Medium was launched in August 2012 by Twitter co-founder Evan Williams as a way for social media users to publish ideas and stories. Over the past few years, Medium has quickly become one of the most popular online publishing platforms where people can publish their own original content and collaborate on writing. With growth comes a host of legal issues to consider. In the latest installment of its In-house Insider feature, Media Law Monitor sat down with lawyers Sarah Agudo, head of legal, and Alex Feerst, corporate counsel, to discuss the day-to-day challenges the Medium legal team faces.

1. What does a typical day look like for Medium's legal team? 

Alex Feerst: Like many lawyers, some days start fast and early—you wake up, glance at your phone and there's a backup of emails and slacks from things that happened overnight or in other time zones. For example, maybe we wake up to a bunch of tweets from people in Malaysia or China, saying Medium's been blocked. If they're pressing, one of us will start handling it right away. We both come to the office with a long list of short tasks, a moderate list of things that will take sustained work, and one or two big ideas.

Sarah Agudo: Probably by about 9:45 we've both temporarily abandoned our lists, sync up, and figure out what to focus on for the day. It's a balance between taking care of all the issues that come up—contracts, product questions, a tricky takedown request—and making real progress on something bigger, like figuring out how to restructure the employee stock-option plan to better align everyone's incentives or develop a plan for takedown requests in a foreign jurisdiction.

AF: We work together a lot. The office is open plan and we sit at neighboring desks. We ask and give each other constant reality checks and hand work back and forth pretty much all day. It's a team sport.

2. What legal issues do you deal with the most in your position? 

SA: Between the two of us, we keep all the legal plates spinning, including general corporate work like fundraising, board matters, and M&A, employment and immigration work, all of our commercial contracts, product counseling, and intellectual property and privacy issues related to users and content on Medium. We also spend a fair amount of time setting and implementing trust and safety policy.

3. Which is what? 

AF: Trust and safety is basically anything affecting how users interact with content and each other on Medium. Our goal is to optimize those qualities in our ecosystem. So, for example, user-generated content (UGC) copyright and trademark issues are considered trust and safety issues because they concern whether content or user accounts are being used ethically and lawfully. Trust and safety also includes content that has been reported as potentially violating our Terms of Service, Privacy Policy or Rules (which prohibit things like doxxing or harassment). With the amount of UGC that goes up on Medium every day, there's a constant stream of these issues. Some are pretty routine or at least recognizable, but plenty are surprising and complex.

SA: We have a team that investigates, takes action and responds to grievances. Some of the harder calls, or complaints with some complexity in the underlying law, get escalated to us. We argue over the tough calls. We apply the relevant law or our site rules. As we get hard cases, sometimes we tweak those rules as we learn. Every decision affects Medium's ecosystem, so we think hard about the rules and each application.

4. So what's really difficult for you and your team? When do you have OMG moments? 

AF: Every single day. We shake our heads. The number of jurisdictions we're in adds complexity. On the content side, on any given day, we might get escalated to us issues not just from the U.S., but also various EU countries, Brazil, India, Turkey, or Togo. We may have a strong view on how a Californian's publicity rights work, but how about someone writing in from Marseille, France about a post detailing a personal relationship without permission, or a photo taken in a public place in Berlin, a screenshot of a heated text exchange between someone in Ireland and someone in Korea. Some places don't have the protections for intermediaries or relative clarity of U.S. law.

SA: We're tasked with doing more than the minimum required under the law. Our challenge is to figure out how to keep Medium open but civil. What types of personal information constitutes a privacy violation when posted, or what things go over the line from just mean into harassment or bullying or hate speech? We wrestle with new cases that come up every day and think carefully about how to apply our rules fairly and consistently. We want freedom of speech on Medium. But we also believe that the era where online norms tended towards standing aside while users threaten each other, spout vitriol, or post information that might put someone in danger is over.

5. Is it difficult to advise non-lawyers about legal issues? 

SA: In some ways, sure. We don't want to be the hall monitors who come in and stop someone from realizing their vision for a product. We want law and product to fit together.

AF: Right, so when we do product counseling, we try to bake it in from inception. We deputize all our engineers and content folks as the front line. They're the ones spotting issues and developing instincts for when they should come find us. We hold regular sessions with employees on things like privacy and regulatory guidelines so their daily work integrates their evolving instincts.

SA: Our goal is for employees to think about these issues as they frame product features and content projects. Rather than coming to us right before a launch to say, "Oh, by the way, is this feature legal?" we want them coming to us on Day One saying, "We have an idea to build a feature that works like this…."

AF: That way the legal thinking is embedded in the product, rather than a compliance solution that's bolted on later. We basically want the smart people we work with to look at the legal or trust and safety issues as another set of interesting constraints that inform how we design and build.

SA: And as another chance to do right by our users and co-workers. We give them a lot of trust, and, by and large, people come to us early and with enthusiasm for how to problem solve rather than dreading a legal compliance meeting that's going to burst their bubble.

AF: We don't want to just say no, try again; we want to spark curiosity about how the law structures their work and then harness the energy that comes from that. People tell us we're fun for lawyers, but who knows.

6. In what ways does a new media company like Medium grapple with issues that are associated with more traditional media? 

AF: So, most of what's on Medium is UGC. This includes many publications on Medium that are run and edited by users. All we do is provide the platform and tools. For that side of the business, you get tech-company type issues. Both of us grew up as lawyers in the Bay Area, so these are the sorts of the things we're familiar with and love to work on—privacy and data issues, copyright, technology licenses, and generally running the company in line with the legal norms that tech workers in San Francisco are used to—minimal noncompete and nonsolicitation clauses, potentially valuable trade secrets.

SA: Over time we've had some in-house publications, like Matter and Steven Levy's tech publication, Backchannel. These publications, among other things, worked as laboratories and exemplars for user-run publications. They produced polished and award-winning journalism and showed what you can do with Medium. These have more traditional content issues.

AF: They also conversely taught us about product. In addition to all of the users out there in world, we had a group of opinionated journalists and editors across the office who would come explain what they were trying to do, why they wanted certain features, or what was getting in their way. This sort of constant in-house focus grouping helped us learn tons, from legal and product perspectives, about how people use Medium—what kind of amazing work they would produce and what messes they might make. Our in-house people did plenty of both.

SA: There are also in-between areas like content curation, a team of folks organizing UGC, making it more logically or interestingly structured, more findable, and more in line with what a given community of readers and writers has on its mind at a given time.

7. What kind of things DO you expect from outside counsel, or Wish they would know? 

AF: Sometimes I think I went from being outside counsel to being confused by outside counsel in three days. For me, the best kind of interactions with outside counsel involve thoughtful, candid and succinct answers to two questions: (1). Is it legal? and (2). Is it wise? I prefer real talk to being obviously managed, like something from an old friend who's unafraid to deliver hard truths when necessary. I love working with people who can show me the biggest possible picture—the forces and motivations at work, the legal levers and practical pitfalls of a position, the downstream and implications of a decision, the range of outcomes, and the knock-on effects for other parts of our business and industry.

SA: I agree that real talk versus being managed is key. We value people who are willing to cut to the chase and to go with us when we question the way things are traditionally done but also feel comfortable pushing back. We get a lot from having outside counsel feel like part of the legal team and company rather than like service providers, to people who are curious about the product or whether a particular decision really fits with the company's values. We try to be pragmatic. We both first practiced at law firms and try to be mindful about how the work actually gets done—simple things like saying to an associate "this is not urgent" or "this one small part is important now, the rest is for future curiosity." We don't get much out of unnecessary scrambling or hedging against exceedingly unlikely scenarios. Medium's a startup, so we prefer short phone calls to long emails and pretty much never want a monogrammed memo or a copied-and-pasted treatise.

8. What advice do you have for other media lawyers? 

SA: Umm—lawyering is often more than lawyering? Sometimes it's about setting up events that won't happen for a while, or may never—a negotiation position, a way to differentiate our product, a form of clear notice, or a de-escalated relationship. For decisions we make that are product-related or public facing, we think a lot about "how will this make our users feel?" Part of Medium's thinking here is that treating users really well is a competitive advantage and also part of leading the way to an internet that is more open, high-trust and civil. So, we try to make these lofty-sounding ideas concrete in things like our user-facing legal documents, such as our rules and privacy policy. Writing functional terms of service that set forth the normal set of rights among the usual suspects in familiar language was just the starting point. We agonize over how to write them in very clear, plain language that is transparent about the underlying rights—things that will make the product (deservedly) feel trustworthy and approachable to people who want to read and write on Medium.

AF: When we rolled out our last terms-of-service update, we got all kinds of emails and tweets in response, but some of them went like this one: "Literally and by far the best update to terms of service type email I've ever received. Blows the others away. This is how I would treat updates to my terms of service and privacy policy if I had such things. I'm impressed, just wanted to give kudos to the legal team." We didn't just keep the company safe and the legal plumbing clear. The terms of service connected with someone. And in the process of giving notice and disclaiming and structuring rights and responsibilities, it gave them a positive feeling about Medium. That was a good day.

As of July 2016, Sarah Agudo has joined Snapchat.

Jaya Kasibhatla is an associate in the DWT media group, based in our New York office.