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

by Scott Berkun

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.

if you don't have a plan, then you never worry if your plan is wrong.

the map is not the territory.

If you make an elaborate map, you forget the world may change for the worse while you're staring ...

you learn more from the present since it has your full attention.

let the project define the plan. Only a fool chooses tools before studying the job to be done.

There is little worse than working on something in small increments for months, only to discover, near the end, that the only solution for the last increment requires redoing everything you've done so far.

as was the case with many Microsoft products, and now WordPress too, many little features, each designed on its own, compete for attention at the expense of the customer's experience.

Laughter paves the way for many things. It's one way to build intimacy between people, something every healthy team needs.

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.

The culture in any organization is shaped every day by the behavior of the most powerful person in the room.

If the most powerful person is silent, this signals passive acceptance of whatever is going on.

It's a common habit of CEOs: they spend so much of their day with people vying for their attention that there's little need to for them to worry about schedules.

On Skype or IRC, all of the secondary feedback people give each other were gone. You know only the words they type. He'd earned a reputation for being terse, occasionally cryptic, and, to some, quite intimidating online.

As the company grew and demands on Matt's time increased, his ability to participate in decisions fell, contributing to the terseness others experienced.

Designing is best done first on paper. It's cheap and fast, making it easy to try many ideas well before anyone's ego is invested.

Projects accumulate a pile of annoying tasks people postpone, but in order to ship the product, that pile must be emptied. 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.

at the end of any project, you're left with a pile of things no one wants to do and are the hardest to do (or, worse, no one is quite sure how to do them).

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

If his or her performance stays the same or improves, you win. If it goes poorly, you still win, as you've demonstrated your willingness to experiment, encouraging everyone who works for you to continue looking for ways to improve their performance.

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

You never see the Skype chats you're not in. Remote work demands social proactivity.

given how old e-mail is: it's older than the web itself by more than a decade.

Technology does have an impact on behavior, but culture comes first.

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.

E-mail empowers the sender. They can put in your inbox whatever they like

E-mail is a closed channel. There's no way to see an e-mail if you are not on the “to” list, forcing work groups to err on the side of including everyone.

E-mail decays over time.

Some conversations need to be real time.

Voice has more data.

Some conversations need fewer people.

Many conversations need to be visual.

Thread hijacking.

ADD kills big ideas.

How much did they read?

Is silence acceptance?

It's easy for people to dismiss a thread if the first thing they see in the comments is a long debate between two people about a detail you don't care much about.

“Matt bombing.” This was when a team was working on something on a P2, heading in one direction. Then late in the thread, often at a point where some people felt there was already rough consensus, Matt would drop in, leave a comment advocating a different direction, and then disappear (not necessarily intentionally).

Matt was brilliant, but it was hard to believe he had the same depth of understanding on every aspect on the thread that those on the project did.

meant that when Matt joined a thread and confused people, it was my job to sort it out by directly asking Matt to clarify or working as a team to respond.

Matt set good examples for praising in public and critiquing in private.

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.

Many things managers do create unnecessary and unhelpful friction. From insisting on unnecessarily detailed plans, to long, stressful project review meetings, much of the boring machinery identified as management has more value for the manager's ego than the quality of work produced.

The only honest test of the value of any management activity is to run projects without some of them and observe how well people perform with a lighter touch.

worry among managers is that this test would reveal that quality improves when they do less managing.

Like a puck on an air hockey table floating around aimlessly, ideas need something to work against—a mallet or a wall—to use as leverage.

There must be someone challenging ideas in ways their creators don't necessarily like in order for those creators to see the blind spots in their thinking.

Breakthroughs await in those ...