The Distributed Podcast is an in-depth conversation about the future of work — with the companies and leaders driving it. Hosted by Co-Founder of WordPress and CEO of Automattic Matt Mullenweg. Subscribe >
Join us for the latest episode of Distributed, as Matt Mullenweg interviews Jack Dorsey, co-founder and CEO of Twitter and Square. They discuss how both companies have embraced remote collaboration, the underrated value of deliberate work, and how questioning preconceived models from the get-go can change everything.
This spring, Jack Dorsey told Twitter and Square employees they could work from home forever if they choose. But a year earlier –– before the global pandemic happened –– he had already started working from home two days a week. There wasn’t the noise or the distraction. It was a place and a time where he felt more freedom and creativity.
Now, he reflects on how his way of working has evolved alongside Twitter and Square over the past year. From leading thousands of employees as a self-described introvert, to why he planned (and still does) to work from Africa for an extended period (spoiler: largely, to support entrepreneurs on the continent), Matt and Jack share ideas for combining the deliberate, thoughtful pace of asynchronous work with the serendipity that occurs in the office.
“If we can run the company without missing a beat,” says Dorsey of planning to work in Africa, “it really opens the door for a lot, especially our ability to hire anywhere as well.”
Tune in to learn how meetings work at fully distributed Twitter and Square, what open source and the punk scene have in common, why bringing thoughtfulness into collaboration is more important than ever, and if Jack Dorsey ever wants to go back to the old board meetings. Plus a whole lot more.
The full episode transcript is below. Thanks to Sriram Krishnan for help preparing for this episode.
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.
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.