The Year Without Pants: WordPress.com and the Future of Work

by Scott Berkun

Automatticians had to know themselves well and be outgoing online. Many were. They couldn't depend on coworkers' catching their mood or a boss recognizing something different in their behavior unless it was visible in how they expressed themselves through the narrower, text-dominant channels of remote work.

The realization that everyone is different when you talk to them alone is a secret to success in life. In private you have their full attention.

Making good things is about managing hundreds of trade-off decisions, and that's one of my best skills. Regarding clarity, most teams in the working world are starving for it. Layers of hierarchy create conflicting goals. Many teams have leaders who've never experienced clarity in their entire lives: they don't know what to look for, much less what to do when they find it. Thinking clearly, as trite as it sounds, was my strength.

Being a good lead is all about switching hats: knowing which level of abstraction to work at to solve a problem. It's rarely a question of intelligence; instead, it's picking the right perspective to use on a particular challenge.

To understand who people really are, start a fire. When everything is going fine, you see only the safest parts of people's character. It's only when something is burning that you find out who people really are. Of course, it's wrong to set a fire on purpose, but if you have a small fire already burning, let it burn and see who, if anyone, complains, runs away, or comes to help. Similar truths are discovered by breaking rules: you need to break some to learn which are just for show and which ones matter.

Today many managers love the saying, “You are what you measure.” They're convinced measurement is the secret to success and seek metrics to track—sometimes called KPIs, or key performance indicators, much like IBM executives did back then. Some companies, including Google, insist on having metrics to evaluate any decision, goal, or feature. Despite the popularity of this belief, it's easy to get lost in the very metrics that are supposed to help you find your way.

All metrics create temptations. Even with great intentions and smart minds, data runs you faster and faster into a stupid self-destructive circle. Data can't decide things for you. It can help you see things more clearly if captured carefully, but that's not the same as deciding. Just as there is an advice paradox, there is a data paradox: no matter how much data you have, you still depend on your intuition for deciding how to interpret and then apply the data.

When a culture shifts too far into faith in data, people with great intuitions leave. They'll find employment where their judgment is valued rather than remain as an annoyance in some powerful equation maker's report. Making great things requires both intuition and logic, not a dominance of one over the other. Beauty, inspiration, and pleasure are qualities that corporations hope customers find in their products, yet none are easily measured.

Automattic is fascinating for its complex relationship with data.

He wanted a data-influenced culture, not a data-driven one. He didn't make data the center of the conversation but wanted to ensure they were part of it. His balance of respect for both intuition and analysis was one of his most notable qualities.

Making things is hard regardless of your philosophy or what adage you frame on your wall.

The more experienced that managers are, the longer the list of bad things they've seen that they're trying to avoid. This is what I call defensive management, since it's designed to prevent a long list of bad things from happening. Defensive management is blind to recognizing how obsessing about preventing bad things also prevents good things from happening or sometimes even prevents anything from happening at all.

As a rule, everyone who launched something was expected to stay online for a few hours to ensure things went smoothly.

At Automattic, the traps of trying to make things safe are resisted, although people are motivated more by their sense of independence than an awareness of a grand philosophical principle. The basic notion is that if people are smart and respect not blowing things up, too many safety measures get in the way.

The lesson for Automattic was: features weren't the problem. We had plenty of features and compared favorably with competitors. Adding more features would have little impact on moving more people through the sequence of publishing unless those features helped users get over the first hurdles, and few did.

The bottleneck is never code or creativity; it's lack of clarity.

Most of the ancient and Renaissance masters he admired didn't feel the same way. It sometimes takes ugly effort to make beautiful things. People who love great things but are ignorant of how they're made are mystified by how dirty they have to get their own hands to make anything at all: they think the mess means they're doing something wrong, when mostly it just means they're finally doing real work. This isn't to say you should deliberately create mess and chaos (that'd be silly), but to fear it as a sure sign of error shows ignorance and nothing more.

There was no debate. We all agreed that Team Social should take it on. But there were no practical considerations. When would we start? No idea. How would it work? No idea. But those concerns never came up, as they rarely do when young men get lost in their own ideas. To start big projects, you must have the capacity for delusion. All the rational people, despite their brilliance, are too reasonable to start crazy things. And working against us in this sense was that we'd spent the day walking in the footsteps of Socrates, Plato, and Aristotle, spurring us all to believe in our grandest dreams.

Laughter paves the way for many things. It's one way to build intimacy between people, something every healthy team needs. Humor has always been a primary part of how I lead. If I can get someone to laugh, they're at ease. If they see me laugh at things, they're at ease. It creates emotional space, a kind of trust, to use in a relationship.

Laughter leads to running jokes, and running jokes lead to a shared history, and a shared history is culture.

In extreme situations, people sacrifice their lives for their culture. While cultures form organically, someone has to be the instigator and get things in motion, reinforcing the good and reducing the bad. In many ways, this was me, always looking for little ways to improve the odds. But it was always clear to me that the master facilitator of culture was Mullenweg.

I'd never had a boss before who so naturally took care of the people around him. He has a generosity of spirit that is undeniably sincere, and it comes across in the large, when he's on stage as the leader of the WordPress mission, but also in the small, when you're with him and a handful of others, sharing a few beers.

I'm certain of the following: Self-motivated people thrive when granted independence. Managers who want better performance must provide what their staff needs.

If a technology annoys you, it probably has more to do with how the people around you use it than the technology itself.

mail madness, or e-mailopathy, is the name I have for the psychological disorder where people are so overwhelmed by the waves of e-mail they receive that they protect their psyche by never reading any of it. Instead they skim e-mails quickly and write and send replies even quicker, like a paranoid, drunk blindfolded man pulling the trigger of a fully loaded AK-47.

Technology does have an impact on behavior, but culture comes first. An easily overlooked factor is that most Automatticians have tangible jobs: writing code, designing screens, answering tickets. They're not in the stressful limbo of abstraction that middle managers and consultants live in. Instead there's little posturing or showing off. People who know how to build things don't worry about turf. They know they can always make more. It's often people whose jobs are abstractions that see a company as a zero-sum game where they have to fight and defend what's theirs to stay alive or get promoted.

That pragmatism changes the nature of how people communicate. There were few turf battles, approval seekings, or the grandstanding that dominate many miserable e-mail threads.

Some conversations need to be real time. Brainstorming and teaching require high interactivity, but blogs are designed for latency. If you are exploring an idea, or debugging something, and want the best possible communication, go real time (IRC/Skype).

Voice has more data. We are a text-centric culture here, but voices have more data. We get tons of information (humor, attitude, nuance) you can't get from text. When in doubt, go voice. A 20 post P2 thread can sometimes be replaced by a 3 minute Skype call (Efficiency ftw).

Some conversations need fewer people. P2s are open to all. Some threads narrow to 2 people going back and forth, and they should get a room (email/Skype/hotel). They can report back if a conclusion was reached. Other times 10 people are involved, bu...

Many conversations need to be visual. As a rule, I never want to talk about a UI feature without a screenshot: A rough sketch explains more than 5 paragraphs of text (e.g. an idea in text may not work in pixels). All designers should be visualizers for P2 threads, saying “do you mean something like this? (show s...

Thread hijacking. This is when you carefully write a post, and then a comment comes along asking a tangential question that everyone finds more interesting. If your thread gets hijacked, start it again—don't as...

ADD kills big ideas. Big ideas require more thinking before commenting. Given post A (clever idea on some little thing) vs. post B (radical sweeping idea on some big thing), post A will tend to get more comments. It's easier to respond and say “cool!” or “+1.” Post B requires more investment to comment, so it gets less of them. This is misleading—it ...

How much did they read? If someone jumps in on a thread, there's no way to know how much they read. Did they just read the previous comment? Did they read the whole thing, but not understand it? Very hard to intuit just from a comment what...

Is silence acceptance? If you post and no one comments, does that mean they read it and they agree? Read it and don't care? Or didn't read it? No way to know without poking at people. Lead...

I find P2 great for documenting things, ok for soliciting feedback on something, but pretty terrible for having a “discussion”. If I want to discuss something with someone (or a group of people) I just ping them on IRC. Skype, phone, etc. also work for discussions. No need to have a discussion with myself on a P2.

My work style was direct by Automattic standards. I've always demanded that my bosses explain things I don't understand. I want to be taught, not told. I don't mind being proven wrong or trumped provided I learn something, but I did not follow decrees well. This makes me an excellent or frustrating person to have working for you depending on how often you like to explain yourself, as Mullenweg discovered in our occasionally long debates. Once we had a four-hour Skype argument about how a single screen should be designed, a debate that in hindsight we've agreed could have been resolved with a short voice call (yes, our debate was typed).

The countermeasure for Matt bombing is what's called “managing up.” As the lead for Team Social, my job for the team was to have as few public ruffles with Matt as possible. It was my job to anticipate potential land mines with Matt, or anyone else, and resolve them proactively instead of trying to put out fires on our P2. It also meant that when Matt joined a thread and confused people, it was my job to sort it out by directly asking Matt to clarify or working as a team to respond.

Online it's hard to know when you've intimidated someone because silence means different things. In real life when you hurt someone's feelings, you can see it in his or her eyes and feel something in your heart. Every employee in the company, including Matt, Toni, and me, lost touch with the empathy we'd have in certain situations for people who had less authority than we did.

During my year at Automattic, no one ever yelled at me. I was never in a meeting that made me angry or want to storm out. The worst kinds of workplace moments simply weren't there. You can get only so angry at someone typing at you. People were polite, almost painfully so. But the best things about workplaces, like sharing an epiphany after working for hours at a whiteboard, were gone too. Working remotely mellowed everything out, dropping the intensity of both the highs and the lows. Depending on your previous experience, this made things better or worse.

Many Automatticians, including Mullenweg, believe that distributed work is the best possible arrangement.

Jerry Hirschberg, the former head of design for Nissan, had a theory of work he called Creative Abrasion.1 He believed you need the right amount of friction for good work to happen—not too much and not too little—and that few managers get it right.

Knowing how much friction is needed and when to apply it is the skill that successful leaders, from the coach of a competitive basketball team to the conductor of an orchestra, must master.

The only honest test of the value of any management activity is to run projects without some of them and observe how well people perform with a lighter touch. It's a test few leaders have the courage to take. The worry among managers is that this test would reveal that quality improves when they do less managing. It might just turn out that an executive whose division always demands eighty-hour workweeks might really just need a manager who knows how to hire well, put a few healthy frictions in place, and get out of the way.

Automattic is fascinating for how little built-in friction it had—or, more accurately, how much negative friction Toni Schneider and Mullenweg deliberately prevented. The ultimate friction most creative people face—the burden of meeting schedules and deadlines—was rare.

The saving grace at Automattic was passion. They naturally found inspiration in the world, from WordPress, or from each other. An open vacation policy had little negative impact on people who would choose to work on their own time anyway.

When Tumblr, a lightweight blogging tool, became a media darling in 2010, with growth numbers that any analyst would see as a threat to WordPress, not much changed at Automattic. It was common to see P2 posts referencing trendy articles proclaiming the death of blogging and articles pointing to the rise of Facebook, Twitter, and Tumblr as ending the era of blogs—articles that rarely mentioned WordPress's continued growth, as those services frequently linked to the deeper content that blogs provided.

Open source cultures naturally see the world as positive sum, with room for everyone, but the capacity to see the world both ways is the best. Rather than just complain, at a future meet-up we experimented ourselves: Team Social used Tumblr every day for the week.

Automattic continually invests in WordPress, from funding WordCamps to helping organize the WordPress community, but to call those efforts marketing would be cynical. As always with Mullenweg, the investment was in the long-term vibrancy of WordPress, with marketing for WordPress.com a side effect of those investments. Only a handful of teams, including VIP, Polldaddy, Akismet, and VaultPress, had their own sales and marketing efforts. VIP had the strongest, reaching out to major companies looking for WordPress hosting and selling them high-end services. But even they did little in the way of traditional marketing since their targets were exclusive.

The lingo for the challenge is what's called refactoring. The word is a fancy way of saying you're going to take the guts of something one part at a time and rework it without disturbing the rest. I don't like the word because many people who use it confuse words with reality: simply because you have a fancy word for something doesn't make you any smarter. It probably makes you stupider because you confuse your precise vocabulary with precise skills. The problem with problem-solving methods, which all business methodologies are, is that they are abstractions, but the world is not abstract. Real work contains hard parts that no method can dictate for you.