I recently finished reading ‘The Year Without Pants: WordPress.com and the Future of Work‘ by Scott Berkun. Berkun is a career technologist and project manager — he made a name for himself leading the Internet Explorer team at Microsoft during the mid-90’s ‘Browser Wars.’ In ‘The Year Without Pants‘, Berkun details his time working for Automattic, one of the most successful internet companies of recent memory (and the technology on which ThoughtCatalog.com runs.) Automattic is unique — built on open-source culture, the company most notably has no physical office. Instead, Automattic’s 229 employees are scattered across 170 cities and 30 countries.

From his traditional background, Berkun’s observations on the good and the bad of Automattic’s culture make for unique insights on both timeless business wisdom and on the future of work as we know it. I recommend for anyone involved in collaborative environments to buy the book, but here are some quotes that particularly stood out for me:

The problem with modern work, and one that sheds light on the future, is how loaded workplaces are with cultural baggage. We faithfully follow practices we can’t explain rationally. Why is it that work has to start at 9:00 a.m. and end at 5 p.m.? Why are you required to wear a tie if you’re a man and a skirt if you’re a woman? Why are meetings sixty minutes long by default, and not thirty? We have little evidence these habits produce better work. Instead we follow these practices because we were forced to when we entered the workforce, and over time, they became so familiar we’ve forgotten they are merely inventions. All traditions are inventions; it’s just a question of how old the invention is. There is nothing wrong with tradition until you want progress: progress demands change, and change demands a reevalution of what the traditions are for and how they are practiced. (74-75)

On customer service as the front lines of business

[On listening to support calls at Microsoft]These efforts were useful, but they were impersonal. Listening to someone else or reading a report doesn’t put a fist in your gut the way being the person responsible for fixing the problem does. Making everyone work in support forces everyone to take customers seriously, which we should since they pay our salaries. Despite my distaste for it, the idea of making all employees participate in support was fantastic. (13)

On ‘business experts’

Here’s why famous experts who write books never go back to regular jobs: regular jobs are hard. Regular jobs mean you answer to others. Regular jobs mean you do regular, often repetitive, things. Regular jobs mean you are not the center of attention and have to follow rules made by other people. Anyone who’s an expert, guru, executive or coach has likely lost any real sense of what real work is. We assume that because we can give advice on something, we are superior to those who take the advice, but that’s not true.” (25)

On management tricks

Every year new trends in work become popular in spite of their futility for most organizations that try them. These trends are often touted as revolutions and frequently are identified with a high-profile company of the day. Concepts like casual Fridays, brainstorming sessions, Lean, Six Sigma, Agile, matrixed organizations, or even 20 percent time (Google’s policy of supporting pet projects) are management ideas that became popular in huge waves, heralded as silver bullets for workplaces. The promise of a trend is grand, but the result never is. Rarely do the consultants championing, and profiting from, these ideas disclose how superficial the results will be unless they’re placed in a culture healthy enough to support them. 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 best approach, perhaps the only approach, is an honest examination of culture. But culture is harder to understand than a meeting technique or a creativity method. And culture is scary because unlike techniques, which are all about logic, culture is based on emotion. Few people have the skills to evaluate, much less change, a culture, even if they have the courage to try. It’s far safer to simply wait for the next trend to come along and rally behind it, hoping the excitement for the new method distracts everyone from noticing how little impact the previous method had. (29)

The seeds of foundation

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 generous, 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. (36)

On support functions vs. core functions

One major mistake Schneider had seen was how companies confused supporting roles, like legal, human resources, and information technology, with product creation roles like design and development. 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 creative what equipment they can use. If one group has to be inefficient, it should be the support group, not the creative. If supporting roles, including management, dominate, the quality of products can only suffer. (38)

On finding great people

It takes more passion to choose, on your own, to build a website, a mobile application, or a company than to follow years of instructions to get a degree. A GPA is not a strong indicator of passion, except for the dubious motivations of wanting to find the right answer to other people’s questions. Degree programs are highly structured and have the greatest appeal to people who depend on structure. (79)

Many employees at Automattic were what’s called T-shaped, meaning they had one very deep skill set, and a wide range of moderate proficiencies. Although I was hired as a lead, my deep skill set in this sense was interaction design. Diversity of skill makes people self-sufficient. They didn’t need much help to start projects and were unafraid to learn skills to finish them. This self-sufficiency prevented the need for paternalistic management. (79)

Although [another] company is not distributed, employees’ desks are on wheels, and they can choose for themselves what projects they want to join, literally rolling down the hallway to become part of the project while it lasts. The Valve company handbook, leaked online in 2012, says, “We don’t have any management, and nobody ‘reports to’ anybody else. We do have a founder/president, but even he isn’t your manager. This company is yours to steer – toward opportunities and away from risks. You have the power to green-light projects. You have the power to ship products. (80)

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. (81)

The skill of good managers

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. (93)

Patience is a manifestation of trust. It conveys to the other person that he or she is worth the time. (93)

On craftsmanship

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. (130)

A project management trap worth remembering

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… This means that 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.) It should never be a surprise that progress seems to slow as the finish line approaches. (147)

An upside and downside of office-free working

Meetings at Automattic were always qualified disasters. They happened so rarely, certainly in-person ones, and had so little urgency there was little pressure to get better at running them. Most of the world has deadlines. If you don’t have deadlines, the need to be good at efficient decision making fades away. (125)

During my year at Automattic, no one ever yelled at me. I was never in a meeting that made me angry or want to storm out. The worst kinds of workplace moments simply weren’t there. You can get only so angry at someone typing at you. People were polite, almost painfully so. But the best things about workplaces, like sharing an epiphany after working for hours at a whiteboard, were gone too. Working remotely mellowed everything out, dropping the intensity of both the highs and the lows. Depending on your previous experience, this made things better or worse. (159)

For people with poor discipline, this freedom can be a problem, just as any other kind of freedom can be. (151)

How to test the value of management

The 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 tough. It’s a test few leaders have the courage to take. (161)

Among the clues for sorting out the truth is how a leader handles things going wrong – not the show that happens in front of the 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. (215)

“Real work contains hard parts”

The problem with problem-solving methods, which all business methodologies are, is that they are abstractions, but the world is not abstract. Real work contains hard parts that no method can dictate for you. (168)

The burden of private information

To offer Adam the job meant disclosing my leaving, and once that ice is broken, it’s best to let everyone know quickly. No one should be expected to carry the burden of a secret their peers would love to know. (225)

The future of work

The most dangerous tradition we hold about work is that it must be serious and meaningless. (230)

It’s not a new, radical idea for work to have meaning and for workers to have both great freedom and pride in the work itself. Instead, those ideas are rooted in the origins of work; we’ve just lost our way. (232)

It’s a shockingly recent notion that work and play should be mutually exclusive things. We learn about ourselves and each other through play, which helps us work together. (233)