How Community Helped a Leader Seize Opportunity at a Challenging Time

John Paul Rollert: What do you do when a great opportunity presents itself but it doesn’t come wrapped in a big red bow? I’ve been thinking about that question a lot as we go through this unprecedented time. And that’s why I was really excited to speak with an old friend, Nabiha Syed. Nabiha is the president of the Markup, a nonprofit journalism initiative that focuses on technology in society, and a faculty affiliate at the Columbia School of Journalism. Nabiha, thank you so much for joining us.

Nabiha Syed: Thank you for having me. I’m so excited to chat with you.

John Paul Rollert: Now, Nabiha, when you became president of the Markup, it wasn’t exactly under ideal circumstances. Can you take us back and tell us a little bit about the challenges you faced?

Nabiha Syed: Sure, so I’ll rewind a little bit and I’ll ask you what might it feel like to have the perfect job at the perfect time? Because I thought I had that. I was at Buzzfeed as their in-house news litigator. I’d come off a crazy stint of some really high-profile cases, the Steele dossier cases. And I was ready for a break and sort of, like, just from heaven, I got a perfect opportunity.

A reporter that I knew, Julia Angwin, who’s now the editor-in-chief of the Markup, reached out to me and said, “We’re starting a new news organization. It’ll have really juicy legal issues because we are investigating the biggest, most powerful actors in the world—big tech companies. We just got $20 million so we have some money in the bank, and we need a general counsel, but not right now. In some months, like, I don’t know, nine, 10 months. How does that sound?”

I had just found out that I was expecting and I needed a break and I was like, “Oh my God, this is perfect. I’m going to have my baby, have a break, join this organization as their general counsel. It’s the perfect next step. Fantastic.”

I left Buzzfeed and I thought, “Oh my God, I’m just going to enjoy this time.” And I’ve worked pretty consistently since I was a teenager. So the idea of having a break felt amazing. I went off to China as part of the commission on US-China relations, went on a long trip, came back, decided to go down to DC to see my friend argue a Supreme Court case, which is important because when you go to the Supreme Court, you put your phone in a little cubbyhole and you don’t see it for a couple of hours.

I then come outside after hearing my friend argue a Supreme Court case, her very first—what a notable, huge endeavor. And I look at my phone, and there are 63 missed calls. Unusual.

So I decided to call back the first number. And it’s a friend of mine who’s a reporter at the New York Times. And she goes, “Hi, honey, how are you? What’s happening with your job?” And I was like, “Oh my God, great news. So I actually left Buzzfeed. I’ve been on this long trip to China. I’m going to start at this place called the Markup. Like, after I have my baby, I’m super excited about it.” And there’s silence. And she goes, “Have you checked Twitter?”

Now in this age, having someone say, “Have you checked Twitter?” when you’re asserting a set of facts is horrifying. So I’m like, “I haven’t.” And she goes, “You should probably do that. Call me back later, though.” Hang up.

So I check Twitter and I see that there had been a bit of now well-documented management tumult. The previous president of the Markup had cast out the editor-in-chief, which is the reason I’d been drawn to the organization. The staff had walked out as protest, and this perfect job that I thought I had, that I’d been prepared for, ready for, with the perfect timeline, up in smoke, gone.

John Paul Rollert: And so, Nabiha, just to be clear, this catches you entirely off guard. All of the thinking you had done, the research you had done, none of it had prepared you for the possibility that you might be walking right into a minefield.

Nabiha Syed: Exactly. I, you know, you think—. Startups are always unpredictable, but you think a fairly decently well-capitalized one that hasn’t even launched yet, you got a little bit of time before the drama starts. And so I was presented with this really interesting moment, where I believe in the mission, I believe that there should be a data-driven journalism organization investigating the tech you know—Facebook, Google, Apple—and the tech you don’t know—tenant-screening algorithms, that kind of thing. Like, it should exist.

So I start on sort of a persuasion campaign of explaining to the investors in this organization, “This thing should exist, right?” And talking a lot to the team that walked out, trying to understand, is something salvageable here. And in those conversations, the proposal comes to the table of: “What would you, what do you think about being the president of this organization? And I got to tell you, it’s like, I’m eight months pregnant. I am exhausted ‘cause I’ve been, you know, putting together business plans for the organization, trying to persuade everyone involved that actually there is something here, but me, a person who had never even been a general counsel before—I’d been a counsel of a large organization, but I’d never been a general counsel, much less the president of an organization that had gone through this kind of tumult and to launch it.

And I really . . . I can’t tell you how I just kept thinking, “Is this right for me? Can I do this? Do I know how?” And the answer to the latter one was, “No, I don’t know how,” but I got tremendous advice from a number of mentors of mine that were like, “No one ever knows how. It’s a leap of faith. It’s a bet. There is no such thing as the perfect job at the perfect time.”

The fiction that I thought I had at the outset, it doesn’t exist, right? It doesn’t exist. So you sometimes just have to look at it and say, “This isn’t the greatest timing. I don’t exactly know how to do this job, but I know that I’m going to roll up my sleeves and do the work that needs to get done.” And that is what I decided to do.

John Paul Rollert: So I was hoping you might walk us through a little bit of the deliberation process here. On the one hand, you are talking to these mentors and you’re trying to get their counsel to size up this new opportunity that’s been presented to you. And of course, you’ve already signed on for one opportunity at the Markup to begin with, to become general counsel. That responsibility would have been challenging enough, although it’s true, as you note, that it would have been consistent with some of the work you were already doing at Buzzfeed. And now you have this new opportunity to become the president of the organization. Far more, kind of, leadership responsibility, a kind of wider suite of demands on your time. And that’s an exciting opportunity. But of course, one that’s challenging, in part because the organization is facing a lot of turbulence. And at the same time, as you note, you’re eight months pregnant. So I was hoping you might be able to tell us, for you, how you ultimately made your way through that calculus and decided that this opportunity was not only one that you could handle, but that it was one that you wanted to tackle right now.

Nabiha Syed: Ooh, it’s such a good question. With one mentor in particular, he sat me down, and I won’t forget this, we went out to go get lunch and he just grabbed a napkin and he was like, tell me all the pieces that scare you. And I was like, what do you mean? And he’s like, from the outside, I look at you as a person who frequently runs into burning buildings. You’ve been a litigator in these high-profile, bet-the-company cases. You get called in when everything is falling to pieces. That’s what’s happening here. So what is the piece, let’s just actually make it tangible, what are you afraid of?

And I just thought that that was such a good exercise of, like, pen to paper, what is it that you don’t know? And I was like, well, I don’t really know. I’m not sure I know how to run a business. How do I set up a model? And he’s like, good. OK, well, so how much runway do you have? Who are the people who would help you do this? What are the beginnings of an idea that you might have? And as I started talking them through, he’s like, you do actually have ideas here. Now, the way I set up the business model was predicated on in-person events, which as 2020 unfolded turns out is not the business model we’ll be using. But it was just this exercise in taking these sort of amorphous concerns and making them concrete, crystal, and realizing that in your networks, you have the resources to solve many of those problems, right? Like there are people you can call upon, and that’s the benefit of being a relationship-oriented person.

The last thing I’ll say that he reminded me of that I think is very helpful, is it’s actually a gift to know what you know and know what you don’t know and be humble about that. Right? So actually the fear that you have of “I don’t know how to do all parts of this job” is good. Identify it. And then walk with humility into those responsibilities, saying like, “I haven’t done this before. Don’t know how to do it, have some instincts. I want to check them and I want to go from there,” and that helps you with your leadership to approach it that way.

John Paul Rollert: So it sounds like he was saying, “Hey, Nabiha, let’s evaluate your blind spots and see, on the one hand, how worrisome they are, and on the other, how we might overcome them.”

Nabiha Syed: Yeah, absolutely.

John Paul Rollert: So to a certain extent that kind of walks us through the professional considerations you had to sort out when deciding to take on this job, but of course there are personal considerations as well, too, that you also have to factor in. It’s not just merely a matter of, can I do this job? Am I prepared enough? Do I want to do this job? There are also a kind of set of different considerations, these personal considerations you had to factor in as well too. And I was wondering at that time, how did you kind of bring them into the decision-making process and how did they ultimately shape the decision you made to take on this opportunity?

Nabiha Syed: Yeah, it was one where I had the fortune of not only having an amazingly supportive partner who was like, if you want to do this, like, this is an ensemble-cast situation. Like, we will make this work. I also have a mom who herself, when she was pregnant with me, sort of surprisingly, she realized that it was the 1980s and it was difficult to start off as an architect in those times as a woman who was also expecting. And she was only able to do her work and really, like, start this architecture firm and really do a tremendous amount of work because she had familial support. And so when I was saying like, “Mom, look, I don’t know how I can do this,” she’s like, “I’ll come out to New York and I’ll be there for some months.” And my sister was like, “Yeah, me too. I can work remotely for a little bit. So why don’t I come for a while?”

So between, like, that care infrastructure in my family and friends who were like, “If you ever need a babysitter, if you ever need anything, if you need help, we got this,” I was really able to sort of look at that calculus and say, this isn’t just me taking care of a family, this is looking at the universe, the infrastructure I have in my life and saying, this is a time where I’m going to need your help because I’m not going to be able to take leave. Which was a very personal decision, right? It’s like, I have to launch this organization in a timeline that overlaps with what would otherwise be considered maternity leave. Do I feel OK with that?

And, you know, a lot of that was luck. If I had had a difficult medical process thereafter, it would have been hard, but I got lucky. And I had resources. I had relationships. I had a community I could call upon. And I think we underplay the importance of that in leadership. It’s just not a solo journey. This is really, you’re going at it with a group of people who are supporting you. And that’s a huge piece of it.

John Paul Rollert: So that’s interesting to hear you say that when it comes to leadership, you think that we don’t often think about that need for community support. Why is that, do you think? Is it because we presume when we’re leaders that we need to think about the needs of everyone else and we’re therefore often reticent or unused to asking, “What is it that we need, ultimately to be successful?”

Nabiha Syed: I think that’s exactly it. I think there is a tendency for leaders to be like, “I am the leader. I am doing all of this,” you know, sort of the cult of I and me comes into play. And there is a way we valorize these sort of lone-wolf leaders who are brilliant geniuses and can do all of this. And I guess I would argue for something that is much more situated in communities.

Like, my decision to do this was influenced by a professional community of mentors who were like, “Yeah, you got this. You can do it.” Of my personal community that was like, “Yep, on this front, we have it too.” And that continues to this day. I frequently have issues where I’m like, “Whew, I’m not sure I know how to handle this one.” And I will call up a friend who runs another company and say, “How do you deal with this?”

And even in the organization itself, it helps build credibility, I think, to say, like, “You know, this is what we are doing. Yes, it’s a decision that I’m making, but I want your buy-in. I want you to participate. I want to co-create this organization with you.” And again, you are a part of the community also. And so, I think that kind of embedded thinking, realizing that you’re embedded in a network of relationships, helps you make hard choices and navigate, I think, historically uncertain times, which the first year of our organization certainly faced.

John Paul Rollert: I wonder, looking back if you think there’s anything you did, maybe any kind of professional philosophy you carried with you that allowed you to build this kind of community you could rely on in these moments when you were trying to figure out what professionally you want to do with your life.

Nabiha Syed: That’s a really good question. I would say, I think I am, I’m pretty open about my life and open about the fact that, like, I think that people around me are stakeholders in my life and I’m a stakeholder in their life, right? It goes both ways. And so, you know, over the years, if someone ever calls and says, like, “Do you have 15 minutes to help me think through a question?” I’ll be like, “Yeah, sure. I got 15 minutes, right? I probably don’t have much more than that, but I do have 15 minutes.” And I think when you go about the world that way, just realizing that, like, everyone is going to need help at some time. So you just, like, pay it forward when someone else needs help and you know that the day will come when you need help too. I cashed in all my “oh my God, help me” chips during this time. I just was like, “I’m here, please, everyone help me think this through.” And I think you just kinda gotta approach the world in that way, like, one day you will need help too.

John Paul Rollert: So is there any kind of sense of intentionality in the way that you go about building this community you have around you?

Nabiha Syed: It’s funny. It’s not intentional, but it is rooted in something that I have found quite helpful in my life, which is: I am very curious. I want to know how everything works. So if I meet someone who’s, like, “I’m a wastewater engineer.” I’m like, “Tell me everything about that. All I want to know are all of the different pieces.” So it’s been really easy when someone’s like, “Do you have 15 minutes ‘cause I have a problem?” I’m like, “Ooh, a problem. I want to understand what’s going on.” And you kind of just collect them along the way in your career of like, “Oh, well, someone had this issue and we thought through it like this. This is how it resolved itself.” And that just ends up helping so much. But it’s just rooted in curiosity.

John Paul Rollert: So what you’re really describing are two kinds of communities. There’s that personal community we build around ourselves to help us make decisions, to offer us that support when we need it, to allow us to know that if we’re going to take on this challenge, we can do so competently while keeping our peace of mind. And yet at the same time, there’s also that professional community. In this case, a community that you are entering that has gone through something of a traumatic event that is looking to kind of get itself back on track. And of course, you are taking on this responsibility when they can all tell that you are, as you note, eight months pregnant. So how, in going into that situation, going into this professional community, did you work as the leader within that community to kind of reestablish somewhat of a sense of smoother sailing? How did you reassure them that you all could get the job done in the way that others gave you that sense of assurance that you could take on this responsibility in the first place?

Nabiha Syed: It was not easy. I think I’d gotten some money in the bank because I had been involved in sort of putting the pieces of Humpty Dumpty back together during this sort of dramatic process. So they knew I was invested in the mission enough that I was willing to put my time, even amidst a time of uncertainty, into the endeavor. But I think there were certainly some, like, “Well, how are you going to do this given that you’re, you know, in a family way?” And that was just a lot of conversations where I was like, “Look, we’re launching in February and a lot of this is, we all have our lanes of what we’re meant to do, right? So you focus on what you’re going to do.”

And so it involved a lot of, at the outset, clarity that this is a team. Everyone is pulling their own weight. I know the area that’s my responsibility right now and I have that under control. And here’s how. Here’s what that looks like. And so, in addition to the humility value, right? There’s a transparency value of saying, “I get that you have worries. Let me read you in to what this looks like, what the path is to launching on February 25th, the deadline we will meet. And that’s how we’re going to go.”

What I couldn’t have planned for was, of course, that a week after we launched the organization there was a historical global pandemic. But those same values of humility and transparency, right? Of like, “I don’t know what’s happening, but we are closing the office out of an abundance of caution. No, I don’t know when we’re going to be back in the office because no one knows that, but here’s what we know. Here’s the choices we’re making. Here’s how, you know”—even the decision of: How long do you keep the office closed? was one where I was calling upon other professionals, other leaders in New York to be like, “So, hey CNN, are you opening? New York Times, are you opening? OK, none of you are opening. We’re not opening either.” And then communicating that to staff too, which is of course, as a pack we are deciding it’s not safe. And so I really feel like that early exercise, you know, I was forced into humility and transparency as operating modes out of necessity. Out of a bit of personal desire of, like, that’s how I like to operate in the world. But they were the best two traits to help carry us through the weird year that we’ve been in.

John Paul Rollert: And so by leading with this spirit of humility and transparency, it sounds like you kind of created a rapport with the people that you were working with that gave a kind of added sense of trust that you could draw on when you all faced this event that for everyone in the world was unprecedented in our lifetimes, a global pandemic. Here you are in January of 2020, about to launch this new venture. You’ve gotten over all of this drama that had kind of preceded the previous few months. And at this point in time, you’re faced with a new set of challenges, extraordinary challenges. And it sounds like that kind of spirit of humility and transparency really benefited you at that moment to help convince the people around you that notwithstanding these new challenges, you’d also find a way to get over them as well.

Nabiha Syed: Absolutely, absolutely. And I will say I think we’re very fortunate as a news organization that humility and transparency actually align very much with the organizational values we have. So at this organization, we pair journalists with technologists to investigate with rigor a lot of these sort of big, thorny structural issues around technology reshaping our lives.

We also have a method that we call show your work, which sounds straightforward, but I think is secretly a little radical. And what it is is that when we publish a story, a big investigation, we’ll say, “Here’s our data set that we relied on. Here’s the methodology of how we did this research. Here are the experts that we went to when we had them kick the tires on our methodology. Here’s what we know, and here’s what we don’t know. So we are actually humble and transparent about our limitations, and here’s the whole investigation and the whole package.”

And that’s why we’ve been able to have stories that in year one have had states change their coronavirus websites. We were cited in congressional hearings. We’ve been cited in a number of lawsuits, a Supreme Court brief. We’ve had a surprising amount of impact, given that we’ve been around for, you know, a number of months. So it aligns with that.

And the reason why, right, the reason why we do the show your work, isn’t just a gimmick. It’s because traditionally trust in journalism was something afforded to institutions that people are like, “Of course I trust the New York Times. Of course I trust the Washington Post.” That’s just not the reality of the operating environment of now, right? People do not trust the media. They don’t trust the traditional ways that media has garnered trust by being objective or neutral. So we have to design, organizationally, we have an approach of garnering trust through transparency. That is exactly what I did in my leadership journey. And I think having those values align and connecting the dots of, like, what you guys do in your day-to-day to build trust is what I am doing in my day-to-day to build trust with you and that sort of connectivity and connecting those dots, I think helps all of it transition in a tumultuous time to culture building via Zoom, which is a lot of what we did.

John Paul Rollert: (chuckles) And I expect as well, too, it would give a spirit of authenticity to the leadership you’re exercising and the decisions that you’re making in the organization.

Nabiha Syed: Yeah, absolutely, right. And it ties into things like being open to failure, realizing, you know, when I shut down the office for the first time, I was like, we’ll be back in a month. See you later. No, we were not back in a month. Right, and so it helps you, it just creates this space to be open, to be honest about failures, to say, “Well, we rethought that. Let’s try again.” And having all of that is just, I think, necessary for any venture, not just an early-stage startup.

John Paul Rollert: So you told us a little bit about this personal and professional calculus you went through when deciding to become president of the Markup. The people you spoke with, the different kinds of concerns you had to weigh out. It’s now a little over a year since the Markup launch, so you have the benefit of hindsight. And I’m curious, looking back, and looking through that decision-making process, in what respect do you think you were most right looking back and in a good or a bad sense, in what respect were you most wrong? I’d be curious to hear that.

Nabiha Syed: Ooh, it’s such a good question. So I think I am, what I have been called in the past, by previous managers, a time optimist, which means that I think that many things can be done in a short amount of time out of a sense of optimism and like, go-getter. I had not ever encountered anything like the emotional strain of a sprawling pandemic. And I have to say, I really, like, I was right that that sort of time optimism, go-getter, like, you know what, anything can be done. We can figure it out. I was right about that—to a limit, right? Like, you can only cheerlead people into so much. And at some point you have to realize, like, people are hitting a pandemic wall. People are tired. They’re scared. They’re caregivers in a variety of ways, right? Not only to children, but maybe to parents or other people in their communities. And realizing that we have to contextualize what we ask of people in the workplace amidst the reality of the world they operate in, right, which you couldn’t avoid over the last year when someone’s like, holding a kid while they’re on a call with you or calling from the parking lot of a nursing home, where they’re trying to see a loved one. That was something that I hadn’t fully understood or grappled with and was unavoidable over the last year.

But I will say that I think realizing that people do, whether you realize it or not, show up in the workplace as their full selves, right? The way that they interact with their team may be inflected by what they’re dealing with at home. And just realizing that you have to be honest and open about that, that you have to account for that, while also having clear expectations for folks, right? Saying like, “Look, OK, if you can’t do the work at this time, let’s figure out a solution.” So you have to run a business, but you have a business full of humans. Your talent is humans. And realizing that that is at the center of every business decision that you’re making. I think it was a pretty important realization over the last year of just how nuanced that balance can be.

John Paul Rollert: In light of all of those challenges, has it shaped the mission of the Markup, where you were, say, last February versus where you are today?

Nabiha Syed: Yeah, I think for us, we realized the urgency of our mission when everything, for many of us, leapt onto screens sort of shockingly in the month of March 2020, right? Things that we would have done in person were now telemedicine, school via Zoom, court appearances that were happening over tele, you know, different teleconference mechanisms. Everything was on a screen that may involve an invisible exchange of data or information that people didn’t realize. And for us, it really meant it just underscored the importance of the mission. It wasn’t that, like, tech was a piece of life over there. Tech was actually the infrastructure by which we interact in a society with one another. And that means that you just have a very different urgency to that mission when you wake up.

And I will say things like the January 6th insurrection attempt, right, really underscored the fact that misinformation online is probably something we should understand, right? Propaganda, the way people organize, a variety of other—we have to understand it, and it can’t wait. We have to understand it now if we’re going to have a functioning society. And so I think that we couldn’t have planned for, but that was—could not have planned for that. But it really underscores why we are doing what we’re doing in a way that’s really immediate and tangible and not just, like, an intellectual interest that some folks might have.

John Paul Rollert: So, Nabiha, by way of a final question, it’s a little over a year now since you faced this question as to whether or not to take on this additional leadership opportunity at the Markup by becoming president of that organization, and by stepping in at a time when even before the COVID-19 crisis, it was going through a great deal of turbulence, and having made the decision to kind of take on that challenge, I’m curious if there’s any kind of abiding lesson you might have to share with people, especially those who may be at the beginning of their career and find themselves being given these opportunities that are golden opportunities like the ones that you had that don’t necessarily come wrapped in this big red bow. Is there any lesson from your experience that you’d share with them?

Nabiha Syed: There’s never going to be a perfect time. The takeaway is nothing is ever—the stars are not going to align, and everything’s going to be great, and the next step will be obvious to you. It will always be messy. And the question is really, can you manage that mess? Like, does the messiness of it align with skills that you want to grow, with talents you know you have? And if it does, you have to take a leap of faith. But the idea that the perfect thing will come to you and it will be the next incremental step, a fiction I myself believed earlier in 2020, that’s not real. And so don’t let the perfect be the enemy of the good. The perfect time is not coming. Now is the time for you to go do something.

John Paul Rollert: Yeah, from my vantage point, it’s not so much that leaders never encounter messes. It’s that they know how to clean them up and how to convince others to pitch in. It’s a really valuable message, and I’m so glad that you shared it. Nabiha Syed, thank you so much for joining us.

Nabiha Syed: Thank you for having me.