Matt W. Kane

Year without Pants

Scott Berkun—20I3.


  • Since location is irrelevant, Automattic, the company that runs, can hire the best talent in the world, wherever they are.


  • You can tell from my chats with Hanni and Barry that they were charming. And smart. And with only text, they conveyed personality and warmth. To work at a remote company demanded great communication skills, and everyone had them. It was one of the great initial delights. Every corporation has the same platitudes for the importance of clear communication yet utterly tails to practice it. There was little jargon at Automattic. No “de-prioritized action items” or “catalyzing of cross functional objectives.” People wrote plainly, without pretense and with great charm.


  • They decided to force customers to answer three good questions:
    • What did you do?
    • What did you see?
    • What did you expect?


  • Often founders don’t fully understand the seeds they’ve planted until much later.
  • Schneider had specific ideas about how to make a great company culture, ideas that Mullenweg shared. 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 “me 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 creative 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.
  • He wrote a creed that would appear on official documents, including in my offer letter:
    • I will never stop learning. I won’t just work on things that are assigned to me. I know there’s no such thing as a status quo. I will build our business sustainably through passionate and loyal customers. I will never pass up an opportunity to help out a colleague, and I’ll remember the days before I knew everything. I am more motivated by impact than money, and I know that Open Source is one of the most powerful ideas of our generation. I will communicate as much as possible, because it’s the oxygen of a distributed company. I am in a marathon, not a sprint, and no matter how far away the goal is, the only way to get there is by putting one foot in front of another every day. Given time, there is no problem that’s insurmountable.
  • Unlike proclamations about culture that are easy to put in speeches and emails, it’s the small decisions that define the culture


  • The unwelcome bonus nail in this coffin of a meeting—a nail so definitive it rendered the meeting; unsavable even by a nuclear-powered crowbar—was my choice to lead an around-the-room-introduction, the soul-draining I death knell of millions of unloved meetings throughout history.
  • Most people doubt online meetings can work, but they somehow overlook that most in-person meetings don’t work either.
  • And even if you didn’t see them. Everyone understood that all of the channels were logged, meaning you could go to an internal website and find a searchable history of every conversation ever held in IRC in the company. This seemed extreme to me at first, but I realized every corporation in America has the right to look at employee e-mails. Corporate communications are corporate property. At least at Automattic, the rules were clear and fair: everyone, not just executives, had access. Mullenweg and Adams explained to me the company line that if anyone missed a conversation or was new to the company, he or she could go back and see the actual discussion. This was one of many practices inherited from the WordPress open source project itself. The trade-off seemed to be the fact that knowing that they were being recorded changed what people were willing to say. I’d never seen a company with a policy like this, and I decided I’d have to wait and see if that were true.


  • 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 are a disease born of good intentions gone I 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.
  • The big bet of many retreats is the location. The hope is that a resort in the woods or a trip to a special city will provide a fresh environment away from the daily routines, a change that stimulates new thinking. But they forget the most important thing that location cannot change: the company culture. No matter where they go, they take dozens of forgotten assumptions about how work is done along with them. The more an event is driven by the people in power, the more it will reinforce the status quo. This is why these big meetings start with promises of growth and innovation and end with a vague sense of disappointment. Somehow the stakes are low, which means that if the results are poor, no one minds. There will be no firings or demotions for running a bad off-site.
  • The general work flow at Automattic had seven steps:
    • I. Pick a problem. A basic problem or idea for is chosen. It could be something like, “It’s too hard to print blog posts,” or, “Let users share from WordPress to Facebook.” There are always hundreds of ideas and dozens of opinions about which ideas are important. There’s no formal system for deciding, but many came from Mullenweg or as suggestions from the Happiness folks. After an idea is chosen, discussion begins on how it should work.
    • 2. Write a hunch announcement and a support page. Most features are announced to the world after they go live on 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.
    • 3. Consider what data will tell you it works. Since it’s a live service, learn from what users are doing. The plan for a new feature must consider how its positive or negative impact on customers can be measured. For example, if the goal is to improve the number of comments bloggers get from readers, we’d track how many comments visitors write each day before and after the change.
    • 4. Get to work. Designers design. Programmers program. Periodically someone checks the launch announcement to remind everyone of the goal. As more is learned about what’s possible, the announcement becomes more precise. Sometimes the feature pivots into something different and better.
    • 5. Launch. When the goal of the work has been met, the feature launches. It’s often smaller in scope than the initial idea, but that’s seen as a good thing. The code goes live, and there is much rejoicing.
    • 6. Learn. Data is captured instantly and discussed, often hourly. By the folks who did the work. Bugs are found and fixed. For larger features, several rounds of revisions are made to the design.
    • 7. Repeat.
  • The fundamental mistake companies that talk about innovation make is keeping barriers to entry high. They make it hard to even try out ideas, blind to how much experimentation you need to sort the good ideas from the bad.


  • There are many theories about why teams of four to six work best, but the simplest is ego. With about five people, there’s always enough oxygen in the room. It means on average that every person gets to speak once every five times, which is enough for everyone to feel they are at the center of things. At this level of participation. Their pride can be invested in the team instead of focused inwardly on themselves. The US and other national armies made similar observations about the magic of small unit sizes, and it’s the basis for how they’ve trained soldiers since I948. Larger groups were less likely to fire their weapons to defend themselves, but if they were trained in small units, their rates of fire increased. From this perspective, a team of ten to twenty people is unlikely to function in the same way as a small team does. It’s likely that smaller units will naturally form despite what the organization chart says.
  • I couldn’t help but consider what Washington Roebling, one of the engineers of the Brooklyn Bridge, once wrote: “Man is after all a finite being in capacities and powers of doing actual work. But when it comes to planning, one mind can in a few hours think out enough work to keep a thousand men employed for years.”
  • 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 are because of the programmers. They are everything. They are not factory employees; they are craftspeople, craftspeople that are the fundamental creative engine of making software. Although my job title was program manager, I wasn’t granted power to run around making demands all day. There would be days I’d need to make demands, but I’d have to earn them.
  • When a new team forms or the central project gets cancelled, there are lingering doubts on everyone’s mind. And the more unusual the circumstances are, the bigger the doubts are. Leaders have two good choices with that uncertainty: use that tension to your advantage or diffuse the tension.
  • I’m the kind of leader who kills uncertainty. I want to identify the doubts and nail them to the wall. They might linger there for weeks, but by making everyone’s private fears public, they become far less dangerous.
  • I explained I knew full well that hiring me was an experiment. But I told them I liked experiments, and they should too. Experiments were awesome. The only way you learn is by doing things where you don’t know the outcome. The only problem with experiments is not when the go wrong, but when you can’t end them. I explained that Mullenweg and I had discussed the challenges. If any of the experiments we were doing, from teams to my leadership choices, to even the nature of my employment, didn’t work out. They should let me or Mullenweg know. Either we’d fix it, or I’d leave. Until that happened, I was open to everyone’s ideas for how our team should work.
  • It seems now like an odd conversation. But as awkward as it sounds, what I’d offered is the unspoken truth in any healthy organization. Every new manager is a kind of experiment. And any experiment that goes wrong should be changed. I can’t recall ever reading a book on management that prescribed bringing this up directly. But it seemed obvious. If I couldn’t earn trust in the Hovercard project, I had to find other turf to start with. More than anything else, I wanted them to know that whatever questions they had about me or our situation were valid and that I was thinking about them too. Bringing it up together surfaced those doubts so we could work out answers together. As the lead, I could raise these issues without being confrontational, whereas they could not. So I did it. But I also made the argument for why it might work I had experience with just about everything that goes right and wrong projects and with teams.
  • My last point was the singular way I’d evaluate my success: to get the best value for Automattic out of every hour they worked. Every decision I was going to make as lead—what projects we worked on, what bugs we fixed, what questions we asked—would be about maximizing their value. Not every feature or bug fix had the same value to customers, and therefore to Automattic, and my role as lead was to keep the work on everyone’s plate to have the greatest value possible. I expressed this in terms of how valuable their time was to me rather than them as a resource for me to exploit
  • I had two questions that had been on my mind that I asked them as group:
    • 1. How do you know if you’re doing a good job?
    • 2. How should we handle within-team conversations on our P2?


  • Failed predictions aside, a common presumption is that the future will be uniform and singular, discounting how chaotic the world is at any time William Gibson famously wrote, “The future is here, it’s just not evenly distributed.”But the past is unevenly distributed in the present too. At the same time we have poor families working on! Farms with their bare hands, urban organic chefs are heralded as innovators for using rustic cooking methods and college dropouts get venture capital funding for start-ups based on the centuries-old concept of to-do lists. There are so many kinds of work and the notions of the past and future are so circular that only a fool would confidently predict what’s next.
  • The problem with modem work, and one that sheds light on the future, is how loaded workplaces are with cultural baggage. We faithfully follow practices we can’t explain rationally. Why is it that work has to start at 9:00 a.m. and end at 5:00 p.m.?
  • Any manager who eliminates superfluous traditions takes a step toward progress.
  • Every tradition we hold dear was once a new idea someone proposed, tried, and found valuable, often inspired by a previous tradition that had been outgrown. The responsibility of people in power is to continually eliminate useless traditions and introduce valuable ones.
  • The volunteer culture Automattic inherited from WordPress, where contributors were under no obligation to participate, defined a landscape that granted wide autonomy to employees. Schneider and Mullenweg went to great lengths to keep support roles, like legal, human resources, and even IT, from infringing on the autonomy of creative roles like engineering and design. The most striking expression of this is that management is seen as a support role.
  • Is often safer to be in chains then to be free.

CHAPTER 9 working the team.

  • You get more mileage if you make people laugh, even if it’s at themselves, at the same. Time you’re reminding them of something they’ve forgotten.
  • 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 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 appears is listening.
  • How people who are respected treat you defines how everyone else will treat you.
  • Over my career, I’ve often been asked how I could manage programmers without doing programming myself. I believe I can manage anyone making anything provided two things are true: clarity and trust. If there is clarity between us on the goal and how we’ll know when we’re done, then we can speak the same language about what we need to do to get there. I knew enough about programming to call bullshit when needed and ask insightful questions. 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.
  • Patience is a manifestation of trust.

CHAPTER I0: how to start a fire.

  • 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.
  • Engineering 101 includes the concepts of incoming rates (the rate at which new problems are discovered) and fix rates (how fast they’re being fixed). It’s a very rough metric, but if Incoming > Fix, quality is probably going down, and if Incoming < Fix, quality is likely going up. This helps project leaders understand what’s going on across the project. Even hospitals and fast food restaurants use metrics like these to decide if they have enough staff or how long the average customer is going to have to wait.

CHAPTER 11: real artist’s ship

  • The absence of a grand schedule removed the constant fear of falling behind that many projects create and replaced it with small but frequent payoffs that we were making things better.
  • A major reason it works at Automattic is belief in counterintuitive philosophy: safeguards don’t make you safe; they make you lazy.

CHAPTER 12: Athens lost and found

Chapter 13: double down

  • It’s never a surprise in great projects to find grueling work somewhere along the way—work that never upholds the same aesthetic as the final results. Tales of the hard parts often fail to make it it into the brochures or the corporate tours.

Chapter 14: there can only be one

  • 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. Sharing laughter also creates a bank account of positive energy you can withdraw from, or borrow against, when dealing with tough issues at work.
  • Laughter leads to running jokes, and running jokes lead to a shared history, and a shared history is culture. What is a friend, a brother or sister, or a partner but someone you share important stories with? Families, tribes, and teams all function in similar ways. Building bonds through rites of passages and shared experiences. 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.
  • If ever you wonder about why a family or a company is the way it is, always look up first. The culture in any organization is shaped every day by the behavior of the most powerful person in the room lets it happen.
  • 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.

Chapter 15: the future of work, part two.

  • As I pointed out earlier in the book, remote work, and many other perks Automattic used. Will work or fail because of company culture, not because of the perk itself. Since by now you know how my team functioned, in this chapter I’ll explore the general challenges with working distributedly and without e-mail.
    • Self-motivated people thrive when granted independence.
    • Managers who want better performance must provide what their staff needs.
  • Remote work is a kind of trust, and trust works two ways. Recently Yahoo CEO Marissa Mayer banned remote work from her company, claiming it made people less productive. She might have been right: in her company, people may have abused the trust that remote work grants employees. Some employees abuse free office supplies from the copy room. Others lie about taking sick days.
  • Outsiders assume remote work means working from home, but that’s an important inaccuracy. The true directive is that employees can locate themselves wherever they want. You could work from your back deck. Or you could rent an office in a co-working space or travel around South America in a used Jeep with good Wi-Fi. In all cases it is up to you as an employee to figure out how to be productive. This is true everywhere, of course, but with less structure from management, there are fewer places to hide bad habits. For people with poor discipline, this freedom can be a problem, just as any other kind of freedom can be.
  • Remote work demand social proactivity
  • 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
  • I find P2 great for documenting things, ok for soliciting feedback on something, but pretty terrible for having “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.

Chapter 16: innovation and friction

  • 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 a conductor of an orchestra, must master.

Chapter 17: the intense debate.

Chapter 18: follow the sun.

Chapter 19: the rise of the jet pack.

  • Mullenweg clarified the importance of the project, and as a good leader should, he offered whatever resources I needed. 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.
  • By the time they finally got to the user interface work, so many constraints exist that even the best designers in the world couldn’t salvage the project. The answer is simple: design the user interface first. This is a mandate at any organization that makes things people love to use.

Chapter 20: show me the money.

Chapter 21: Portland and the collective.

  • 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.
  • One afternoon after lunch, designer Noel Jackson and I ranted! About things on we thought could be better. The home page was discussed, and we agreed it had major problems. It was odd that the Sign Up button, the most important button on the page, was on the right side of the screen It’s basic design knowledge that people who use Western languages read left to right, meaning that what you put on the left is seen first. We rallied on the many reasons that it was worth trying the other way and about how odd it was that we hadn’t tried it. The company had done many A/B tests and redesigns, but somehow this critical real estate had been ignored. Just as there was no team for the store, there was no team for the home page either.
  • Finally Noel shook his head and went to grab his laptop. I asked him what he was doing, and he said, “I’m fixing this now.” And he did. In a few minutes, he rewrote the code for the page to move the bar to the left. We’d also discussed simplifying the design, which he did. Evan Solomon, an expert with A/B testing, helped us measure the impact. This simple change improved signups by 10 percent. Ten minutes of work for a 10 percent increase in one of our primary metrics: an amazing payoff for the price of low-hanging fruit. This story exemplifies my confusion over Automattic, and it reflects what Lance Willet had said to me back at Seaside: “Welcome to the Chaos.” Big opportunities were everywhere. But few grabbed them. Was it a risk-averse culture, despite how much freedom there was to take risks? Was it the personalities of the people hired? Was it a side effect of team divisions? Was it something about P2s? Or was it an effect of the behavior Matt and Toni cultivated? In fact, all of these were factors. It took only ten minutes of work by Noel to remind me both how open the playing field was at Automattic and at the same time how few were willing to grab the ball and run with it. It was a cultural paradox I still have not resolved.
  • Managers often wrap their egos around meetings. And long meetings ensure they always feel that they’re the center of attention, even if the meeting is a waste of time for everyone else.

Chapter 22: the Bureau of socialization.

  • The first day of a new team on a short deadline is fascinating anthropology. Everyone tries to figure everyone else out—who is talented, who has the same taste, who is easy or hard to work with, who has the status.

Chapter 23: exit through Hawaii.

Chapter 24: the future of work, part three

  • But I can tell you this: they have answered many important questions the working world is afraid to even ask. The most dangerous tradition we hold about work is that it must be serious and meaningless. We believe that we are paid money to compensate us for work and 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. While money provide status, status doesn’t guarantee meaning. They are paid well because of how poorly works compensates their souls.
  • The popularity of Dilbert, The Office, and any other of the pop-culture windows on cubicle life attests to the dark absurdism with which many Americans have come to view as their white-collar work