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

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try new things. That is the only way they are going to achieve the ambitious goals they have—by being open to trying new ideas. So I don’t have a hard line about recommending that every company should switch to being distributed. But I do have a hard line about this: if you are managing things, what new things are you trying? Automattic offers a whole suite of things to use. If Automattic did these 12 interesting experiments, many managers and executives should be able to try at least one or two. That’s what I hope people get from the book.

X: Lots of individuals are probably attracted to the idea of working remotely from their organization. What kinds of people are cut out to succeed at this, and what kinds are not?

SB: There’s a chapter in the book that tries to talk about how this all fits into the future of work. In there, I offer that that the people who do better at distributed companies or remote work are the ones who have a little bit more self-discipline. They don’t require being in the same room with a bunch of other people who are working to be motivated to work. They are good at managing their time. There is just more independence in an environment like this, and less social structure to depend on to get work done. So people who struggle to want to go to work and manage their time and manage their attention will probably have a harder time, because they don’t have a boss checking them every day and looking over their shoulder, or a coworker reminding them to do this or that. They are more autonomous.

X: That must be part of the point of Automattic’s hire-by-trial process—finding the people who can work autonomously.

SB: Yes, it fits with that. The project that you get, you have to manage yourself. There is no one there giving you a step-by-step on what to do every day. You are expected to go and do it on your own. A lot of talented people are uncomfortable with that much autonomy and that’s an indication that you probably wouldn’t do well in an open, chaotic environment like Automattic’s.

X: One of the sub-themes in the book is about the blogging and chat tools, like Skype and IRC and the company’s internal P2 blogs, that Automattic employees use internally to stay connected. You write near the end of the book: “It might be that progressive companies like Automattic are open to the idea that technology can return some of the meaning of work we’ve lost.” Can you explain a little bit more what you meant by that?

SB: It’s liberating when none of these tools are official or mandated—when employees are told, ‘We hired you and you know what you’ve got to get done and it’s up to you to decide what tools are going to be most useful.’ That gives meaning to people who are passionate about their work—that management and the company itself is not a hindrance, not a source of friction. Instead it’s a support structure.

Automattic does a great job at this. For all of my criticism about P2 and IRC—and a lot of the people in the company agree with me and use different things at different times—there are no draconian rules about using these tools. You’re free to choose. Which is no surprise, given the open-source roots of WordPress itself.

X: Speaking personally, e-mail is the scourge of my existence—there’s just far too much incoming stuff, and dealing with all of it takes too much time away from my actual work. On the other hand, maybe that is my actual work. And it’s not clear that any of these other tools would work in our organization—we’ve tried some and they haven’t caught on internally. It sounds like you’re not a huge partisan of any particular technology as “the answer.”

SB: I’m really ambivalent about every tool that exists. They can be abused, and they can be used well. The culture around them and the habits of the people you work with really define how well they work.

In most organizations, the experience of e-mail is poor because e-mail is abused. Too much information is sent over e-mail, when there are better alternatives for certain kinds of information. But it’s hard to blame e-mail technology itself, which hasn’t changed much over the last couple of decades. We have changed, and our habits have changed.

It’s really hard to change a culture that is centered on one tool to another tool. It requires leadership and clear notions about what the problems are that motivate the changes. You’d have to highlight for people the frustrations of e-mail and argue that these are the kinds of communication that would be better held over here [using another tool]. Blogs and comment boards are a much better way to deal with certain kinds of communication. But all tools have value, and all tools can be problematic depending on how they are used.

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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.