Getting Legal Work Done in a Distributed Environment: Paul Sieminski with Chad Main on Technically Legal

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500-page bound merger agreements, office printers, and libraries lined with law books. Legal work looks a lot different now that most in-house counsel (and law firms for that matter) have adopted some form of distributed work. 

But that doesn’t mean the work itself has changed. Contracts still need to be written and signed, litigation still needs to happen, and employment law might be more important than ever. What’s become clear over a year into a global pandemic is that legal work can be even more effective without the office. To make it happen, however, lawyers need to adapt their communication mediums and technology in a way that fits company culture and mission. 

Automattic’s General Counsel, Paul Sieminski, recently joined the Technically Legal podcast to talk about how legal work can thrive in a fully distributed company. “It’s aimed at a legal audience, and I love to remind my fellow layers how much value we can add to a distributed organization,” said Paul of his appearance on the podcast. “We are trained to communicate clearly, and especially to write cogently and persuasively.  These are invaluable skills in any environment, but especially in an environment where writing is paramount…like a distributed company.”  Paul has written on the topic in other places, such as Modern Counsel

He talks about communication starting just after the 23:00 mark with host Chad Main. For that discussion, and legal topics spanning the advantages of creating a searchable document database, to what tools and protocols we use to communicate transparently while protecting confidentiality, you can learn more about legal work in the distributed model by listening to the full episode here.

Growing as a Leader: Matt Mullenweg on the Starting Greatness Podcast with Mike Maples Jr.

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“Was there a palpable time when you felt like…you had to have a new kind of thought as you got bigger?” asks Mike Maples Jr., host of the Starting Greatness podcast in an April conversation with Automattic founder and CEO Matt Mullenweg.

Matt shares several such pivotal moments in an episode full of stories and insight from the growth of Automattic, and of his own journey and leadership evolution.

“For better or worse, you become close personal friends with everyone because you’re kind of in the trenches,” Matt said, sharing a story about when the company almost accepted an acquisition offer at a time of friction among the small, but growing, Automattic team. “So when you fight, it kind of feels like you’re fighting with your partner, your significant other.”

Matt reflects on a journey from his Palm Pilot user group to first meeting Jeffrey Zeldman of A List Apart (and now a Principal Designer at Automattic), and later his first visit to San Francisco, all before committing full-time to WordPress and Automattic. Mike and Matt also touch on the difference between a learn-it-all and a know-it-all, and even some books that have been influential along the way.

Maples, partner in venture capital firm Floodgate, has also hosted Annie Duke, Mark Cuban, Tim Ferriss and David Sacks in the second season of Starting Greatness, a podcast dedicated to startup founders who want to go from “nothing to awesome, super fast.” You can listen to the full Starting Greatness episode, and all others, right here.

Another year of distributed work. A brand new set of questions.

In May of 2020, I wrote about the move to adopting a distributed model and how change happens slowly, and then all at once. Today most companies are approaching a year of distributed work and looking ahead at another. While the dust has started to settle for most companies, new questions are emerging — from who shoulders tax burdens for remote employees, to what ongoing support looks like for employees and their families. 

These questions go well beyond the productivity and collaboration topics that typically accompany any discussion around distributed work. And the answers are more important than ever as companies that want to return to the physical office look at another year away from it — and for others that plan to permanently embrace distributed work. A recent article by Chip Cutter and Emily Glazer in the Wall Street Journal examines what another year of remote working looks like along with some insights into how some companies are tackling some big, thorny issues.

Discussions about the future of work, such as whether to reduce the salaries of employees who have left high-cost cities, are priority items in board meetings and senior executive sessions across industries, according to chief executives, board members and corporate advisers. Listen to this article 6 minutes Among the questions companies are trying to resolve: Who should shoulder tax costs as employees move to new locations while working remotely? And what is the most effective way to support working parents? Companies say there is much at stake, from the happiness and productivity of employees to regulatory consequences, if they get these decisions wrong. 

Head to the Wall Street Journal to read the rest of the article.

Episode 26: Jack Dorsey and Matt Mullenweg on Remote Collaboration, Finding Serendipity, and the Art of Deliberate Work

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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.

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