from those same staff, who are busy with other things.
long-term sustainability from every angle 
Where are discussions about long-term sustainability planning? I really want to see serious Endowment planning, and contingency plans that include "How to run Wiki[p]edia on a shoestring". Is there a relevant thread somewhere / where to start one? Endowments and long-term support should have roadmaps.
- Types of sustainability, from above: support by a network of independent friends and collaborators; more diverse long-term funding sources; broader support from skilled volunteers in most areas of organization; and a more modular structure, so that core operations improve even as peripheral initiatives come and go.
- Note that if organization size and short-term support grow hand-in-hand without corresponding improvements in contingencies and long-term support, the projects as a whole grow less stable.
Broadly improved mirrors and research clusters 
What active discussions are there about more and better mirrors and research clusters?
A number of research groups would like to support such a thing, providing dump mirroring, stats generation, &c. in a way that many researchers could access the results, run their own scripts on central servers, &c. As an example, the Harvard-MIT Data Center provides permanent hosting for similar sets of public data, and clusters on which to run stats and other scripts.
- I personally want to see more than a few major mirror sites for WP and Commons dumps. There is no reason for there to be fewer than a few dozen which are kept meticulously up to date, and there should certainly be well-seeded torrents of larger datasets such as the commons images.
- Resources to fund/staff related projects should be available at a number of research centers, particularly those on the internet2 backbone.
Sharing draft community ideas 
Is there a way to make http://wikimediafoundation.org/wiki/Special:RecentChanges more active, by including drafts of ideas working through the foundation staff? I'd like to identify barriers to doing this and address them. (Those I know of include the desire to avoid public confrontations, or to avoid wasting time responding to questions about unfinished thought)
Advantages to early, frequent publishing:
- projects such as the usability project don't get much actual input in the structure / timeframe requested despite being of almost universal interest to readers and editors
- drafts that never make it off the drawing board can inspire other good ideas; and some never make it off
- publishing drafts is what wikis are made for. If this is painful, address the root of the cause, not the symptom - fix the broken parts of community response, pick out ombudsmen to address back and forth about such material, &c.
- while the structure and division of internal writing recapitulates internal org structure, the optimal division of labor in the community will not. minimize this founder effect by minimizing the incubation period.
Drawing in ideas from new audiences 
- Currently the audience of readers and editors is definitely not a balanced cross-section of society. It is heavily biased towards younger tech-savvy men, among other things. How can we draw in opinions from people who are currently carved out of the project and their feedback loops entirely? At a less absolute level, how can we increase participation from those who don't partake in meta-discussions, but are deeply engaged in reading, reuse in their lives, or editing?
- Start with an agile iterative planning process with test-driven strategy development... http://www.youtube.com/watch?v=l1wKO3rID9g
More seriously, for embracing people beyond our current meta-contributors, we could have fun and compose a "what should Wikipedia become?" teaser and a painless way to submit an idea. Customize the teaser for a few major audiences:
- professors, scientists and students
- readers, authors, and librarians
- artists, music and pop culture lovers
- wikiaddicts (on WP, other mediawiki sites, other major wikis)
- inventors, analysts, futurists
- business, government, and legal leaders
Have an online submission form for people who wouldn't otherwise be comfortable leaving a note on a wiki, which posts the results on a wiki discussion page and doubles as a nice membership drive - asking for optional account info afterwards.
Get some inventive artists to help with postcard images, find sponsors at major websites and physical institutions to post badges on their websites or print their own little cards. Get sites devoted to idea generation to host their own short contests for the best suggestions. Encourage the current community to pass this on to their secondary communities (stastistically, those should be better balanced in almost every dimension. my mother for instance would draw in her music history friends and doctors' and pediatric organizations). Post on forums of groups with shared interests -- all of the shared knowledge, open education, and free software groups -- to think about our known biases (link to stats) and share this request for comments appropriately.
Invite specific thoughts and comments from presidents, rock stars, authors, encyclopedia editors-in-chief (I'm thinking of Kaczorowski), ship-steering captains and CEOs that will inspire casual readers to read more than a sentence about the request. [great for site notices and blurbs of all formats]
Outreach to those interested in WP variants for educational niches 
Every major field has a leading light who would like to see a wikipedia variant that will better address her own work [a proper source compendium for local laws, a monitored compendium of medical advice, a catalog of published works, &c &c], and most have individual funded projects that struggle to launch single-topic wikis. Direct input from them is better than browsing the web, discovering their fledgling projects, and writing the webmaster email.
Find advocates from existing initiatives 
Troll the concept space of existing WP initiatives in different languages and editing circles. There isn't yet a Long-Range Planning WikiProject but there's no time like the present. Ask each niche initiative to find a non-wikipedian interested in helping the project connect with creative minds who work diligently on knoledge-sharing and can help it grow.