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

by Scott Berkun

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.

But values aren't something you have; they're something you use. Anyone can proclaim to believe in anything. The question is how much of their actions reflect those beliefs.

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

Making lists is a great way to clarify thinking. You put down thoughts, refine them, order them, and even share them with other people. And if you're willing to do the hard work of putting a list in priority order, you can condense great visions into a few simple sentences.

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.

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.

Remote work is merely physical independence, and the biggest challenge people who work remotely face is managing their own psychology. Since they have more independence, they need to be masters of their own habits to be productive, whether it's avoiding distractions, staying disciplined on projects, or even replacing the social life that comes from conventional work with other friendships.

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.

Being a good lead is all about switching hats: knowing which level of abstraction to work at to solve a problem. It's rarely a question of intelligence; instead, it's picking the right perspective to use on a particular challenge.

All metrics create temptations. Even with great intentions and smart minds, data runs you faster and faster into a stupid self-destructive circle.

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.

When a culture shifts too far into faith in data, people with great intuitions leave. They'll find employment where their judgment is valued rather than remain as an annoyance in some powerful equation maker's report.

Merely shipping something does not make you an artist. However, the only way the world learns of what makers makes, whether it's art or trash, is when they're brave enough to say it's done and put it out into the world.

The more experienced that managers are, the longer the list of bad things they've seen that they're trying to avoid. This is what I call defensive management, since it's designed to prevent a long list of bad things from happening. 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.

By not having too many safeguards, we were trusted to pay full attention. Keeping things a little dangerous made things safer.

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

People who love great things but are ignorant of how they're made are mystified by how dirty they have to get their own hands to make anything at all: they think the mess means they're doing something wrong, when mostly it just means they're

finally doing real work. This isn't to say you should deliberately create mess and chaos (that'd be silly), but to fear it as a sure sign of error shows ignorance and nothing more.

In the old days, Microsoft used to deliberately understaff teams to help

keep pretense and BS low. Too much understaffing causes misery, but if you cut it right and delegate ownership liberally, morale and productivity stay high. Passionate people love to feel like empowered underdogs.

vaporware can go on for years with people endlessly believing in something no one is working on, preventing plenty of good plans from starting because of an unchallenged mythology.

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.

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.

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

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.

If it's important, prove it. Importance is always relative to other projects, not verbal fairy dust to

sprinkle over your staff.

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.

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 last act of good leaders is to ensure things go well when they're gone.

The same ego that drives grand leaders defeats them in the end because they can't accept the notion that someone will replace them.

Succession planning must be part of any long-term leader's thinking, and it has to be done now.

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. While money provides status, status doesn't guarantee meaning. They're paid well because of how poorly work compensates their souls. Some people don't have souls, of course, but they're beyond the scope of this book. Among those with souls and high-paying but empty jobs, there's a denial of how what they seek is hard to get in the way they're trying to get it.