Shedding Light

My Leadership Philosophy

Posted on January 29, 2019 by Josepha

My twitter bio ends with this statement “I’m bad at writing recipes, great at cooking the food.” That has always meant to imply that, while I may be good at doing something, I don’t really know what goes into it all the time. When I set out to define my leadership philosophy, I didn’t realize how hard it would be to put all my thoughts and philosophies into words.

I’ve been guiding and advising future leaders for many years, as a mentor and overall advocate, and my advice hasn’t changed much in that time. My concept of good leadership is informed by being a woman in a male-dominated field, a person of color in a primarily white-dominated world, and a general faith in the power of a good-hearted group of people.

Is documentation really a DEI* initiative?

Posted on June 21 by Josepha

Have you ever stopped to ask why documentation gets created? Those little bits of paper that arrive with your latest online purchase or crammed into that IKEA box, those make sense. They are there to tell you how to use the thing in the box. Their primary function is explanatory, but you could argue that “documentation” as we know it can broadly include these functions:

To describe the use, care, purpose, or design of something
To train or inform someone
To introduce you to features in a product

If you’ve never considered how documentation could be seen as a *diversity, equity, and inclusion effort, I’ve got a few things that will probably help open up that area of thought for you.

Documentation makes learning available – When you write down how to use something, then that information is available at any time for anyone. It removes potential barriers to entry of having to know the right people or having time to set aside for classroom learning. It also enables translation of your words so that learning isn’t limited to those who speak the same languages you do.
Documentation lets you account for many audiences – Documentation also creates the opportunity to account for different ways of learning. Some people are able to learn and retain information simply through reading it, but if you have a video or audio component to your docs, then you can also provide that learning opportunity to visual and auditory learners. And of course, kinesthetic learners will solidify what they’ve learned as they practice.
Documentation clarifies entry points – This one is probably specific to open source or communities, but any time that you document “the way things work” in a community you are making it easier for other people to get involved. And the more we can help people get involved in our communities without making them know specific movers and shakers the more resilient and effective our organizations become.

Had you ever looked at documentation from that point of view? What are other ways that “writing the docs” could bring more diversity into your communities?

Dungeons and Dragons for Team Trainings

Posted on May 20 by Josepha

If you’re not familiar with Dungeons and Dragons (or table top games in general), the best way to describe it is “collaborative story crafting where a group of characters try to solve problems, save folks in trouble, and survive quests that they uncover along the way”. A colleague of mine, Andrea Middleton, once used a Dungeons and Dragons style session to introduce contributors to some basic issues that arise during the course of organizing an event, and ever since that session folks have asked for more trainings in the same style. I had the opportunity to do this recently myself, so I thought I would share some tips for hosting a training adventure of your own.

Getting Prepared

When you’re hosting these sessions, it’s important to do some documentation before you meet. You will be playing the role of everyone except the people who are in the room so there is a lot to think through. But also, don’t worry about getting too granular since your team will be a little unpredictable—just know the general shape, the main players, and the key elements.

Make a list of what to learn – Spend some time thinking about any skills gaps or knowledge gaps within the team. Is this a basic training on everyday tasks or more complex? Are they already familiar with working as a team or are they just starting to form?
Find a scenario where you can practice – Brainstorm some scenarios that will provide opportunities to learn one or more things from that list. For instance, if you want them to learn where the company directory is, then maybe your scenario takes place at a registration desk.
What do they need to know already – Determine any pre knowledge that will be required. If it’s a lot, consider sending it ahead of time. If it’s mostly “know where to ask questions” you’re probably their best resource. 🙂
Outline your story – start at the end with your learning outcomes and work your way forward. Make particular note of any decisions that would cause the outcome to branch. Try to think through what the best way through the problem is, but also the most common first steps, missteps, and failures.
- In my session, Missteps triggered a random encounter or external input and Failures triggered “It’s a trap” moments where the problem became worse.
Know the required parts of the story – Note any important facts or people they should seek out while they are collectively working through solutions. What information will they try to find? What information must they find? Are there specific people who they have to find or they will get stuck?

Getting Adventursome

Before you host your session, determine how familiar your group is with this type of game. Not everyone plays games let alone adventuring table top games. If people have never played before, make sure you give them an overview of the process (or send them your favorite one shot). Also, if you are going to use this to track goals and progress over time, consider some sort of “character sheet” to document progress. Don’t get too rigid with the mechanics, though. You want them to come out having succeeded at the learning objective!

Welcome everyone! Explain how each turn will work and have them roll initiative (so you know what order they will go in). Since there’s no Dex to break ties, I just had my players roll to break their own ties. 🙂
Read the scenario and ask the highest roller what they want to do. Table talk and discussion is encouraged, so it’s important to confirm with your player that they have decided on an action. Once they have completed their action, read out the results of the action and move on to the next highest roller.
Make notes of the table talk and progress. You don’t want to move them through anything too quickly. They should have a chance to discuss, ask questions, and ponder possible outcomes. This is a time for them not only research and explore the problem, but also to learn how to work together toward their common goal.
Don’t let them flounder! If they get too stuck, you do have some options:
- Remind them that you are a resource (“I’m playing all parts except you all, so feel free to ask me anything.”).
- Roll in a random encounter (“a friendly community member DMs you to ask…”).
- Roll in a skills check (if they asked almost the right question, roll a Charisma to see if they get some extra info. Do they need information that they aren’t aware of or can’t find? Roll a Knowledge/History.)
Rinse and repeat until the problem is solved! As far as one shots go, these might be pretty much on rails, with a few clear alternative endings/solutions.

Getting Closure

Once you’re finished, I recommend doing a little debrief if you have time. If you take good notes during their session, you’ll be able to go back and look at the various branches and see what could have been done differently.

This is a loose concept based on my recent experience. If you end up trying this, let me know in the comments!

To my global community: Start Small

Posted on February 25 by Josepha

When I woke up on Thursday, I was met with the devastating news that the Russian-Ukraine conflict had escalated. My first thought was, of course, whether anyone in the WordPress community lived in any affected areas. Then, I questioned what I could possibly do about it from halfway around the world.

I can’t comment on the specific politics of this conflict and, for what it’s worth, I can’t for the life of me think of the “right” thing to say. But when I don’t know where to start, I generally like to start small. So, I’ll share what I’ve been thinking about for my communities these past few days.

While I am certain that my words—no matter how carefully chosen—cannot possibly change the hearts and minds of nations with which I am wholly unaffiliated, I am equally certain that in my own communities there are people who are longing to learn how to help. I know I am.

As the world faces war, it’s also the same world in which kindness, community, and integrity co-exist—you are testament to that. WordPress is built on the commitment of thousands of contributors from all over the world to a unified mission. I’m sure many of you are in solidarity with those affected by this week’s events.

If you want to show your support, check in on your fellow contributors, friends, or families and let them know it’s okay to ask for help. You can also donate to a nonprofit that offers material relief or refuge to those in Ukraine. And of course, do what you can to stay informed. The world is a much more connected place today than it’s ever been. With all eyes bearing witness, learning, and paying attention, we are better equipped to move toward resolution.

But as you do all of these things to support your community, however you’re defining it, remember that you do not personally hold all the responsibility for “making things work” today. We are all here as part of a passionate and compassionate global community—please be gentle with yourselves and others.

State of the Word 2021 | Q&A

Posted on January 4 by Josepha

It was a treat for me to see some folks in-person and online at Matt Mullenweg’s State of the Word on December 14th. For me, the thrill of his annual keynote is hearing his perspective of the year and what questions it raises in the community. Unfortunately, we didn’t get to all of the questions! We only had a handful of pre-submitted questions which I’ve included along with their answers in my post below. After those, I’ve listed all the questions that were received during State of the Word (with the exception of the banana shake questions 😉

How do we do this?

All unanswered questions have been assigned reference numbers (Q1, Q2, Q3, etc) and any corresponding answers that come in the comments will be labeled similarly (A1, A2, A3, etc). Just like twitter, but slower! 🙂

Pre-Submitted Questions

Matt, me, and my team are building a decentralized publishing infrastructure to bridge WordPress users to Web3. We hope to help content creators leverage blockchain to reach the end goal of democratic publishing. Especially for heavily censored places where people don’t have the freedom to distribute and access information. What do you think WordPress would evolve in the Openverse/metaverse, and how could we deliver the right tool to the WP community? Thanks for answering my questions, and if there’s a chance, I would love to get in touch for a follow-up conversation with you or the team.
– Phoebe Poon

Web3 is currently a collection of ideas, aspirations, and technologies and, in this context, refers to a decentralized web built on cryptocurrencies and the blockchain.

It’s important to note that decentralization is not exclusive or inherent to the blockchain and crypto. Solid, a project from Tim Berners-Lee and MIT, is an excellent example of this. Self-hosted, open-source WordPress sites are already a great example of decentralization on the web, where users already own their data. The blockchain itself may be trustless and decentralized, but the gateways to access it and abstract it for users might not be. Openverse is an open-source, centralized tool to enable the discovery of openly-licensed media that challenges proprietary libraries of stock photography, licensed audio, and more. – Zack Krida, Openverse project lead.

I’m curious how many people use WordPress Block Editor vs. Classic Editor, raw numbers, and percentages. I’m looking forward to tuning into the event on Dec. 14th.
– Mathew Wallace

The Gutenberg plugin has over 300,000 active installations, while Classic Editor plugin has over 5 million. It’s hard to draw any specific conclusions from these numbers since each plugin serves a different purpose. Having the Classic Editor plugin provides users and clients with a choice of how to create their content, so folks who have that plugin installed could still be publishing primarily with the Block Editor.

My question is about the plugin review team: This is a very special team. It is closed, has only two members, and although we have nearly 60k plugins now, 100+ more coming every week, the team never got more members. The team has power (reject plugins, closing plugins, ban users, etc.), and it has no rotating policy, although the work is very stressful. WordCamp organizers have a rotating policy; why do we have no rotating policy for the plugin review team? And/Or how can we prevent misuse of powers here?
– Torsten Landsiedel

Great question. We have had several people on the plugin review team at various points. Unfortunately, there have been cases of legal threats and illegal harassment against the team’s members, and I will not expose community volunteers to that. That said, there are other community teams involved in reviewing disputes about blocked accounts, and there are plans in place to automate any checks we can, so humans are involved in the parts humans do best. – Josepha, WordPress Project Executive Director

I am afraid that the block editor is dividing the community we are so proud of. As a long time community member, many people come to me as a “representative” person (WordCamp & meetup organizer, speaker, moderator, GTE, etc.) and complain about Gutenberg. Devs are complaining about the fast moving target, the incomplete documentation, and the changes. Users complain about full screen mode and UX problems (especially with older themes). How can you help us volunteers or the people in general to have a smoother transition?
– Torsten Landsiedel

Although the recommendation is to build themes as block themes and migrate existing themes to blocks, older themes are still supported. In this direction, the Widgets Editor was released in 5.8 to support Legacy Widgets in the Block Editor and add native blocks in Widgets Areas. However, it is recommended to implement migration paths from Widgets to blocks.

With the advent of FSE in WordPress 5.9, the new Site Editor will supersede the Customizer, hidden by default. Still, whenever WordPress detects hooks that need the Customizer in themes and plugins, it will be available automatically. Further, companies participating in the Five for the Future initiative are increasing the number of sponsored contributors focused on developer advocacy and documentation to help smooth this transition. – Matías Ventura, Gutenberg project lead

Hi Matt, first, thank you for providing this space to ask a few questions. My questions relate to the newly formed PHP Foundation and the future of PHP. In your 2015 State of The Word, you told the community to learn JavaScript deeply. With Automattic as an integral part of the newly formed PHP Foundation, is it time to learn PHP deeply? Any chance you might like to read the tea leaves and share your thoughts about the future of WordPress, JavaScript clients with PHP servers? Where do you suggest we (the community) focus our efforts in 2022?
– Rita Best

PHP is a foundational language for WordPress, so many people in the ecosystem already know it deeply. That said, it’s always smart to know your software’s tech stack well. The WordPress project has benefitted so much from the PHP project and community. This sponsorship is giving back in the way that I hope companies in the WordPress ecosystem give back to our project—think of it as a proactive Five for the Future contribution to PHP. – Matt Mullenweg, WordPress project lead

Finding Solid Ground on Day 591 of N*

Posted on August 30, 2021 by Josepha

*where N=unknown

I used to think there was nothing more stressful than being in the midst of a stressful thing. When you’re in the middle of something, it’s all raw and electric and the ways out aren’t always a sure bet. In the past nearly 600 days, I’ve learned that there is something more stressful—being in the midst of a situation with an undetermined length.

The first time a team member brought the news of COVID-19 to my attention Jan 17, 2020. And during the following months as we were all trying to pivot and work through the apparent crisis, I remember thinking that this wouldn’t have a huge effect on us. “WordPress has been distributed forever, we won’t have many adjustments to make.”

Life Imitated Work

What I hadn’t anticipated was that the processes of our work (Zoom calls, coordinating across timezones, collaborating/communicating primarily via text) were going to become the processes of every other area of our lives. For many of us we now not only have distributed work, we have distributed learning/teaching, distributed exercise/wellness, and distributed celebrations/grieving.

And when every part of your life mirrors the way you work, it can be hard to separate your self from your work.

Earlier this year, my Chief of Staff shared a podcast with me that was exploring the dangers of letting the definition of your work become the definition of your self. I learned that “career enmeshment” is the borrowed term used to describe this phenomenon, and while folks may have ways to cope with this in normal circumstances, I know that that past 18 months are not very normal.

First, Some Grounding

As we approach the time of year where organizations of every stripe (non-profit, for-profit, commercial, or otherwise) start gathering plans for the near future, you might find that it’s hard to get your bearings when the world is so unpredictable. When you can’t be sure which way is up, it’s always best to start by finding the ground.

That can be as simple as listing your recent projects and tying them directly back to your organization’s mission.

As an example, here is how that would look for WordPress project maintainers. In 2020, maintainers did the following work that shows a commitment to “democratize publishing”.

Contributed to an ongoing contributor-focused effort to increase diversity, equity, and inclusion in WordPress through:
1. transparent communication (i.e. regular project round up posts, live streamed working sessions, etc),
2. mentorship (Core cohorts, LearnWP cohorts, etc),
3. and the willingness to help new contributors learn by failing safely (WP5.6).
Contributed to ongoing user-focused efforts to not only lower barriers of entry, but also to reduce the effort to level-up through:
1. the proliferation of block patterns,
2. small (but meaningful) a11y changes over time,
3. and the regular shipping of self-serve content on learn.wordpress.org.
Contributed to an ongoing ecosystem-focused effort to make the web a safer place through:
1. user facing auto-update functionality,
2. dedicated attention to HackerOne reporting,
3. and the thankless work to keep our underlying technology up to date.

As WordPress maintainers, you all met the challenges of 2020 where they were, and did great work to grow through them, rather than let them stop your progress.

Second, Some Reconnection

After you’ve gotten your mind around what you know, it’s time to spend some time reconnected with what you believe. Knowing what inspires you, what drives you, and who you are when you aren’t working can help reconnect you to the values that bring you to your work every day.

Break things into smaller wins – Many of us make plans that focus on single massive goals in a year, but this is the year to instead have smaller milestones to look forward to. Instead of big plans that could be foiled by things outside your control, it makes sense to create more frequent creative/celebratory/processing moments. I have said before that “the value of routine can’t be overstated”, and these little speed bumps in our routine can remind us to reset.
Know your concern vs your influence – None of us can control the vaccine rollout plan, but you can probably commit to “X pushups a day” or “Y minutes of fresh air”. We make time for what’s important, and following through on even the smallest challenge to yourself, helps to remind you that you have inherent value outside of what you’re able to do for others.
Get it out of your head – It can be hard to unplug right now, since screens are the safest interface with the world at the moment. And you might have Slack on all your devices just in case you remember something you meant to do. Instead, write it down (via paper, or a blog, etc) and process your list in the morning. The mental activity of remembering to do something can make you very anxious, and writing it down makes sure you don’t forget it.

What things do you do?

There are countless ways for us to re-engage with who we are, and to clear our minds for creative thinking/problem-solving. What are some of the things you do?

Books All Leaders Should Read

Posted on June 29, 2021 by Josepha

There are four books that have shaped the way I approach my work. Any time that a volunteer or team member tells me that they are ready to level up their leadership, I recommend some combination of these books.

On recent news about the FSF board of directors

Posted on April 2, 2021 by Josepha

I want to take a moment to respond to the recent news of Richard Stallman’s return to the Free Software Foundation’s board. In short, I do not support his return as a board member.

It makes me proud that the WordPress project embodies the best traditions of open source and retires outdated traditions, or shibboleths, that do not have a place in our mission: to democratize publishing and grow the open web. For years, this community has been committed to championing underrepresented voices and maintaining a safe and welcoming environment for those we rarely see in open source.

WordPress and the community that supports it has made an effort to move open source methodologies into a space that applies at the scale of the people who participate, not just the software we create. The high standards for welcoming behavior are held across the board. WordPress contributors lead with accountability, acknowledgment of error, and a genuine desire to grow based on feedback. Under the guidance of many thoughtful leaders, WordPress makes space for those who are committed to growth.

The work is never finished, both on WordPress and the community that WordPress seeks to foster. I look forward to working with everyone willing to help us make WordPress, and the web, a better place.

Leading at Any Level

Posted on March 5, 2021 by Josepha

The concept of leading at any level comes up frequently and focuses on the idea that leadership isn’t the sole responsibility of those at the top of an organization. This idea happens to fit well with my definition of leadership in general, which is that you are a leader if you have anyone who looks to you for support, guidance, or trusts you with collaboration.

You might notice that I didn’t include anything about reporting structures, employment, or hierarchy and that’s intentional. I think that you can lead from where ever you are in your organization, because I don’t believe that “telling people what to do” is the ultimate expression of what it is to lead.

There are leadership tasks that will always be the sole responsibility of top-down leaders, such as vision setting or responding to crises, but the day-to-day work of keeping momentum and upholding values belongs to everyone. And in WordPress—where we have top-down coordination, but prefer to rely on leading by coalition—our most successful* leaders are those who understand how to lead from where ever they are.

The Pillars of Leading at Any Level

All parts of leadership can be taught, so if this concept is new to you I’ve got a quick list to get you started.

Supporting the Culture (or how we engage, motivate, guide)
- Set an example – Guidance doesn’t start and stop with active advice that you’re providing. If people ask for your guidance, they will also watch what you do (or don’t do) to know what is acceptable in the community.
- Set the tone – You are responsible for the tone you bring to the space. Meeting attendees, community members, and team mates will take their cues from leading voices, and it’s up to us to make our spaces welcoming and ethical.
- Communicate clearly – Share what you know and don’t know clearly. When possible, be transparent about decision making so it’s clear that disagreements are safe and give people insight into the full journey.
Supporting the People (or how we train, enable, nurture)
- Acknowledgement – Open source acknowledges good experimentation and honors past work. As leaders in open source we should also acknowledge our contributors by setting up in a space where they can fail safely (like new contributor meetings), and thanking them for their contributions.
- Redirection – I think that solving the software’s biggest problems according to users is always the primary agenda. Early redirection of passionate contributors can offset future resentments when their passions lie with non-priority things. Letting someone know that they can work on it, but we can’t guarantee it will ship is the right and ethical thing to do.
- “Yes, and…” or “No, but…” – Respond to questions in a way that makes people feel comfortable asking. Encouraging exploration is part of how we commit to the open source idea of good ideas coming from anywhere. Respond to questions in a way that encourages future exploration for the asker (which can be hard when you’ve done it for the 100th time) and tells them that it’s good to ask.
Supporting the Changes (or how we respond to crisis)
- Caveat: Many crisis responses require named leadership, but for those responses that don’t this list will help.
- Be Balanced – Differentiating between urgent issues and emergent issues is hard, especially if you don’t have the full context. But putting some thought into what the impact might be can be a good start.
- Be Present – Leading in a crisis requires a lot of time and attention. Staying visible in public spaces (and not resorting to private spaces by default) is uncomfortable but necessary. When you have to have closed sessions, and you will, report back on what was said.
- Be Judicious – Discern how best to combat the most urgent issue amongst many emerging issues. Knowing whether to fight a fire with fire/water/vacuum takes some practice, but at the very least have a sense of what will make a crisis worse.

* What do I consider a successful leader? Successful leaders aren’t defined by how many decisions they have to make or how many people report to them. They are defined by how many leaders they send out into the world. They are defined by their consistent engagement with their community, that results in sustainable practices and proactive avoidance of burnout. They are defined by the resilience of an organization that can survive long after they have left by ensuring they aren’t a single point of failure, by encouraging people to participate, and by committing to guarding their own resilience. And, in any organization where coalitions are key, successful leaders are those who when faced with making really uncomfortable choices, can help people find the reasons to commit despite their disagreement.

Purpose Driven Projects

Posted on February 22, 2021 by Josepha

One of the hardest parts of working in open source projects is figuring out how to incorporate product management. In my experience, product management requires opinionated direction that doesn’t always seem to fit the open source ideals of “good ideas can come from anywhere” or the egalitarian ethos of a do-ocracy. Since any contributor can submit a patch, every contributor holds the very broad mandate of building and maintaining the WordPress software and project.

But—as anyone who did a group project in school can attest—when everyone is responsible for something, no one is responsible, and “death by committee” can really sneak up on you. Which is why a lot of projects (school or otherwise) end up with a manager.

Product Managers

It seems that there are as many definitions of a product manager as there are people who manage products. For many WordPress contributor teams, there’s historically been the expectation that each developer/wrangler/designer should function as their own product manager. Since the WordPress CMS’ project vision is generally done by the project lead and shared in the State of the Word, it’s sometimes hard to know how to manage products that relate to WordPress, and what it looks like in practice.

What if the individual work of being a product manager wasn’t about making decisions about what features are where, but instead the work is checking whether our suggested solutions are keeping track of their purpose? What if the work of managing a product is checking that identified and scoped features are still on the right track to the goal?

Questions to Start With

This all seems like a really big task, especially if you’ve ever read about my theory of care and influence in the WordPress community. But if this makes sense to you, and you would like to try, I have a quick set of questions that can help you get started.

What is the problem we’re solving? Your event wants to try printing name tags on-demand in the registration line, as opposed to ahead of the event. The problem being solved is allowing late registering attendees (users) to still have their own official badge.
Who does this solution benefit the most? There are three groups that should see benefits with this solution: Attendees who get to have their own printed commemorative badge; Organizers who can leave registrations open for longer; and Volunteers by making the registration line faster since you don’t have to sort/organize/find each badge.
How does the user’s experience improve with this solution? This solution seemed like a net benefit for the attendee (badge, longer window to register, shorter time in line), and that’s who we want to have the most benefit! 🙂
Is the impact well balanced with the level of effort to accomplish this solution? In this case, the level of effort is wrapped up in training on new machines and the cost, but that seems like it can balance so many benefits for the user.

Ta da! You did it!

Like so many things I share about leadership, this is something that requires consistency over time. Sustainable changes are best made through iteration, with the understanding that mistakes are opportunities to learn.

If this doesn’t work for your teams in the long run, it can still be a great starting point as you figure out what does work for you.

Six Years in WordPress

Posted on February 2, 2021 by Josepha

Today is my six year anniversary of becoming a full-time, sponsored contributor to the WordPress open source project. There are many ways I would describe it—rewarding, complex, cutting edge, difficult, ever-changing, meaningful—but at the end of the day, I want to be able to describe it like this:

For the past six years, I have supported a software that stands to bring more equity into the world, by unlocking opportunity and believing in the freedoms of open source. I have supported a community that strives to remove barriers to entry for that software, by uncovering what was once arcane and connecting to one another for strength. And I have supported a space that works to welcome those from whom we hear the least, but who could benefit the most from the tools that WordPress enables for them.

Happy Six Years to me! And cheers to the community that I serve!