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

by Scott Berkun

I withheld judgment. The wise engage all new things with an open mind.

In anthropology terms, this superficial mimicry is called a cargo cult, a reference to the misguided worship of abandoned airplane landing strips among tribes hoping for the goods that airplanes had delivered to return.

No technique, no matter how good, can turn stupid coworkers into smart ones. And no method can magically make employees trust each other or their boss if they have good reason not to.

The inability to scale is one of the stupidest arguments against a possibly great idea: greatness rarely scales, and that's part of what made it great in the first place.

Event planners crush curiosity under the weight of agendas, topic lists, working groups, and exercises, all crammed together like a bad, hyperactive vacation.

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.”

William Gibson famously wrote, “The future is here, it's just not evenly distributed.”

This is the advice paradox: no matter how much advice you have, you must still decide intuitively what to use and what to avoid.

There is nothing wrong with tradition until you want progress: progress demands change, and change demands a reevaluation of what the traditions are for and how they are practiced.

The responsibility of people in power is to continually eliminate useless traditions and introduce valuable ones. An organization where nothing ever changes is not a workplace but a living museum.

In his classic book The Soul of a New Machine, Tracy Kidder noticed that Data General's efforts to hire people with strong internal motivations changed things: “Labor was no longer coerced. Labor volunteered. When you signed up you in effect declared, ‘I want to do this job and I'll give it my heart and soul.’”6

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.

Typo

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.

If you ask the old-timers, Automattic believed in the broken window theory, the idea popularized by Jane Jacobs in her book The Death and Life of Great American Cities.1 She examined why some neighborhoods in New York City were safer than others and concluded that neighborhoods that were well maintained by their inhabitants, including small things like picking up trash and fixing broken windows, tended to have less crime.

The broken windows theory has been challenged for not being the primary reason some neighborhoods were safer, but the premise—little things done well consistently can have big effects—has merit.

When a culture shifts too far into faith in data, people with great intuitions leave.

If you want to explain the difference between Apple, BMW, and IKEA and Microsoft, Fiat, and Walmart, KPIs alone will not help you.

I'd seen this before. The solution is vision. Someone has to define what we're trying to get to and clarify which ideas are both more and less important in completing that vision. To simplify a design requires thinking holistically—how the whole thing fits together for the user—rather than how good any idea seems on its own.

Ambiguity makes everyone tolerant of incompetence.

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

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.

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. It's a relationship cushion.

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.

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.

It's easier to get feedback and make adjustments with how a team works if you're in the same room. 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!” and walk off having validated all of your bogus assumptions about your awesomeness for another year. The reality check is to consider how many things you've wanted to say to people you've worked with that if they were open to it, could have helped them do better work but that you've been afraid to mention.

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?