Category Archives: leadership

Letters to an open source contributor: Leadership

Much of my work in WordPress over the past decade has involved coaching and training leaders working in open source, and as I wind down this part of my career, I find I have a lot to say on the topic! I’m going to try to follow my own advice and be brief here, but I do not promise.

If you’re just getting started hearing me talk about leadership, I recommend a previous post of mine: What happens when you won’t admit (or don’t realize) you’re a leader. That piece resonated with a large number of people I’ve worked with in WP, so I’m recommending it as supplemental reading for this article.

Oh! And the other important thing to know, going into the leadership advice I will share below, is that I firmly believe in leadership at any level of an organization. Open source embraces this idea, in that our organizations are usually less hierarchical and, because the work is accomplished by the people who show up at the time, more fluid when it comes to who we look to, when we’re navigating a problem.

So! With those ideas in mind, let’s dig into more advice for leaders in open source.

Don’t make yourself indispensable

One of the most powerful things I’ve learned from Josepha is that

If you can’t be replaced, then you can’t be promoted.

– Josepha Haden Chomphosy, Executive Director of WordPress

I know, I just told you that open source isn’t very hierarchical, and I wasn’t lying. This concept applies to flat/open source organizations more like this:

If you can’t be replaced, then you can’t ever work on cool new stuff. Because if you do, all the cool old stuff you built… will end, or break.

Teaching people how to do the work that you do? It’s time-consuming, and can be a real challenge. But the people who do this — who document their code, who design in public, who create a succession plan and train their replacements — those people get the best that open source has to offer. They get to create amazing new features, programs, events, etc… and then they get to see those things keep growing, even when they move on to the next thing.

Recruiting, training, and cultivating your successor will make you much freer and more nimble, in an organization. It’s also the best way to ensure your work has a lasting effect.

Love your beginners

Photo by Ron Lach on Pexels.com

If you want your project/initiative/coalition to grow, you need to welcome new people into it. One of the things about new people = they don’t know everything yet. Don’t fall into the trap of thinking that ignorance is the same as stupidity — answer questions (even the ones you answer a lot!) with warmth and grace.

Also, be aware that beginners are a rare and valuable resource. They see things with fewer preconceived notions than the people who’ve been around for a long time. They question things that tenured contributors don’t even notice anymore, or have given up complaining about but still dislike.

Beginners are also an endangered resource! If you can get them to stick around a while, and train them for a while, then guess what? They’re not beginners anymore! So be sure to engage with your new people while they’re still new, and can help you fill in some blind spots or clarify where your outreach or messaging is still confusing.

Open source your decisions and thought process

Working in public is one of the hardest things we do, in open source, but profoundly worthwhile. Transparent processes and work patterns result in well-documented decisions, which lead to higher-quality contributions in the future.

I had this realization a few years back, when I was complaining (not for change, btw) about how many suggestions my team got, that didn’t demonstrate an understanding of what our work was about, or why things were set up a certain way.

“Why don’t they understand that [thing that was obvious to me at the time]?!?,” I fumed. And then it hit me: BECAUSE I HAD NEVER TOLD THEM.

Me, about me.

When you keep your concerns, doubts, convictions, and theories private, then the people who show up to collaborate with you… are slower to connect with both you and the problems you’re trying to solve together. Maybe so slow that you never connect in the first place.

But thought leadership can scale pretty elegantly, if you are willing to work in the open and diligently share your goals, observations, reasoning, and philosophies. It’s not easy, but it works.

Play the long game

Things tend to move slowly in large organizations, even if you have all the power in the world. Groups with broad impact are powerful but tend not to be nimble. So you will run into a roadblock or traffic jam in something you’re trying to accomplish.

When this happens, try not to force it. Do your best to take the long view, and bide your time. I have accomplished a lot of things in WordPress that I wasn’t sure were possible, sometimes simply because I stuck around longer than the people who were blocking my progress.

Be patient, pace yourself, and keep a few ideas on the back burner, for when conditions might be right for them. The story only ends when you stop writing it.

Looking for more advice?

If you’re joining this open source advice series in progress, you might enjoy the other articles, too!

  1. Intro: Letters to an open source contributor
  2. Communication
  3. Collaboration
  4. Criticizing for change

I think I have a few more of these articles in me, so stay tuned!

Letters to an open source contributor: Communication

Josepha likes to say, “all problems are, at their heart, communication problems,” and I couldn’t agree more. The most powerful tool in your open source toolbox is not an understanding of code or usability, but rather the ability to express yourself and understand what other people are trying to say.

Here are some qualities I have observed among highly successful contributors in open source:

Brevity

Avoid “walls of text,” long paragraphs, and complex sentences.

Inexperienced or insecure contributors sometimes try to establish credibility or persuade their audience by writing a LOT of words. This is a mistake. Verbose communication requires people to work extra-hard to understand what you think or want. By the time they think they understand you, they are likely irritated that they’ve had to work so hard, or they have untested assumptions about why you’re burying them in words.

This is not easy advice for me to follow, because I love words and complex sentences! So when I’m writing to communicate in open source, I make a first draft and then cut words and sentences as far as I can. I sometimes joke that most of my writing time is actually spent deleting!

In open source, time is short and information overload is constant. You appear aggressive and disrespectful when you only communicate in long, complex messages. Be kind; be brief.

Humility

Don’t try to establish credibility by trying to appear smarter than other people; it just makes you look like a jerk. No one wants to work with someone who brags about their skills or calls attention to other people’s ignorance.

Photo by Magda Ehlers on Pexels.com

No one was born knowing any computer language, or any fact, about open source or WordPress. Even if people were snotty to you as you were learning — remember how bad that felt, and don’t perpetuate the pattern. Rise above, and be kind to those who know less than you.

Showing off rarely makes you popular in open source, but humility and helpfulness nearly always do.

Consideration

Open source projects are, if they’re lucky, global organizations full of very different people. Working in the open, with lots of people who are very different from you, is a great way to build something extraordinary.

Photo by Dio Hasbi Saniskoro on Pexels.com

To communicate effectively in those conditions, you must consider how your messages will be received by people from many different backgrounds and cultures. This isn’t just about refraining from slurs, swearing, broad generalizations, and gendered language — though, please avoid all that too! Really, I mean it!

But considerate communication is also:

  • thinking about how to include more people into the conversation, regardless of time zone,
  • allowing enough time for people with different availability to join a discussion or project,
  • assuming positive intent,
  • using group Slack pings sparingly, and
  • thinking about how people will feel, when they read your message(s).

We also communicate considerately by focusing our criticism on the problem, rather than the people. Personal attacks won’t get you anywhere that you really want to be.

Over and above

For even more open source/WordPress communication tips, check out these lessons from the WordPress contributor training course!

What did I miss?

Hey, other experienced open source contributors, what else do you think people need to know, about communicating successfully in open source? Add your advice in a comment on this post!

Even more tenderness, even more compassion

In the US, we hear the pandemic is ending. A billion people have been vaccinated worldwide, and government restrictions are relaxing in many places. I’ve been fully vaccinated, and my pod will be fully vaccinated by next weekend. I have plans to see family members I haven’t seen in almost a year, and I’m so grateful for the hard work and science that went into the rapid creation of the COVID vaccines. 

And I’m sad. I’m so very sad, and so very angry, and so very, very, VERY tired.

I thought I knew exactly how tired I could get, because 2020. This time last year, I was tired in my bones — the stress of uncertainty, invisible risk everywhere, supply chain failure, the late stages of the Trump re-election campaign and presidency… it was exhausting.

So much of that rotten stuff is gone now, and I don’t feel better.

UGH! I just don’t feel better, and it makes me both mad and afraid. Anyone with chronic mental illness or a history of trauma will be familiar with the thoughts that surge: “What if I never feel better again? What if my capacity for joy and peace is just gone? What if this broke me permanently, like nothing else has been able to do… quite… so far?”

I keep talking to people who feel the same way. “Things are getting better,” we tell each other. “Why don’t I feel better? I feel so sad, so unhappy; why?” We look at each other in shared, helpless, irritated anguish. 

Here’s the thing about traumatic events: when a crisis hits, many people (like me) shift into survival mode, and focus on getting through the crisis with minimum damage and risk. I’m excellent at this, and so is my partner. We both survived traumatic events in our past, so survival mode is even familiar, in an almost-comforting way. You put as many feelings aside as you can, and you get the job done. One foot in front of the other; take a breath, and keep moving. 

But of course feelings don’t just go away because I’ve gotten too busy for them. And when it’s time to get out of survival mode, the feelings are there, and they suck. 

This is a kind of delayed grief, even a delayed reaction to trauma, and as far as I know, the only way out is through.

Image of a small dejected child, head lowered, with hair covering face. Child is wearing a fluorescent yellow shirt. Image is very dark.

I know I’m not alone in this — all around me, I see co-workers, friends, and family struggling with exhaustion and deeply painful emotions. This is a time to be tender with ourselves. “But I’ve been reaching for gentleness, for patience and kindness all year, and last year too!” my stubborn brain might say, “Surely it’s time for something else!” 

“It’s time for even more,” says my heart. “It’s time for even more tenderness, even more compassion.” However you get there: whether you start by being compassionate with someone else, and then find that same compassion for yourself… or if you need to start with yourself first, and then bring it to others. 

Because you can’t get blood from a stone. Productivity may have to wait a while longer; goals may be delayed. Quality might have to slip in some places. We’re not back to normal yet; not even close.

If we must be wretched a while longer, let us do so with grace, and grant grace to others.

What happens when you won’t admit (or don’t realize) you’re a leader

Hello, my name is Andrea, and I’m a recovering leader-in-denial.

I’ve spent much of my life stepping (usually reluctantly) into leadership roles, while also eagerly looking for someone else who could lead better than me — so I could stop being in charge! And that rarely happened, much to my surprise and chagrin, but only recently did I realize that was because… I am actually gifted at leadership.

“I smell imposter syndrome!” you’ll say — and you are correct! But having my own imposter syndrome pointed out to me… was not the thing that helped me get past it. The lightning bolt for me, was when I realized that my unwillingness to embrace a leadership role was causing me to screw up the actual work of leading.

Read on for my observations on how leading without admitting or realizing that you’re in charge… is really inefficient and hard!

  1. You’ll probably avoid doing *all* of the job. Many times I have stepped into a leadership role because I was in a group of people who had no direction. I would wait for someone to step up and take charge, and wait some more, and wait some MORE, and finally it was too much for me. So I would speak up and say, “Hey everyone, let’s go this way!” and then shut up again. Little bursts of leadership and strategy are usually better than nothing, but having a consistent and engaged leader is WAY more effective.
  2. You are more likely to undermine yourself and confuse others. If you think you shouldn’t be doing something, you are more likely to do that thing in a half-hearted or apologetic manner. Alternately, you might act passive aggressively, resenting that you’re in a position that you find uncomfortable. I don’t endorse an authoritarian approach to leadership, but you can lead collaboratively without apologizing for holding people accountable or setting limits.
  3. You probably think you’re failing if everyone isn’t happy all the time. Now, I like making people happy, and I think that leaders should care about the health and welfare of the people on their team. As a leader, you have a duty of care, but that duty does not always extend to “please all of the people, all of the time.” Leaders have to make choices, and some choices aren’t crowd-pleasers. Reluctant leaders or leaders-in-denial tend to stay in reaction mode — which is frequently conflict- and tough-decision averse.
  4. You are more likely to get in the way of your people. There’s a leadership adage that says, “when the conductor picks up an instrument, the orchestra falls apart.” The conductor doesn’t grab the violin when it’s time for the solo, or when the violinist is off key. If you’re laboring under the assumption that your primary value to the group is not that of leading, then you’re going to be looking for any excuse to put down that work and go back to individual contribution, sometimes by taking over the work of someone who might just need a little (or a lot of) support to do a better job.
  5. You won’t work on improving your skills. Good leadership is learned behavior, and learned behavior benefits from study and practice. By rejecting the fact that you’re a leader, you immediately cut yourself off from opportunities to get better at leadership in an intentional way. And when you do something badly, then you reinforce the idea that you’re not well-suited for it…. it’s a catch-22!
  6. You exempt yourself as a role model. People from marginalized groups don’t have a long list of excellent leaders to model ourselves after. That might even be one of the reasons you don’t see yourself as a leader — because you don’t look/sound/work like many of the leaders you saw while growing up. When people from traditionally marginalized groups courageously inhabit a leadership role despite all their misgivings, they change the very face of leadership.

I’ve learned a lot about myself on this leadership journey so far, which I love to do. I may have started out by accident — and I won’t say it’s the easiest thing I’ve ever done — but it’s a lot easier and more rewarding now that I’m bringing intent and awareness to the work. If any of this resonates with you, I’d love to hear about it! 

Leadership Lessons from Lincoln

The cover of the book Leadership in Turbulent Times by Doris Kearns Goodwin

I’m reading the book Leadership in Turbulent Times, by Doris Kearns Goodwin, and really enjoying it. Here are some of my notes on the chapter about lessons that can be taken from the leadership of Abraham Lincoln, specifically around his work on the Emancipation Proclamation.

Anticipate contending viewpoints.

Lincoln has my full respect for creating a presidential cabinet full of people who frequently opposed him. Dissent from his advisors was something he cherished, because it allowed him to “stress-test” his ideas and decisions before taking them out into the wider world. Many leaders, in a misguided attempt to reduce conflict, surround themselves with people “smart enough” to agree with them all the time. Lincoln’s cabinet served him as a group of powerful “beta testers,” and by the time they were done discussing and railing against the Proclamation, he knew how he would need to convince the country to come along with him.

He had deliberately built a team of men who represented the major geographical, political, and ideological factions of the Union. For months past, he had listened intently as they wrestled among themselves about how best to preserve this Union. At various junctures, diverse members had assailed Lincoln as too radical, too conservative, brazenly dictatorial, or dangerously feckless. He had welcomed the wide range of opinions they provided as he turned the subject over in his mind, debating “first the one side and then the other of every question arising,” until, through hard mental work, his own position had emerged. His process of decision making, born of his characteristic ability to entertain a full carousel of vantage points at a single time, seemed to some painfully slow, but once he had finally come to a determination to act, it was no longer a question of WHAT—only WHEN.

Goodwin, Doris Kearns. Leadership: In Turbulent Times (p. 218). Simon & Schuster. Kindle Edition.

But how did he keep this critical, dissenting group of men engaged, and working together with him, even when he was determined to do what they disagreed with?

Understand the emotional needs of each member of the team.

Lincoln took the time to really understand the men in his cabinet, to find out what they needed to feel effective and engaged, and then he tended to their needs. He also recognized when a cabinet member was struggling, and made time to talk to them or just spend time with them outside of work. He carved out time to spend one-on-one with each member of the cabinet, careful to avoid the impression of favoritism.

Not only that, but he sought out opportunities to praise his people:

“Every one likes a compliment,” Lincoln observed; everyone needs praise for the work they are doing. Frequently, he penned handwritten notes to his colleagues, extending his gratitude for their actions. He publicly acknowledged that Seward’s suggestion to await a military victory before issuing the Proclamation was an original and useful contribution. When he had to issue an order to Welles, he assured his “Neptune” that it was not his intention to insinuate “that you have been remiss in the performance of the arduous and responsible duties of your Department, which I take pleasure in affirming had, in your hands, been conducted with admirable success.” When compelled to remove one of Chase’s appointees, he understood that the prickly Chase might well be resentful. Not wanting the situation to deteriorate, he called on Chase that evening. Placing his long arms on Chase’s shoulders, he patiently explained why the decision was necessary. Though the ambitious Chase often chafed under Lincoln’s authority, he acknowledged “the President has always treated me with such personal kindness and has always manifested such fairness and integrity of purpose, that I have not found myself free to throw up my trust . . . so I still work on.”

Goodwin, Doris Kearns. Leadership: In Turbulent Times (p. 224). Simon & Schuster. Kindle Edition.
First Reading of the Emancipation Proclamation by President Lincoln, by Francis Bicknell Carpenter

Combine transactional and transformational leadership.

If these terms don’t make a lot of sense to you, don’t despair! Goodwin explains:

Transactional leaders operate pragmatically. They appeal to the self-interest of their followers, using quid pro quos, bargains, trades, and rewards to solicit support and influence the behavior of their followers. Transformational leaders inspire followers to identify with something larger than themselves—the organization, the community, the region, the country—and finally, to the more abstract identification with the ideals of that country. Such leaders call for sacrifice in the pursuit of moral principles and higher goals, validating such altruism by looking beyond the present moment to frame a future worth striving for.

Goodwin, Doris Kearns. Leadership: In Turbulent Times (pp. 234-235). Simon & Schuster. Kindle Edition.

What was fascinating to me about Lincoln’s brand of leadership is how he combined both approaches, adapting to the group he was trying to convince to get behind the Proclamation. In a public letter read aloud at a rally in his hometown of Springfield, Illinois, he argued that by freeing the enslaved people of color in the South and enlisting black men in the Union Army, the Union would gain an advantage in the war: a fundamentally pragmatic approach. Once having secured the agreement of his objectors that black troops would help their shared cause, he switched to a transformational argument:

“If they stake their lives for us, they must be prompted by the strongest motives—even the promise of freedom. And the promise being made, must be kept.” — Lincoln

Goodwin, Doris Kearns. Leadership: In Turbulent Times (pp. 235-236). Simon & Schuster. Kindle Edition.

The proof was in the pudding. By the end of the Civil War, the majority of soldiers saw “emancipation and the restoration of the Union as inseparably linked,” says Goodwin.

Find ways to cope with pressure, maintain balance, replenish energy.

One of Lincoln’s favorite ways to relax was by going to the theater. (I know, right?) He was apparently drawn to Shakespeare’s darker, more tragic plays, like Macbeth, Hamlet, and King Lear. How relaxing, sir! But when the stress got so bad that he couldn’t sleep, he would wake up his aide John Hay and read aloud from Shakespeare’s comedies.

His appreciation of tragedy was matched by his appreciation of silliness, anecdote, burlesque. The narrow seam between tragedy and comedy afforded Lincoln what he called his “literary recreation.” When engaged in a comic tale, his laugh, the artist Carpenter noted, resembled the “neigh of a wild horse.” A friend observed that Lincoln’s laugh served as a “life preserver” for him. Hay recalled that only when “my heavy eye-lids caught his considerate notice would he stop & sent me to bed.” Recitation was Lincoln’s way of sharing in a common humanity during an uncommon, inhumanly isolating time.

Goodwin, Doris Kearns. Leadership: In Turbulent Times (p. 229). Simon & Schuster. Kindle Edition.

Put ambition for the collective interest above self-interest.

The Emancipation Proclamation was issued on September 22, 1862 came into effect on January 1, 1863. Lincoln ran for reelection in 1864, at a time that the Union’s victory was in serious doubt, and opposition to the Proclamation was still very strong. Lincoln’s party suggested to him that the only way he would be reelected, would be to start peace talks with the South and not push the emancipation issue with them.

Bureau of Engraving and Printing portrait of Lincoln as president

“I confess that I desire to be re-elected,” Lincoln acknowledged. “I have the common pride of humanity to wish my past four years administration endorsed,” and at the same time, “I want to finish this job.” Nonetheless, he rejected Raymond’s plea that he dispatch a commissioner to Richmond to meet with Confederate president Jefferson Davis. To sound out conditions for peace without demanding the end of slavery Lincoln considered “utter ruination.” He would rather face electoral defeat than renounce emancipation. He “should be damned in time & in eternity,” he vehemently declared, if he abandoned his commitment to the twin goals of Union and freedom. Moreover, those who accused him of “carrying on this war for the sole purpose of abolition” must understand that “no human power can subdue this rebellion without using the Emancipation lever.” The word firmness is insufficient to connote the iron will with which Abraham Lincoln now stood his ground.

Goodwin, Doris Kearns. Leadership: In Turbulent Times (p. 239). Simon & Schuster. Kindle Edition.

In the end, Lincoln won reelection in a landslide, owing much of his success winning 7 out of 10 of Union soldier votes. These were the men who were most at risk in a continuing war, but they overwhelming showed their support for the cause that Lincoln had inspired them to believe in, too.

I’m really enjoying this book, and I hope you’ve enjoyed reading about some of my favorite takeaways from the Lincoln chapter. Next up: how Theodore Roosevelt did crisis management! I can’t wait.

Musings from speculative fiction: Queen of the Tearling

As a lifelong fan of speculative fiction (science fiction and fantasy), I read the genre for both leisure and intellectual stimulus. When a book or series captures my attention, it’s usually because at least a few of the following things are true: the plot is well-constructed, the characters are interesting/engaging, the writing is competent, and something in the story is relevant to my life (past or present).

Cover art for Queen of the Tearling, first book in the trilogy

The plot of the Tearling trilogy centers around a young woman who lived in isolation with two foster parents until she turned 19, at which point she leaves home to reclaim her dead mother’s throne. She is supported by a small group of soldiers, the Queen’s Guard, but has no real political support within the nobility, military, or clergy. She makes some rash through ethical political decisions upon taking the throne from her profoundly corrupt uncle — decisions that her impoverished nation does not have the power to back up. Luckily, magic saves her in a number of dangerous situations and shores up her credibility with her few supporters and the people.

I’m now reading the second book in the series, The Invasion of the Tearling, and what keeps hooking me is how her guard keeps urging this 19yo queen to avoid alienating other influential people in the kingdom… which she does anyway, because they’re all pretty corrupt and terrible. Her people maintain surveillance on her enemies but fail to share the information they have gathered with her. Thus (or perhaps despite this?) she keeps making rash decisions that seem to be lining her up for inevitable failure. I figure magic will intervene, but I really want to shout at the lot of them.

That said, it’s interesting to think about how one’s ability to lead is weakened by insecure connections both inside and outside one’s organization. Kelsea Glynn and her supporters apparently accept that there are some things she should not know, which makes it harder for her to do her job, and harder for her supporters to do theirs. Whatever obstacles my team and I face, I hope that we always go into it fully united through communication and unity of purpose — especially since we can’t count on magical sapphires to bail us out of sticky situations.