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Reading/Strategy/Strategy Process

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About Choices Possibilities Tests

Earlier this month, some members of the Reading team spent two days learning how to go through the exercise of "playing to win" methodology of strategy. The meeting, by all means, was not set or designed to come up with a strategy for the movement in two days, in a closed room, by less than a dozen of people - the focus was on learning how to go through the thinking process, how to evaluate our concerns, and how we cascade our choices and solutions for suggested issues. The Reading department is relatively new, with mostly remote staff. Coming together to learn through the exercise was an important step towards systematizing the planning process and aligning the ideas moving forward. We also have a slidedeck from the first meeting and you can check the Q&A for further questions.

Kristen Lans and Jon Katz during the meeting

How the process works

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  • Defining problems,
  • Bucketing,
  • Picking one problem to go through
  • Generating choices for how to over come the problem
  • Generating possibilities that each choice could entail
  • Narrowing down possibilities
  • Defining obstacles that would make the assumed possibilities not effective
  • Designing tests to evaluate obstacles

Step 1: Identifying issues

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For starters the team started by brainstorming pressing issues. In less than 30 minutes a whole wall was already covered with problems. Below is the list. It is understandable that lots of [citation needed] might be brought up. However, due to the nature of the problems, some issues are long standing and crystal clear, or else, qualitative rather than quantitative

  • The below issues were tagged according to 5 themes
Content Delivery (CoD) Partnerships (PAR) Community (COM) Perception (PER) Organizational Capacity (ORG)


  • Identity crisis around reference versus learning ORG
  • We don’t manage change well ORG
  • Balancing resourcing, innovation, and maintenance ORG
  • We are bad with people: communicating and listening. We don’t understand our community of different users ORG COM CoD
  • Because of how giant we are, we struggle to scale. ORG
  • Our decline in North America traffic endangers our fund raising model PAR COM
  • Lack of shared understanding around primary stakeholders ORG COM
  • We have a mentality of “Us + Them” ORG COM PER PAR
  • Being both a tech company + non-profit is challenging ORG COM
  • Factionalism within the foundation + the movement makes it hard to collaborate ORG COM PAR
  • No framework to gracefully handle tension in our world ORG COM
  • As a Reading team we lack diversity ORG COM
  • Lack of understanding around reader/editor relationship PER COM
  • Not effective at problem solving with community ORG COM
  • We have only one way for users to consume content PAR CoD
  • Foundation fails to support non-encyclopedia projects and we are wasting opportunities ORG COM
  • Not doing a good job in partnerships ORG PAR
  • Not playing in the education space, which means our competition occupies and takes away from us PAR
  • We lack a lean-back experience CoD
  • The web is changing and we don’t have a clear understanding of our place CoD
  • People in other countries are not aware of Wikipedia PER PAR
  • Goals of editors and readers are not always the same COM
  • The web has new contribution/presentation methods that are not present in Wikimedia CoD ORG PAR
  • People feel unsure about the quality and accuracy of our info PER
  • Our technical platform needs investment in order to reflect user expectations ORG COM
  • Proprietary web trends marginalize us and lock us out of potential markets and conflict with our values CoD PAR
  • We don’t participate in the creation of standards PAR
  • We’re not engaged in the conversations around open standards PER PAR
  • Competition is better at presenting information CoD
  • We don’t serve our users who don’t speak English CoD PAR
  • Other channels and formats are diverting attention CoD
  • Audiences might veer towards more passive/distracting/trivial activities CoD PER
  • We don’t optimize content for learning across different audiences and different needs CoD
  • No obvious way for readers to engage in knowledge contribution PER
  • We are not playing (visible) in important spaces - educational search engines, social, etc. ORG
  • People aren’t reaching us because of intermediaries (other platforms) CoD
  • Dealing with decline of desktop web ORG CoD
  • Our content is being consumed without participation back PER PAR
  • Readers don’t understand how Wikipedia works PER
  • The world needs better access to open knowledge to deal with pressing issues of the day ███
  • Wikipedia has failed to become relevant on mobile presentation-wise CoD
  • People need trusted, easy-to-understand information that could impact quality of life PAR
  • Wikipedia is not seen as an authoritative source PER
  • We don’t have partners PAR
  • We don’t know what we should partner on PAR
  • Too many possible partnerships PAR
  • We don’t partner with the largest syndicator of our content in a measurable, impactful way CoD
  • Users are not reaching us and the web is getting more closed PAR
  • Third parties may be diluting our content CoD PAR
  • We know there are pipelines but not how to leverage them PAR
  • Not enough local content PER
STEP ONE: For the themes below, think of what choices do we have that can solve the problem, add your choices here

Step 2: Clustering

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The eight themes emerged from the above problems those where:

Lack of feedback loops that effectively incorporate a variety of users We don’t have a shared vision for the next generation of user experiences Lost opportunities when users access content through third parties We don't understand our variety of community of users External Perception: people don't understand how Wikipedia works Organizational Capacity problems and lack of efficient framework of collective decision making The web is changing while squashing our values Our core capabilities, infrastructures, and workflows are not optimized for emerging platforms, experiences, and communities

Step 3: Partially completing the process on one theme: Our core capabilities, infrastructures, and workflows are not optimized for emerging platforms, experiences, and communities

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The process requires constructing distinct choices to solve the issue, and then deriving possible ways of solving the issue. After describing possible ways of solving the issue, the process requires further exploration about what would need to be true about the industry, customers, capabilities and cost model relative to other players, and the reaction of other players. The following table describes just one potential choice. During the face to face session, the team delved more deeply into just a couple of relatively simpler possibilities from the table:

  • Focus on improving our end user experiences Possibility 1: enable readers to share content to read inside and outside Wikis
  • Focus on enabling others to improve end user experiences Possibility 1: Set of pre-built content for embedding existing Wikimedia content.

These two possibilities are by no means complete strategies in their own right. The team will explore more possibilities. And of possibilities that appear viable as part of a cohesive strategy, the team will construct cascades about the markets, products, capabilities, and management systems required to support such possibilities, as well as some lightweight tests that can be conducted to reasonably determine the viability of the possibilities.

Problem Choices Possibilities
Our core capabilities, infrastructures, and workflows are not optimized for emerging platforms, experiences, and communities Focus on improving our end user experiences.
  • Amazing mobile lookup experience (fast, accurate) for mass market in global north.
  • Optimize experience for users coming from specific referrers (eg. Google, etc)
  • Make a kick ass long form reading experience.
  • Restructure display to focus on media.
  • Strengthen dev advocacy to engage U/X + developer experts to improve reading UX.
  • Enable readers to share content to read inside and outside Wikis
  • Stop focusing on search and emphasize discovery/browsing in UI.
  • Leverage communities to organize related content to create deep-dive educational experience.
  • Create new reading experience tailored for users in the global south.
Focus on enabling others to improve end user experiences.
  • Set of pre-built content for embedding existing Wikimedia content.
  • Grant rich/deep access to inform - platform/tools beyond scope of general reference.
  • WMF-as-a-service: spin WP into its own entity and all/any projects become customers of the service.
  • WMF encourages an ecosystem of frontend experimentation.
  • WMF supports 3rd party dev/design of WMF incubated projects.
  • Project agnostic:
    1. Become THE broker of open access data, targeting specific channel partners.
    2. Messaging apps/platforms.
    3. Media companies
    4. Platform companies
    5. Specific verticals (eg. medical specific wikis)
    6. Including the existing communities
    7. The more data we broker, the more durable

Next Steps

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  • Let's carry on the process together:
    Follow the process, and for our targeted problem think of possible choices. For Every choice, generate a number of possibilities that the choice entails. After than, design tests to verify concerns against possibilities.
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