Strengths and Challenges: Organization

In my post following up on project strengths and challenges, I sorted the requests from contributors into three different groups. I also addressed some of the major communication issues that were identified and I’ve been thinking about how best to manage each of the two tasks I assigned myself.

The asynchronous AMAs are going to have a public Slack channel for collecting questions (#leadership-ama) and public posts on this site with the answers (using the tag #ama).

The Weekly Digest has been a little harder. I have a good idea of the information I need, but it’s been a lot of work from team reps and I always want to be respectful of everyone’s time. So, I was hoping you all would join me in an experiment.

A New Concept of Team Leadership

Let’s refresh our memories of the major organization issues that were identified:

  • Understanding of roles, leadership structures, and decision making
  • Understanding of self-sponsored volunteering vs company-sponsored and how much time any volunteer has available to contribute
  • Proactive identification of issues that could affect the whole project
  • Smoother transitions for component maintainers (both with code and without code)
  • Ways to help WordPress make a positive change in the broader context of the web

These issues (along with a desire to be good stewards of volunteer time and talent), led the Community Team to try a structure that included reps who had training on basic open source/WordPress philosophies as well as some leadership best practices. You can read more about that on their site if you’d like.

I would like to take a cue from the success the Community Team has had with clarifying their roles and structures. I suggest we experiment by identifying single team leads who have training and clearly established responsibilities/expectations.

I think that by doing this, we could clarify what the organization needs from leaders of contributor teams and how to elevate concerns of the teams more effectively. We also “open source” our foundations of leadership and make it easier for contributors to move in and out of volunteering as their time allows. I think we could easily address a lot of worries accepting un-ending maintainership and burnout while we’re at it.

Share your feedback!

I’ve seen this work really well on the Community Team, so to be candid, I really believe this experiment will be a success. I’d love to know what you think of this idea. If you have thoughts about how this might help or hinder the important work we do in WordPress, please share them in a comment on this post!

Our Strengths and Challenges

Hello all, and thanks for welcoming me so warmly. I’m new to this role of Executive Director, but this is my third year helping our wonderful community work together. During that time, I’ve worked with a lot of teams and have been able to see what seems to be working well for most of us.

For the most part, the WordPress contributors excel at:

  1. Sharing knowledge freely, for the common good
  2. Seeking efficient and effective solutions to complex problems
  3. Communicating courteously in our shared public spaces
  4. Pointing out exceptions and possible risks in implementation
  5. Raising concerns about fairness and possible conflicts of interest
  6. Jumping in to help when the need is great

Working with multiple teams across the project has also given me the chance to identify some things we all struggle with. I’ve received feedback from contributors, too, about where they feel more support is needed. Here are some of the places where I see we (contributors of all types) can have the most impact over the course of the year.

For the most part, WordPress contributors need help with:

  1. Coordinating on collaborative work between teams
  2. Aligning our work better to project goals/values
  3. Understanding team roles, leadership structures, and decision making
  4. Clarifying the differences between open source and open commit
  5. Tracking conversations and progress across the project
  6. Raising project-wide concerns more easily
  7. Improving how we recognize and celebrate success

We can start solving some of these things right away (please join me in using this P2 for talking about project-wide work for starters). Others will take some exploration and planning.

What is missing from this list? What kind of support do you need to do your best work? Which of the above do you think is most urgent? Share your thoughts in a comment on this post

After people have had a chance to weigh in, I’ll follow up with some next steps!

Weekly Digest | Week 10

For all teams, maintainers, and contributors: Daylight Saving season is upon us. Many teams adjust timing of meetings based on the EU dates and you can, too! You can learn more about each of these teams at

From the Development Teams

From the Design Teams

  • Shipped: Improvements to the Custom Color Picker.
  • Shipped: The Block Management modal has made an adjustment from “Disabling” blocks to “Hiding” blocks.
  • Discussion: How to show a “hidden” block is still being discussed; please share your feedback!
  • Action: Testing for responsive controls in blocks is ramping up. Read more about the testing plan and how to participate on
  • Action: Design work on the Showcase is underway, and there is a call for helpers.

From the Programs Teams

From the Operations Teams

Open Calls

  • Design
    • No additional calls
  • Testing
  • Development
    • Training needs some theme devs with a little extra time (#, #)
    • Accessibility would like feedback on #29022 and #33030
    • Cron would like a logic check of #44818

Noteworthy Dates

  • Mar 10 – DST starts in the US
  • Mar 13 – 5.1.1 release date
  • Mar 21 – WordPress 5.2 Beta 1 (feature freeze)
  • Mar 31 – DST starts in the EU
  • Apr 7 – DST ends in AUS
  • Apr 23 – Proposed 5.2 release date
  • May 11 – Global WordPress Translation Day 4


5.0 Release Retrospective Kickoff

Even though we are many months past the 5.0 release date, this is one of those times where “better late than never” is true. The few times that a release retrospective has been held, it was hosted on, and consisted of open-ended questions with answers in the comments.

However, as I’ve looked back over past releases, it is clear that code isn’t the only thing that goes into a successful release. So, I’m going to try a different way (kudos to @karmatosed) to hold an asynchronous and open retrospective here on our shared blog/P2.

It’s not entirely possible to do a traditional retrospective in a project this size, so I’m going to try something a little different. I’m collecting feedback in the survey linked below. The feedback that is shared will be anonymized and published to this blog, so if you’re not yet subscribed, now is the time to do it!

5.0 Retrospective Survey

The survey asks for your username, which is specifically for my use in case I need to follow up with some clarifying questions. It’s open for two weeks, until Friday, March 15.

Strengths and Challenges: Follow Up

I really appreciate all of the thoughtful feedback I received on my post “Our Strengths and Challenges”. Many concerns were shared — I’ve done my best to synthesize them below — and I think there are some immediate changes we can make to address some of these difficulties. But first, let’s take a look at what we’ve uncovered.

Shared Challenges

From my reading, contributor requests can be grouped into three areas:


  • Clearly stated project goals and values
  • Consolidation of discussions and needed skills across the project
  • Better coordination between teams
  • Clearer responsibilities and goals for teams
  • Collaborative conflict resolution methods


  • Understanding of roles, leadership structures, and decision making
  • Understanding of self-sponsored volunteering vs company-sponsored and how much time any volunteer has available to contribute
  • Proactive identification of issues that could affect the whole project
  • Smoother hand-off for component maintainers (both with code and without code)
  • Ways to help WordPress make a positive change in the broader context of the web


  • Awareness that active contributors come from all over the globe
  • Better recognition and celebration of successes
  • Understanding of how to participate in vision-setting and prioritization

How Can I Help

As we (the WordPress community) work toward addressing these concerns, I think we’ll see easier planning, a reduction in burnout, an increase in meaningful participation, and easier collaboration.

The communication requests seem to be something I can help with right now. I’d like to start with these two changes:

  • Weekly digest on this site
  • Regular asynchronous AMAs in Slack or on this site (I don’t know the best place to host this)

I would love to hear which of these things listed above you all feel would have the highest impact. Or if you think they will all have equal impact, I suppose. 🙂 Let me know your thoughts in the comments below!

Expanding WordPress Leadership

Today I want to announce two new roles in the WordPress project, and the people who will be filling them. Both of these roles will help me lead the project more efficiently while also making better use of both of their individual talents to benefit WordPress and the web.

First, Josepha Haden ( @chanthaboune ) will take on the role of Executive Director. She will oversee and direct all contributor teams in their work to build and maintain WordPress. Josepha has done a lot of great work in WordPress over the past few years, so many of you will already know her. I’m sure you’ll all enjoy working with her as much as I do.

Secondly, Joost de Valk ( @joostdevalk ) will take on the role of Marketing & Communications Lead. You might know him as a long time core contributor and plugin author. His role will be to lead the marketing team and oversee improving, related websites, and all its outlets.

Please join me in congratulating Josepha and Joost. With these changes as well as the 9 focuses for the year, I am excited about what 2019 (and beyond!) has in store for WordPress.

Proposal: Five for the Future acknowledgement page

tl;dr: let’s increase the number of companies that dedicate employee time to WordPress by building a tool that allows companies to make public pledges of dedicated time.


In 2014, @matt launched the Five for the Future initiative, saying that “organizations that want to grow the WordPress pie (and not just their piece of it) should dedicate 5% of their people to working on something to do with Core — be it development, documentation, security, support forums, theme reviews, training, testing, translation or whatever it might be that helps move WordPress’ mission forward.” WordPress-based organizations responded by contributing more dedicated time to the open source project, which has helped WordPress grow to power 31% of the Web.

A discussion was held at the 2017 WordPress Community Summit about how we could encourage more companies to contribute more dedicated employee time. @liljimmi suggested that if there were a page where all companies participating in Five for the Future were listed, then smaller companies would see that they could have an impact too. This got a lot of people thinking about outreach to companies of all sizes, and how we could encourage participation in Five for the Future.

A year or so later, here’s a proposal that takes this concept and runs with it! Main collaborators on this program proposal include: @chanthaboune, @hlashbrooke, @_dorsvenabili, @iandunn, @angelasjin, @coreymckrill, and myself. Hand-sketches are from me; other mock-ups by @iandunn and @mapk.

Props to Tracy for the idea that sparked this, and thanks to the many people who gave early candid feedback. 

Exceptionally long proposal after the jump!

Project goals

  1. Acknowledge companies that sponsor volunteers to work on the WordPress project.
  2. Motivate more companies to sponsor more volunteers.

Potential challenges

  1. Defining the kind of contribution that would “qualify” for this.
  2. Identifying what contributions come from people whose work is being sponsored by a company.
  3. Deciding what qualifies a company to appear on the page (minimum number of hours, licensing practice, company size, etc).
  4. Holding companies accountable, if we think that’s important.
  5. Defining how we treat companies and sponsored employees on

How do other projects do this?

How do other open source and/or volunteer organizations acknowledge and recruit contributors, specifically support from companies? We looked at the following organizations in a comparative analysis:

Key takeaways

  • Nearly all of these organizations make an appeal to contributors with the promises that their contributions will have a powerful impact, that they will be recognized for their work, and that their work will help the project/organization thrive for years to come.
  • Most open source projects place more emphasis on individual contributors, and don’t directly acknowledge companies that support the project by sponsoring contributors. Drupal is a notable exception to this practice.
  • Gamification is common. Badges are very popular, as well as being able to filter by the most commits (Github is a very common tool for this). Python even gives cash awards to noteworthy contributors.

Possible approaches

Option 1: The activity stream firehose

One option would be a completely automated system. All volunteers would share what company, if any, sponsored their contributions. Contributions could be shown in an activity stream, in which activities are grouped by company, and sorted by the most recent contribution. Additional sorting and filtering options would be available.

A hand-written example of the activity stream idea, with a list of contributor actions divided by company. There is a "sort by" drop-down list on the top right, with the options: company, contributor, activity, and date.

Advantages: No administrative work/moderation needed.
Disadvantages: Information overload; company visibility is low.

Option 2: Curated case studies

Another option would be a page that shares the goal and vision of the 5ftF program. Included would be rotating examples of participating contributors, like case studies curated from a broad cross-section of the open source project.

A mock-up of a Five for the Future page with a header, a short description of the program, and some lorem ipsum, and Featured Contributor case studies (Helen Hou-Sandí and Jan Dembowski) on the right side bar.

Advantages: compelling content, lots of useful information.
Disadvantages: selecting contributors to highlight could be contentious; limited number of companies acknowledged; lots of administrative work to maintain content.

Option 3: Pledged contributions

Companies make a public pledge to dedicate a certain amount of time to the open source project. Then their employees complete and confirm the information about intended team and intended time. All pledges would be public and listed on

Advantages: Company/volunteer reported & verified; would not require much ongoing moderation.
Disadvantages: Potential for abuse/misrepresentation.

Proposed approach

After considering these three possible structures for a Five for the Future program, I think the most effective method is a pledge program: allowing companies to publicly declare how much dedicated employee time they plan to donate to the WordPress project.

This approach would work towards key goals for the Five for the Future initiative:

  1. Recognize the companies that sponsor volunteers to regularly work on the WordPress project.
  2. Ensure a stable contributor base, by motivating more companies to sponsor more volunteers.

The program would allow companies of any size to submit a pledge indicating the number of hours they intend to commit to the WordPress project. After making the pledge, the company notifies its contributing employees, who then edit their profiles to indicate the company that is sponsoring their time. This will allow a contributor’s sponsored time to be credited to the company that is enabling them to contribute much more time than they (presumably) could give, if unsupported.

On their profiles, all contributors will be able to share how many hours a week they dedicate to the project, and on which team(s). If a contributor’s work is part of Five for the Future, they will be able to link to their company’s pledge on their individual profile.

Privacy note: The intent here is that a contributor must intentionally link their individual profile to a published pledge. No matter what a company pledges, the individual contributor won’t show up on that pledge unless they link to the pledge and save. Then the company contact associated with that pledge will have to accept the link — active consent should be required on both sides.

This will help contributor teams identify what people have been pledged to work on their projects, which should help with recruiting people to work on specific, possibly longer-term, team projects. Once a pledge has been made, companies and individuals will be encouraged to keep their details up to date as needed.

A hand-sketched example of a profile, with the added feature of a section on the right-aligned sidebar that says "Dedicated time: (box with "40" inside it) hours to (box with "community" inside it).

Historically, we have recognized individuals for their contributions to WordPress, without connecting that work to their companies, even if their time has been sponsored. By asking companies to make a pledge of time, we hope to offer increased recognition to all parties who actively participate in the Five for the Future initiative.

Companies that have made a pledge will be listed in a public, searchable, and filterable archive that displays:

  • company name & logo
  • company size
  • number of contributing employees
  • number of hours pledged
  • teams contributed to

Here’s an example:

As we receive more information from Five for the Future companies, we can consider whether we recognize companies further by publishing individual company pages. We hope that this will also encourage additional companies to make their own pledges and commit employee time to the WordPress project.

Companies and sponsored contributors will be expected to update and resubmit their pledge after a period of time – this will make sure that the page remains current at all times. For privacy reasons, individual contributors won’t be listed on a pledge unless they choose to link to the pledge. Companies that wish to make a Five for the Future pledge will be asked to agree to follow project etiquette and meet our expectations for promotion on

And another thing…

Despite the disadvantages of the curated case studies idea, that’s still a great way to show organizations what kind of impact their participation in Five for the Future can have. If possible, we’d like to include a case study or two on the Five for the Future landing page on, which would also include some persistent content like: “Why donate employee time to the WordPress project?” and/or “Convince your boss to donate your time to” For case studies, we’d want to rotate the content at least every 6 months. We may want to feature contributors who are doing some of the less “glamorous” or visible work that nevertheless has a strong positive impact on WordPress.

Measuring Success

How will we know this is making a difference — what can we count?

  • number of people whose paid time was pledged to the project
  • number of companies participating
  • percentage of teams with at least 1 sponsored contributor
  • number of pledged hours
  • number of people sponsored at least 20 hours/week ; number of people sponsored for 40 hours/week


We’d love your thoughts on this approach to Five for the Future acknowledgement! Here are some specific questions, but please ask about anything that concerns you, in a comment on this post.

  1. Should we require users to be logged in to to be able pledge? (This would stop spam and make editing easier in the futur.e)
  2. Should we auto-publish pledge submissions, or should a moderator review them first?
  3. Should we set a minimum company size for participation in this pledge program?
  4. Do you think this might help teams find people to work on less “glamorous” contributions?

Marketing Team Update – September 21, 2018

The Marketing Team is a strategic resource for other WordPress teams. We also provide copywriting services. Our volunteers are well-equipped and eager. We work independently using in Trello but use our weekly slack meeting to focus on updates.

We meet in Slack every Wednesday morning at 8:00 a.m. Pacific Time as a catch up on our tasks. However, anyone can chat in our Slack channel about anything at any time.

What is the Marketing Team Doing?

Admittedly, it’s been a while since I posted our last update. Apologies.

Quite a few of the Team Reps were at the Contributor Day at WordCamp Nijmegen and we also promoted Siobhan Cunningham to Team Rep.

Publish. Publish. Publish.

We’ve been publishing like crazy — as fast as an open source collaborative can, anyway. We’d love social shares, feedback, and, of course, ideas.

Closemarketing & Java Traveler – WordPress Case Study

WordPress News Survey 2018 Report

How WordPress Easily Links Content and eCommerce to Complex Back-end Systems: A Case Study

Transforming WordPress for the Modern Newsroom

What is the difference between and

Slide Deck for Meetups: Contribute To WordPress

We’re Here for You

If your team would like strategic advice or copywriting, please ping either me (@gidgey on Slack) or @mcdwayne. We’ll set up a Trello card and get to work.

As always, our meeting notes are published on our blog weekly.


Community Team Chats – September 20 2018

(Note: I am almost done posting four months of chats after a period of inactivity. Unfortunately we couldn’t find anyone in the team to do this task, so bear with me while I update everything!)

The Community Team meets twice a month, first and third Thursday, at two different times to cover different timezones.

Agenda and Slack logs from September 20: 11:00 UTC and 20:00 UTC

Deputy Check-in

All good, busy with tons of applications and we are trying to catch up with those!

P2 posts needing feedback/action

Proposal to Increase the Maximum Ticket Price for WordCamps
Note that we are not telling WordCamps to increase their ticket prices, but we are having a (long) conversation about the possibility to raise the maximum possible price that would be allowed to go for if they need to.
All Camps are still encouraged to make their prices as affordable as possible

Input Requested: “Building A Diverse Speaker Roster” Document
The Diversity Outreach Speaker Training group created a document for WordPress Meetups and WordCamps about Building A Diverse Speaker Roster and they need our input. 

Announcements/Updates/Highlighted posts

#community, #community-team

Mobile Team Update – September 25th

We don’t have a new beta build going out this week since we skipped one release cycle, but you can still join the beta program and test version 10.9 of the WordPress mobile apps.
Sign up here to join the beta program on iOS or follow this link on your Android device, tap on Become a beta tester.

Highlights for the last two weeks:

  • iOS: We started working on Xcode 10/Swift 4.2 migrations and added actionable calls to actions to all empty states.
  • Android: We made great progress in a new framework to better handle lists pagination.
  • Gutenberg mobile: We placed the groundwork for the image block, better format toolbar support and enabled Gutenberg-web automatic mobile test suite run on all web PRs.