Ex-Ancestry CEO: How AI is Forcing Companies to Rethink Everything

What does it actually take to lead in the age of AI? On this episode of Digital Disruption, we’re joined by Deborah Liu, former CEO of Ancestry and former VP of Facebook Marketplace at Meta. Deborah joins Geoff to share a candid, practical look at modern leadership in 2026. Drawing on her experience scaling billion-user platforms and transforming legacy organizations, she explains why “adding AI” isn’t a strategy and what it truly means to build an AI-native company. They unpack Facebook’s mobile-first pivot and what it teaches about leading through disruption, why adaptability may be the most important executive skill of the next decade, and how CEOs should think about AI governance, security, and enterprise guardrails. Deborah also discusses building with a founder mindset inside large organizations and creating a culture where innovation comes from the bottom up. This conversation also explores the human side of leadership and why communication makes up 80% of the job. Deborah was most recently President and CEO of Ancestry, where she brought the legacy company into its next phase of growth. In her prior role at Meta, she turned persistence into a platform. The idea for Facebook Marketplace came to her during her first interview, though it took six years of strategic thinking and tenacious advocacy to build what would become a global marketplace serving over a billion people. She also architected Facebook’s first mobile ad products and payments infrastructure, proving that the most powerful solutions emerge when you connect the right people, ideas, and opportunities. Her 20+ years in tech began with integration work at PayPal and eBay — complex projects that taught her how to see the connections others miss. In this video: 00:00 Intro 01:00 What Being a CEO Means in 2026 06:30 Rebuilding a legacy company for the AI era 07:20 Facebook’s mobile-first pivot (stock price crisis) 10:45 The power of top-down buy-in 12:00 Big bets vs incremental change 15:00 The “Future Us” decision-making framework 19:35 How to build great products 21:00 Fall in love with the problem, not the solution 22:45 AI: Blessing or curse for product teams? 24:30 AI governance, security & data risks 26:45 Are developers becoming obsolete? 28:30 Why senior engineers are more valuable in AI 30:00 Should CEOs own AI strategy? 34:30 Magic wand dinners & listening as a leader 36:00 Remote work vs in-person culture 40:00 Breaking the CEO archetype 44:00 Failure as a career advantage 47:00 Communication is 80% of leadership 51:00 Why experts often fail as managers 53:30 Building a culture of innovation 58:00 Scaling infrastructure to unlock product velocity 1:10:00 Parenthood & career stalls (the honest truth) 1:15:00 Networking for introverts 1:20:00 Adaptability: The most important skill of the next decade 1:21:30 Closing thoughts Connect with Deborah: LinkedIn: https://www.linkedin.com/in/deborahliu/ X: https://x.com/debliu_ Our links: Visit our website: https://www.infotech.com/?utm_source=youtube&utm_medium=social&utm_campaign=podcast Follow us on YouTube: https://www.youtube.com/@InfoTechRG

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Geoff Nielson?

  Hey everyone, I'm super excited to be sitting down with Deb Liu. She's the former CEO of Ancestry, mastermind and VP of Facebook Marketplace at Meta, and a longtime product leader who spearheaded the integration between PayPal and eBay. What I love about Deb isn't just that she was the CEO of a billion-dollar tech company, or the creator of an online marketplace for a billion people. It's that she shatters the archetype of the entitled CEO, and knows what it takes to get her hands dirty and build something great. She's a wellspring of executive-level insight, while also being radically open about her own challenges. I want to ask her what tech CEOs need to be thinking about in the age of AI, what we can learn from the tech companies to do it best,

• 0:42Geoff Nielson?

  but also what it takes to climb the ladder to the chief executive office. Let's find out.

• 0:52Geoff Nielson?

  Deb, thanks so much for being here. Super excited to have you on the podcast here today. Maybe to start things off, I'm curious, you know, from your perspective, what does being a CEO mean in 2026, in this sort of age of AI? And especially, you know, you've been a tech CEO. What's changed in the past five years at that kind of highest leadership level?

• 1:14Speaker 01

  Well, I think the expectations are now changing so much. Like, for example, I, you know, I stepped down as CEO last year, but I still stay really close in touch with the company. I sit on a couple of boards and I talk to CEOs all the time. And, you know, what's changed the most is the expectations. And also this time of transition. You think about, okay, so think about three years after the internet came out. That's 1998, right? And then think about the 10 years since then. If you were in a company, or CEO of a company in 1998 that was not using the internet, you are not internet native. What were you doing at the time? And then 10 years later, which companies came along and who won and lost? And I think there's a lot of companies that are run by people who, you know, these companies have been around 10, 20, and Ancestry was around for 40 years.

• 1:58Speaker 01

  And we've gone through a lot of digital disruptions and yet on the other side, this one is probably coming faster and harder than ever before because it's not just changing how we work, it's changing how work is done, it's changing how information is shared, it's changing actually so much of the superstructure of what a company is, which is, you know, you hire young people, you train them in your art, you have them move through the ranks. And yet now so much work can be done in a way that was never done before. And so I think that set of expectations to change. Boards are like, show us your AI strategy. And the answer is if you, if I asked you for an internet strategy in 1998, what would it have been if you were at Sears? Or a travel company or an airline, right? And so I do think that we don't look back at precedent from history

• 2:43Speaker 01

  and understand what that feeling is like for someone today. And yet the expectations are ratcheting up faster than ever.

• 2:50Geoff Nielson?

  I, I, I think that's a really interesting framing of that. And I'm curious, you know, from your perspective, because you know what ancestry, you know, I, I think even you've described it as inheriting a little bit of a legacy company, right? One that was built in kind of an earlier age of the internet and working to modernize it. So, you know, as you said, people expect in AI, investors specifically expect an AI strategy and how you're going to build a more modern organization. What does that look like? I mean, I, I assume it doesn't look like, you know, just being Sears and saying, no AI for us, sorry. But as you think about how you improve your product, how you improve your organization, what like, what are the types of questions you should be answering as you take your business into the modern age?

• 3:35Speaker 01

  Well, I think the first question I, I hear that's probably wrong is how do I bring AI in? But AI is a tool and it's a channel and it's a strategy. But you have to really understand what AI could mean. If you were rebuilding your company today as an AI native company, what would that look like? And I think that's the first question that every company should ask is if I were starting over today with this TAM, this mission, this brand, and I was starting at AI native, what would I do? Because that doesn't say, I think there's a lot of companies are like, I'll sprinkle a little bit AI, right? I will get some Claude code in, I'll use, you know, cursor, I'll get a little chat GPT for everybody and we're all set. Like, that's a strategy. And that's what happened in the internet age, right?

• 4:17Speaker 01

  A lot of companies were like, well, just use the internet as a channel, it's just one other channel, like every other channel. And yet it took over the world and it changed entire industries. And I think that's what's happening today is companies aren't sure what to do. So they sprinkle a little AI here, a little AI there. But if, if you actually did a massive rethinking, I'm going to rethink my company as if someone were going to come to disrupt me. And by the way, the cost of disruption is now so much lower than it's ever been before, because the cost of building software is now much lower than it's ever been before. And you rethink your company from the ground up and said, if I were building an AI native version of my company, what would that look like today? And then what would I do now with the assets that I have that would give me advantage for the next 10 years?

• 4:56Speaker 01

  And I think those are really important questions that companies need to really wrestle with, which is, you know, by the way, a thousand people could be trying to replicate your company. They don't all have to win. A handful of them can succeed and disrupt you in a way that you could ever imagined. There were many companies that tried to do what eBay and Amazon tried to do. There were many other companies that, you know, try, you look at the music industry, right? And how much that's changed. It doesn't even look anywhere near like what it used to look like. And so really thinking hard about what does, you know, building from the ground up look like? And then saying, okay, but what are our assets? What do we have that someone else from the outside does not have? It's, you know, customers, brand, it's loyalty. There was a VC, a prominent VC who said to me, the best companies don't have customers, they have hostages.

• 5:42Speaker 01

  And I laughed when he said that, but it's true, right? It's people who are so loyal, they feel like they can never leave, for whatever reason that is. And if you have that reason, you'll win if you can figure out how to bring AI to make that, those people you serve, better off.

• 5:59Geoff Nielson?

  I love the business-first approach there. And I'm, you know, personally, I really like all the, you know, the callbacks to kind of the internet age. And I always laugh and think about like the, you know, I remember and it was like, oh, like Pizza Hut has a website now, but you can't order pizza. It just like is basically a poster on the internet that says Pizza Hut exists. And I feel like that's sort of the, the approach of a lot of companies now who are using AI, right? As, as you said, they're just using AI for the sake of it. So, you know, there's kind of this interesting challenge, which you said it's, how do we rebuild our company? If we, no matter when we were founded, if we think about this holistically, what should we be doing differently?

• 6:41Geoff Nielson?

  And Deb, if we look at organizations that aren't doing this, which, you know, sadly, I feel like is most of them, is the reason like fear, is it a lack of courage at the leadership level that they're going to be too disruptive? And if you want to be successful, how do you actually get from point A to point B? Because I mean, the idea that, okay, we're just going to blow up everything and build something new, like I'm, that's not quite the right answer. But, but, you know, what does this look like in your experience when you're really getting through, you know, the nuts and bolts of a, you know, a fundamental shift like that?

• 7:18Speaker 01

  Well, I remember the time, so I was at Facebook in 2009 and I spent 11 years there. And we were going through the mobile revolution. So it's 2011, 2012. And the stock price, we went public and our stock price was halved. And I think it was something like $19. So it's somewhere in the $700 today. But it's $19. And it was because we hadn't figured out mobile. We hadn't figured out mobile monetization. And we were a desktop company, right? And so we were like, everybody was a desktop product manager. Everyone was a desktop P I. These people coded, they, everything oriented in the company was like, make our website amazing and the experience amazing. Right? And suddenly it was like, actually, we need to think about it a different way. And at first, we weren't building even a mobile app.

• 8:02Speaker 01

  And there was a team inside the company who was like, we should have a native mobile app for Android and and iOS. And it was not that, not everybody even agreed to that. I know it seems crazy coming back, looking back at that. And there was a team who was like, no, we are going to build this and every other team is going to help us get there. And we're going to take all of our features and return them mobile. But we didn't even have any mobile engineers in most of the teams. And so, you know, at one point, Mark realized how, you know, that transformation had to happen. And he's like, we are now a mobile-first company. And he declared it and he said, every single screenshot, every product, everything has to be mobile native first. And so he's like, I don't want to look at anything that is not mobile first.

• 8:43Speaker 01

  And he overnight changed that you were not allowed to walk into his office and present any idea. No product reviews could happen unless it was a mobile-first product. Think about that transformation, literally a group of people who've been building products for years and years and years a certain way. Suddenly had to do it a completely different way. But it forced us to think differently. Because at the time, there are not that many mobile product managers, mobile engineers. And so we had to actually think about the world in a very different way, our products in a different way, how users interact in a different way. You know, and it made us better because we were forced to do that. And so it wasn't that we replaced all the teams with someone else or we reorg the entire company. Instead, it was actually saying, hey, I'm going to change what is said and what is built such that

• 9:28Speaker 01

  what comes into the room and what gets reviewed from the top is going to look this way. And suddenly we thought that way. Our designers became mobile-first, our product managers, our engineers, our AI was like, and it really, I mean, within a year or two, like, everybody was mobile native. And it was very interesting. And then they actually had to bring back a team to actually work on the desktop. So it was fascinating because you swing so far to one side. And and I built Facebook Marketplace. And at one point, we were arguing about whether we needed a desktop version. And it turns out that we were a great place to sell cars and and rent apartments. But nobody wants to rent apartments and cars from a phone because they want to open multiple tabs. And so, again, you go so far one way and then you swing the pendulum back.

• 10:08Speaker 01

  But I do think that really swinging the pendulum towards AI and saying, what would that look like if we were AI native? If we were AI first? And then come back and say, okay, and here's the things we wouldn't do is a great way to actually balance that out.

• 10:22Geoff Nielson?

  The story about going mobile first with Facebook is it's so interesting to me. And you talk about the stock price halving. And I mean, you had a you had a front row seat to this, but like it was a big bet. And it kind of seems to me there's like, there's a road where nobody puts up their hand and says, we're going mobile first. And like, does Facebook even survive in that world? Or does it end up in the dustbin of history? Like, was that a bet the farm decision at the time?

• 10:49Speaker 01

  Well, I think it's one of those things where hindsight is always 2020, right? It seems really obvious today, but at the time we were like, well, you know, there was a group of people who said, what if we just built and react native? And just, you know, built great mobile websites, you know, and things like that. So there were people who had different points of view. And in the end, we built the native apps, right? And and I think that was we were better for it. But I think eventually somebody would have figured it out. There were a lot of really smart people. But I think the thing that made the difference was not the team saying they want to do it, but it was buy in from the top, because that's when everybody did it. You know, it's one thing to be a side team working on something and they, you know, Tom Allison was one of the leaders there. He's now running Facebook app. He's, you know, he's just like, we're going to do this and then we're going to get people come alongside us.

• 11:32Speaker 01

  But, you know, without the, everybody's moving in this direction, that mobile app wouldn't have had a lot of features, because each of the feature teams had to build their feature into the mobile app, one piece at a time. And so getting the buy in is what made it a rich experience. He could have still had a pretty simple and good experience, but it wouldn't have been the rich experience people expected on a desktop.

• 11:52Geoff Nielson?

  If you work in IT, Infotech Research Group is a name you need to know. No matter what your needs are, Infotech has you covered. AI strategy? Covered. Disaster recovery? Covered. Vendor negotiation? Covered. Infotech supports you with the best practice research and a team of analysts standing by, ready to help you tackle your toughest challenges. Check it out at the link below and don't forget to like and subscribe. You know, just by way of background for me, you know, I spent, you know, seven years leading digital, you know, product development teams and an innovation group here. And what's interesting to me about that story is that, you know, what, what Mark didn't do is say, oh, we're going to spin up some, as you said, we're not going to spin up some side team and

• 12:35Geoff Nielson?

  study it and have like an innovation lab. Like, he kind of like, you know, cut the proverbial knot and just said, we're going all in here. This is our big bet. And I'm curious, you know, with, with your experience, what you've seen with other leaders, how you've acted as a leader, you know, what your stance is on that type of approach? When is like a big, you know, bet the farm approach right? Should you be more incremental? And like, can anybody other than the CEO do this? Or is this really kind of the most important thing a CEO can do for the organization?

• 13:11Speaker 01

  Well, I think that in the things like bet the farm, like, you know, for example, prior to my, my joining Ancestry, the last CEO and the last leadership team said, we are going to move to the cloud. We had our own data centers and they did a lift and shift to AWS. And that was a multi-year painful process because this is a company that's been hosting its own servers, hosting everything. It was one of the first online digital subscriptions that was ever launched on the internet. And, you know, the move to the cloud was not easy and it took up a ton of resources. We had to stop building a lot of things. And then, you know, and I was there for the kind of finish of the migration and then actually, like, you know, a lot of optimization and the work we had to do to make it work on AWS.

• 13:52Speaker 01

  And but the, but by moving to AWS, that unlocks the actual ability to use like AI models and do all of these things that we could never have done before because, you know, you now everything's in the cloud. And, and I think that's an important lesson, which is sometimes some things are not going to immediately pay off, right? So much is like, it wasn't like there was some financial number at the end. It's like, if we move from our data centers to, you know, our servers from to AWS, it's going to save us exactly this much amount of money. That's not how it works, but it does open you up to so many other opportunities. And I think the challenge sometimes is when you bet the farm, you make these decisions, they don't pencil out the time. And this was true for international expansion for Ancestry. We, you know, we had discussed international expansion. We

• 14:35Speaker 01

  were in multiple countries, but there were many more countries we want to go to. But we didn't have a platform to do it. So we're shipping country by country and it was taking a long time. And every time the decision came up, they would defer it another year, whether I was there or not. So by the time I got there, we had also deferred it because we said, well, it doesn't pencil out, right? But at some point, and then one day I said to our leadership team, what is the, you know, what is the future us sitting here in this room in three years, which we had decided to be? Because it's going to take over a year, probably a year and a half, two years to launch this. And we're like, yeah, of course, we wish we had showed this. Like, my son always says, the best time to plant a tree was 20 years ago. Next best time is today. It's his favorite quote, for some reason. And one of the things that's true is that I wish the leadership team of 10 years ago had made this decision

• 15:18Speaker 01

  to build the platform, but they didn't. And the leadership team that I was leading two years ago would have made that decision, but they didn't either. And so I said, but what do the future us in three years wish we had started? Because that journey is a multi-year process. And so I just think sometimes you have to have conviction. And I think that's true of AI as well. I've, you know, in the firm that I'm working at now, and I just co-founded, we talked to some companies, like, super forward-leaning. They're like, we want to be AI-forward, AI-native. And others are like, why would I want to do that? It's going to disrupt my business model. And it's very interesting to see the economy. They're in the same space, but have completely different points of view as to where the world's going to go. And in five years, that thing will, you know, those decisions will play out.

• 15:59Geoff Nielson?

  I'm just chuckling to myself about the, that would disrupt my, my business model. Because it's like, yeah, that's, that's the point. That's, that's what we're here to do. But, but I love, I love the framing device of the, what, what would we wish we had done three years from now? I think that's like a really, really nice north star for decision-making there. I'm curious, you know, just as you were talking about that, one of the other challenges in tech, in product, in leadership in general, is difficulty killing projects or killing initiatives. And like you said, there's like, these things just get kicked down the road again and again. Do you have any sort of, you know, insight around?

• 16:45Geoff Nielson?

  Just your philosophy on how and when that project should die?

• 16:51Speaker 01

  Well, first, I think, you know, I use the analogy, whenever we kill something, it's of pruning, right? That a tree is more healthy, or a bush is more healthy if you prune it, because you're not having dead, you know, parts of the tree taking up resources, and you're actually giving more life, and it actually revitalizes the plant. And so, you know, pruning is actually a really good thing. I think there's a lot of companies that have these, and we had this as well, a lot of my projects, and over the years, was what we called zombie features. Right? A few people use it, they love it, and you don't want to get rid of it because they might be upset, but at the same time, it costs just as much to maintain it as it does any other feature that's used by a hundred times as many people. And so, what are you, you know, what are you spending your time on?

• 17:33Speaker 01

  And there's no such thing, by the way, I tell you in tech, there's no such thing as maintenance mode. Because things deteriorate over time. New code gets shipped, and then it breaks the thing from the old code, and you have to go back and fix it. And the more complexity that you have, the harder it is for you to maintain your new code and your old code. And so, one of the things that I think is really important is thinking about pruning. Which is, I always ask, and I ask this from a perspective of like, when people aren't sure they want to keep somebody on their team, or, you know, they're not sure if, I always ask them, hey, you know, if you're given a choice today, would you hire this person back today? The same thing is, given the choice today, would you build this feature today? And the answer is no. Then what are you doing? You already have all the information you have.

• 18:16Speaker 01

  Either you need to coach that person to get them to be the person that you need to be, or you need to make that feature as successful as it needs to be, or you give it three months and then get it out. Because at the end of the day, that's just sucking up resources from the rest of a more vibrant opportunity. And I think people have a sunk cost fallacy and opportunity cost, you know, opportunity cost ignorance. Because sunk cost fallacy is like, I've just put so much into this, and it didn't work. So I'm going to keep pouring resources in it. And then they don't realize that everything you keep alive, there's an opportunity cost, a real, true cost of maintaining it, of supporting customers, of actually like really, you know, fixing bugs. And that true cost is something that weighs on the organization.

• 18:58Speaker 01

  And over time, it's one of those things where you just keep adding straw on the camel's back. But at some point, it just, it becomes too complex to launch new features.

• 19:07Geoff Nielson?

  Yeah, everything you're saying is like resonating very strongly with me from, you know, from a lot of my experience in that space. And I completely agree, right? It just like, at some point, it like diminishes your velocity and your responsiveness as an organization. Because, oh, what about the impact on, you know, product line A or B or C? And it just gets, it gets heavier and heavier. But I did want to flip that around a little bit and maybe talk about building great products. Because you've, you know, Devin, your career, you've built some really amazing stuff with a number of different organizations. How do you, how do you think about that? You know, what are the questions you should be asking? Is it, is it as simple as, you know, a stroke of just, you know, inspiration?

• 19:51Geoff Nielson?

  Or how do you, how do you come up with a great product? And if you have, you know, the germ or the seed of a great idea, how do you make sure that it actually, you know, to you, continue the tree analogy, like blossoms into something great? And you don't take too many, you know, wrong steps that, that, you know, make it die on the vine? We're way overboard on the plant analogies now.

• 20:13Speaker 01

  So one of the things I do is really thinking hard. I've worked on a lot of things, there's zero to one within a large company. And that is not usually the, a popular place for people to be because all those things die on the vine. There's a lot of issues with it. But I've had so much fun doing so many things I wouldn't have had the resources or support to do outside. And, and that kind of founder mindset is what I brought into every product that I've ever done. And one of the things that I think is extremely important is really thinking hard about, what is the problem you're trying to solve in the world? And is it worth solving? Often we have this thing, it's like, we have this thing, we want to build X product. And I'm like, no, no, what problem are you trying to solve? You know, the product is the answer, but what's the question you're asking?

• 20:55Speaker 01

  And often the, when you ask customers what they want and what they, and what they tell you is different than what actually you build. Because when you iterate, you see that they want something completely different. And to fall in love with the problem, not the solution. Often people are like, I need to build X, like I need to build a marketplace for X. I need to build, you know, Y, like a way to just, you know. And I'm like, but what is the, what is the human need you're solving? And how are you going about that? And I think that's an important way for me, which was when you see something happen organically. And a lot of what I built was, you know, people show you, and we call it people centric development, which is people show you the answer because they're trying to solve a problem with the tools, the very poor tools you're giving them.

• 21:36Speaker 01

  And you say, hey, if I just build a great tool, then they're going to use it, right? And so really thinking through that question and then thinking, what am I? What is my organization and my team? What is the unique take on this? Like, why, what is our right to win? And I think often people are like, well, you know, somebody go X has worked. We could just do X. And I'm like, yeah, but there's something about your team, your distribution, your customer base, your brand that gives you a right to win in a way that someone else doesn't. How do you lean into that as well? And so fall in love the problem, what is your right to win? And then thinking about what is, what, you know, at the end, if you're successful,

• 22:17Speaker 01

  what is your, what is your vision such that if you succeed at this, what is the outcome? Because often people say, oh, I want to build X, but the TAM is not big enough. There's not enough people who want this. If the outcome is you solved a problem for 10 companies and, you know, each with 100 customers, is that enough to really build this? And say, really saying, if I solve this problem, this is the thing that's changed in the world. And then seeing if that's big enough and worth enough your time to make it happen.

• 22:45Geoff Nielson?

  I, I, I really appreciate that answer. And again, it'll, it aligns sort of with my thinking on it. I want to bring AI back into the mix because my, my sense is right now AI is almost a blessing and a curse, if that makes sense. It's a blessing because, you know, as you said, there's this whole new tool set available to help us, you know, solve these problems or, you know, just, yeah, just have these tools in our toolkit that we've never had before. At the same time, I sometimes worry, you know, you talk about the, you know, the, to use an analogy again, like with AI, it's kind of become the hammer and, and like organizations, like suddenly they only see nails and it becomes, how can we use AI for this and for this and for this?

• 23:28Geoff Nielson?

  And it's taken so much of the oxygen out of the room, out of. More creative problem solving, or at least that's one of my hypotheses. I'm curious if you see the same thing. And how, what's the right and the wrong way to use AI as a tool in this broader exercise?

• 23:46Speaker 01

  Well, I think right now, you know, there's, I'll use the analogy of what's happening in high schools and colleges. Right. Which is in high schools, in my kids' high school, basically AI is supposed to be banned from any, they can't use it at all. They use kind of one of the, you know, tools, like turn it in that says, hey, did AI write this? And so kids have almost no proficiency in using AI because of that. They get to college and some classes are fully banned and others are like, use whatever you want. And I think the question is this, are, how do you build the fundamental muscles to use the tools of future? If you don't practice, so if the answer is nothing, then you have no skills. But if you use it, over rely on it, you don't understand the fundamentals that actually get you so that you understand what the answer is.

• 24:30Speaker 01

  And I think somewhere in between is where companies are. Some companies are just like, you know, I'll just like shove our strategy into this, you know, and our decks into this, you know, tool. And it's just going to spit out the answer. But human judgment is actually, this AI is the summary and average of all human judgment of things that have been published over time. And what you're doing is something that's plowing new ground. I mean, presumably your company is doing something that's new. If everyone's already done it before, you're in a commodity business, right? And so how is it going to give you an answer? If you just ask it, you know, tell me what everyone else has done for, you know, looking back in time. That's not going to give you a great answer, but instead using your judgment and actually, you know, using it as a thought partner. Thinking through what are the questions you want to ask?

• 25:15Speaker 01

  That is a skill like any other. And so sometimes I think we're just over relying on it. And then some companies are like, I don't use it at all. You know, we don't, we don't really use AI. We give people ChatGPT and we're good. And that's also the wrong answer because it could be so powerful and unlocking value within your company that you had not noticed before because you have a lot of workflows that are very manual. You have a lot of tools that don't make sense and you could combine them. You have all these things that you could do, but you're just like, nope. I think I see AI as just a chat, you know, a chat window and that's it. And I think somewhere in the spectrum is where most companies are. They're struggling to figure out where do they sit. It's kind of like between high school and, you know, kids cheating in college, which is like, I just use AI for everything, but I've learned nothing.

• 25:56Speaker 01

  And I worry a lot because there's kind of, how do we teach people to be smart users? So that you're using judgment, but also discernment. And I think discernment is very important. It's like, what is useful and what is not? And I think organizations are really struggling with that, both on the government side, as well as really, um, you know, data usage, like are you putting customer data in there? How is, how's it being used? And then what are you extracting and how are you using that data as well? Because if all your competitors use the same tool, you're going to get the same answer also. And is that, you know, uh, is that the outcome you want also?

• 26:31Geoff Nielson?

  It, it, it's something that I think a lot about and I want to, you know, pick a very specific use case that I think is probably, you know, near and dear to your heart, which is the impact of AI on product teams and development. Uh, you know, just like, you know, code development engineers, all that good stuff. And, you know, there, there's been a lot of obituaries written lately for, you know, developers, like AI has made them obsolete. It's all about vibe coding. I'm curious, in your experience and, and from, you know, everyone you've been speaking with and working with, you know, how real is that? What, what is the future of those functions where AI exists? And, and what's the best way for these teams to be structured and making use of them?

• 27:16Speaker 01

  Well, it's fascinating. There was a chart that I recently, a chart that I recently had that I put together, which was basically the hiring for senior engineers is actually going up, but going down for junior engineers. And so that means that AI requires a type of understanding, not just of the AI tools. Because I think younger, you know, especially more junior developers are were actually native to using a lot of these tools. It's understanding how do you use AI within the superstructure of a company? With other applications already there, you know, not everything is like, somebody's like, you can go in Claude Code and build everything. And I'm like, yeah, if you have no databases, no data, no customers you have to secure, you have no dependencies and databases from 20 years ago to honor and all these rules and privacy things and GDPR.

• 28:00Speaker 01

  Sure, you can build something green fields, but and that's what a lot of junior developers are doing. There's that's how they learn. But when you're in a company, you have to fit this into the shape of a box, which is like, here's 15 products that can't be touched. You know, we have PCI compliance over here and GDPR requirements over here. And if you delete an account, it has to be quarantined here. That is a skill that is very highly in demand because you can spit out code for a feature. But how do you fit it in the, you know, company shaped hole that where this product belongs? And I think that's where you're seeing a lot of more senior engineers being hired because they understand how to work within that complexity and bring AI into it. But that also means that, you know, new companies can be started by junior engineers that can start from scratch,

• 28:44Speaker 01

  but it's very hard to fit within existing companies. I think beyond that, you know, what's happening is there's more and more need for, for example, security engineers. Because AI spits out code, but it is not necessarily secure. You've seen there was a few studies that said that something it was something like 30 or 40% of AI built applications have catastrophic security issues. And or even like a cookie banner, like it just doesn't automatically say, oh, you need a cookie banner to launch this product. You know, there's going to be a lot of AI driven products that are not compliant with a lot of the local laws, a lot of the requirements to even exist. And that takes discernment as well. And so you can't just trust AI to do all those things. And I think that's why you're seeing the dichotomy between senior and junior hiring.

• 29:28Speaker 01

  But also it requires thinking and yes, they could produce the code, but someone has to say which part of the code makes the most sense? And how do we use it? And then how do we secure it?

• 29:40Geoff Nielson?

  It's all of these are concerns that are on my mind and I'm worried that there's companies that are going kind of off in the wrong direction here because they're not maybe appreciating, you know, the technical complexities of doing this. And, you know, I'm curious on your perspective, Deb, but, you know, it seems like there's almost at a CEO and board level, this belief that like AI is easy, or as you said, like you just kind of sprinkle it here and there. And one of the trends I've been following right now is this trend, you know, there was a BCG report fairly recently saying that CEOs are increasingly taking over AI, that it's not living with a CTO or a CIO, even in tech companies, it's

• 30:20Geoff Nielson?

  at the CEO level. And, you know, my concern is that if we don't have this, you know, enterprise technology involvement, we don't catch all these like very important technical concerns around security, around architecture, around integration, around, you know, issues like cookies, as you mentioned. You know, you've been a CEO in an organization like this. What's, once again, like, what's the right approach and what's the wrong approach here to be, you know, governing and structuring how an organization implements AI?

• 30:53Speaker 01

  Well, I think first, it's really asking the right questions, you know, so for every CEO is asking the right questions, which is not just how do I bring AI in, but what does it mean to use AI in our organization? And this was the how do we become a native, you know, asking those questions as a leadership team. But, you know, there's a difference between the what and the how. So the what is what are we doing with AI in our company that, you know, this is becoming AI native, it's actually bringing in AI into our strategy, it's bringing it to the boardroom, it's bringing governance. But then there's the how, how do you secure it? How do you implement it? How do you retrain? And I think often we don't separate those two things. The what is we just munch it all together and say, oh, the CTO will just take care of this and we'll just make sure we can, you know, we have a comms person to tell people, the employees how to use it, and the legal team will just

• 31:37Speaker 01

  make sure everything's in compliance. And you're like, no, that's not how it works because it's such a different technology. It requires everybody to align on the what and then align on the how. And you know, a lot of organizations, if you're not careful, will not think about it that way and not think about the governance required to actually bring it in. But then also how it's implemented. What are the guardrails? And I think, you know, it is such a powerful technology. But recently, you've heard people talk about how, you know, it's like military plans were uploaded into a commercial chat GPT. You know, people are uploading, they're like, oh, I upload my, you know, my W2 to get analysis. And I'm like, you realize you have, yeah, all the things necessary. And we have no idea how LLMs ingest that information and you can never take it back.

• 32:23Speaker 01

  And so I just think it's very, you know, people are doing this at companies, people are doing this in government. And that's a very dangerous thing. And so having clear governance and understanding of what the guardrails are, how much customer data, you know, what are the governance on using customer data and leveraging for the models? And then taking on the other side is like, what is the outcome we want? And really sitting and aligning, which is this is the, what is the future us wish we did today? To get us to where we think the future is going. You know, the companies that, you know, did not thrive in the mobile and internet age were the ones who just said, well, we'll just tack this on, we'll just sprinkle it on. The ones who said, you know what? They're going to be competitors who are AI native, who are internet native, who are mobile native, who are going to disrupt us,

• 33:06Speaker 01

  are the ones that you actually had a strategy. And whether they executed or not, they had a chance to actually win in the next stage.

• 33:15Geoff Nielson?

  There's, um, there was something you said in a different podcast that caught my attention and really resonated with me, which is you talked about, you know, I'll paraphrase here, but basically said that a successful executive needs to be a builder, not just somebody who's, you know, understanding the what, but the implication is creating stuff in the how. Can you unpack that a little bit and just share a little bit about how that's influenced, you know, your decision making and approach as a senior leader?

• 33:47Speaker 01

  Yeah, I think as a senior leader, often you can float above everything, right? There's like the kind of guru senior leader who's like, I just tell people and it gets done. And I'm like, look, a great leader is a conductor. They understand the music. They don't have to play every instrument, but they understand what great music looks like. And they put together the right team, but they also call out when things aren't working. And I think sometimes you could just say, well, I just, I have a conductor for that. And like, but not hearing the music upfront and in detail is a very dangerous thing because you can get very disconnected by what's happening on the ground. And one of the things I think is very important for senior executives is to really understand at the deeper level, what's happening when the music is not quite right.

• 34:29Speaker 01

  And, you know, really getting into the details because, you know, people don't come to you and say, hey, I saw this problem. Right? So one of the things I did at Ancestry is I hosted magic wand dinners. And people would, 10 people would come and have dinner. And it would be throughout the organization. You know, some people worked in customer service and member, member services. Others worked in our proteinology group and others were like, you know, engineers, product managers, people in law, the legal team, HR. And we just had dinner together. And I would ask, you know, what is, if you had a magic wand, what would you change about the company? The process, the teams? And they brought up things that they would never say in another, you know, another place. But I think hearing helps you understand what some of the challenges are,

• 35:13Speaker 01

  but also what some of the opportunities are too. And if you're really disconnected from, you know, hearing what people are saying, it's a very dangerous thing because you're not understanding what employees are saying. But these are the employees who are listening to your customers every single day. And they have a level of empathy that can't be summarized in the one pager on like how customer sentiment is.

• 35:34Geoff Nielson?

  I really, really like the idea of magic wand dinners and, and, you know, even just hearing about it briefly, it's such a like, to me, obvious tactic for getting to, being able to hear the true concerns of people and figure out from your, your own staff, how to make the, the company better. One of the ideas rattling around in my head though, that, you know, I'd love to get your reaction to is even the notion of, hey, yeah, we're all having dinner together.

• 36:03Geoff Nielson?

  Is it feels like it's eroding in this world where, you know, when we think about the modern workforce, so much of it is remote. We're not often in the same room. We're not in the same city anymore. We're kind of all over the place. And, and so, you know, maybe this is the difficult question. Maybe it's not, but you know, what does that look like? Do you, are you sort of all in on, we need a team to be in the same room together? What's the right way to think about how to structure a workforce between, you know, onsite and remote?

• 36:36Speaker 01

  Well, I think that there is, it's one of those things where we, when we got together, it was magical. And yet people were, you know, it's like, oh, there's a ton of travel. How do we get together? And I think there's something really special about these, these side room conversations. What happens? We, we call it what happens after the meeting, which is the conversation behind the conversation. And, you know, one of the things that you really miss is, you know, when you hang up, you know, the Zoom, it's over, right? But there's always the follow up conversation, what's happening on Slack? And so creating moments, it doesn't have to be every single day, but it has to be moments where people are connecting, where having dinner, where you just have a conversation around what's working and what's not working with people that you might never have met. I mean, there's something really important about that.

• 37:21Speaker 01

  It doesn't have to be five days a week in the office, but it has to be, you know, people don't work in complete isolation because you're not actually getting everything on the table. People just don't, it's like you have an idea and you'll just lean over and talk to the person behind you, but you wouldn't slap them and say, hey, Jeff, I have this idea. What do you think? You know, because that just seems so formal, right? And I think we're missing a little bit of the informal communication. And being able to replicate that is important. And so whether I've, you know, I've, I have friends who run companies where they say, hey, look, we just, we do home week once a week, like once a month or once every quarter. We're like together for a week and we just like, you know, pack all the time together. So at least we know each other. And others are like, hey, look, we just do two days, you know, in the office.

• 38:05Speaker 01

  But I think the fully remote teams, I think that can work, but then you have to create those moments and it's artificial. And you have to be very thoughtful about creating that culture.

• 38:16Geoff Nielson?

  Yeah, and that's exactly what I'm getting at. And you know, I'm talking to you now as someone who is and has been a team lead, both in person and remote. And yet, to your point, it just feels like there's tasks and certainly like a level of creativity that just doesn't lend itself well to being fully, fully remote, like a whiteboard exercise. Like, hey, I just had this idea. And you know, there's lots. I'm the same way. Like, I'm not advocating for like, hey, we need people in the office five days a week, every week. But it feels like there's just like, there's something very human and something very creative that's missing if you're just not ever in the same room as your colleagues. Is that, is that your experience as well?

• 39:00Speaker 01

  Yeah, I mean, I think it's, how do you build connection? I think for a long time during remote work, it worked really well because people had all the connections from before. And then as those erode and you hire, you know, hundreds of new people and suddenly, you know, a third of the company has not ever met each other. You know, that's, that happened to some companies during COVID. And I think it just really, you know, you have less of those relationships. And those relationships and those serendipitous moments, those are the ones that really matter because that's where ideas happen, where people talk about, you know, something that they've been, that's been on their mind, where they get support for something where, you know, the next meeting is going to get pitched. And I think, you know, creating enough of those moments so that you can carry it through the year is important.

• 39:45Geoff Nielson?

  I, no, I agree. And I think that's, that's very well said. So, yeah, I think we're, I think we're pretty aligned on that one. I do want to shift gears a little bit and talk about CEO-hood, if I can. And, you know, CEOs are kind of a funny thing in the sense that it feels like culturally right now, there's like, you know, almost like a backlash against CEOs. And there's this narrative of, oh, you know, especially with, you know, layoffs happening, CEOs are people who, you know, they shake a bunch of hands and they're these extroverted older white guys and they lay off a bunch of people and they get a, you know, a big bag of money for doing that. And it's this-

• 40:26Geoff Nielson?

  You know, you, it's almost cartoony, but this is kind of propagated. And Deb, you know, what strikes me about you in, you know, a lot of more obvious and more subtle ways is that, you know, you, you've been a successful CEO, you've been a successful senior leader in a way that's, I think, a completely different mold from what people often think of when they think of as a CEO. And I think that's a really good thing. And you've talked previously about, you know, introversion and being able to lead even if you're not, you know, what I've called in the past, like sort of a type A leader personality. What does that look like to you? And, you know, what's your message to people who would want to take on more of a leadership role,

• 41:11Geoff Nielson?

  but think, you know, oh, maybe, maybe I can't do this because of my personality type or how I look or, you know, not being the traditional profile in that space?

• 41:23Speaker 01

  Yeah, well, first, I rose through tech, which is Asian women in particular, 13% of tech workers who enter and 3% of executives. So they fall off at a much higher rate than any other group of people, I believe, who's at that size where, you know, it's a, it's a pretty large group, but they rarely make it to the top. And, you know, I think part of it is how do you lead that's authentic to you, but also adapt to the environment? And I think that those are two things which are very hard for people to navigate. I meet a lot of people who are like, well, I'm just introverted, so I'm not going to talk at meetings. And I say, you know, I coach a lot of people. So I've coached over a thousand people over the years. I do these kind of quick calls and, and I said, well, you know,

• 42:05Speaker 01

  if your, if your dream job were available and they said you needed to, let's just say your dream job is in Japan. They're like, you need to learn Japanese, but you can go run our Japanese, you know, our Japan office and open our new Japan office. Why didn't you go learn Japanese for your dream job? You would figure it out. Well, here's the thing, if you aspire to leadership, communication is 80% of that job. If you say, well, it's not going to do it, do you think you're going to be successful? You know, and I think as a woman leader, there was a study that said, that men and women are seen as leaders differently. So men are seen as leaders that they're competent, but women have to be competent and warm. And in the two by two matrix of competence and warmth, there's a lot of women who are not born warm.

• 42:49Speaker 01

  I am not, I'm one of those people. And I had to decide, what does that mean? And do I just say, you know what? I don't want to be a leader. Or do I figure out what being warm really means? And I think I came off very cold because I was an introvert. So I was like, I kept to myself. I got things done. I was very hyper competent. And I'm like, if I were just hyper competent, I'm going to succeed in the workplace. And I was absolutely wrong. And so I have a lot of women who tell me, well, I'm not warm. So, you know, and I just, you know, I don't want to wear a mask. I don't want to fake it. And I realized something, which is, you know, why do we adapt to other things? You, we weren't all born learning to walk. We weren't born, you know, public speaking skills. We weren't born knowing how to code. So if those are skills, why don't we treat warmth?

• 43:34Speaker 01

  Why don't we treat leadership? Why don't we treat, you know, speaking up as skills that can be learned? And suddenly, if you turn it from a, this is a fixed thing, like I was born this way, to a learning mindset, I can actually learn these skills. It's amazing what's possible. And I learned those things the hard way, which is I failed multiple times just saying, this is who I am. Take it or leave it, because it worked really well in school. Right? You take the SAT, you get straight A's, you get your 4.0, and then you check the box and you graduate. And then you go into the workforce. And what success looks like is completely different. And it requires you to learn a set of skills that you never previously had.

• 44:14Geoff Nielson?

  You brought up failure. And to me, that's like a really interesting point, because, you know, I expect you've seen the same thing, where there's just an awful lot of people who believe like, I can't fail, I'm not allowed to fail. Like, if I, if I speak up or I say the wrong thing, people will think I'm dumb. Or like, it feels very fear motivated. And that's not what I, that's not what I'm hearing you say about failure. How do, how do you conceptualize failure?

• 44:39Speaker 01

  Well, so there was a study that I was reading about, where people who, they looked at early researchers that got an NIH grant. And then they looked at the group of people right below them. And they said, you know, the people who were said, who were given a no versus a yes on their first try. The people who were given a no actually went on to have better research careers than those who just got the yes the first time. And part of it is, they said it was because failure made them rethink and double down or leave. And so they just had to rethink. And I think it's one of those things where the people who are most successful in life that you see and you admire, it's not that they never failed. Those are the people who actually took the failures and took a lesson from it and use it as a stepping stone. So, you know, how do you turn a stumbling block

• 45:23Speaker 01

  into a stepping stone into the thing that you want to achieve? And I think one of the things that we forget is that, you know, I use this quote from Chuck Sandoval, like, life is 10% what happens to me, 90% what I choose to do about it. And those who are like, well, I failed, can't ever do this again, they're the ones who sit on that rock and say, you know, I'm not going to continue this climb. But those who are like, actually, this rock's going to, you know, I get it, it sucked, but it's going to, I'm going to double down and redouble my efforts. Those are the people who rise further and faster. And so, a lot of that is the mindset of, you know, do you allow failure to, to teach you, it's just another thing that teaches you a lesson and makes you stronger. And there's analogy of the trees in the biosphere. So, they've grown

• 46:08Speaker 01

  these trees in the biosphere. They grew super fast because there's no wind, there's no rain, you know, there's not all these, you know, elements. And then they realized the trees got super tall and then they snapped. They just fell over and snapped. And they realized that the wind and the rain, the bending of the trees during these storms actually created these micro tears. And then those micro tears were filled with the type of new wood that would made it much stronger. And it reinforced so that they could grow longer and stronger over time. And without adversity, trees will fail. And I think that's the same, it's true of our careers. We avoid adversity, we avoid failure, we don't learn anything. Because then every, we think everything we did was right.

• 46:48Geoff Nielson?

  I was, um, this is a silly reference, but I've got young kids and I was watching, I was watching an episode of Bluey, and I don't know if that's the wrong era for your kids. But the dad on, the dad on Bluey was trying to be zen and he said, the obstacle is not in the way of your path, the obstacle is the path. Which was, I thought, very deep for like, a show for toddlers. But I really like that, you know, like, to me, it's reframing it as this is, it's exactly what you said, right? The trees need to learn how to bend. It reinforces them. And yeah, it's very easy to get wrapped up into this idea that like, oh, the people who have made it or at the top are really successful. They're successful because success is just sort of

• 47:30Geoff Nielson?

  like this linear thing. And they're the people who have never failed and will never fail. And yeah, it's nice to hear. It's always nice to hear from people who, you know, have that lived experience and are willing to put up their hand and be like, I can tell you from experience, that's not true. I've failed lots of times and lived to tell the tale. And it sounds like that's your experience as well.

• 47:51Speaker 01

  Absolutely, absolutely.

• 47:53Geoff Nielson?

  Yeah. I want to come back to something you said earlier, which is, and I may misquote the number, but you said something like 80% of being an executive or senior leader is about communication and just the importance of communication. And that's something that is maybe an overlooked, you know, skill or ability in people who are a little bit farther down the career ladder. Can we unpack that a little bit? Like, what is good communication? What is the communication that sets a strong leader apart from an average leader or a weak leader? And if you were coaching someone who was looking to up their communication game, what advice would you give them?

• 48:35Speaker 01

  Well, first, I think, you know, when you're, when you're, you know, new or an entry level employee, your whole job is doing. Every single day you're doing, right? You are moving this task forward, you're doing that, and you're checking a checklist. As you rise in the organization, your job is to do through others. So, you know, the first time you're a manager, you don't, you can't do the job anymore. You're actually managing people doing the job. Then you become a manager of managers, then a manager of organization, a GM. And as you rise, you don't get to do the job. But you also have to be careful not to tell everybody how to do their job. And so communication is, now you're communicating, what does success look like? What are our values? What are our, you know, what, how do we want to serve our customers? What is it that we, that we represent as a company?

• 49:20Speaker 01

  And suddenly you're going from, hey, this marketing brief has to be really good, to what do, how do we want to present in the world? You know, how do we want to think about our strategy? Because a very good and successful leader isn't making decisions anymore. They're enabling great decisions to be made. You know, what I loved about working at Facebook was Mark said, you know what? If you have an idea and Tom had an idea to build the mobile app, I had an idea to build Facebook Marketplace. He would support planting those seeds. But he said, the culture is you can do hackathons. There's an outlet if you have an idea. Some of the best products were not products that he would have chosen to build. But you know, when the, when the opportunity came, he supported them. And I think that's where it's really important. It's like, what kind of culture do you want?

• 50:05Speaker 01

  And what are you cultivating? And so one of the things about communication, though, is we ignore it as, as critical skill. Because the first thing when we talk is we think about what we're going to say. But instead, the best thing you can do is think about how it's going to land to the other person. Which means you say a different thing to someone who's a brand new employee, to somebody who's your senior executives, to someone who's on the board, someone who's your investor. And really learning to tune your message to what's landing. What is the other person hearing? What filter are they using? And how do you deliver that? Those are really critical skills.

• 50:41Geoff Nielson?

  You talked about competence and warmth and that you had to work more on the warmth side. But I'm curious, Deb, you know, you're someone who started with more of a technical background. And you rose up the ranks from a technical background to, you know, increasingly, you know, senior roles, all the way up the flagpole to CEO. Was that, that's something that I know a lot of people in technical roles struggle with is say like, oh, it's a different competency. I don't have those skills. I couldn't gain those skills. Is that something you struggled with as you jumped to, as you said, a manager level, a manager of manager level? And you know, how did you, how did you overcome that? And what did that look like for you?

• 51:24Speaker 01

  Yeah, so I remember when I first became a manager, I was a few years out, a couple of years out of business school. And my manager's like, hey, the team's gotten too big for me to manage. I'd like to make you a manager. And I just remember how frustrated I was working with some of the junior employees that we had just hired because they had never done the job before. And I was like, I could do this so much faster than they could. It's driving me crazy to teach them. And he said, yes, but then your career will never scale. Because you can only do so much as one person. But when you're scaling and leading through others, you have to learn how to teach them how to do the thing that you do the best. And that was a really important lesson. My manager went on to step away from the team and I took over the team. And I should had no business running the product team for the biggest business at PayPal.

• 52:09Speaker 01

  Um, and you know, I was just a few years out of business school and I had only been a product manager. I think like two, three years. But the point was, you know, he had taught me to look at the perspective of, how do you think about your career? What is the future you want? And then how, what are the things you're doing today to get you there? If I continue to like micromanage the APMs, it would have been a disaster, right? But instead I learned to teach them and turn to learn to lead them and support them. And that taught me a lesson, which was so often the expert is a terrible manager. And by the way, we do this all the time. It's like you take the best product manager, the best engineer, the best salesperson, and you make them the manager and they suck because managing is a totally different skill than doing.

• 52:55Speaker 01

  And you know, you think about the, you know, some of the best coaches were not great players. You know, but they could see a different skill set, which is strategy, you know, rostering, like putting your teams together or training. But they weren't themselves, not necessarily the top superstar players. And I think that's true of so many things. And too, I think learning management is a skill and learning communication is a skill is really important if you want to rise in an organization.

• 53:22Geoff Nielson?

  I, I completely agree. And there's just, I'm just processing all of that. And there's a theme that we've kind of been talking about in a number of these, you know, in a lot, a number of these answers here, which is the importance of, I think, listening as a leader and as an increasingly senior leader, making sure you're, you've got a feedback mechanism within the organization. And finding a way to balance that with having some sort of vision or ability to say, yes, this is right. I'm placing my chips here. And I find myself coming back, Deb, to the example with Mark and going mobile first. And you just said, Tom was the one who proposed the Facebook mobile app. How do you conceptualize this as a leader?

• 54:07Geoff Nielson?

  And how do people like Mark do that? Like, how do you balance the ability to take things from other people, to be listening, but also not just end up so reactive that you're not willing to put your own touch on things or prioritize what matters most?

• 54:23Speaker 01

  Well, I think that what I loved about my time at Facebook was that it was a company where the culture was very bottoms up, where anyone could have an idea, no matter who you were. And part of the magic one dinners was people came up with product ideas. They had process ideas and opportunities for how could we build our business? And one of the dinners was where it came up with the idea for Pro Tools, which was sort of tools for really pro genealogists who really wanted to go deeper in their family research. And so creating opportunities and outlets for people's ideas, because these are the people who are on the front lines, who are talking to your customers, who know what the questions are to ask. Those are the people you want to hear from. But if you create no outlet for them to ever bring forward their ideas,

• 55:07Speaker 01

  because our roadmap's locked for the next two years, you can't do anything, I think you lose out on a lot of really special opportunities. Because often, when you reach a certain level in a company, you don't see the day to day anymore, right? Everything is a summary of a summary of a summary, and now it's all written by AI. It's like, customer feedback is not rich anymore when you have a summary that's three levels smoothed out. And so having real opportunities and creating a culture where thought leadership can come from anywhere and ideas can come from anywhere is super important. Then you have to have a process to distill the information, because there are a lot of also bad ideas, too. And so how do you create a culture of pruning so that you're actually focused on the real ideas that are going to make a difference?

• 55:54Geoff Nielson?

  The I'm fixating a little bit on the point about AI and this like, you know, the smoothing and the summary of a summary of a summary. I mean, I've I've lived that. And it seems to reinforce just the human connection here and being able to have, no matter what level you're at, that that that human connection there, which, you know, it feels like a valuable lesson. And the and the pruning part, too, to me, is interesting because it seems like it can be a challenge to solicit ideas, but also be comfortable telling people that is a bad idea, you know, versus a good idea, because if you're not careful calibrating that, you know, you can actually discourage, you know, employees sharing their ideas. Is that a challenge you had?

• 56:38Geoff Nielson?

  And how do you make sure that you're able to prune without creating too much discouragement?

• 56:43Speaker 01

  Well, I think first, first, you know, there's a lot of ideas that are not well formed. And so really asking people, well, who's this for? You know, you know, just put together even just like a 15 minute brief, which is like, who is this for? How big is this opportunity? Where do you think this could take us? Often, you know, the idea is then people having to think the next level down are now saying, oh, actually, maybe not that many people would do it. How will we build it like, you know? And it forces kind of the conversation to go from just a like off the top of your head to a deeper conversation of like, what would that look like? And, you know, I think the people who actually spend the time to do that will now think through the idea. And a lot of times they say, oh, that's not going to work. But then the times they're still pushing for it. Then it's like, well, why do you think this is going to work? And what is it that why should we be doing this?

• 57:28Speaker 01

  And what can we accomplish there? And so really thinking a in a process, like having a process to get through those ideas. I see this happen where the thing about, you know, innovation within a company is often people, what you said earlier, it's like they have an innovation team that sits on the side where it doesn't matter.

• 57:46Speaker 01

  But innovation actually is the lifeblood of a company. You can't just make it a side project for somebody. Or you have one executive who innovates for everybody. That's not how real work is done. It's actually the people who are working day to day that have the best ideas because they understand what's happening in the company, what the assets are, what is buildable, and also what customers want. And so building a culture where, you know, and celebrating the ideas that make it through to shipping. So one of the things we do is like we used to have hackathons. And then we celebrate the things that made it to the to live. And like, it wasn't everything, like hackathons would have like dozens and dozens of projects. But the one or two things that made it live made it people feel like, hey, there's an outlet for this, the customer saw it. It made it through. And so I think that's an important part of it is like,

• 58:30Speaker 01

  do create a place for those ideas, but then also an outlet for it as well.

• 58:36Geoff Nielson?

  I really like that. And yeah, it's, it feels like a great way to tie together those challenges. And to your point, the celebration, I think, probably goes along there, a long way there. And I'm chuckling too, because I led that side innovation team. And we had that exact challenge, right? Which is as soon as people believe like, well, we're not, we're not innovating anymore. The innovation team is, you know, that was one of the reasons we ended up kind of dissolving the way that team was structured, because it's not, it's not productive for the rest of the business there.

• 59:11Geoff Nielson?

  Sorry, I had a question and I totally lost my, my train of thought there. Oh, I wanted to ask you, Deb. From your time at Ancestry, what would you say was your proudest accomplishment?

• 59:26Speaker 01

  I think, you know, the thing that I really, it's hard to show what it is because customers didn't see it. But it was how we build things. We actually were able to ship more products than we ever were before. We were able to innovate, you know, we were like, there's so many things and the infrastructure and the substructure of the company that we had to change to make it possible to ship new features to customers. Because we had done the lift and shift to from A, from our data center to AWS. And in that, We also had to like actually open up the opportunity to build. So we stopped building a lot of things for a while. But then we were able to open up new opportunities. And so we built, for example, you know, through lines, which was you could actually see your DNA from your parents.

• 1:00:08Speaker 01

  So even if your parents passed, like my have, you could see your ethnicity estimates from your parents and then your grandparents. That was something that was never possible before. Same thing, we were able to look at edit history and collaboration on your family tree. Things that we could never have built without a lot of, you know, investment in really the infrastructure. But that infrastructure means that for every team and every product going forward, it can move faster. It can get to customers faster and we can iterate faster as well.

• 1:00:37Geoff Nielson?

  I, I, I love that answer and I, I'm curious, like, I guess it's a big question, but how? How, how did you do that? Cause that's a cultural shift, right? Like, that's not just, oh, we ship this one thing or it's not singular. It, it's like a layer within the organization where you change the way people, the, the way people do things. How, how did you go about doing that?

• 1:00:59Speaker 01

  Well, first, I mean, our CTO was really incredible. He had become the CTO at the same time I came in. And he had been at the company and he had led a lot of the AWS migration. And he was able to really rework how we did engineering. For example, we used to have kind of more siloed teams who worked on their own code bases. And then he was able to do kind of, you know, people being able to code across the company and work together. So that helped a lot. We changed our process, our roadmapping process. There were, you know, it's funny when you describe it, cause it seems very mundane. It's like, we changed our roadmapping process and we published a roadmap and we changed our product process. But what it unlocked was, you, it, things are either happen fast or slow because of everything that happens before the product.

• 1:01:40Speaker 01

  And often people are like, oh, my favorite product is X, but what's behind it is this iceberg of all the things necessary to make it possible to do that thing. And when I describe, you know, how it was possible for us to ship things like Pro Tools in just a few months. It's because we had done all of the groundwork for the year and a half, two years before that, where we could build A B. We had built an A B testing that we had built, you know, the infrastructure. We had, you know, ranking and M L and, and all of these things that we had invested in were coming to fruition for us to build something that we could, you know. And it's not just that infrastructure that stays on for the next feature and the next feature and the next feature. And so I know it's not sexy, but at the same time, actually really thinking hard about.

• 1:02:24Speaker 01

  Is your platform, you know, something that enables or is it hinders? And if it's not something that enables, you really need to rethink the platform first because every other feature is stuck behind that.

• 1:02:36Geoff Nielson?

  I'm just chuckling because the word that came to my mind was platform for what you had built. And that's exactly it. Like it's a platform, you know, in the broader sense of the word. But it makes absolute sense to be able to have that platform that then becomes the the jump off point to, you know, do everything else, the, you know, the part of the iceberg that's that's under the water. I wanted to, I wanted to go back to something you said earlier, though, which is the, the part about mentoring a thousand people, which I think is amazing, by the way. I think it's such an amazing, you know, gift that you've given, that you've, you know, the gift of time and the gift of wisdom and your experience. I'm curious, for the people that you're mentoring,

• 1:03:16Geoff Nielson?

  at that scale, what are the, what are the themes in terms of what people are worried about, what they need help with? And where you find you're able to, you know, create the most leverage or help people the most?

• 1:03:28Speaker 01

  It started when I was leading product recruiting at Facebook and I used to teach a new hire class. And I said, I have an open door policy. You can schedule 15 minutes with me anytime if you need help. And suddenly, you know, and it would be like one or two calls a week, you know, people would stop by my office and, and then, you know, over time, it just built up where, you know, and then I opened it up to everybody. And a lot of people reach out and I do a 15 minute call while I was traveling and, you know, the thing that I I see the most is people need permission. They they come to me with a problem. But I'm like, the reason you're calling me is you want permission for me to say you can leave this job. Or you can, you know, you can basically quit because you have a toxic manager.

• 1:04:10Speaker 01

  Or you're struggling with something. People don't ask a question unless there's something wrong. I see that as a huge theme, which is, you know, often people feel very powerless for a bunch of reasons. And they need someone just to say, I hear you, I see you, and I see that this is a problem. You can leave and you can leave your team and your product. I know how much you love it, but this is not a good situation for you. So that happens a lot. I also get a lot of calls when people are between roles, where they're trying to make a decision, either within the company or exiting the company. And often they'll tell me all these things and then I'll say, well, where do you want to be in five years, 10 years? And they don't know. And I said, well, the problem is unlike college where everyone, you know, is, everyone kind of graduates at the same time. You kind of enter as a major in the same time.

• 1:04:55Speaker 01

  You go to sophomore, something, yeah. You, careers, jobs come along and they're, it's asynchronous, right? And so you don't know. But I'm like, if you don't know where you're going to go, what are you evaluating every job against? Are you just saying, hey, it's better than the current job I have? But instead, really having a thoughtful, you know, three years from now, here's who I want to be. Five years from now, how do I make it there? And is this getting me closer or further away? That happens quite a bit, too. And, you know, often people will say, let me think about it and call you back. And then they say, okay, this is what, this is what I hope to accomplish for the next five years. And then we actually reevaluate. Finally, people ask me specifically about like, should I do X or should I do Y? Usually it's like between jobs or change jobs or change roles or change products.

• 1:05:41Speaker 01

  And usually they tell me, I just said, describe what it would be to stay, describe what it would be to go. And then you can tell from their enthusiasm and what they're trying to sell you, what they actually want to do. 80% of the time, they tell you the answer. And then I'm like, well, why are you calling me? You already know the answer. And so it's been really fascinating to hear, you know, different problems from different people throughout the years. And it's been really gratifying as well.

• 1:06:05Geoff Nielson?

  It, it's funny how, how big a theme that, that sense of permission, or I just need a sounding board. I need some sort of validation that I'm not crazy or that my logic makes sense or what I'm experiencing makes sense. The, the piece you went over in the middle, which was, Where do I want to be in five years? Which is, you know, I have to imagine that is a pretty challenging exercise for a lot of people. And if the answer is CEO, well, I mean, that's kind of like, that makes the exercise a lot easier. And especially if you think that there's a lot of roads to get there. If the answer is not CEO, which is, you know, you've been a CEO. If the answer is not CEO, what are some of the answers that you hear?

• 1:06:48Geoff Nielson?

  I'm curious, just from your perspective and for maybe anyone who's listening and is thinking, well, I don't think I want to be a CEO, but that makes it a lot harder to answer. What are the categories of answers? Or what are some of the more common ways that people structure that as a way to have that North Star?

• 1:07:05Speaker 01

  Well, so some people just say, hey, look, like I, you know, I want to start a company at some point. You know, I want to be a founder. That's pretty clear because if you're going into a very, very large company like Apple as a, you know, as an analyst, like, are you going to get the skill set? Because your, your, your span of control is going to be very small, right? And so, you know, or if your choice is going to, you know, these three different startups, but they're in different spaces. There's other people who say, hey, you know, what I really want to do is I need something. I want to be able to start a family. So in the meantime, what do I do? And so that's a very different thing where some people are like, I want to push hard. But, you know, at that point, I want to have kids. And again, you know, I read the book Lean In.

• 1:07:47Speaker 01

  Cheryl's giving me the Lean In talk when I was debating whether to join Facebook. And, you know, I think it's really important to understand how your life and your work is going to intersect. And I wrote an article about this in order of a lot of the women who've asked me this question, about what is the reality of maternity leave? And then the reality of being a parent and, you know, especially in tech. And, you know, my career stalled out for six years during the time I had my three kids. And you know, eventually it took off, but it's not a given, right? And so I share that very candidly because it's not always going to be easy. Um, there's others who are like, hey, look, I just want to have, I want to work on something I really care about. Like, meaning is really important to me.

• 1:08:29Speaker 01

  So whether it's climate or it's AI or it's something, then I'm like, okay, then chase that. You know, because for some people, it's not the title, it's not the money, it's the, I want to work on something that's like world transformative. And then, you know, but then I'm like, well, why would you take this like, you know, risk management role at a payments company then? If you feel like, you know, are you going to have as much impact than if you, you know, do something directly in the things you care about? And so I think it's one of those things where really having a vision of who you want to be helps filter out all the things you don't want. And it also gives you a sense of whether this is going to add to your bingo card to get to where you want to go.

• 1:09:07Geoff Nielson?

  Hearing, hearing you say, um, you know, with, with a rear view mirror, that your career stalled out for six years. I, I think in some ways, you know, for me and for a lot of people is, is really validating, especially in relation to parenthood. Because I think, you know, there's a lot of people out there who believe, okay, well, I've got kids now. And it's my career is stalled out, therefore it will stay stalled out. Like I've missed the track, like I can't get back on the track. And the, the fact that you're, that, you know, you're, you know, living and breathing proof of like, you know, I, I, I don't want to, I don't want to oversimplify your entire journey, but saying like, who cares? Like you can, things turn out okay, you can still end up somewhere really great.

• 1:09:52Geoff Nielson?

  And that for a lot of people, that may be a worthwhile trade off. Is that something that people talk to you about and that you've, you know, given specific coaching on?

• 1:10:01Speaker 01

  Absolutely. I think after I wrote that article in particular, um, I think it's really, we don't want to talk about it, right? We don't talk about the sacrifice of having families and, you know, it's not always that, it's not always easy. And one of the things that I really You know, write about very openly is because I've gotten to the other side. And I can, you know, talk about some of the challenges. But there's many people for whom during those six years, they just give up. Because during those six years, I tried to quit twice. I was almost one of those statistics, but but but for very specific reasons, I didn't. And, you know, I thank those mentors, you know, every day for for, you know, helping me through that. Because it just feels so frustrating. You are swimming through molasses. I had a baby with colic and two toddlers.

• 1:10:46Speaker 01

  And it was, you know, my dad had stage four cancer. And I was like, what am I doing? You know, and, you know, I. But on the other side, I'm glad that I pushed through. The thing is, people always say like, nobody ever says this out loud. And I'm going to say this out loud to all of your your parents, your parent listeners. Get help, like hire help. Because that is so important. We always pretend we can do it all, right? You can do everything. That's not true. Most of the people who are very successful, and by the way, something like 70 or 80% of men who are in the C suite have a stay at home spouse. And only 20% of the women in the C suite. Why do you think there's only 20% of women in the C suite? Also, is it correlation or causation, right? Because, you know, I have an incredibly supportive husband, but

• 1:11:31Speaker 01

  we, you know, we got help all of those years. And I think a lot of people want to say, well, I did it all myself. And I'm like, no, no, no. The people you see are successful have tons of help, whether from their family, whether from their village, whether they have to hire help. That is so important to success. And I wish people didn't hide it so much. Because it does a disservice, because then people feel like, well, I can't handle this. She got to CEO and she didn't need help. And I'm like, no, no, no, I had a lot of help. And, you know, I had a lot of help from my family. I had a lot of help from my husband. And I hope that we don't write other people out of our stories and make it seem like we did it alone.

• 1:12:07Geoff Nielson?

  I I really, really appreciate you, Deb, not just not just sharing that story, but the the openness that you bring to it. Because I think there's. There's just sort of a stigma out there about a lot of this in general, that if you're going to be successful at work, it means sort of almost like shedding your human side. You need to be an automaton employee. And, you know, how dare I be dealing with, you know, the sickness or death of a loved one or family, the family side of things. And to be able to say, you know, you will go through these things and that's okay. And you can be successful. You know, you can have career success in spite of that.

• 1:12:49Geoff Nielson?

  To me, that's just such a powerful message for people to hear. And I don't know, it's just, it's really resonating with me because that speaks to, it speaks to the world that I think we want to build and the cultures that we want to build. And yeah, I'm sorry if I'm being a bit effusive here, but it's just, it's like a refreshing take, I think, from a lot of the, you know, traditional messaging you hear from senior leaders.

• 1:13:15Speaker 01

  Well, I think sometimes we, it's like, you know, we spend more time at work with our teammates than we do at home with our families. You're at work eight, 10 hours. You know, you're actually spending physical time when you're in the office with them. And that's really, you know, something we don't talk that much about. Recently, I wrote an article called Make Friends at Work, because the friends that I've made from work are the ones who have, you know, I've invested in companies, I buy some of them, they've gotten me jobs, I've gotten them jobs. You know, I've like referred them to boards, they have been references for me. You know, these are people you live your life with, but they also want to know who the real you is. And I hate when people say, oh, you know, we're not, we're not at work to make friends. And I'm like, no, that's true, you're here to work.

• 1:13:57Speaker 01

  But at the same time, you're missing a whole dimension of richness if you're not building friendships and community. And so I do think it's really tragic. It's kind of this like transactional approach to work. You know, the reason I am, the product that most people know me for is Facebook Marketplace. I championed that product for many years. And it is, the product came about because I am a mom. And I was the only mom PM at Facebook for many years. And I helped recruit the next mom PMs. And if you think about it, uh, it, cause I could see a world no one else could see, which was all of the people in my local community buying and selling bikes and strollers and, you know, cribs from each other.

• 1:14:38Speaker 01

  And that was, you know, a world that it was a blind spot for, you know, a company where everybody was twenty something at the time and I had three kids. And so, you know, what makes you special is something you don't have to hide. It's something that could be iconic in the things that make you you.

• 1:14:57Geoff Nielson?

  I, I, I, I love the story. I love the message. I feel like I'm saying that way too much and people are gonna get tired of me, uh, uh, of me saying that, but I think it's a, it's a really, really nice message. Um, ju- just sort of along those lines, and I should start to think about wrapping up at some point, but, um, making friends at work, probably more difficult for an introvert than for an extrovert.

• 1:15:20Speaker 01

  Yes.

• 1:15:20Geoff Nielson?

  Um, and there's that dreaded word that people talk about, which is networking. And, oh, I hate networking and wow, I can't be six, you know, do I really have to network? I, based on the conversation we've been having so far, I have to believe you have a take on this and that there's an angle here that is more useful for introverts than you just have to go out there and network. What, what do you tell, you know, people like you or who may have been like you about building these bridges and these connections?

• 1:15:53Speaker 01

  Well, you know, I was somebody who was, you know, as I said, very introverted, especially at work. And it was really hard, but, you know, one of the things that, um, when I was in, uh, but, cause I went to engineering school. So I grew up in a small town in the deep south. And looking as I do, there were a lot of comments about like, you go back to where you came from. What are you? Those types of things. And so I was like, if I just make myself smaller and less visible, then people will stop saying those things to me. And I, you know, I was already an introvert, so I just got more and more introverted as I went along. Then I went to engineering school at Duke and you, the great thing is you can get through engineering school and never talk to anybody. You know, you can do, you know, I had great, I had friends, but like, we did problem sets in silence in the library, you know, together. That was our social interaction. And, um, and then I went to consulting and I was at Boston Consulting Group.

• 1:16:38Speaker 01

  And I didn't get the highest rating and I've always been like the type A, you know, perfect score, four point O kind of person. And I didn't get the highest rating and I asked the partner, why did I not get the top rating? And he's like, you're kind of bad at this, the client part of client service. And that's what we do. And I was like, what do you mean? He's like, you're supposed to hang out with the client, talk to them, socialize and, you know, get drinks up. And I was just like, why? My work is objectively good.

• 1:17:02Speaker 01

  And that's when you got the first lesson of like book smarts and objectively, you can have great PowerPoints, great strategy. And, you know, even your presentations could be very good. But if you're not actually connecting with the clients, this is a client service relationship business. And I got that all wrong. And I realized this and I went to business school and, you know, business school, by the way, a third or half of your grade is class participation. I was like, oh crap. Um, and one of the things that, uh, David, is I took an organizational behavior class. And at the end, they asked a question, what are you going to change because of what you learned in this class? And I said, I'm going to be an extrovert at work. And it was really hard because I just, at the end of the day, my husband would want to talk because he's a lawyer and he spent all day like working on contracts and by himself in his office. And then he want to talk and I'm like, I'm out of words for the day.

• 1:17:48Speaker 01

  But I realized something, which is people crave connection. And if you say, well, you know, you don't, I'm, I'm, I'm just, I don't know with, you would never go into a meeting and, you know, talk to a friend and say, I'm going to withhold my ideas from you. I'm going to make it hard for you to get to know me. But that's like the ridiculous unintentional ridiculous strategies. My friend Carolize Zaki says, it's like, you know, you go through life doing things. And then if you actually said that was your strategy, you would be like, that's stupid. And it's like, you wouldn't go to work and say, I'm going to withhold all my good ideas because I don't like talking. I'm not going to make friends here because I don't like people. You know, I'm going to make them work really hard to get to know me because, you know, I'm an introvert. That's a dumb idea, but yet we do that because that's where our comfort level is.

• 1:18:32Speaker 01

  So instead I looked at it from the other perspective, which is how do I make other people comfortable? Yes, I'm uncomfortable, but how do I look at it from their perspective? And suddenly that really changed the way I learned to show up. And I think that matters a lot, which is, you know, how do you want to be who you are and have people be a part of your life? And, you know, when we say networking, I think it seems so like clinical, right? It's so transactional. But what if I just said you're going to just like connect with some people and get to know some interesting people? Suddenly, it's like less foreboding, right? It's not, I have this transaction, I need to get your LinkedIn connected, your phone number. Instead, it's what if I just spend the evening getting to know some interesting people? And so, you know, I just invited my coworkers to my house.

• 1:19:17Speaker 01

  These are, I worked with these people 20 years ago PayPal. And they came to my house and had dinner and reconnected. And, you know, I've been friends with most of them through that whole time. And it's because I learned to do that before I got to PayPal in business school that I was able to make those friendships. And they became people who I had a chance to work with again, and I've had the chance to get jobs with again and, you know, live life with.

• 1:19:41Geoff Nielson?

  That's, that's awesome. And I, I think is, you know, in some ways, exactly what I expected to hear in terms of the, you know, just kind of destroying the myth of networking as being this cold clinical thing. But it, it, it's such a cool story. Deb, we've covered, we've covered a lot of ground here. And, you know, I've, I've been very thankful for so many of the insights that you've shared. You know, for, for business leaders in particular, for people who are trying to get their career to the next level or take their organization to the, the next level. You know, do you have any parting words of guidance that you would, you know, want to share with them as they think about, you know, how they, how they do something better tomorrow than today?

• 1:20:22Speaker 01

  Well, I think the first in an age of AI, always be learning. Adaptability is going to be the most important skill over the next 10 years that it hasn't necessarily been in the last 10 years. You know, if you think about careers, often we like, everyone is like focusing on expertise. You get better and better and better. And now it's how do you assimilate new information? How do you learn? How do you adapt? And so that skill set is going to be valued more than anything else. And I encourage you to try new things, you know, take a vibe putting class, learn what's possible with AI, build something. You'll talk to people, network, as you say, with people who are the cutting edge because you'll see the world of possibilities of bringing this tool into what you do every day and thus making your role in the company more, more important.

• 1:21:07Speaker 01

  But also that you're able to actually bring it to your company so that it will be more successful in the long term. And, you know, in turn, you're able to help others get there.

• 1:21:17Geoff Nielson?

  That's great. I really, really feel that that resonates with me and I really appreciate that advice. Deb, I wanted to say such a big thank you for coming on to the program today. I've really, really appreciated the conversation and not just your insights, but your candor and your openness in challenging some of the stigmas that we find, not just with AI, but with interpersonal relationships, with what it means to be a person at work and how anybody can be successful. So I wanted to say a really big thank you for that.

• 1:21:47Speaker 01

  Thank you. Thanks for inviting me.

• 1:21:51Geoff Nielson?

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