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The Year Without Pants


My take: really good book. Full of knowledge, forward-thinking, interesting story as well.


p. 28 Much of what bad managers do is assume their job simply to find new things to jam and new places to jam them into, without ever believing they need to understand how the system - the system of people known as culture - works.

p. 29 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.

p.36 Often founders don’t fully understand the seeds they’ve planted until much later. Talent is hard to find, especially at new organizations, which allows leaders to justify rushing to hire people who are selfish, arrogant, or combative. This is poison for culture, assuming you want a culture of geneous, confident collaborators. Starting a company, or even a project team, is an exceedingly hard challenge, but in the scramble to survive, founders often hire to solve immediate needs and simultaneously create long-term problems.

p.54 What good is something that scales well if it sucks? Why is size the ultimate goal or even a goal at all? If you’re the kind of person who loves Seaside or the place where you work, you don’t need it to be any bigger than it is. 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.

p.61 More than anything else, I recognized that the big cultural bet wasn’t on process but on people. Instead of betting on the enforcement of an elaborate fifty-step process or the magical talents of management, Automattic put the onus on individuals. It was like a small startup company where every employee was empowered, out of necessity, to make many decisions free of approvals from the long list of grumpy corporate gatekeepers.

p.61 It’s always a bad idea to name things after how they work or to fit into brand strategy. The best feature names simply describe what the thing does. (JavaScript)

p.66 It’s likely that smaller units will naturally form despite what the organization chart says.

p.67 No one sees the importance until long after, and then they all share the same lie about the wave they saw coming way back when.

p.98 Little things done well consistently can have big effects

p.99 I tried to remember Mullenweg’s attitude of letting that which did not matter, not matter. Maybe with the right culture and talent, you didn’t need some of the fundamental things experts claim you need.

p.101 If my frustrations weren’t matched by the frustrations of the people doing the work, perhaps it was my problem and not theirs.

p.103 Just as there is an advice paradox, there’s 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. There's no good KPI for measuring KPIs.

p.126 The bottleneck is never code or creativity; it’s lack of clarity.

p.134 The prevailing attitude at Automattic was that any big project is simply a series of smaller ones, and I liked this.

p.134 The only sane way to work is to let the project define the plan. Only a fool chooses tools before studying the job to be done.

p.136 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.

p.147 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.

p.147 It should never be a surprise that progress seems to slow as the finish line approaches, even if everyone is working just a hard as they were before.

p.161 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.

p.161 The only honest test of the value of any management activity is to run projects without some of them and observe how well people do with a lighter touch. It’s a test few leaders have the courage to take. The worry among managers is that this test would reveal that quality improves when they do less managing. It might just turn out that an executive whose division always demands eighty-hour work weeks might really just need a manager who know show to hire well, put a few healthy frictions in place, and get out of the way.

p.163 In these days of continuous deployment, grand strategies seem quaint, but for many Fortune 500 companies, it’s still the way they plan their work.

p.187 Of the many P2s at the company, one was called Money. It was a quiet place. Since there was no team dedicated to the store or to revenue, it was no one’s primary job to actively work on it. One side effect of having teams is there will always be things that fall through the cracks. Teams create territories. This is a force for good since it helps people focus and feel pride. But it creates problems for projects that fall between teams. If you try to cover everything, the teams are unfocused, and if you cover too little, there’s no room for growth. But even if you carefully design teams, the turf needs to be conceptual, not territorial. Organizations become bureaucratic as soon as people devine their job around a specific rule, or feature, rather than a goal. For example, if you tell me my job is to cook fries, I will resist anything that threatens the existence of french fries, since when they go away, so does my job. But if you tell me my job is to make side dishes for customers, I’ll be open to changing from fries to onion rings or other side dishes, even ones we’ve yet to invent, since my identity isn’t tied to a particular side dish, but instead to the role side dishes play.

p.193 Many of Automattic’s employees, although talented, work in places where there’s less demand and fewer high-profile companies to choose from.

p.215 Among the clues for sorting out the truth is how a leader handles things going wrong - not the show that happens in front of crowds but in the daily meetings and decisions where there is no audience. If they genuinely share credit but take the lion’s share of blame, you might just have someone sincerely invested in doing what’s best. A leader who shields others from things that get in the way inspires everyone to do the same. It’s small habits like these that shift a culture away from the pointless exercises of finger pointing and dodging blame and toward a contagious confidence that the best work of your career is possible right now. The feeling that there’s nothing in your way is something few feel often in their careers, if they ever feel it at all.

p.215 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.

p.216 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?

p.222 For all my planning, scheming, and influencing as a team lead, sometimes talent, chaos, and chemistry are all you need for good work.