There are three 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.
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.
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It makes me proud that the WordPress project embodies the best traditions of open source and retires outdated traditions, or shibboleths, that do not have a place in our mission: to democratize publishing and grow the open web.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.
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 ideas 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 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 their consistent engagement with their community, that results in sustainable practices and proactive avoidance of burnout. Excellent leaders have made sure that their organization 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.
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.
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?
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.
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!
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. 🙂
World Mental Health Day is observed on 10 October every year, with the overall objective of raising awareness of mental health issues around the world and mobilizing efforts in support of mental health. The Day provides an opportunity for all stakeholders working on mental health issues to talk about their work, and what more needs to be done to make mental health care a reality for people worldwide.
World Health Organization
While I don’t specialize in mental health, I think everyone should consider themselves a stakeholder in their own mental health at the very least. For many of us, knowledge work is an active part of our weekly work routine. And even for those who don’t associate themselves with that, I encourage everyone to consider mental health as one of the many facets of health that we must all invest in (mental, physical, emotional, etc).
During my sabbatical this year, I spent a week exploring the state of my mental health and thinking of all the ways that I do and don’t care for myself enough. I ended up creating a mental health journal (as I affectionately call it) that is filled with space to clear my head, notes to myself for when I feel down, and things to track while we’re all experiencing the pandemic-specific slippage of time.
This little book is something that has come in handy almost every day since I created it. It helps me get out of my own way, and remember what “my way” is, regardless of whether I’m in the midst of an emerging crisis or floating through the unending emotional drain of a global pandemic.
I’m not much for flip throughs (I can’t imagine that anyone cares what I have to say that much), but I’ll share some of the primary components and can follow up with a flip through if folks would find that easier.
What’s In It
I used a Happy Planner notebook, in the mini size. I’ve been using their products for years because of the extensibility and quality, not to mention the disc bound system is very forgiving of errors and changed plans.
I have four sections: Goals, Track, Think, Know
This section is mostly as expected, with a laundry list of projects to do and habits to hone. It also has some pages with key questions for goal-setting (what would I do if money didn’t matter, what small changes could I make to improve my quality of life, what activities do I dread the most).
I also take time to write down why I have chosen some of my goals, because if I have learned one thing in life it’s that no plans survive contact with reality.
This section, in the time of COVID, is used to track the passage of time and to remind me of the things I do that don’t require being attached to a computer. Not because I can’t figure it out for myself, but because decision fatigue is a real thing. In those moments when you find yourself once again at the end of your crisis response reserves, it’s nice to flip open a page and see that your past self was looking out for you.
For me, this section includes visual layouts of:
things I’ve tracked so I can make changes
optimal routines for my work week
what makes me feel happy or sad
the books I’ve read
my hobby stretch goals
and when I last took time for myself
It also includes two weekly prompts for gratitude and big wins – moments that often go unremarked on right now.
This section is the best and the worst. It’s just blank pages that I’ve doodled some titles onto. The titles are all big, existential questions that I want to explore (so I can write about them here), or small and relentless fears that are hindering my progress through my everyday life. Because I am a happy planner, most of these pages have some supportive and semi-inspirational quotes to go along with them.
But mostly it’s just a non-judgemental place for me to clear my head and admit to what scares me.
And speaking of blind panic.
This section is my favorite. It has one sheet that logs important dates in my career (and a new page that charts my path) and the rest is just illustrations and doodles of things I have come to believe as a leader.
It has quotes that I say to my team leads all the time. It has my main recommendations about how to stay resilient. It has a tree of questions for when I’m worried. And page after page of guiding thoughts for when I feel the most at sea.
I add to these pages, and refer to them for self-guidance, almost daily. It is clear to me, now more than ever, that I know who I am and what my purpose in life is. It is my sincerest hope that what I reflect into the world matches.
What’s In You
I know that pen and paper isn’t for everyone, so I make the following recommendations lightly.
I think that some of what we will lose the most in future retellings of this time period is how fiercely human this reality made many of us. We will lose our handwritten notes, we will lose how we tried to improve our circumstances, and we will lose how we tried to help each other.
I will always write here, on this site, as I have for a decade. But I think there’s something to be said for the slow, tactile experience of creating something physical that can help you now and can capture who you were for the future.
I’m from rural Arkansas and all my life my family has had a garden. The gardens varied in size and purpose, but tending to plants is something I saw my parents do all my life. So when COVID-19 knocked us on our heels and confined us to our homes, it made sense that I should use my extended time at home trying to keep greenery alive.
I started with a single tomato; a vine-y, indeterminate hybrid called Early Girl. I soon got brave and added four basil plants (this is too many basil plants) and after a friendly chat with a neighbor received a gift of five assorted seedlings.
I didn’t know what to do at this point. Or more accurately, I didn’t know that there was more to do than putting them in the ground and watering them occasionally. My parents always made it look easy, though I have decided that my dad must be in constant communion with the gods of nature.
It is not easy. I am not good at it. I am an objectively terrible gardener.
So, predictably, I used my sabbatical to learn absolutely everything I could about gardening. Equally predictably, the lessons I learned reminded me of leadership lessons that I’ve struggled to learn along the way.
Plant today what you need tomorrow. Planning out a garden, it turns out, required a lot of time and knowledge. You have to know what plants are friends or enemies (because gardens are just zoos for plants), and if you want to use seeds or seedlings. You have to guess how much one plant will produce, and you have to guess how much support they will need in the future (because you have to do that early before it gets out of hand).
Give them space to grow, or create space later. I did not quite believe the information about how to space the plants. The basil got lined up in a tight, orderly row, and later I had to transplant them. Transplanting a plant is cutting it out of the ground, moving it, and hoping that it looks sad because the view is worse, not because it’s contemplating death. Even after that, I didn’t account for the wild tomato which then strangled one of the basils. Because… gardens are just zoos for plants.
Track what matters and do something with it. I set up a tidy gardening journal for myself, and I’m tracking all sorts of nonsense that I definitely don’t need and won’t use. Like… the planting depth of seeds, even though I started with seedlings. And the preferred pH of the soil even though I’m not testing it. But also some useful things like, the type of food each one needs, and when I last pruned them. How much water they need versus what I actually gave them (and I made changes appropriately).
Prune purposely and decisively. I learned so much about pruning tomatoes, friends. With indeterminate tomatoes you have to prune the vines or they will leave their enclosure and take over your lawn (gardens are zoos). But for many of my plants, I learned that you have to prune the old parts to keep the plants healthy. And, sometimes you have to prune the healthy parts so the plant will focus on producing vegetables.
Let them settle into any changes. It was really scary when I moved plants and watched them wilt, knowing I had to wait for them to regain their balance. I thought I had killed every plant in my yard at least once, including those that I was intentionally pruning. And despite my truly terrible plant husbandry, they had a drive to thrive and have come through the other side happy and healthy.
Plant today what you need tomorrow. Your work, no matter what you do, will take time. If you know what your goals are, you can start the process now and patiently guide it to where it needs to go.
Give them space to grow, or create space later. In order to flourish, you need to allow room to move into. Or, prepare a move once they’ve outgrown the space you planned.
Track what matters and do something with it. I used to say “if you don’t track it, you can’t change it” but I think it’s true the other way around, too. If you’re not going to change it, consider why you’re keeping track of it. Know what allows your team to reach their full potential, and monitor how well you help them do it.
Prune purposely and decisively. Whether it’s unassigning ill-suited tasks, or putting a stop to toxic behaviors, avoiding your own pain by doing something halfway can set the entire organism up for failure.
Let them settle into any changes. One thing about leadership that never gets easier for me is trusting that what I am observing is what is actually happening. And when I make changes, the cultivation period after that is excruciating. Patience in the face of slow growth that I can’t always see, tests my faith in myself.
But here’s the thing…
I know I said I was bad at gardening, and… there are days when I feel that I’m bad at leading. But my garden is actually thriving. I rehabilitated a cucumber plant and some roses. I harvested 8lbs of tomatoes every other day at the height of their growth period. I have tiny little peppers clinging to life on a pepper bush.
The plants are not picture perfect. They are not staying in their containers, but they are well-fed, supported as much as they are willing to be, and happily making more vegetables than I can shake a stick at.
And shouldn’t that be true for those we lead, too? That perfection shouldn’t be measured on what we wish someone could do, but rather one what they were built to do.
Over the course of my career, especially as I was learning to lead, I made a lot of mistakes. Most turned out fine in the end, but basically all of them required me to go and find an adult. And as I became more proficient as a leader, there were two truths that used to shock me a lot:
I am the adult now. If I need help, I have to find adultier adults.
At some point my mentors were also shocked to find that they were the adults.
All of my leadership skills were earned not learned, and I am here to debunk this myth for you: leaders don’t always know the answers and they aren’t always fearless. My mentors—the people who have taught me how to do this—what they had that I didn’t have was a network of advisors, and a few excellent tactics to work through inaction.
A Few Excellent Tactics
I use these tactics routinely, not as a way to hack my productivity, but as a way to ground myself in where my autonomy lies. As an added bonus, they can also help you address specific, short-term fears in a way that I have found to be truly empowering.
For When You’re Afraid Use the 10-10-10 Rule. This can help you to identify if the thing you’re afraid of is a short-term problem. You pretend you made the decision right now, and ask yourself how you would feel 10 minutes from now, 10 weeks/months from now, and 10 months/years from now. If you’re afraid to contradict someone (10 minutes), and you know that the change will be complex (10 weeks), but you’re certain that the long-term benefits balance it all out (10 months), then you know that you can stand the discomfort of the decision.
Next Level: Check for the area of effect – are you using single use potions or spells that help all surrounding allies. If challenging a path forward will inconvenience two people, but save multiple hours of work for seven, that might be a fair trade.
For When You’re Overwhelmed Use the Eisenhower Matrix. This can help you identify where your time is best spent. For every task that is on your plate you determine if it’s urgent or not, and whether it’s important or not. Where each tasks lands in those quadrants will tell you how you should handle them. If it’s Urgent + Important, then you should focus on completing the tasks. It’s it’s Not Urgent + Important, then you can plan for a time to do that. So on and so forth.
Next Level: The practice of identifying the differences between urgent/emergent/routine tasks can help us to find more autonomy in the decisions we make. This decision matrix can help define what you can affect change on, so you can have a more proactive pattern of approaching your work (also known as circles of concern and influence).
For When There Are No Good Options Use the Maximin Strategy. This can help you identify how to minimize the potential negative impact. When faced with nothing but bad choices, you think through who is impacted and how. Thinking through how big the negative impacts can be, can give you some way of ranking options that originally all felt less than optimal. At the very least, it will quickly clarify which options are not possible.
Next Level: If you can state clearly why you decided against any option, then it can help identify why you would say yes. It’s so often the case that there are many possible “yes”es and far fewer “no”s. Discovering one will help reveal the others.
It happens. Your advisors might have some insights, but they aren’t perfect either. If you don’t know how to proceed, but you must choose something, then remember these things.
Limit information gathering to what’s immediately relevant.
A mistake is only as dire as the outcome that follows it.
And when you do make a mistake, think of it as a lesson learned.