Building collaboration into annual planning: An experimental new approach

Collaboration is something near and dear to our hearts at the Wikimedia Foundation. It is the secret ingredient that brings life to our projects; it allows us to draw on the diverse wisdom of everyone involved so that we can get closer to our vision of a world where everyone has access to the sum of all knowledge. It is so important to us that it is enshrined in the organization’s values.
Given that, we at the Foundation decided to approach our annual planning—the process where we hash out the work we anticipate doing in the coming year—a little differently this time around, by making it much more collaborative. Many more stakeholders across the organization were involved, and we designed the process with the intention of supporting different parts of the organization to share as much information as possible, discover where plans were competing or overlapping, and generally bring us all closer to shared understanding and alignment of our programmatic plans.
As we have done the past few years, we also involved the Wikimedia community through the Funds Dissemination Committee (FDC). Feedback from the FDC on the upcoming year’s plans was published on May 15. In addition to helping the organization plan its annual budgets, this process also allows us to communicate and validate our high-level plans with our stakeholders outside of the Foundation.
Traditionally, defining an annual plan for an organization happens amongst the highest levels of leadership and is handed down to the rest of the organization to execute. But the Foundation is not a traditional organization, and we wanted to see what would happen if we expressed our values through how we approached our planning. We knew it would be difficult – as anyone involved in our projects knows, collaboration is rarely easy. But our hypothesis was that we would end up with a better, richer annual plan that was better understood by our staff and stakeholders, and more coherently aligned across the organization.

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The cornerstone of our effort to make annual the planning process more collaborative was the annual plan Collaboration Jam (nicknamed “The Collab Jam”). The Collab Jam was a three-day event in late February organized and facilitated by Kristen Lans and Arthur Richards with additional support from the Team Practices Group.
According to the English Wikipedia article on “Jam session”, “to ‘jam’ is to improvise music without extensive preparation or predefined arrangements … [jam sessions] are often used by musicians to develop new material (music) and find suitable arrangements.” This is precisely what we hoped to achieve with our plans, rather than with music. Our goals for the Collab Jam were to:

• Develop shared understanding between program leads of all the proposed annual plans
• Identify where there’s thematic overlap and/or divergence between programs
• Identify interdepartmental dependencies across all programs

In addition to these goals, the event offered participants an opportunity to learn about new ways to flex their collaborative muscles through experiencing a variety of participation formats and activities designed to support collaboration.
The event was timed early in the overall planning process when plans were in an initial draft form. We did this with the hope of identifying where there might be overlap and/or divergence in plans, as well as interdependencies, early on in the process before people spent a lot of time developing plans that would later need to be reworked to account for these things. The downside to timing it this way was that there was some important information that was not yet available to those responsible for their department’s planning. However, we hoped these early conversations would set the stage for ongoing coordination between departments as new information came to light and plans took shape during the course of the planning process. Representatives from each Foundation department engaging in programmatic planning (Legal, Communications, Advancement, Product, Technology, and Community Engagement) attended the in-person event.
On the first day of the Collab Jam, we organized a “trade show” activity, where each department had a station where they would present their draft plans. At timed intervals, the participants in the event would rotate to a station to listen to departmental plans, ask questions, and share any information they had that might be of value to the presenting department. This gave everyone a chance to hear the initial plans of each department and provide meaningful feedback and information that might make the plans clearer, more realistic, and aligned.
On the second day of the Collab Jam, the representatives from each department reviewed the feedback and information they received on Day One to get clear on what they might need from other departments, as well as what other departments might need from them relating to their plans. This served as preparation for the third and final day of the Jam, where the goal was to identify  interdepartmental dependencies to support better decision-making throughout the remainder of the annual planning timeline.
For the third day, we set up “MegaGrid”—a large Kanban board where everyone would be able to track all of the conversations they needed to have. Participants populated the board with post-it notes describing the conversation they needed to have and with whom. As the day went on, participants would move the post-it notes along the board depending on the current status of the conversation: to-do, doing, done. This gave visibility to everyone about what work was left to be done, and helped people identify which conversations they should try to have next. We also added a competitive element to the day by saying that departments that resolved the most conversations would win the Collab Jam (congratulations to the Foundation’s Legal team!).
Feedback about the event from surveyed participants highlighted learning, fun, and the usefulness of the format as strengths. Areas for improvement largely focused on making sure that the right people are in attendance, and that the event occurs at the right stage of the overall annual planning process. We expect that this year’s retrospective on the overall annual planning process will provide more feedback on the learning, value, and overall utility of the event for annual planning at the Foundation.
Arthur Richards, Senior Agile Coach: Organizational Collaboration, Team Practices
Kristen Lans, Director, Team Practices
Wikimedia Foundation