Navigating a leadership crisis

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KATHERINE MAHER: On the cab to JFK, the night before I left, I went, “is this really the right decision?”

It’s an incredibly high wire act to pull off navigating an organization through a moment where it has been thrust into this sort of geopolitical spotlight. I was incredibly concerned about whether I was going to be able to rise to that moment.

But I’ve spent a lot of time in the Middle East. I’ve spent time in Israel. I have people that I love very dearly in these communities.

We need to find a way, of course, to recognize that Paddy’s comments really did create harm and hurt. And also, we need to find ways to ensure that Web Summit doesn’t shy away from topics. 

Maybe this is the original sin of the tech sector, is that everybody stood up and said, “Hey, we’re here to change the world.” And people said, “Great, okay, well, we’re going to make you live up to your promises.”

BOB SAFIAN: That’s Katherine Maher, the new CEO of Web Summit, who came aboard recently in the midst of a crisis that, while not as heavily covered as OpenAI’s, was just as existential.

I’m Bob Safian, former editor of Fast Company, Founder of The Flux Group and host of Masters of Scale: Rapid Response.

I wanted to talk to Katherine because leadership tumult happens in almost every organization at some point, and there are good ways and bad ways of dealing with it. 

In late October, Web Summit’s founder and CEO, Paddy Cosgrave, posted social comments that described Israel’s actions against Hamas as “war crimes.” The uproar that followed threatened to derail Web Summit’s signature event, in Lisbon, Portugal, just a couple of weeks away, with sponsors including Amazon and Google, pulling out. 

Cosgrave stepped down as CEO, and in came Katherine Maher, the former CEO of Wikimedia Foundation, which runs Wikipedia. In this episode of Rapid Response, Katherine shares how that transition came about, her hopes, her strategies, and how she steadied the situation around the Lisbon event, which successfully drew over 70,000 tech leaders from 153 countries.

Plus, she shares her perspective on the OpenAI situation and more. Let’s jump in. 

[AD BREAK]

SAFIAN: I’m Bob Safian and I’m here with the CEO of Web Summit, Katherine Maher. Katherine, thanks for joining us.

MAHER: It’s great to be here.

SAFIAN: So you have just finished your first Web Summit as CEO in Lisbon. And I’m eager to hear how it went. But first, I want to ask you, what in the world is going on at OpenAI? It’s been such a whirlwind.

MAHER: I think like everybody else, the weekend was just full of… what’s your best baseless speculation, what’s your best rumor mongering? Wrong answers only, sort of conversations. I mean, look, it’s an unfolding moment still, but I think one thing that I am interested in, because of my background, is the role that governance played in all of this. And really understanding the purpose of a board and what their objectives are. Pro commerce, pro productization, get out to market, start building a client base, versus… we’re a research lab and our nonprofit mission. And I think there’s a fundamental tension here. That misalignment of the governance structure, the corporate structure, the mission, integrity and purpose. All of that feels like that was a fundamental disconnect.

Copy LinkKatherine Maher on her decision to join Web Summit as the CEO

SAFIAN: You also had some tumult around your entry into this new role. Really just a few weeks ago, Web Summit’s founder, Paddy Cosgrave, abruptly resigned as CEO in the wake of comments he made about the Israel-Hamas war. Can you take us through how and when you first heard about his social media comments about war crimes and how that then evolved to you getting connected with Web Summit directly?

MAHER: I had been traveling in Dubai, at an event, and it was on the flight home, sitting there waiting for the plane to take off. I open up my phone, and I’m scrolling through the news, and I went, oh, Paddy resigned. And I don’t know Paddy well, but I’ve been to Web Summit, and I really enjoyed the experience. And I knew he’s pretty outspoken on social. And so I read about his comments, and I thought, okay, well, I’ll be really curious how this all shakes out. And by the time I landed at the other end of my flight, which was in Austin, Texas, I had a message from a friend of Paddy’s who said, “Hey, would you be willing to take a call?”

They’re looking for a new CEO. And so I got on the phone, initially with Paddy, and then with the board and the executive team, and the conversation sort of went from there.

SAFIAN: Were there questions you had of them, things you needed to be reassured about, so you understood what you were getting into?

MAHER: I wanted to understand how much autonomy and independence I was going to have. It’s a privately held company. And what influence did the shareholders have? 

I think the biggest distinction that I was looking at was, is this a company in crisis or is this a company going through a crisis? I’ve seen both, and I’ve worked in both. And the latter is, you enter into something that has fairly solid bones, and it’s about: how do you steer through that moment?

Through asking pointed questions and really sort of testing the way that they responded, I felt very confident that the team was incredibly solid. I knew the product was solid, and it felt as though that was something I was willing to step into. May or may not have questioned that decision a few times between there and actually getting on the plane to go.

SAFIAN: So it sounds like you had second thoughts.

MAHER: I didn’t have second thoughts about the product. Again, I think Web Summit is fantastic. I enjoyed it so much when I had attended. I know the role that it plays, and I was really confident that it needed to exist. My hesitation was, it’s an incredibly high wire act to pull off navigating an organization through a moment where it has been thrust into this sort of geopolitical spotlight, that it’s well over its skis, so to speak. And I knew that people would want to hear from me. And that is a very difficult conversation to have, and there’s very few things that you can say that won’t be misinterpreted or misheard. I was incredibly concerned about whether I was going to be able to rise to that moment.

And that was why, on the cab to JFK, the night before I left, I went, is this really the right decision? But, the thing that I kept coming back to is, I’ve spent a lot of time in the Middle East. I’ve spent time in Israel. I have people that I love very dearly in these communities. And I recognized in a very real way how much pain and suffering people were feeling. And that is probably the only thing that is appropriate.

Copy LinkThe commercial implications behind Web Summit founder Paddy Cosgrave’s comments about the Israel-Hamas war

SAFIAN: Part of the backlash against Paddy’s comments were from big tech firms, who were saying they were going to potentially pull out of the 2023 event. So, there were commercial implications on the kind of communication you were going to have.

MAHER: Yeah. When I stepped in, we’d already heard from some of the larger partners, such as Amazon and Google, that they weren’t going to be coming. They were public about that. The first question that I had was, well, is there any chance that we could convince any partners to come back? The answer was, for some, it is actually like a physical impossibility. The limitations of the build out for the conference itself are such that, these decisions, once they’re made, you’re talking shipping containers and teams. So that’s going to be tough. 

Then the next question is, what about folks who are still feeling as though they’ve got some degree of uncertainty? Or are there people who can come back in some speaking capacity or things along those lines? And we were successful in having conversations with partners and bringing them back to the table. The thing that we heard was that the decision to move quickly for Paddy’s resignation to find a new CEO, brought some degree of stability and certainty.

Once I’d sort of been clear about the tone, the tenor, the purpose of what this event is and how we would move to the future, we started to hear, okay, let’s start talking about the next event. Whether that is our event in Doha, our event in Rio, our event in Toronto, or Lisbon in 2024.

SAFIAN: We’ve seen Elon Musk’s social posts take a bite out of X/Twitter’s revenue, big advertisers retreating, Apple, IBM, others. Do you feel like that’s appropriate, that sort of boycotts by business, in service of social or political aims, is what part of the job of being a CEO is today? 

MAHER: It’s not just about what CEOs want. In the technology industry in particular, there’s a lot of expectation that companies have some sort of values alignment. Maybe this is the original sin of the tech sector, is that everybody stood up and said, Hey, we’re here to change the world. And people said, great, okay, well, we’re going to make you live up to your promises. If you say that you’re not going to be an evil force in the world, well, what does that actually mean? And now we’re going to force you to engage in that in a rigorous dialogue, and we as employees came to you because we believed in that mission. And so, you’re not the only one who gets to make a determination about whether that mission exists or not.

Whether that is a good thing or a bad thing as an investor, maybe not. But I actually think that given the pervasiveness of the industry’s role in shaping every aspect of society, it’s probably completely appropriate that we’re holding companies to account. You know it is a CEO’s prerogative to know when to speak and when not to speak. When I was in my last role at Wikipedia, we were very clear that we would speak about anything that potentially could harm our mission, whether that was censorship or freedom of expression, freedom of inquiry, and the like. And then we were very clear that we would speak about anything that could be harmful to our staff. So, limitations on mobility, the immigration bans, these were things that had a direct impact on our ability to be successful and for our employees to feel as though there was someone looking out for them. Every CEO, every company, is going to have different boundaries and different limitations and have to be really thoughtful about that.

Copy LinkWhy Web Summit needs to exist

SAFIAN: You said earlier that Web Summit needed to exist. Why does it need to exist? I mean, there are a lot of events and conferences in the world.

MAHER: I have spent a lot of time in decision-making rooms that are populated exclusively by C-Suites. There’s a lot of norm shaping that happens in those rooms. There are very few events in front of an audience of 10, 15,000 people, which is sort of the capacity that we offer on our biggest stage, in addition to the 70,000 people who are at our events. You have incredibly important discussions that happen on the stage, in the corridors, about the future of what technology should be, or even sort of whose voices matter.

Web Summit takes tremendous pride in the work that we do around gender parity, in terms of our speakers, in terms of our attendees. We also take a similar approach to innovators from the LGBTQ community, from minority groups or marginalized groups, or the global south. You don’t see that at most conferences. At Web Summit, it’s absolutely there to support entrepreneurs. It’s absolutely there to support people who have the big idea. It is a place in which deals get done. It is a place where checks are written. And it is also a place where conversations are had.

To put us in Lisbon, where there’s a far greater access to a different attendee base, I think that’s a really healthy reminder of the fact that this discourse is global, and it must be, and it needs to be.

SAFIAN: And I guess this emphasis on a cultural openness is part of what made Paddy’s comments so challenging for the organization, something that needed to be dealt with so quickly.

MAHER: One of the things that I said on my opening night remarks were that we need to find a way, of course, to recognize that Paddy’s comments really did create harm and hurt for members of this Web Summit community. And also, we need to find ways to ensure that Web Summit doesn’t shy away from topics. We should have conversations that challenge us on stage. That’s a healthy way of engaging in intellectual curiosity and debate. Anything worth doing in the world is going to challenge somebody. Let’s just make sure that we’re doing that in a way that’s really respectful, that sees our collective humanity or our individual humanity in doing that, and creates the space for openness for those conversations to happen.

SAFIAN: So you stay in the cab, you go to JFK, you fly your way to Lisbon, it’s Web Summit’s signature event, but it isn’t really your event, because you’ve just inherited it. 

MAHER: That’s right.

SAFIAN: Although you’ve been there before. So, what was your plan for your role in that environment?

MAHER: On day one of Web Summit, all sorts of folks’ microphones poked in my face and say, “Well, what’s going to be different about Web Summit under your leadership?” And I’m like, you guys know that this has all been being planned for literally months now? It’s not as though this bears my stamp. My role coming in was supporting the team. 

And in this particular moment, that was, being the public face of the event, being available to partners, our sponsors, telling attendees what to expect on stage, and setting the tone.

SAFIAN: There’ve been demonstrations here in Brooklyn, where we both live, about the Israel-Hamas battle, even just yesterday. Were you concerned about demonstrations at the Summit? Were there any?

MAHER: We did talk about this, especially given that I stood up and said, look, I think that we need to have a right to express ourselves. Well, what does the right to expression look like? As it turns out, unscheduled protests in Portugal are actually illegal. That’s obviously something we’re not familiar with here in the U.S. That is what I learned about Portugal. So that would be sort of out on the street, we didn’t see any of that. Within the venue, what we agreed was that every speaker would have the right, and every attendee would have the right, to show up as they wanted to show up. If you wanted to wear something, if you wanted to carry something on your person to make a statement about anything, that as long as it wasn’t incitement or it was within the bounds of safety for other attendees, that’s okay. If you wanted to make some sort of statement with your presence at somebody else’s speaking moment, as long as that was silent and respectful and not bothering attendees, we would give that moment as well. If you were going to be disruptive in some sort of way, well then, our normal rules and conditions of entry and participation apply.

So one of the changes that we made was we actually foregrounded those code of conduct policies, so that every attendee, when you show up at Web Summit, you have to sort of click through your app as your badge when you go to registration. You actually had to proactively ascent to that code of conduct, so that attendees were reminded that that was what we expected out of them was respectful participation.

SAFIAN: Katherine’s calm and clarity amid the storm around Web Summit, and the consistent communication around what’s known and unknown, stands in stark contrast to what we’ve seen unfold at other tech firms in crisis.

After the break, we’ll hear about lessons from her time running Wikipedia, and why she prefers a startup-like work environment. We’ll be right back.

[AD BREAK]

SAFIAN: Before the break, we heard Web Summit CEO, Katherine Maher, talk about the crisis she walked into and how she’s navigating it. Now, she shares lessons from her time running Wikipedia, why she prefers a startup-like work environment, and more. 

Copy LinkUniting three tech markets in Qatar

You’ve got Web Summit in Qatar, in Doha, coming up in February. Especially with events going on in Israel, that may be a more fraught location than one you would’ve chosen for your next event. Is that complicated?

MAHER: Many people have expressed their thoughts about it to me, yes. If you want to get into the geopolitics of it, the New Yorker actually has a really great piece about Qatar’s emerging role as a neutral party that brings people to the table. What I would focus on is not, oh my goodness, are we going to a country in the Middle East? What I would focus on is, it has access to three of the world’s largest markets that are the least well represented in the global technology ecosystem and least well served. If you look at South Asia, seriously deep connections to Qatar, specifically. It’s like two and a half, three hours to India. It’s so close.

Then you have, obviously, the Middle East, and that’s 350 million people, the vast majority of which are under the age of 35. And that means they’re digitally native. It is a market that has traditionally been underserved because there hasn’t been a lot of development of digital products in the Arabic language. And then you have Africa. If you’re sleeping on Africa, you’re sort of missing the boat for the next century. By the time we hit 2050, one in four people on the planet are going to be African. By the time we’re at the end of this century, that’s 40% of the world’s population that is going to be African. The velocity of emerging markets in Africa, transitioning into middle income status is higher than any other region on the planet.

And what Web Summit Doha offers us is the ability to bring all three of these markets together, which is, if I’m an investor, if I’m a start-up, if I am a major corporate partner, I’m going, how do I access this more deeply? I’m so excited about what we’re going to see there.

SAFIAN: So passionate about technology and what’s possible here, huh?

MAHER: I got my start working for UNICEF on the role of technology and transforming healthcare outcomes for mothers with HIV, who were giving birth to children, who could be HIV free, if they were able to take their medicines on time every day. And I was working in rural Zambia. And what we realized was that mobile phones meant that people now had alarm clocks in their pockets that were reliable. You could take your medication at the same time, you could communicate with your community health worker. And in doing so, you were able to have an entire generation of people who were able to be born without HIV.

And so, technology can be absolutely transformative. And I see that possibility in every new technological innovation.

Web Summit actually offers us the opportunity to have these conversations, recognize all of that opportunity. You can build the next unicorn, and it might even do something good in the world. And also, how are we going to talk about what the unintended consequences are? How are we going to talk about the responsibility to society and to people in the process?

Copy LinkWhat Katherine Maher learned from her time at Wikipedia

SAFIAN: You were previously CEO of the Wikimedia Foundation. How is that experience as CEO informing your approach?

MAHER: Wikipedia is a global consumer product. It has a billion users plus per month. We ran every aspect of our own technical stack. We rolled our own DNS. We were absolutely in the guts of everything that we did. The ability for us to run that operation at the scale that we did, with the size of the team that we had, on the budget that we had, meant that every decision was a tradeoff. You’re trying to make decisions in an incredibly compressed time period, with a tremendous amount of pressure, and sort of limited capacity. You’re having to prioritize.

That’s what Wikipedia felt like every single day, despite the fact that it’s a 20 year old site that everybody knows. How do we compete in this incredibly competitive industry, as a top ten website? Everybody that’s using our content, reusing our content, mining our content to build the large language models of the future… it was a very intense experience. Web Summit’s a different product, but the real time aspect of it is there. So Web Summit is just as global.

It is also in a competitive market, where we have to be very thoughtful about how we’re positioning ourselves, but also how we’re relating to all these different partners and stakeholders. And how we respond in real time to what’s of interest and value in the world is quite similar. Wikimedia is negotiating ambiguity in real time, in a way that, where everything that happens in the world would happen on our pages. Everything that happens in the world is pertinent to Web Summit, because everything is technology and technology is everything. And so that is a familiar place. I’m still getting up to speed, but that feels very familiar to me.

SAFIAN: And culturally, it sounds like even though it’s been around for a while, as Wikipedia has, it still feels and operates like a startup, or you want it to, you need it to.

MAHER: I think it’s healthy to. It feels like a startup in the sense that there is a high degree of awareness that execution is everything and you’re only as good as your last event. It feels like a startup in the sense that we’re always seeking what’s the fresh angle. I like that environment. I mean, I’m somebody who seems to really enjoy running towards the burning building. And so for me, that tension feels as though it’s a fun place to be. It’s a place at the edge.

Copy LinkWhat will be different about Web Summit

SAFIAN: So Lisbon, Doha, there’s Web Summit Rio in April. There’s June, your North America event, Collision in Toronto. What’s going to be different about the operations and the events with you at the helm?

MAHER: We have a great depth when it comes to startups and the consumer facing productization of existing technologies. I am quite keen to have technologists on our stages, talking about where innovation and research are going and how that might project us forward into the future.

Our name is Web Summit, but we are much more than the Web. And so, what are we thinking about when we think about technology? What does that actually mean? Is it fundamental R&D? Is it applied sciences and biomedical and material science? Is it climate and climate tech? I hope we’ll see more of that on our stage. So much of where really, truly interesting things that are going to be transformative to our world, are not yet part of our event. So I’m looking forward to bringing that in. 

And then I think that it’s essential for us to be a platform that brings people in from truly everywhere. I want to make sure that Web Summit continues to be a place where we’re challenging what truly global technology actually is. And then I guess the last thing that I’ll say is, how do we ensure that that conversation about our social obligations as innovators, entrepreneurs, technologists, is met? Because ultimately the things that we’re building, my strong belief is that they have to be in service of the societies that we live in. And I know that not everybody agrees with me on that, but that is what makes for really good conversation. And I want that to be a part of our stages.

SAFIAN: Well, this has been great. Thank you so much for doing this.

MAHER: My pleasure, Bob. Thanks for having me.

SAFIAN: What strikes me when listening to Katherine is how her leadership style combines both calmness and enthusiasm. Things often don’t go as planned in business. Sometimes the disruption is self-inflicted, sometimes it’s unavoidable. Regardless, finding the way forward doesn’t have to be a panic. Clarity of thought enables clarity of action. And that’s what delivers lasting progress. 

I’m Bob Safian, thanks for listening.