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

by Scott Berkun

Making everyone work in support forces everyone to take customers seriously, which we should since they pay our salaries.

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.

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.

Your Meetings Will Be Typed

Most people doubt online meetings can work, but they somehow overlook that most in-person meetings don't work either.

I knew if I kept our meetings on important decisions and little else, we'd do fine, whether in person or online.

A company rule was that anyone could join any channel.

if anyone missed a conversation or was new to the company, he or she could go back and see the actual discussion.

The trade-off seemed to be the fact that knowing that they were being recorded changed what people were willing to say.

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.

I did not believe in multitasking unless I was doing something trivial, a state I wanted to avoid.

A simple process affords three things: 1. It is easy to launch projects. 2. If it's easy to launch, small projects will get launched. 3. If small things are launched, there is a fast feedback loop about what worked and what didn't, which can be quickly improved because of #1. 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. I've visited companies that use big meetings, with far too many cooks in the room, to rank ideas based on one-sentence descriptions. It was madness.

the only reason anything good ships is because of the programmers. They are everything.

A central element in Automattic culture was results first.

all you saw of your coworkers was the code they produced, the designs they made, the tickets they resolved, or the comments they wrote.

If removing a restriction improves performance or has no impact on performance but improves morale, everyone wins.

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

the biggest challenge people who work remotely face is managing their own psychology.

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

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.

Regarding clarity, most teams in the working world are starving for it. Layers of hierarchy create conflicting goals.

the saving question was always, “How will this impact the user experience?”

Patience is a manifestation of trust. It conveys to the other person that he or she is worth the time.

It's only when something is burning that you find out who people really are.

truths are discovered by breaking rules: you need to break some to learn which are just for show and which ones matter.

The trap is that even if you find a good metric that avoids the trap IBM fell into, people will naturally, even subconsciously, work to game the metric.

You see a similar downward spiral at schools that try to measure teacher performance. They create new student tests for evaluating teachers that reduce time teachers have to teach real lessons, which lowers their scores, which, sad surprise, leads to more testing.

Data can't decide things for you.

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.

Beauty, inspiration, and pleasure are qualities that corporations hope customers find in their products, yet none are easily measured. If you want to explain the difference between Apple, BMW, and IKEA and Microsoft, Fiat, and Walmart, KPIs alone will not help you.

Although he was not using these as a hammer to end arguments, he regularly referred to data as part of his thinking. He wanted a data-influenced culture, not a data-driven one.

“Real Artists Ship.”

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.

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.

But the problem isn't functionality. Functionality means a piece of software is capable of doing something. Merely having a function doesn't say anything about how many people can figure it out or are even interested in trying.

It's design, not functionality, that determines if people will succeed or fail in fulfilling the promises products have made to them.

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

For strategic investments, you don't want to have to continually do the same work twice.

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

Passionate people love to feel like empowered underdogs.

After years of leading projects, the best thing I've learned is that I have to periodically shift between thinking small (bazaar) and thinking long term (cathedral).

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

Things that are less fun to do are usually harder to do, which means the pile isn't ordinary work but a pile of unloved, unwanted, complex work: 1. We do things we like first. 2. We do things we don't like last. 3. The things we don't like tend to be harder. 4. Late changes have cascading effects.

It should never be a surprise that progress seems to slow as the finish line approaches, even if everyone is working just as hard as they were before.

Self-motivated people thrive when granted independence. Managers who want better performance must provide what their staff needs.

If you want longevity, you can't just bet on tradition; you have to continually invest in the future.

GitHub has always been a fully distributed company, naturally reaching many of the same conclusions as Automattic about autonomy, empowerment, and trust.