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

by Scott Berkun

The wise engage all new things with an open mind.

Anyone who's an expert, guru, executive, or coach has likely lost any real sense of what real work is. We assume that because we can give advice on something, we are superior to those who take the advice, but that's not true.

One major mistake Schneider had seen was how companies confused supporting roles, like legal, human resources, and information technology, with product creation roles like design and development. Product creators are the true talent of any corporation, especially one claiming to bet on innovation. The other roles don't create products and should be there to serve those who do. A classic betrayal of this idea is when the IT department dictates to creatives what equipment they can use. If one group has to be inefficient, it should be the support group, not the creatives. If the supporting roles, including management, dominate, the quality of products can only suffer.

Making good ordered lists is the fundamental thing any effective leader does, and it's the heart of popular planning methods like Kanban and SCRUM.

One trick is to be the scribe. If you take on the task of taking notes, people have a chance to see how you think. If they find your recording of what happened clear and honest, you get a trust point. If the way you summarize complex things is concise but still accurate, you get another.

What's sad is that right now, as you read this, there are hundreds of similar organizational off-sites and retreat meetings happening, and the thousands of people attending them have the same central, desperate struggle: to stay awake. The crushing boredom that plagues these events is a disease born of good intentions gone wrong. No manager wants to bore people; they just can't help themselves, and the bureaucracies they work in make it worse. Event planners crush curiosity under the weight of agendas, topic lists, working groups, and exercises, all crammed together like a bad, hyperactive vacation. The slippery slope toward misery starts with all major players having their own agenda, their own thing they're championing this quarter, and they push to make it part of the official schedule. And as their peers respond in kind, a series of endless slices are made into every day, and every hour, until there is no room to breathe. And nothing is real. There is no actual work being done. Instead it's all metawork, or discussions about future work. It's a sea of abstraction.

Write a launch announcement and a support page. Most features are announced to the world after they go live on WordPress.com. But long before launch, a draft launch announcement is written. This sounds strange. How can you write an announcement for something that doesn't exist? The point is that if you can't imagine a compellingly simple explanation for customers, then you don't really understand why the feature is worth building. Writing the announcement first is a forcing function. You're forced to question if your idea is more exciting for you as the maker than it will be for your customer. If it is, rethink the idea or pick a different one.

He told me the central way he'd evaluate me was the quality of what made it out the door. It wasn't about the ideas I had or how I managed schedules. It wasn't how I ran meetings or how well liked I was. Those were all secondary. What mattered was what we shipped. And he told me the only reason anything good ships is because of the programmers. They are everything. They are not factory employees; they are craftspeople, craftspeople who are the fundamental creative engine of making software.

The responsibility of people in power is to continually eliminate useless traditions and introduce valuable ones.

The most striking expression of this is that management is seen as a support role. The company stays as flat as possible for this reason. Schneider described his philosophy in this way: 1. Hire great people. 2. Set good priorities. 3. Remove distractions. 4. Stay out of the way.

Self-sufficient passionate people are hard to find. No manager puts up job postings that state “Wanted: infantile dullards with narrow abilities and fragile motivations.” But like attracts like. Every time a company settles for a mediocre hire, it becomes harder to recruit the best. And just as Mike Little joined Mullenweg to start WordPress, finding the first match sets the tone. Once you have two or three like-minded people, a culture forms that attracts more people with similar values and repels those that don't.

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. If you talk to two children in front of their mom and then each alone, you hear different things. The mystery for why some people you know succeed or fail in life is how courageous they are in pulling people aside and how effective they are in those private conversations we never see. Only a fool thinks all decisions are made in meetings. To pitch an idea successfully is often possible only in informal, intimate situations. The same goes for speaking the deepest truths and having them heard. Almost no one can convince an entire conference room of coworkers with a speech. That happens only in the movies. Some things are never said, or heard, if more than one pair of ears is listening.

safeguards don't make you safe; they make you lazy. People drive faster, not more slowly, in cars with antilock brakes. American football players take more risks, not fewer, because of their padding.

Often acquisitions create a paradox: they're hard to fit into a company for the same reason they're attractive to acquire. The thing you want to buy reflects a different way of thinking, which has value, but that difference is at odds with the culture you already have. Like an organ transplant, natural antibodies will fight against having the new organ fit in. And the more you do to force it in, the less of what you wanted to acquire in the first place remains. The vast majority of acquisitions fail for this reason. Few executives recognize the paradox, or think themselves immune to it.

The absence of dedicated quality assurance people made every employee accountable for quality, which is rare if there are many QA people around.

In every meeting in every organization around the world where bad behavior is happening, there is someone with the most power in the room who can do something about it. What that person does shapes the culture. If the most powerful person is silent, this signals passive acceptance of whatever is going on. And if that person speaks up to say, “Good idea,” or, “Thanks for asking a clarifying question,” everyone notices and will be more likely to do those things. It's deep in human nature to look to the top to define our own behavior, even at a company as autonomous as Automattic.

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.

Too often teams are imprisoned by methodologies when they should be empowered by them (a sentiment captured in the Manifesto for Agile Software Development, a set of simple principles for making software1). Methodologies are often another bad friction that managers impose, putting more faith in a bunch of rules than in the people they've hired.

The first time that a team that has never done estimates before does them, accuracy is poor, as is how much they care about the consequences.

It's a great bullshit test of any boss who says, “X is important.” If she doesn't match that statement with resources, she's incompetent, insincere, or both. If it's important, prove it. Importance is always relative to other projects, not verbal fairy dust to sprinkle over your staff.

design the user interface first. This is a mandate at any organization that makes things people love to use.

Employees can yell and complain, but there is no louder message to management that something is wrong than forcing them to watch a great employee walk out the door.

In any organization, large projects require leverage, but few employees have any. People who have grand ideas but little influence wonder why no one supports them. They think the lack of support is a judgment on their ideas rather than the politics of authority. Ideas are evaluated differently depending on the mouth they come out of.

A leader who shields others from things that get in the way inspires everyone to do the same. It's small habits like these that shift a culture away from the pointless exercises of finger pointing and dodging blame and toward a contagious confidence that the best work of your career is possible right now. The feeling that there's nothing in your way is something few feel often in their careers, if they ever feel it at all.

One-on-ones. During the meet-up, I'd schedule time with everyone to talk in private. The conversation centered on the same four big personal questions I asked everyone in e-mail once a month: What's going well? What's not? What do you want me to do more of? What do you want me to do less of?

The next day Mullenweg tuned in to chat with us and answer any questions about the leadership change. To his credit, this is precisely the kind of kickoff any new lead deserves. It verified for everyone that the company was behind the change and empowered Adams to have a good start with all the support he needed.

The most dangerous tradition we hold about work is that it must be serious and meaningless. We believe that we're paid money to compensate us for work not worthwhile on its own. People who are paid the most are often the most confused, for they know in their hearts how little meaning there is in what they do, for others and for themselves.

It's a shockingly recent notion that work and play should be mutually exclusive things. We learn about ourselves and each other through play, which helps us work together. Not everyone believes this, of course, but I do.