Although the term "meetup" is being used here, it would probably be best to think of this as a community visioning group, or a brainstorming session. Meetings should have a relaxed feeling. Feel free to invite partners or friends, and avoid a "classroom" feeling. This should be a creative process!

General Best Practices

Key considerations:

Document who attended
Present this as a community oriented process, not as a “top-down” process.
Empower people: if you find there’s something that your group can do and is willing to do, then do it!
Follow-up: Keep in touch and continue to refine your ideas.
Report out! Post finding, ideas, and stories on http://strategy.wikimedia.org.

Finding a group

In some cases, groups that meet to discuss strategic planning will be previously formed (for instance, a chapter). In other cases, you may need to form them. Some ideas:

Look for people on a local mailing list and post there to find out who might be interested.
Ask about a geolocating site-notice who to ask? where to ask?
Search userpages for active users in your immediate area

The perfect place

The perfect location can be anything:

A local coffee shop
A classroom at a local college
A community center
Your living room
A park
An IRC chat room (you're welcome to use #wikimedia-strategy)

Meetups specific to the strategy project

Opening exercises

It’s important to have a time for participants to introduce themselves; you may find it valuable to find a way to get past the tendency to introduce as “I’m X, from Y” and get to know each other personally.

Provide sheets of paper (11X17 or larger) and markers. Ask participants to silently draw the answers to the following questions.:

1. What does a community-driven, strategic planning process look like?  
2. How do you envision your role in this process?  
3. What excites you about our challenge?  
4. What would be the outcome of a successful, strategic planning process?

Allow 15 minutes for drawing, and then reconvene in groups of 4 or 5 to discuss what each participant drew. Some examples from a previous workshop are posted at http://www.flickr.com/photos/blueoxen/sets/72157621968831576/

Or

Ask participants to introduce themselves and tell the group about two things that make them smile, or two things of beauty.

Process Overview

Express the purpose of the meetup. Is it to work on a particular issue? It it to create a set of recommendations around a particular Emerging Strategic Priority? Is it to discuss the role of strategic planning in general? Is it to create a specific task force? Document this goal and publish it with your report-out.

Provide an overview of the Strategic Planning Process:

Phase I: Level-setting

This phase starts with the question, "Where is Wikimedia now?" We'll be encouraging stakeholders to engage with this process, and we'll be applying a variety of research methods to gather input and establish a shared fact base (hence the title "level-setting") to provide context for the planning effort. Our goals are to synthesize what we collectively know and point out the gaps in that knowledge. The Bridgespan Group will gather this information and develop a guiding paper for the next phase of this process. The paper will be published on this Wiki on October 1, 2009.

In particular, we will be:

Creating and maintaining the space for this conversation and work to happen (this Wiki).
Developing an outreach plan to engage with as many stakeholders as possible.
Collecting and discussing proposals, and encouraging people to implement what they can and what they care about. (See Proposal:Call for Proposals for an explanation of why we're doing this, and what we hope will emerge from this.)
Developing a fact base.
Putting out a broad call for participation on September 14, 2009, which would include applications to participate in task forces for Phase II, starting on October 8, 2009. (See below for details.)

More details at Process/Phase I.

Phase II: Deep dives

We expect this phase to run from October 2009 through December 2009.

We'll be synthesizing input from Phase I into insights, recommendations and options for the Wikimedia movement and stakeholders (including the Wikimedia Foundation, Wikimedia Chapters, and so forth).

We'll pose strategic questions to task forces, which will be formed principally from the current Wikimedia community, but will also include external volunteers bringing specific expertise to certain problems.

In addition, the community will have the opportunity to evaluate both proposals and the key questions gathered in Phase I.

Phase III: Synthesis

We expect this phase to run from December 2009 through March 2010.

The Strategy Task Force (as described in Task forces) will be evaluating and synthesizing the different recommendations from the Task Forces into a cohesive document on this Wiki. All participants will have a chance to contribute to the discussion and development of that document.

Phase IV: Business Planning/ Call to Action

We expect this phase to run from January 2010 through July 2010.

Based on the recommendations that emerge from the synthesis, we hope that people in the community will start committing to the different roles and responsibilities that emerge (in addition to continuing to iterate and refine the work done in phases I through III).

The Wikimedia Foundation, for example, will be developing a business plan with the help of The Bridgespan Group, where it will decide what role it needs to play in this higher-level strategy and how best to execute those roles.

Take Action

Visioning 1: Using the stakesholders listed at Wikimedia_stakeholders, discuss how to best involve each set of people in the strategic planning process. What are the costs inherent in contacting each group? What is the best way to engage each? What are the challenges that are likely to be encountered? What groups may have been forgotten?

Visioning 2: Ask participants to discuss their vision: what will Wikimedia look like in five years? What will the wiki movement or the free culture movement look like in five years?

Task Forces: Ask participants to decide what three subjects most interest the group, and form ad hoc task forces around them. What resources can the Foundation or participants in the strategic planning process provide? What is the mandate (the clear goal) of the task force? Form a task force, publishing the mandate and the membership on the strategic planning wiki. Report back the results of the task force’s work.

Other questions: What other questions are important to your group? Document the questions and the answers and provide them on the strategy wiki. What local concerns should be addressed? How does the strategic planning process affect your chapter?