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.

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!

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