leadership

There’s Risk in the Resolution

Posted on by Josepha

Late last year I attended a wonderful leadership session that walked us through closing the book on 2022 and preparing ourselves for the opportunities coming in the new year. There were 30 or so leaders representing a vast array of sectors, and in our opening breakout session we were invited to look at a number of individual images or quotes and select one or two that really called to us as a kōan for 2023.

The image I chose was something like this:

Carlos Ramírez in full competition at the UCI BMX World Cup, Bogotá 2021
Felipe Ayarza, CC BY-SA 4.0 https://creativecommons.org/licenses/by-sa/4.0, via Wikimedia Commons

Now at first glance, there are a few obvious choices for what a photo like this might mean. It might mean that I expect the year to be fast-paced with a series of ups and downs. It could mean that I anticipate the weightless feeling of escaping something holding me back. It could also mean that I have grown a sudden interest in death sports.

But there is also a hidden sort of element to it and that’s what drew me to this photo.

If you are like me—a planning, strategic thinking, “yes, but how did we get here” type person—then you probably know that that photo implies countless hours of training, practice, and probably a handful of painful lessons. No one ever got to the point where they are floating, attached to nothing, free from the aid of wings or the safety of a harness without years of intense dedication.

For any sport like this (gymnastics, motocross, dance, surfing, anything) one of the earliest things you have to learn is how to fall well. Since what goes up must come down, you are told early on how to land safely. How to limit the risk (of injury) in the resolution (of reuniting with Earth).

From Phase to Phase

I just wrapped up the latest episode of the WordPress Briefing. In it I talk about what the end of Phase 2 for the Gutenberg project does and does not mean for our everyday users. Throughout the writing and recording of that episode, all I could think of was this photo and that one phrase I immediately associated with it: “there’s risk in the resolution”.

From a big picture, long-term perspective it is easy to look at a project that successfully got off the ground and assume that the rest will take care of itself. There is an extent to which that’s true. Honing the skills, seeing the opportunities, and then having the wherewithal to put it all together in a way that creates enough speed and momentum to get you in the right place at the right time—yea, that’s hard. Once that’s done, the rest is just “get back down and continue safely forward”. But if you haven’t been told how to get down safely or how to convert that momentum into forward movement, then it’s more likely that you’ll run into difficulty doing those things.

Does that mean that I’m worried about the rest of our work on Gutenberg? No. I believe that the WordPress community can and does close the chapter on important projects all the time. If anyone can make this a joyous return to Earth, it’s the people supporting this project. But I also believe that they can because they have been for nearly 20 years.

Does it mean that I’ll be relying on our collective knowledge more than ever? Absolutely.

p.s. – a mantra

I have a list of reminders on my lock screen. If I remember, I’ll share one at the bottom of each of my posts in 2023, because we can never know who is in need of a little encouragement.

To grow, you must be willing to let your present and future be totally unlike your past. Your history is not your destiny.

Alan Cohen

The Four Os of Meeting Preparedness*

Posted on by Josepha

There are quite a few resources from WordPress contributors over the years about how to identify and resolve conflicts in open source projects. There are posts that cover why conflict occurs, the structure of conflicts over time, and what to keep in mind while in the middle of conflicts.

I’d like to share some additional explanation of my Four Os checklist, a tool that I use to make sure I know the facts of a situation as well as the feelings. This was first shared on Andrea Middleton’s primer on Conflict De-escalation in Open Source which I also highly recommend.

Why Prepare for a Meeting

If you’ve never mediated a discussion or helped to de-escalate a disagreement before, you will be surprised just how much the emotional state of the participants in the room can affect you. To make sure you are a well-grounded, calm-headed guide, there are two things you have to know going in: Know the facts, and Know the fights

In the heat of the moment, your short term memory can fail you, so having done the work ahead of time to assess the situation is important. Also, if you have asked all participants in a mediated discussion to answer these questions as well, then it’s easy to see where there are agreements, so folks can focus on working through the disagreements.

This is my primary checklist before heading into any conflict resolution work:

The Four Os

  1. Origin: Before you can help anyone through a conflict, it’s important to know what caused the conflict. Getting an understanding of the context, the catalysts, and the primary concerns gives you the lay of the land and the beginnings of a map to see what is real. Questions that you can ask yourself:
    • What made this meeting necessary?
    • What are the circumstances around it?
    • What made this unsolvable on its own?
    • What are the perceived risks? What are the actual risks?
    • Are there imbalances of power, knowledge, or access that you can see?
  2. Objective: Knowing the purpose of a meeting is a differentiator between good leaders and great leaders. Awareness of what needs to happen during this valuable shared time together will help keep the discussion focused and increase your chances of a workable solution.
    • What do you want to happen in this meeting?
    • Is this a “see the other side” conversation or a “debate the solutions” discussion?
    • How do you expect the other participants to engage?
  3. Obstacles: If you’re new to strategic planning or communications, it can feel counter productive to think of all the ways that your plan can fail. However, I believe strongly that the only way we can keep ourselves from falling along a journey is to look for the rocks and sticks in our path.
    • What do you think might interfere with this objective?
    • What’s your plan if that comes up?
  4. Outcome: Give some thought to what you want to have happen as a result of this meeting. The best way to look at it as on a spectrum from the minimum hope is for next steps all the way through to the best long-term changes that come from resolving this conflict.
    • What do you want to walk out of the meeting with?
    • What’s your desired outcome?
    • What are the best next steps?
    • What compromises are available (where everyone has to let go of something)?
    • If this is resolved perfectly, a year from now what is different?

Bon Courage!

These might not all apply to every situation you encounter. Not all conflicts have deep and meaningful context (and that’s a good thing), sometimes it comes down to miscommunication. When we’re working across cultures, sometimes the role of an impartial guide through some facts and feelings is the thing we need most.

* I know this is a terrible name, but honestly, it’s all I can come up with. 🙂

Free man writing on white

Is documentation really a DEI* initiative?

Posted on 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.

  1. 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.
  2. 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.
  3. 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?

polyhedral dice on wooden surface

Dungeons and Dragons for Team Trainings

Posted on 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.

  1. 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?
  2. 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. 
  3. 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. 🙂
  4. 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.
  5. 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!

  1. 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. 🙂
  2. 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.
  3. 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.
  4. 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.)
  5. 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 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.

Finding Solid Ground on Day 591 of N*

Posted on 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”.

  1. 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).
  2. 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.
  3. 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?

Cropped shot of a antique

Books All Leaders Should Read

Posted on 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.

Recommended Reading

  1. Leaders Eat Last by Simon Sinek
  2. The Coaching Habit by Michael Bungay Stanier
  3. Daring Greatly by Brené Brown
  4. Reboot: Leadership and the Art of Growing Up by Jerry Colonna

In case leadership reading isn’t your favorite, here are the quotes that turned my head in new directions:

Great leaders truly care about those they are privileged to lead and understand that the true cost of the leadership privilege comes at the expense of self-interest.

Simon Sinek, Leaders Eat Last

Leaders would sooner sacrifice what is theirs to save what is ours. And they would never sacrifice what is ours to save what is theirs. This is what it means to be a leader. It means they choose to go first into danger, headfirst toward the unknown. And when we feel sure they will keep us safe, we will march behind them and work tirelessly to see their visions come to life and proudly call ourselves their followers.

Simon Sinek, Leaders Eat Last

We live in a world where most people still subscribe to the belief that shame is a good tool for keeping people in line. Not only is this wrong, but it’s dangerous. Shame is highly correlated with addiction, violence, aggression, depression, eating disorders, and bullying.

Brené Brown, Daring Greatly

We’ve survived and are surviving events that have torn at our sense of safety with such force that we’ve experienced them as trauma even if we weren’t directly involved.

Brené Brown, Daring Greatly

The essence of strategy is choosing what not to do.

Michael Bungay Stanier, The Coaching Habit

When you build a coaching habit, you can more easily break out of three vicious circles that plague our workplaces: creating overdependence, getting overwhelmed and becoming disconnected.

Michael Bungay Stanier, The Coaching Habit

Strong back and open heart. This is warrior stance, I tell him. The strong back of fiscal discipline. The strong back of clarity and vision, of drive and direction. The strong back of delegating responsibility and holding people accountable. The strong back of knowing right from wrong. But it’s also the open heart. It’s giving a shit about people, purpose, meaning. It’s working toward something greater than merely boosting your ego, greater than just soothing your worries and chasing your demons away. It’s leading from within, drawing on the core of your being, on all that has shaped you.

Jerry Colonna, Reboot: Leadership and the Art of Growing Up

Leading at Any Level

Posted on 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 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.

  1. 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.
  2. 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.
  3. 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! 🙂
  4. 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.

A WordPress Dinner Party

Posted on by Josepha

At the top of 2020, I observed my fifth anniversary of being a sponsored contributor to WordPress, and am proud to say I led the first all-women and non-binary release team in our project’s history. When I applied for the position I was an advocate for diversity in technology, and I hoped this was a chance to make my time more impactful. I came to the work without any preconceptions of what open source was or should be. I didn’t even have a strong concept of the “best ways” to increase diversity. I just had my experience, my self-taught notions of leadership, and a desire to bring people together toward something bigger.

During my first year I met so many people, but especially sought out other women and people of color. WordPress had always seemed to be an oasis of welcoming in a field that is known to be the opposite, and I wanted to compare my experience with others like me. I felt that I had found a community with the contributors I met, that we had common ground.

And in 2017, I had this startling moment of doubt.

Chairs at the Table

I responded to a hashtag on twitter (#WITBragDay) this way:

I don’t know if I count as “in tech” but I fight for and inspire women to be in tech.

Amid the support from fellow contributors, I got a message asking why I thought I didn’t count. And I had too many answers.

  • I’m non-technical (in an OSS project).
  • I’m a woman (in a male-dominated field).
  • I’m a person of color.
  • I “just work with people”.
  • And countless more.

Which led right to the question: “Why do you want to inspire other women to be in tech… if you feel like you don’t belong in tech?”

I assumed I was alone in feeling like I didn’t have a place at the table. I assumed that everyone else knew their value, and skills, and could advocate for themselves once they arrived. And my role was just to make sure we had enough places for people to be.

But when I’m leading others, I always encourage people to ask their questions publicly, because you never know who else is too shy to ask the same question.

So I started asking questions.

Place Settings at the Table

I asked my mentors about their early experiences of WordPress contribution. I asked rising contributors when they felt they’d had their first success. I asked long standing contributors about their journey. And I asked people who stopped contributing what led to that decision.

I approached this problem like any project I plan: by getting all the info in one place, looking for risks, and making plans to avoid risks.

So I asked people to start making small changes with me. Little process tweaks in one team, a borrowed welcome wagon concept from another. Nothing major, just being a tiny bit more proactive with our burden of proof so that when diverse voices joined us, they knew they belonged and had some idea of where to go. And contributors took these little changes, modifying them to fit their teams like any good open source community would do.

More Tables and Chairs and Settings

The community kept building on those changes and kept inviting others to join in. Small training cohorts were attempted. There were people who loved documentation (lowering barriers to entry); people who loved mentoring (helping others find their way); and people who just wanted to help any way they could. Then late in 2019, I shared that I hoped for an all-women release by the end of 2020.

It honestly made me nervous. We aren’t perfect, and there were so many things that I thought were missing.

But there were also so many people who wanted to participate, from brand new contributors to OG developers. So we did it. And the release team for WordPress 5.6 was massive. Not because I wanted volume, or because I was playing to the numbers, but because I had observed that our community enjoys learning shoulder to shoulder. Learning by watching, then doing, then trying again when we fail is a key part of how open source works, so it’s a key part of how I wanted to be able to introduce this team to the work.

A Great Dinner Party?

Did I do everything right? Definitely not.
Would I do it again? Maybe.
Was it worth it? Without hesitation, absolutely.

The latest release of WordPress, while a massive undertaking, was the culmination of years of work by hundreds of contributors. Not all of them knew that their contributions would lead to this, and certainly not all of the release team know about the work that came before them.

But isn’t that the beauty of open source in the end? That we benefit infinitely from the work of everyone who came before us, yet can still find ways to bring new benefits for those who come after us? And if this long labor of love encourages even 10% of the release team to return, I will consider it a truly great dinner party. 🙂

This post originally appeared on 24 Days in December, which hosts a series of reflections from PHP and open source community members.