A year in the life of Scott Berkun as he rejoined the workforce in a new type of company; one where most interactions between staff occur on-line.

Book Review: The Year Without Pants, Scott Berkun.

Scott joined Automattic, the company behind the WordPress blogging platform, as a team leader of a development team, a role that had not existed in the company before. It had been his suggestion to introduce teams as a means to enable Automattic to take on bigger sized projects, having consulted with the company about how it should shape itself as it grew. Because it was his pitch to create teams and the inevitable hierarchy that goes with them, Scott felt that he needed to prove that he could lead his team successfully.

The remote nature of the job is why the book has such an eye catching title. If you are sitting in the comfort of your own home every day, working remotely, and communicating almost exclusively by text and voice, do you really need to wear pants?

What interested me in this title is how someone that came from a large, traditional software company would manage with the new-style, remotely operating organisation that is Automattic. Scott spent his formative years in Microsoft, and worked on many of the Internet Explorer iterations during the early years of the Internet’s explosion, before becoming a successful author, coach and consultant. Would his project management background help create structure when combining people together into teams from individual creators, and with people distributed across the world?

Automattic is not like most companies. Many of the employees began by volunteering to fix bugs and write code for WordPress. They did so because they also loved to use the platform. The software that they produce is given away free under an open source license. You can take it and change it but what you produce from it must also be given away.

When he joined Automattic, the idea of teams was new. Before then each employee worked on mostly individual projects, often in complete isolation to the other engineers. The managing director, Matt Mullenweg, kept some overall control of vision and direction, but with the number of employees growing this was becoming difficult to scale.


When you join WordPress, no matter what role you are going to be doing, you must spend an introductory tour on the customer support ticket desk. That means dealing with people who may have little IT experience or with running a blog as well as seasoned users. The questions and problems raised can range from simple queries to difficult problems. Sometime the difficulty was simply to decipher what the user really wanted.

This is a great idea in my opinion. There is no better way to get so intimately in touch with the product as having to solve real user issues. There is no substitute for using the software, and trying to put yourself into someone else’s shoes when getting started.

Starting in the customer support team, or happiness team it was known within Automattic, was a difficult thing for Scott to do, especially as he had grander ambitions for his role in the company. But he got no special treatment. His rate of ticket resolution was informally monitored and it was not long before he felt both the pressure and the sense of community that exists within the team. The support team at WordPress were there to lend a helping hand whenever he came up with a difficult problem.


Most people are better at face to face communication. There are multitudes of visual, almost subliminal signals that arise from body language that give colour to the words being spoken. Even the tone and speed of the voice tell a lot about what is being said. What if most, if not all, of your daily communication with you those you worked with was text based over email or chat? Would you be able to communicate clearly? Would you be understood? What if you try to say something funny; will it be understood correctly?

If you work in the technology industry, you will notice that there is a growing need to be able to maintain relationships over nothing but email and on-line chat. We increasingly have to deal with people working in different time zones, that cause a stilted half-day break between each response. WordPress appears to be ahead of the curve in embracing the on-line, world-straddling workforce. Scott’s experiences provide useful pointers on how to manage this emerging working world.

WordPress regularly bring all the employees together. They spend a week or so every year at a retreat. This helps to cement the bonds and create the shared experiences that teams need to really make them feel like a team. Knowing a person in the flesh helps you understand them when you are communicating over a chat application.

I hope that in the increasingly spread out technology landscape that companies take a lead from WordPress to regularly bring groups of employees that are at different locations together for meet-ups. Whether it is to help form a company vision or to work on or launch exciting projects, it will be time well spent.


The culture at Automattic is unique and stems from both its business model and its rapid rise in use and popularity. The company makes its money through a number of channels. While the main blogging platform, software that can be deployed yourself or used as a hosted service, is available free, there are many paid-for add ons. For example, you can have WordPress.com host your website, but to give it your own, unique URL you have to pay a small subscription. WordPress can register that URL for you also, another source of revenue.

The services range from low end up to VIP type management of accounts for large companies. They get a certain amount of income from advertisements that appear from time to time on peoples blogs (unless they pay for them to not appear).

WordPress grew dramatically because it was free software, of high quality, and because it had an army of volunteers that were passionate about fixing bugs and adding features. Matt Mullenweg turned this into a company of devoted employees that continue with this same principle. They love WordPress and want to make it better all the time,

It can be difficult to put a value on culture, but to me, it’s what keeps you going when times get difficult. From the beginning WordPress had a great culture, and Scott gives a great description of it in the book.

The Bazaar

One final word about the book relates to what Scott calls the bazaar or the cathedral approach to software development. Automattic seemed chaotic when he arrived. Code was released when it was ready, monitored and adjusted as necessary. There was little coordination between releases, and no obvious overall direction. In many ways it resembled a bazaar, with lots of noise, growth in different directions and plenty of colour. Opinions vary widely and there is constant sharing, making the staff, who are based all over the world feel really close.

Contrast that to the cathedral style, where plans are dictated from a hierarchy downwards stemming from executive level or a senior architect. Little room is allowed for free expression and any change is difficult. New ideas are not easy to popularise as they need to fight their way up the hierarchy for approval. Committees end up killing off most of them before they see the light of day.

The bazaar allows ideas to emerge, get built and die or succeed depending on the circumstances. Useful things are constantly emerging and made available to everyone. And yet it may never be possible to shift out of this mode. It may be impossible to steer bazaar thinking to build something like a cathedral.

As someone who has worked in financial services as a software developer, I have first hand experience of cathedral thinking. It can be difficult to get approval to try new things, to take risks. Admittedly there is a lot at stake, but the red tape involved in getting change done or introducing something new can be demoralising.

Can there be some middle ground? Let’s keep the big projects but give teams some room to experiment and try things out. If they don’t work, then kill them off. True innovation requires a bazaar like environment to give it a chance to succeed. Scott makes a compelling case for striving to include both the bazaar and the cathedral in your company’s planning and thinking.