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

by Scott Berkun

E-mail empowers the sender.

E-mail is a closed channel.

E-mail decays over time.

1. Some conversations need to be real time. Brainstorming and teaching require high interactivity,

2. Voice has more data. We are a text-centric culture here, but voices have more data.

4. Many conversations need to be visual.

How much did they read?

Working remotely mellowed everything out, dropping the intensity of both the highs and the lows. Depending on your previous experience, this made

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. Worse, they don't know what to aim for, having never experienced a healthy creative workplace. 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.

Too often teams are imprisoned by methodologies when they should be empowered by them

I didn't care about estimates but needed another level of granularity in lists to help us decide next steps. I was always pushing for lists of things and putting them in order, like good project managers do. I did care about the lists themselves, but early in a project, I cared more about the thinking Adams was forced to do in order to generate the lists. There were two missions clear in my mind: Ensure simplicity. Plan the project to be easily managed.

The natural mistake engineers make is to build from the bottom up. They leave the user interface last, assuming it is the least complex technology. This is wrong. Humans are much more complex than software,

But even if you carefully design teams, the turf needs to be conceptual, not territorial. Organizations become bureaucratic as soon as people define their job around a specific rule, or feature, rather than a goal.

The deal at Automattic was centered on quality of life, not just the quality of life while at work.

I dubbed it NASCAR in reference to how race cars are covered from front to back with logos from different companies, creating a horror show of clashing styles.

(a common occurrence in online discussions known as the bikeshed problem, or Parkinson's law of triviality).

But at the same time, problems that required deeper thinking and bigger bets rarely improved. Even when a debate surfaced about a larger issue, few knew how to convert that debate into a plan.

Developers definitely stay busy, but I don't think we're good, as a culture, at ensuring the most important work gets done. We should have a real issue priority system (pri 1 = wp.com down, pri 2 = data loss, etc.) since without it, all issue reporting is very subjective, and we default to “fix it now.”

Big/Ugly projects we avoid.

4. Conservative ideas. I don't see many people push for big changes, big ideas or crazy thoughts—we're very tactical idea wise—many inspirations are drawn from what competitors are doing.

5. Talent, camaraderie and morale are high.

6. Some things are opaque. Transparency is very high but there are things no one seems to know. 1) How people are compensated 2) How people are hired (criteria for picking people for trial offers / full time offers). #1 is tricky, but #2 isn't. Leads, at minimum, should know more about the process and be involved. You should be teaching us how you've done #5 so well.

Thousands of managers around the world inherit healthy teams in healthy companies, do little of merit, and get great rewards for just being in the right place at the right time. The real story behind some people you meet with fantastic reputations isn't notable talents or skills, but merely an exceptional ability to choose the right time to join and leave particular projects.

What made work at Automattic fun and challenging was how often things changed.

Feedback is hard to come by in life at all. It's easy to give the pretense of feedback: anyone can say to a coworker, “Do you have any feedback for me?” and for the person to say, “No. Not really,” and then for you to say, “Okay, great. Thanks!”

I'd experimented enough to build three traditions into our meet-ups to ensure channels of frequent high-quality feedback:

We'd catch up on everything in each other's personal lives and reconnect without an agenda.

3. 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?

But second, and more important for Automattic, I could let them start to see things from the leader's view.

It's a common weakness among creatives, whether a designer, a writer, or a programmer, to be shy about showing unfinished work.

Once Hugo realized how helpful it was to post hand-drawn sketches and ideas, even if he was sketching ideas from other people, he soared. It told him it didn't matter if the sketches were “right”; what mattered was that his sketch improved the quality of the conversation, which it always did.

Of the many dreams I've had in my life, making great software is one. But the biggest, craziest, and most rewarding dream to chase has been the writing life.

The last act of good leaders is to ensure things go well when they're gone. Many legendary leaders failed at this: Alexander the Great, Julius Caesar, Napoleon, and nearly every monarch in history. As much good as they did in their reigns, most of it was undone by those who followed.

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.

While money provides status, status doesn't guarantee meaning.

Earlier in this book I explained the dangers of data-driven thinking and how the most important things are the hardest to capture in numbers. While we have a universal measure of wealth called money, there is no comparable measurement for meaning. Meaning is personal.

Emotional words like meaning, passion, and soul are scary to people who believe everything in life hinges on pure rationality.

Many people believe that throughout history, work has rarely given people meaning, but that's not true. The history of work is rooted in survival. We hunted and gathered in order to live. Little distinction was made between work and the rest of life. Rather than this making life miserable, it likely made it more meaningful. Every action, however hard, had personal significance. Working with your own hands to catch a fish or build a shelter gave deep satisfaction that few high-paying jobs ever will.

In this sense, companies like Automattic are returning work to its roots. It's not a new, radical idea for work to have meaning and for workers to have both great freedom and pride in the work itself. Instead those ideas are rooted in the origins of work; we've just lost our way. Through the last two centuries, work has become increasingly abstract, which of course, is, in some ways, progress. Fewer people (at least in the First World) are exposed to dangerous, backbreaking labor. But at the same time, we've lost the beneficial effects work used to have on our psychology.

It has been only in the past hundred years that work has become this way. In the centuries of civilization prior, many more of us had crafts and skills that gave us pride.

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.