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

I'm Chad Main, the founder of legal services company Percipient, and this is Technically Legal, a podcast about legal technology and innovation in the legal industry. In today's episode, I have a conversation with Paul Seminsky. He's general counsel for the tech company Automatic, and we talk about distributed workplaces. My conversation today is with Paul Seminsky. He's general counsel for Automattic. Automattic is a company founded by Matt Mullenweg, who is one of the founding developers of WordPress. I'm sure many of you out there are familiar with WordPress. It's an open source content management system that's used in about 40% of all websites out there, including some big ones like The New Yorker and Time Magazine. Although WordPress is open source, Automattic is a for-profit company that builds apps to work within the WordPress environment like WooCommerce, which is a plugin that helps create e-commerce websites. Automattic also owns Tumblr. One of the reasons I wanted Paul to come on the podcast is that Automattic is a fully distributed company with around 1,500 employees in 80 different countries. Automattic is and always has been a distributed company by design. The fact that the company values its distributed nature is even built into the company's creed. With this in mind, I wanted to bring Paul on the show to talk about how he runs a legal department when everyone is working in different places. As we come outta the COVID pandemic, How and where we work is going to be completely different than it was before we went into this pandemic. This is just as true for legal departments and law firms as it is with every other industry. So Paul and I go deep into the new reality of working remotely and how communication is key to the whole process. I pick up my conversation with Paul where he talks about the interplay between the WordPress ecosystem and Automattic.

I think a lot of people have heard of WordPress and not a lot of people have heard of Automattic. WordPress to start is a, um, a piece of open source software. It's the most ubiquitous CMS or content management system or web publishing software on the internet. More than 40% of websites currently are built using WordPress. And it's something that you can go to wordpress.org, click on a link and download yourself completely for free. And so that software and, you know, kind of the ideas behind it I would say, to democratize publishing and to make, you know, that type of powerful software tool available for everyone is really what has animated the WordPress community and is what led to the founding of Automattic, which is a for-profit company. The link to WordPress is basically two things. The fact that the products and services that we do at Automattic, most well known as WordPress.com. Uh, which is, you know, a hosted version of WordPress, WooCommerce, which is the e-commerce component of WordPress. Um, and a number of other products and services, Jetpack, WordPress.com VIP, which is enterprise hosting. All of those are based on the open source free software. And so that's our kind of connection to the WordPress project. Uh, and the other connection is, um, Matt Mullenweg, our founder and CEO, is also the founder of the WordPress project and still very engaged in the development and direction of, uh, of that community and, uh, of the software. So those are kind of the two common themes, but they are, you know, they're very distinct things. And I think, you know, if you just see people around the internet talking about Automattic, they'll sometimes say it's the parent company of WordPress, or they'll just call Automattic, you know, WordPress. Matt's the CEO of WordPress. None of those are technically true. It's, you know, two, two distinct things, but very related.

Let's talk about your legal background. You're the general counsel for Automattic. But I did notice in getting ready for the podcast that there were complaints directed at WordPress. Usually it's content-based. Someone didn't like what was posted on WordPress site. You step in and deal with that. Is it— do you still do that or what's the connection there?

Yeah. So it— because of WordPress as a piece of software is, um, something that you can get yourself for free and host anywhere. There's WordPress sites that are running on GoDaddy, on Bluehost, on any number of hosts around the world, or companies can just host it themselves. People can host it themselves. So it's something that anyone can get. As a company, as Automattic, which is what I work for and I'm, you know, the general counsel for, we have, you know, a small sliver of those sites, um, that we do host on wordpress.com and that we're responsible for. Good timing of the police car to be driving past my window. You've probably heard.

No, I've had that happen before. That's all good.

Yeah, no, no, it's perfect timing talking about police and WordPress.com sites. So those are the sites that we host on our platform, and it's, you know, millions and millions of blogs and websites and things, but it's not the entire universe of all WordPress sites that are out there. It's actually a pretty small percentage, but for those, I mean, we take responsibility, just like any other host of any content does for the sites that are on our platform. We have rules about, you know, and guidelines for what can be published, what's illegal content, what our policies are against, you know, hate speech, copyright infringement, all sorts of those things, just like any other host. So we do enforce those, and we, you know, have a legal team and a trust and safety team that get involved in that. But that's only for the sites that we're that we're responsible for. And there's oftentimes a lot of confusion. You know, if people see a website on the internet that says it was built using WordPress, a lot of times we do get complaints about it directed to us. And we just have to clarify that we're not actually the host of it. So, um, it, it's, it again goes back to that distinction I mentioned that like Automattic itself is not, you know, does not represent the entirety of WordPress.

And how big is the legal team at Automattic?

The legal team is now 10, 10 people. We've grown pretty rapidly in the last couple of years. As late as 2018 or so, we were only 2 or 3, um, and when I started, of course, in 2012, I was the, I was the only lawyer and was the only lawyer for several years.

And so what are the different roles within the legal department now? Do you have someone in charge of litigation, someone in charge of employment? Like, how's it set up?

Yeah, I think that the roles that, I mean, that you, the ones that you mentioned and the ones that you would see at, you know, any other company, any other tech company are the ones that we have. We have people that review our commercial contracts, help with negotiation of business agreements. We have one dedicated employment lawyer, and her job is really interesting just because of our distributed nature. But, you know, in general, most companies of our size will have someone in that role. We have people handling litigation. We have a corporate team and we're hiring, you know, starting to hire a little more specialized roles, I'd say, for areas of the company that are a little bit more regulated and are also growing pretty quickly, like e-commerce. I would, you know, call out as one where we're, you know, hiring people to support that business. Our enterprise business, same thing as, you know, growing to a size where they, you know, need their own dedicated legal support. So it's a pretty common pattern that I think you'll see a lot of high-growth companies follow where they start off with, you know, covering the needed work through generalist type roles and then find that they have a need for more, you know, specialization and certain areas of the business that need the more attention. So we're right at that point right now and you know, just like the rest of Automatic and the legal team are growing, you know, growing pretty quickly.

So, you just referenced it, you're a distributed company and—

Right.

Automatic always has been by design. I think I saw last count is 1,100 employees in 75 countries. Does that sound right?

We are closer to 1,500 now. Mm-hmm. And yeah, we're— I do lose count of the countries at some point. When I started, it was in the 30s and we're definitely into the mid-'70s now. And it's hard. I mean, if you add a bunch of people a year, it's hard to add to the country count because the long tail gets pretty long. So you have to start getting some pretty exotic countries in there to take that count up beyond where it is now.

Yeah, that's true. I didn't think about that. That's a good point. And so speaking of distributed workforce, law firms and legal departments everywhere that may have pre-pandemic worked in an office kind of have to change the way they work. So, you've got this experience with it. As I mentioned, Automattic's always been distributed by design, but you came from big law and then went to Automattic. So, tell me about that change because I assume before you weren't working that remotely when you were at the law firms.

Yeah.

You know, it's interesting. Now, I hadn't thought about this, but now that you mentioned it, I mean, even at the law firm, I was probably— I did feel a little constrained being in the office. I like to work in a Starbucks or take walks or go to client meetings. Like, I, I, I definitely felt, you know, as you point out, I mean, law firms have historically been pretty traditional organizations and definitely were not on the leading edge of being distributed. So the change for me to Automattic was definitely a big one, but I feel like I was just personally pretty flexible and pretty ready for something like that. I don't know that, that all lawyers would be, especially at that time. That was 2012, and my work setup changed quite a bit. The way that I had to communicate with people I worked with changed drastically from being in person and in an office to being Essentially just online at the time. And one of the, I mean, one of the big things now that is almost hard to appreciate now that everybody is working in this fashion in some form is that there were a lot of people, especially in the, in the legal world, that weren't even sure that the company was real and had a hard time just getting their arms around the idea of there being no office whatsoever.

Meaning they, they didn't think Automattic was real. They thought it was just something in the ether.

Yeah, that's right. I mean, they felt that, you know, you had to be, in order to be a business, in order to be a real actual company, you needed a mailing address, you needed conference rooms, you needed an office with a door and a phone. Like without those things, it's almost like your job was not like legitimate in some way. And at the time, you don't hear this term so much anymore, but at the time, definitely I heard, and people referred to Automattic as like a virtual company. Which is, I think they're trying to say, you know, remote or distributed, but like the word virtual, like almost implies that there's something like not fully real about it, you know, it's, um, and, and that was a pretty, you know, a pretty common thing that I had to overcome with, you know, some of the more traditional, you know, organizations that I would work with. And it was kind of falling into my court more than anyone at the company to engage with not just the law firms, but the accounting firms, the banks, the, uh, Secretary of State, uh, you know, you know, um, the courts that had to mail us different legal papers. So we had to basically—

if a court's got to send you a pleading or an order, where does it go?

Exactly. I mean, that's— yeah, that's a, that's a good question that we just had to, you know, kind of figure out and build up from scratch. Because I do think that, you know, one of the, one of the roles of the legal team and a lot of the operational teams we have at Automattic is sort of like bridging the gap between our distributed existence and the way that the traditional non-distributed world works. So for things like that, which we tried a number of different things. We had a coworking space in San Francisco for a while where we could get mail. There wasn't someone there all the time to get things that might have been important. So we ended up getting a post office box and we hired some part-time people to check it regularly and make sure we weren't missing anything. We experimented with having our email sent to a service that would scan it into PDF and put it into our, our LegalQs so that we could review it. I still have to go to the notary a lot. I just go there in person in the Mission. I just have to drive down there. We can do a lot of things now online that used to be only be able to be done in person, but that's definitely for the legal field, something that we always had to try to experiment with and figure out some creative solutions for, because like I said, the non-distributed world was not always set up to accommodate a company like us. It's changing a lot. I mean, the pandemic has really accelerated a lot of what was already happening with organizations going more distributed, but even things like courts and things are now holding hearings on Zoom. And, you know, as everyone knows that practicing law and working in any number of these types of organizations, like it's changed a lot in the past year and there's been a lot more flexibility in areas that you would think would never change possibly.

Do you use the term remote a second ago, but you generally seem to use the term distributed. Do you draw a distinction between those two terms, between a remote workplace versus distributed workplace?

Yeah, I do. I mean, I don't know what the official dictionary definition of how to define these, but the way I think of it would be that, uh, Automattic is a distributed company. And to me, that means that our whole workforce works from a location of their choosing, and there is no central hub. There is no central office. There never has been in our case. When there still is not, and everyone is effectively equal in terms of where they are and their access to the organization, which I would say exists 100% online. I think that's a little bit— it's distinct from remote in that remote to me implies that there is a central place, like an office, where at least some of the employees are every day. And typically it tends to be, you know, the top-level management type people that are in a central place. And then people that are quote unquote working remotely are not in that place. You know, they still have jobs and the organization is set up to accommodate people that are not working in that central place to varying degrees. But there still is this idea that there's a place that you can go or that you should go sometimes. In order to get the full picture of what's going on with the organization. So think of it as sort of like a collection of disparate dots on a page, which is distributed versus one big dot with a bunch of little dots around it, which is like the remote idea. And I think there's, you know, different companies are adopting different flavors of each of those, but distributed is what what I'm used to and what Automattic has always been.

Other than the logistics stuff we talked about, like the courts wanted an address, the accountants were curious, there was no address, did you find it hard to adapt the legal workings of a company to the distributed setup?

I didn't really, no. I mean, I think you just have to— you just have to be very flexible in your thinking and kind of start from first principles rather than trying to make what Automattic was as a distributed company fit like a particular model that you were used to. So things like, you know, all hands meetings or communicating confidential legal advice, meeting with product teams to go over an idea, all of these things that companies do and that lawyers do as part of their job, we still have to do those. I still do that every day, but you just don't do them in the way that a company that has an office would do them. We don't have a conference room that you usher everyone into and close the door behind you. We don't have a big auditorium where everyone goes into every week to, you know, have a town hall with the CEO or what have you in person. We do all of those same things. We just do them in a different way. And there's pros and cons to it, which I can get into a little bit. But I think that the premise of the question or the skepticism I get from some people is just the idea that we've figured out how to do this stuff as organizations, as companies, and changing that up, trying to do it in a different way and in a way that doesn't involve being in person is somehow not possible or not as good, things like that.

We're going to step away from my conversation with Paul for just a couple minutes. When we come back, we're going to talk about a lawyer's superpower, and we're also going to talk about distributed work's 5 levels of autonomy.

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We'll get back to my talk with Paul in just a second, but I wanted to let you know that for every episode of Technically Legal at tlpodcast.com, there's a dedicated episode page with with more information about our guests and links to some of the stuff we talk about. Also, if you want to subscribe to Technically Legal, you can find us on pretty much wherever you get your podcasts. And if you like us enough when you're there, I hope you leave us a favorable review. Okay, let's get back to my talk with Paul Semensky, the general counsel for Autimattic. What do you say to the lawyer? Because I've talked to people even the last month, just kind of old school lawyers, ah, you know, I still need the people in the office. Like, what do you say to the lawyer that comes to you and says, "I don't know how you do it. It just doesn't work for me." Why does it work for legal? You and I talked before. I think it does for a lot, for most of the work, but a lot of people still don't. What do you say to that lawyer?

Well, I mean, to the old, like, senior partner, I would, what I would say to them is talk to your junior associates and see what they prefer, because I think a lot of it is very generational. And if you, you know, spend time with and work with Younger lawyers, younger people that, I mean, really have grown up much more online and are used to this, are used to having text be, you know, their interface to the world, the preferred way they communicate with their friends, the preferred way they had, you know, ingest and communicate information. Like, being distributed and working in this fashion, I think, is much, much, much more natural than the idea of saying you have to be in a certain place. For certain hours or at a certain time in order to do your job. I think there's definitely a generational idea to it. And then for me personally, with the law, you know, I have, gosh, I mean, I'm gonna date myself here, but like 18 years now of experience of working in law firm and in-house, about an even split between the two. And I would say, you know, at the, at the beginning of my career at the law firm, and definitely as, as a junior associate, you feel this the most that You know, a lot of the work you kind of do need like a big conference room, you need a copy center because you're, you know, assembling 500-page merger agreements and putting tabs on them and shoving them into FedEx envelopes and making sure you make the FedEx deadline and doing research in a law library that has books that you need that you can't get., you know, online or that you, you know, can't get at your house. And so, yeah, as a junior associate and when I started my legal career at the law firm, like all of those things were, you know, very much a part of my job and it would be really hard to imagine doing a lot of those things from home. It would've been impossible. But then you just think about how, you know, not the law firm as an organization kind of intentionally developed, but how just the technology, how the way people communicated, how the way deals got done. Evolved and all of those things that I was doing, you know, in 2003 from a conference room in Boston, you know, junior associates are doing a lot of that from home and doing almost all of it by email or some other digital way. And so that's really what enables it to be a, you know, and I, and I think now the law firm and the legal profession really has evolved to the point where of any industry, it's almost like the one that should be the most ready and the most able to embrace working in a distributed way because we're doing, you know, the definition of knowledge work. And once all of those like logistical things around, you know, paper and, and things move online as they have with You know, LexisNexis and the internet in general, and, you know, email, Box, file sharing, virtual data rooms, like all of these things that we used to do with boxes and paper really, um, are, you know, 100% able and, and much more efficient really to do, uh, in a digital way. So that's kind of what opens the door to the rest of the, you know, distributed model falling into place, I think, for a law firm.

I agree. And you keep using the term, which I think is why the practice of law and legal work is well suited for distributed. You keep saying the term communication or communicate. And the reason I bring this up is for two reasons. Number one, it's literally in your company's creed. In Automatic's creed, part of it says, I will communicate as much as possible because it's the oxygen of a distributed company. And because if you're not going to work in the same room, you've got to be able to communicate effectively. And this is why I think a lot of times lawyers and people in assisting them are well suited, because you got to be good communicators to do legal work.

That's really a great observation, and it's something that I do try to communicate to other lawyers, especially last year at the beginning of the pandemic when lawyers in large numbers, you know, because of necessity were moving to working distributed when they had never done it before and were kind of calling me up asking for, you know, this exact type of advice. And I highlight exactly what you just said, which is that the communication in a distributed company is, is everything. And that's what makes the entire model work. You have to be very intentional about it. And you have to, I, I kind of tell people you have to do what feels like over-communicating because without the, the crutch of being in a physical location of running into people in the hallway or being able to pop into someone's office to talk about something or see somebody at lunch to talk about a question, like you, you kind of do lose out on some of those types of opportunities, but I think you do gain a lot more when you're more intentional about communicating and especially about documenting stuff. And as lawyers, it's very interesting to think about because I think that our legal training gives us in a way a superpower in this world, but also kind of serves as our detriment. As most superheroes know, there's always, uh, what tends to be your greatest strength, often, often is your Achilles heel as well. So what I mean by that is that we take for granted the fact that writing is something that we have been trained to do very well. And I say writing and not just communication, because in the distributed company, you do have Zoom meetings, you do have in-person things, but so much more of it is written. And we as lawyers are trained to be good at that and to be very clear and to be unambiguous and to convey ideas in a clear way and to make complex things easy to understand. Like all of these things give us a tremendous advantage in being effective in a distributed company. And I think that as more companies move to this, like the lawyers within the organization can really be, you know, leaders in ways that they may not have been able to do in a more, uh, office-based environment. So I think that's all super, super positive. I would say the flip side of that, the weakness that we have to try to accommodate, is that our training also kind of makes us very legitimately, but I would say, you know, skeptical, if not, you know, openly hostile to the idea of sharing too much. And there's a lot of good reasons for it, you know, attorney-client privilege being one. Confidentiality, things like that, that we think about, you know, just like breathing really puts a brake on that type of open communication. And that can be, I think that can be a little bit of a detriment to the organization and the way that lawyers function within that organization. If, you know, those are the types of things that, you know, that kind of go against what makes the—

let's, let's talk about that though. Let's, let's go back a year. You had your friend calling and go, how do I do this? How do I do this remote work? How do you run your legal team? What tools do you use to communicate effectively, to make sure we're on the same page, but also how are you using them to protect, you know, the confidentiality issues and the sensitive nature of what lawyers have to deal with?

That's a conversation, like, like you mentioned, I have had with a number of people, uh, especially as they've been moving to this model. And I mean, I don't think that any particular setup is right for everybody, so I usually just tell them you know, what we do here at Automattic, and it's a combination of tools to start with to enable the type of distributed work that we do. We have Slack, we use Slack a lot. I think a lot of organizations now have it and use it. And since they've been distributed, probably use it a lot more. So that's one aspect of it. I think that Slack is, is fine for certain things, but just by itself is not going to give you everything you need to have an effective distributed organization.

You making that point as a lawyer? Are you talking about in general you need other tools?

I think in general. No, that's in— I think that's in general because it's fine for, you know, one-on-one conversations in text for sure. It's fine for like smaller group conversations for sure, but it tends to be pretty pretty small snippets of information back and forth, and it's fine for the real-time or close to real-time type, uh, communication. But layered on top of that is a system that we have, and that I, I think every company needs some version of to do the distributed communication right, which is a longer form tool to really preserve documentation and ideas and discussions in a more permanent way.

Are you referring to, you referring to P2?

Yeah, yeah, exactly. In a more long-form way. So we call it P2. It's basically just a network of WordPress blogs. Essentially, we have now hundreds of them for different teams. The legal team has one. The enterprise team has several different groups at Automattic that are working on a project might have a P2 for that particular project. It's a website basically.

I'm glad you brought that up because I want to ask you about it because when I was listening to a few podcasts with, uh, your CEO and he, he kept bringing up P2 and he, he was coming more of the angle of the development teams and different projects you guys are working on. But then I, I, I'm glad to hear you, you're, the legal department's using it too. But tell me what the distinction would be between P2, they're internally automatic for your legal team versus just a knowledge management system. Because at some level that's what, that is what it is, right?

It is what it is. Exactly. Yes. I think that that's, like I said, a decision that each company would make for themselves, like what the best tool for doing that is. But basically, you know, in a distributed environment and really any environment, I think it behooves the organization to really have that repository of knowledge.

Oh yeah, legal is probably one of the most optimal to use it.

Totally. Yeah, and I think I do, and I think back to, you know, my law firm days where, you know, it was probably the very early, earlier days of, of thinking about some sort of online-based knowledge management type system. But you just, I just remember like if you had a question or if you were trying to find some sort of precedent or provision that you could put into a group, you just emailed the entire firm or you emailed the corporate group or you email, you just email these questions around. And if you're there at the law firm long enough, you know, a couple of years, you'll see the same questions just go around by email all the time. And people would sometimes reply all or whatever, and you would just have this really diffuse, you know, set of knowledge around the questions that people just chose to ask everybody. And it wasn't anything that was preserved. It wasn't anything that was consistent. It was, you know, definitely not efficient. Or very searchable, but it was basically how we did it then. And I think it's very different with P2 where, you know, like I said, it's just a collection of WordPress blogs that sort of just endlessly scroll down. You know, it's just like going to any other website where you would have a blog post about a particular topic and then a bunch of comments underneath it to discuss it and to, you know, either reach a decision or, you know, just discuss some of the ideas that are in that post. And it tends to be for the longer, for inform type communication. And over time it does turn into a very permanent searchable record of, you know, the things that you talked about, how you handled certain issues in the past. So you can go back and see what your precedent is. And I think by the nature of working and the nature of working in that way, you do develop this record that tends to be, you know, independently useful as, you know, a knowledge management system, it tends to be super useful for onboarding people. You know, when they start, they can go back to the beginning or, you know, several years ago or the beginning of a project and see how everything has developed before they started. See who's, you know, who has which ideas, see how certain decisions were made. Like it has, you know, a tremendous number of benefits that are kind of a byproduct of just the nature of the distributed work and the nature of just preserving the the information. I would say, and this is one question you asked a little bit earlier, like, that type of thing also is a little bit scary, you know, to lawyers in particular.

Yeah, I was going to ask— I was going to ask you about that because I, I saw this, well, I don't want to go on Slack because they were going to take it as legal advice. Like, what do you say to that? And how, you know, there's some legitimacy to that, that argument. I think it's a little— I don't know if paranoid is the right word— it's a little I don't know what the right word is for that, but how do you prevent against that? Like, don't take this as legal gospel, but here's what I think.

Well, paranoid is what we do, Chad. Again, I mean, it's kind of the theme that I've been talking about. It's just the fact that, I mean, it's not like privilege goes away because we're a distributed company. It's not like the rules of confidentiality don't apply to us. I can't show up in court and say, oh, we're, you know, We're a distributed company, Your Honor. Like, we can't turn these documents over. They're not privileged. I mean, it's all the same. The rules are the same for everybody, and we just have to find a way to, like everything in the legal realm, like balance the risk and, you know, think about it and implement systems that do the best to manage it given the circumstances we have. And the circumstances we have, like I think now every distributed organization, is that so many more things are now in writing and preserved sort of by default. And so you just have to manage, you have to manage that, the risks that are associated with that in, you know, a thoughtful way. And I think that involves, you know, some kind of basic things that any company does, like, you know, deletion of emails and of Slack channels after a certain amount of time, but also the fact that, when we're talking about litigation or when a litigation-type issue comes up and is posted about on P2, just having a protocol for that and over time just developing an understanding with the organization that there are certain things that we have to keep off of that company-wide discussion.

Yeah, I was just thinking about that going back to my litigation days and there were certain cases where you tell the client, just don't email, don't put an email, just—

Yeah, exactly. And so we have to give that advice. You know, sometimes and create, you know, a smaller group or have a Zoom call to discuss things. But I always like to do that in a way that's consistent with the other values and the other things that keep the distributor organization going, which are, you know, transparency and accountability and, you know, explaining and kind of showing your work. And so when this type of issue might come up, we're very transparent about the fact that, you know, we'll, we'll post on the P2. We won't just go silent. We'll say, hey, here's, you know, the risks of talking about this here, as we've done with other cases or litigation matters. We need to take this offline, talk to this small group about it, and, you know, the process will play out from there. And then what I like to do is at the end of a case or when those issues are, you know, kind of resolved or no longer relevant in terms of privilege or confidentiality or what have you, is to go back to that thread or start a new one and just catch everybody up and say, you know, this lawsuit happened here. We kind of had to go dark for this period of time. We explained why. Here's what happened since then, and here's how this was all resolved so that there still is that level of documentation and transparency and accountability. That makes a distributed company work. It just doesn't happen in exactly the same way because of some of the legal concerns and things that are also very important. So, it's just really trying to do the job in a way that works with the organization and not trying to make the organization change too much to fit our own view of the world.

Right. I agree. You were just talking about how historically maybe these conversations would happen in a conference room. So, privilege is still there, but there wasn't a record of it. But then you said a lot of it's in writing, so you got to, you know, take stuff offline. But it's really no different than back in the day where you just really should have— you have your conversation with the control group to preserve privilege. Just talk to people that need to be involved in this conversation so you don't run the risk. It's just adapting to the communication medium, right?

Correct.

Yeah, that's exactly— that's exactly what it is. It's just a different— it's just a different medium, but the issues and the The thinking behind it is all, is all basically the same. And I think that, you know, just getting people used to those ideas and explaining what they are. I mean, everybody in the organization, you'd be surprised, like, is just really interested in some of the legal considerations behind things, interested in understanding what some of these concepts are, like attorney-client privilege and how they work. And so if you kind of lay that out there and explain what's going on and why, people are always, you know, very receptive and, you know, don't, uh, don't resist it too much. You just have to, like anybody else, just have to really be transparent about it and explain, you know, what, what the point is, um, so that people understand.

Again, when I was listening to some of your— some of the podcasts that your company CEO was on, he said something to this effect, and I want to know if you also agree with this. As it relates to legal decisions. He said something to the effect that asynchronous decisions take longer but might actually be better because they're more thought out and more considered. Do you agree with that?

It's an interesting point, and I think at the root of it is, I believe, the idea that the in-person model of decision-making— picture, you know, a group of 5 or 10 people sitting around a conference room table talking about an idea, debating and what have you. There's certain people that are very good at that and have a way of being persuasive in person because they're very outgoing in terms of personality. And they're— yeah, and they're very, you know, very loud, or they can kind of bully people into their position. And that may be, that's a fine way to make decisions, but just question whether all points of view are given the right amount of weight and are considered in the same way. And then if you move that same discussion with all of the same people and all of the same issues to a Slack channel or to a P2 where everyone has to write a thousand words about why their position is the right one, do you come to the same answer? Maybe not. I mean, some people are much better in that format and maybe a little more introverted in the in-person format. And so I tend to see that a lot and around the company, it's super interesting to see, especially when I first started working here and you spend most of your time on the P2s and you see people writing these really long, very passionate P2 posts about something they really care about and you meet them in person and they don't like to make eye contact maybe, they're not the most dynamic speaker in person, but online they're just a very different persona and a very compelling proponent of a lot of ideas. And so just changing that format a little bit you tend to get a lot of different input and a lot of different, maybe different results. And so I think that having that type of room for discussion and giving some people, you know, the ability to have input and giving weight to that input that might not happen in some in-person environments is really, really interesting. And, um, you know, you could even do that in the, in ways that are even more radical or more more blind. Like if you do things like anonymously, or if you do, you know, things all in writing, you might not even know, you know, what gender someone is or where they are in the world or all, all these types of things you sort of can strip away in the kind of the written environment, the distributed environment. And that leads to some really interesting, uh, really interesting, you know, results and possibly better ideas, which I, I do agree with.

That's interesting. It's interesting. Another thing that I've heard consistently too is even if you work distributively, you still need to meet a couple times a year with your team, maybe the company in general. That's very important. Does the legal department meet as a group once or twice a year? What do you do there?

Well, I mean, we haven't in a year.

Yeah.

So I would say, you know, right now we're like everyone else. I would say no, we haven't, um, we haven't met in person for about a year, but typically, yes, we have 1 to 2 meetups for the legal team every year. And that's, you know, the small group of us getting together for about a week. And, you know, it's a mix of, I would say, talking about work-related things, but not, not day-to-day work things. It's, you know, what's our roadmap for the next 6 months? What are the key legal risks that Automattic will be facing over the next couple of years? We'll usually have some guest speakers. From around the company come in to talk about, you know, bigger things that we're working on or the direction of, you know, the company overall. And then, you know, half the time, if not more, I think is just for just the in-person experience, just hanging out and going to dinner together. And that type of in-person interaction I think is really important because it really makes the rest of the year, the rest of the distributed time work when you know somebody's sense of humor, when you know how they communicate, when you know the things they like, when the things they don't like, you have some shared experiences that you can reminisce about and like, you know, joke around about. Like all of that stuff is, is super important. Like I think it's a mistake to think that, you know, if you're distributed and you work from home every day that, you know, somehow that in-person time and some of those things you get from being around each other in an office are not important anymore. I think they are. Yeah, you just have to do it. You just have to get that interaction in a different way. You have to plan it differently.

Yeah, and it's the one thing that you cannot really generate on a Zoom call. I mean, to some extent you can get there, but not—

Right, totally.

Not that level.

Yeah, so that's what we do. And then we have an all-company meetup, you know, for the, for the whole organization, uh, just about. And that's once a year too, where same, same types of thing, type of things happen, um, but just in a much, much bigger setting.

Before I let you go, I want to talk about distributed work's 5 levels of autonomy. It's kind of a theory there at Automatic, and there's 5 levels, one being the lowest where it's a job you have to do in person. Level 2 And correct me if I'm describing these wrong. Companies accepted remote work, but they kind of try to recreate the office environment with some tools. And then level 3 is probably where a lot of us are now, where you see the value of it, starting to invest in some tools needed to do remote work. And then 4, 4 and 5, these are levels that are really hard to aspire to. Is 4 is completely asynchronous. Basically, you open up your talent pool to anywhere in the world, which is where it's probably where Automattic's at, if I had guess, right? Would you agree you guys are 4?

Yeah, I think we're, we're 4 if, if we assume that 5 is sort of like an aspirational—

yeah, and then 5, let's talk about— yeah, what is 5? 5 is nirvana where it outperforms every other entity out there. Like, what is 5 on this, this, this tool, this, uh—

yeah, I mean, I think that's sort of the apotheosis of like what, you know, what our model that we currently have implemented would be. You're talking about complete autonomy. So people work whenever they want to, at any time, in any time zone, in any part of the world that they have. And, you know, all of the advantages of the distributed model exist with, you know, few, if any, of the disadvantages that have all been kind of, you know, addressed and solved for. And, you know, I think that it's something that I would say we aspire to and, you know, other distributed organizations aspire to. But this is also where, like I mentioned a couple times, like the real world sort of is sometimes a hard thing to solve for in the distributed organization that you do have, you know, inconvenient things like time zones and sleep and things like that where, you know, it, you know, sometimes gets in the way of, um, being, you know, fully autonomous and fully asynchronous. But yeah, I think, you know, If you read through that post, you know, I think the level 4 organization, you know, we're automatic. I think, you know, we're, we're pretty, pretty solidly there and have kind of been guiding towards that level and, and operating at that level for a while, which since the beginning, basically, you know, we don't have any of the baggage. I would say if you look at levels, you know, 2 or 3, basically where It seems to kind of assume an organization that, you know, either has an office and wants to keep it or was kind of forced out of the office against their will, which a lot of people have experienced over the last year. And they just kind of have to make it work. And they rely on effectively analogies, you know, to how they did things in the office or how they think things work best in a non-distributed environment and trying to replicate that, trying to replicate, you know, conference rooms and trying to replicate you know, the Friday happy hour every week on Zoom, which a lot of people did and everybody got sick of after, you know, 3 weeks. And, and all of the, all of those things and assuming that you have to make it look as close to what your old life looked like in order for it to be workable. And as I mentioned a couple times, I think like, you know, the distributed model works really well if you just kind of free yourself from those assumptions and just try to build, you know, and think from the ground up of what works the best, assuming that you never go back to that office or that you never want it or you never had it. How would your setup be if, you know, if that was true and what tools would you need? How would you communicate all of those things? And once you start to just think about it that way, which I think a lot of organizations are doing now because they are seeing that, you know, this is going to be a permanent feature of of how they work, what works the best for that.

So that's the parting, that's your parting advice. Free your mind. Free your mind.

That's always my advice. And that's definitely the advice for the distributed model is just think, you know, think from a world where the office doesn't exist and you want to add some, you know, of the in-person things that make distributed work work better, like meetups and in-person time and bonding and things like that, versus the other way around where, you know, the office is sort of the ideal and you have to kind of replicate as much of the office on the internet as you can.

Well, Paul, thanks for your time. I really appreciate it. People want to get a hold of you, how do they find you?

Yeah, I am on I don't want to sound like an influencer and say, hey, follow me on Instagram. But yeah, I'm on Twitter @pseminski and on WordPress, of course, same username @pseminski. And those are probably the easiest places to find me.

Well, that's it for today's episode. As always, we appreciate you listening. If you want to subscribe, you can find us on most major podcast platforms like Apple, Google, Spotify, et cetera, et cetera. When you're there, if you like us enough, we hope you'll give us a favorable review. If you want to find me, you can reach out to me on LinkedIn or email me at cmain@precipient.co. That's cmain@precipient.co. Thanks again for listening. Until next time, this has been Technically Legal.