The Things You Learn about Leadership after 10 Years at a Distributed Company

For many, remote work is a recent phenomenon — a nascent practice brought about by public health concerns. By now, however, there are also quite a few companies that have used various distributed models for years, and the people who’ve been part of their journeys possess deep knowledge about what makes (and occasionally breaks) a fully distributed workforce.

Case in point: Sara Rosso, WordPress.com’s Director of Product Marketing. Sara recently celebrated her 10th anniversary at Automattic, and to mark the occasion she took to her own WordPress.com blog to share 10 leadership lessons she’s learned over the course of a decade working with and leading distributed teams.

Sara’s insights span a wide range — from ways to foster psychological safety in the absence of shared physical space, to tips on how to successfully separate work hours from personal time when they both take place in the same house (if not the same room). One of her standout lessons? Optimizing remote meetings to work for people with diverse communication styles and preferences:

Though written communication is a very strong skill needed in a remote company, there is likely a wide variance of personalities and work styles in the company. A remote company can attract both clear extroverts (like myself) and introverts who would be fine not to meet up even twice a year.

One of the ways I’ve had to learn how to lead team and project synchronous meetings is to be sensitive to all types of personalities. As Automattic has grown, it has gone from a company where I knew who had kids and where they each lived, to video calls with people whom I’d never met, never worked with, and in some cases I wasn’t even sure what country or city they’re sitting in.

As an extrovert I am especially aware I need to make space for others to contribute in a synchronous discussion. However not everyone wants to be included in that moment, especially when that means calling on someone spontaneously. Some of the advice I’d heard in the past for meetings was “call on people who haven’t spoken up” to make sure diverse voices are heard on the call. This is not a one-size-fits-all approach, and can definitely backfire.

To explore tools and strategies based on Sara’s deep experience at Automattic, head over to her blog to read the full post.

Illustration by Lily Padula

Distributed FAQ: How Did P2 Become Automattic’s Signature Mode of Communication?

In Distributed FAQ, Matt Mullenweg addresses some of the most common issues companies, executives, and individuals face as they consider transitioning to a distributed model.


Q. Automattic is known for using internal blogs called P2s for most work-related conversations. How and why did that happen?

A. In Automattic’s early days, we collaborated a lot directly in the code, or on IRC (Internet Relay Chat), a Slack precursor. We quickly realized that it wasn’t great for asynchronous discussions, and when we tried email instead, it didn’t allow for the transparency that is the hallmark of open source (it also brought a lot of noise with it). Finally, we ditched email and moved to an internal blogging system. P2 is the evolution of the blog for the purpose of working within and across teams. It’s organized much like a Yammer or Facebook stream, but on the back end it still operates like a blog, allowing for archiving, advanced search, and rich media embeds. 

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Distributed FAQ: How Do You Create Company Culture When You Rarely See Your Colleagues?

In Distributed FAQ, Matt Mullenweg addresses some of the most common issues companies, executives, and individuals face as they consider transitioning to a distributed model.


Q. Trust and a strong shared culture are two ingredients that help companies thrive. How do you build either when coworkers don’t meet each other in the hallway every day?

A: Culture is what people do when no one is looking. Companies redefine their culture in real time whether they’re distributed or colocated.

In more normal times, meetups are key to Automattic’s culture — employees expect 3-4 weeks of travel per year, one of which is devoted to the company-wide Grand Meetup, and the rest to team and division meetups. We’ve seen that you can build trust and create bonds when you break bread across a table and meet in person, and then use that momentum to power relationships for years when everyone’s back in their home base.

But even these days, when travel is suspended for the foreseeable future, there are many ways to foster trust and to reinforce Automattic’s values and culture. We put a lot of emphasis on social communication at the company, leveraging the same tools we use for our work — P2, Slack, Zoom — to encourage informal interactions. For example, many teams start weekly meetings with a fun, non-work-related question. We created automated systems that can pair people up to chat about any topic they wish, and recently launched Connectomattic, a series of video calls based on shared interests and experiences, from meditation to baking.

Ultimately, we believe in giving teams autonomy to create a culture that works for them.


For more thoughts on culture and trust in distributed settings, listen to Matt’s conversation with Glitch CEO Anil Dash.

  

Distributed FAQ: Hiring

In Distributed FAQ, Matt Mullenweg addresses some of the most common issues companies and executives face as they consider transitioning to a distributed model.


Q: When interviewing candidates, are there any tactics you recommend to better assess candidates’ fit with a distributed workforce?

A: At Automattic, one thing we try to do is set our expectations publicly so they are obvious. We stress our company-wide travel expectations (3-4 weeks a year), and highlight our benefits. We do this to add a layer of self-selection to the process. We also do trial projects, which last a few weeks and are incredibly valuable when making hiring assessments.

Transparency is key. We put a lot of thought into our hiring process to ensure that it reflects our culture in order to manage job applicants’ expectations. For example, we include our Creed as part of the standard offer letter.


Q: We are currently hiring for a few roles and it’s quite likely that the entire process will be remote. Is there anything we need to look out for, or do differently than in a non-distributed context?

A: Our entire hiring process can oftentimes be conducted over Slack.  Every new hire starts with two weeks of support, which is a hands-on opportunity to learn about our products and to develop empathy for our customers. Our support folks — Automattic’s Happiness Engineers — are our welcome wagon.


To learn more about distributed hiring:

  • Listen to Matt’s conversation with Automattic’s Head of Developer Experience, Cate Huston, here on the Distributed Podcast.
  • Read a recent interview with Automattic’s Global Head of Human Resources, Lori McLeese.

The Importance of IRL in a World of Screens

Since launching the Distributed podcast, we’ve learned that most distributed companies host in-real-life (IRL) meetups in order to promote social cohesion and a sense of collaboration among colleagues who might not otherwise ever spend time face-to-face. As much as leaders at distributed companies value the many benefits of remote work, they also recognize the importance of meeting in person. Automattic CEO Matt Mullenweg has blogged about the connection between meeting up IRL and the health of a distributed company, and has encouraged individual teams of Automatticians to meet every year in various locations around the globe. 

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Episode 15: Inside the Grand Meetup

Read more about the Grand Meetup in “The Importance of IRL in a World of Screens.”

Distributed Podcast: Inside the 2019 Grand Meetup

On this episode of the Distributed podcast, we get an insider’s look at the Grand Meetup, Automattic’s annual weeklong all-staff event, where employees have an opportunity to collaborate, learn from one another, and hang out face-to-face. Folks from across the company share what makes this gathering so special, talk about social cohesion in the context of a large distributed company, and reflect on what’s great (and what’s tough) about the distributed lifestyle.

The full episode transcript is below.

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Welcome to the Chaos

“Welcome to the Chaos.”

These are the words every new hire at Automattic sees on their first day, emblazoned across the company’s online handbook. They are designed not to instill fear, but to prepare the newly-minted Automattician for life in a fast-moving, globally-distributed company. Working at Automattic sometimes feels like chaos, but over 950 employees wouldn’t have it any other way.

Sonal Gupta is one of them. She describes the moment she first read those words. They gave her immediate comfort because they confirmed that yes, working in this environment can feel overwhelming, but she wasn’t alone. 

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Observe, Don’t Surveil: Managing Distributed Teams with Respect

Like any new employee, Scott Berkun had the jitters on his first day at Automattic. He was a little older than most of the people at the company, having spent the previous nine years at Microsoft. Although he witnessed firsthand the excitement of the tech giant’s glory days, office life was still rather conventional.

Now, in 2010, Scott was joining a young company with no offices, and — prior to his hiring — no managers. Before Scott joined, everyone in the company reported more or less directly to Automattic’s founder Matt Mullenweg and then-CEO Toni Schneider. Scott had been hired based on his own advice as an Automattic consultant. He had observed that the company had grown too large to operate efficiently with a flat structure. Scott suggested a turn toward a more conventional approach — the company needed hierarchy. 

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How to Build and Strengthen Distributed Engineering Teams

The term “digital nomad” appeared in the ‘90s to describe an emerging class of globetrotting workers. The digital nomad in those days was an edgy, lone-wolf cyberpunk character with little dependence on hearth and home. Freed from the constraints of geography, the digital nomad hops from hotspot to hostel, client to client, living out of a suitcase and funding her lifestyle with contract work. 

Cate Huston is the Head of Developer Experience at Automattic. She embodies the ethos of the modern digital nomad, and maintains a newsletter chronicling her travels. Though she calls the Irish city of Cork home, you’re as likely to find her in any other corner of the world. Yet Cate’s no lone wolf. Modern communication tools have made it possible for Cate to help manage and stay in constant contact with large teams. She’s deeply embedded within the Automattic organization, helping to define how its many engineers engage with stakeholders around the company — and with each other. 

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On Building Automattic

Launching the Distributed podcast has given me space to reflect on the last 14 years at Automattic. In 2019, distributed work has spread throughout the Bay Area and beyond, but when we were getting started, having no corporate headquarters was seen as quirky. Our distributed status has come to define our company, but we didn’t set out to be distributed. It was common in open source projects and our initial team was spread around the world. But over time it became who we are. 

I’m originally from Houston, Texas. In 2003, web developer Mike Little and I, along with a few other online friends, developed a web publishing tool called WordPress. It quickly became popular, but we had no inkling that it could ever be a revenue-generating project. We just wanted to make better publishing tools so that non-engineers could express themselves online with their own blogs. For me, it was satisfying simply to hang out on IRC (an early chatroom protocol) with smart, curious people working on an interesting collaboration. I was spending all my free time online, hanging out and coding with people all over the world, having an absolute blast. 

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