Reimagining Work: Scott Berkun’s Year Without Pants at Automattic

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how the working world is changing. Many people who write books and give lectures don’t ever go back into the fray and see how much of their own advice they can actually practice. I was thinking I should probably go back and manage a team again at some point. I didn’t know when or where, but when Matt suggested this idea, I said this could be it.

Then, thinking through all the crazy, unusual things they do at Automattic, it seemed like a fantastic way to test my own ability as a manager in an environment that was so novel, with no e-mail, an open vacation policy, open source origins—there are all of these things that many people think are the future of work. So it seemed like a great project to kill two birds with one stone, and get my next book out.

X: Going in, were you skeptical about the feasibility of remote work and all this decentralization?

SB: Yeah, I went in skeptical about many things, and I am still a little skeptical in some ways. I wasn’t sure that it actually works, or that it’s a thing that should be emulated. And I wasn’t sure that the notion of forming teams would work in an organizational culture that was so passionately anti-corporate, anti-structure, anti-hierarchy.

X: So, what did you learn? Did you come away less skeptical?

SB: I think one of the biggest things I learned, if I had to pick just one, was about hiring. For all the criticism about how the company actually functions or whether [distributed work] is right or wrong, they do such a good job at hiring that it compensates for most of these other issues. They fact that they hire by trial [all prospective Automattic employees must complete a project before being brought on full-time] is a wake-up call for most of the work world, about how broken our interviewing and hiring practices are.

X: What about remote work itself—what were your before-and-after attitudes about how well it works at Automattic?

SB: I didn’t really have a strong opinion going in. I was skeptical about it, but I think what I learned was that it works fine, if you have a smart team of talented people who are motivated to be collaborators. When it doesn’t work I don’t think it’s because of the tools; it’s because the people aren’t talented, or they don’t like working with each other, or they are given bad direction or leadership by whoever is managing them.

My year there totally proved that remote work can work fine for teams. We did all kinds of different projects, some of which required schedules with dependencies, and some of which were more ad hoc and agile. But if it’s a good team that’s motivated to work and you have the authority to manage them well, then they can do a good job.

The Year Without Pants: and the Future of Work, by Scott Berkun

X: For companies thinking about whether to implement a more distributed structure and allow remote work, what would you say are some of the biggest benefits and pitfalls?

SB: If the goal you have as a leader is to have a culture of people who are passionate and independent and autonomous and aggressive about pursuing ideas, distributed workforces make that likely, because these are people who have to manage their own time and work independently. If, on the other hand, you have a 1970s, MBA mindset and you want command and control and you want to be the center point of all decisions, then distributed work is probably a mistake, because by its own nature it diffuses people and their attention and your decision-making authority.

X: It seems like it’s the kind of structure that would only work at companies where the founders or top executives are comfortable being hands-off, the way Matt Mullenweg and Automattic CEO Toni Schneider seem to be.

SB: Yes, but it’s a philosophy for an executive that I would encourage at any kind of company that’s ambitious about progress. I have experienced managers who are like that—very hands-off—even at Microsoft. Gabe Newell, the CEO of Valve, has a similar philosophy, and Valve is not a distributed company—they do many other things that are unusual but one thing that’s normal is they all work in the same building. So there are definitely others with a similar “benevolent dictator” mindset.

X: You point out in the book that new management fads come and go, and that it can be disastrous to try to graft a structure like remote work onto an organization that doesn’t have the right culture for it. I interpreted that as a kind of “don’t try this at home” warning. But in other places you seem very admiring. Which side do you ultimately come down on? Is Automattic-style decentralization something more companies should emulate, or are you saying it’s probably a bad fit for most organizations?

SB: Your question is a good one, and I totally understand it, but I wouldn’t say either is true. I think the book should be an eye-opener and a call for managers to experiment. There is very little risk in letting an employee say, ‘You know what, I want to try working from home for the next month.’ A manager could say, ‘Okay, why don’t you try that, but I am going to evaluate you on these specific things, and if you can meet those performance objectives, then great, go for it.’ That kind of experimentational attitude is what every manager should have.

The book isn’t meant to be a bible on how to be Automattic. It should be a bible for managers who want to … Next Page »

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3 responses to “Reimagining Work: Scott Berkun’s Year Without Pants at Automattic”

  1. Matt Boyd says:

    Hi Wade, I seriously can’t believe that no one’s commented on this post! A big fan of Scott Berkun and think that he’s on point. I definitely don’t believe that it’s about the tools themselves, but the culture and people that use them. Building a distributed team is definitely a challenge and not for everyone, especially if you require a sort of social structure, although I do believe that this social structure can be created in a distributed team.

    I love the discussion that’s going around regarding distributed teams at this point because as new precedence are set, and new tools arise that make this structure easier to exist, then it’s a no-brainer that distributed teams will start to thrive. Again, I don’t believe it’s all about the tools themselves, but if that social structure can be implemented using these tools, then that’s a great thing.

    I really appreciate this interview and enjoyed reading it! Thanks!

    -Matt Boyd
    Co-founder of Sqwiggle

    • Wade Roush says:

      Hey Matt. Thanks for your comment. I totally agree. As a founder or manager you need to decide what kind of culture and social structure you want in your company, then find people who will thrive in that culture, then find tools to support them. The culture and hte people have to come first.