# A Masterclass in Leadership and Scaling Companies: The Decisions only the CEO Can Make

The Secret To Talent Acquisition and Retention and How To Find The Unscalable Things that are Fundamental To Scale with Christa Quarles, CEO @ Corel Corporation

20VC · Jul 29, 2021 · 46 min · 9,674 words
Speakers: Harry Stebbings, Christa Quarles
Source: https://www.996.fm/episodes/20vc--ep-f133f3d2/

## Cold open

**Harry Stebbings** [0:00]:

Welcome back. This is 20 VC

## Intro

**Harry Stebbings** [0:01]:

with me, Harry Stebbings. Today, we're joined by one of the best operators in the Valley today in my mind. So diving straight in, I'm so thrilled to welcome Christa Quarles, CEO at Corel Corporation, building software solutions that simplify the task journey for knowledge workers. Prior to Corel, Christa spent close to four years as CEO at Opendoor, driving a chapter of transformational change for the company. Before Christa was Chief Business Officer at Nextdoor. And finally, pre Nextdoor, Christa spent close to four years at The Walt Disney Company, where she led Disney Interactive to profitability as Senior Vice President of Interactive Games. If that wasn't enough, Christa is also on the board of Affirm and Kimberly Clark today. I'd also want to say huge thank you to Jeremy Liu at Lightspeed, both for the intro and for some amazing questions, suggestions today. But before we dive into the show state,

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## Conversation

**Harry Stebbings** [2:22]:

Christa, it is such a joy to have you on the show today. I've been so looking forward to this one. I heard so much from Jeremy and from Max before the show, but thank you so much for joining me today.

**Christa Quarles** [2:29]:

I'm so excited to be here and congrats on six years of this and two VC funds later. So it's awesome to be on the show.

**Harry Stebbings** [2:37]:

It is very, very kind of you. I'm still scratching my head wondering how it actually worked, but I'm thrilled that it did. I do have you ask, and I love context. So like, what was your entry point into the world of tech? We look at this glittering career that you've had. What was the entry point?

**Christa Quarles** [2:49]:

I mean, honestly, it was being on the sidelines in Silicon Valley. You know, I come out after business school. It was right around the year 2000, so dotcom one point zero. And all of my friends were getting written up in the New York Times out of Harvard, they were starting these startups. I grew up in Western Pennsylvania. I didn't know My dad worked at a steel company. My mom was a teacher. I just didn't have the exposure to it. And so I had to go out West, and I was like, Well, I'm going to at least just watch the tech companies. So I went to an investment bank where we were taking growth companies public, and it was from that vantage point that it built my pattern recognition. Because we had separated research and banking, and so I was going out and meeting with company after company after company and figuring out which of these is going to go IPO one day? How do I determine this? And a lot of it was just starting to understand business models, leadership profiles, which company was going to make it. Was really the entry point, was just this high sample, really. Sometimes you go to a company, you see that single company. Here, I looked at hundreds of companies. I don't know if it had gotten into the thousands, but certainly many, many companies would meet with CEOs every single day, and it was my job to figure out winners and losers. And I think that was the interesting part. I think where veered off was like, I was super tired of just sitting on the sidelines, armchair quarterbacking, as we say in America. And I was like, I want to go play the game. And so the only way to do it here is to just go to a startup. And so I went to a small gaming company called Playdom, and we were second to Zynga and we were really launching this whole games as a service concept. So we had cloud, we had social, we had new business model. We had everything that you could possibly figure out as new. And that was really the entry point. I dove in, I gave away a giant bonus that I was going to get in my old banking world to go join this company because I was like, Screw it, I'm just going go. And I didn't get paid my bonus That year I left in December and I was going to get paid it three months later, which could have been stupid. But I dived in and went into startup life.

**Harry Stebbings** [4:53]:

I mean, absolutely love that. And I think it's more than paid off. So I think you can forget that bonus. So please. There are a couple of elements that when I was going through your journey that were just too special that I couldn't not dive on honestly. One was Walt Disney, one of the most foundational companies definitely of the last 50. So I have to ask, when you look back at your time there, how did your close to four years there impact how you think about leadership and management today?

**Christa Quarles** [5:18]:

You know, Disney really was foundational, as you say. I mean, first of all, I got up close with Bob Iger and anybody who has the chance or opportunity to learn from him. He's written a great book. Think I it's called What a Ride. But he had this incredible ability to one day conduct high end diplomacy for Disneyland Shanghai, and then the next day debate the finer points of The Sims with me. I was like, How is this possible? How can he go from here to there? And so this ability to kind of deep dive on a topic and come back up and just the breadth of awareness, context setting skillset that that takes. I also carry with me just some funny things. In the Zoom world, Disney paid attention to your executive hygiene. And so did you start a meeting on time? Did you end a meeting on time? How did you conduct the meeting? And so there was a little bit of pomp in there, but I think the craft of leadership was considered. And so I think that's where I got a lot of the early lessons about how to think through. And I would say my time at Disney was during a really transitional and transformational point in its history. It had been this tech leader, honestly, when you think about the early days animation. And then modern media had sort of lost its way, and Netflix was coming around, and they had to reimagine what the future was like. And so when we sold Platoon into Disney, a lot of that was, Hey, consumers are spending different amounts of time with different types of media. We got to understand this. And I think that was Bob who leaned in, maybe it was because he was on the board of Apple, really was about this transition into how the modern consumer is going to spend their media time in this tech transformation and understanding technology. And if you think about it, it's not too dissimilar from the transition a lot of retail companies have made to go direct to consumer. If you think about Disney, Disney was not really direct to consumer. It was direct to a cable company, but it didn't really think about the end user and what did the end user really want to do. And so this idea that like, Oh, I'm going to put something out there. The end user's going to respond, and I'm going to change by virtue of that feedback, these real time feedback loops. We were in direct observation with Disney as they were transitioning business models, and that was just a really exciting time to be at the company. Oh, and we bought Lucas while I was there, so that was cool to hang out at Skywalker Ranch a few times.

**Harry Stebbings** [7:31]:

Pretty pivotal times. I'm going to just ask one thing, though, which is you said about the craft of leadership there. When you blend the different experiences that you've had from the investment banking, Disney, OpenTable, now obviously with Corel, it's so broad, it's terrible, awful interview question. But what does the craft of leadership mean to you today then, blending these different disciplines and experiences?

**Christa Quarles** [7:51]:

I think what's embedded in that is scale. What's fascinating, or what I felt fascinating about Disney, was it was just huge. It would swell to over 100,000 employees during park high season time. The anthropological concept of how do you move that many people around was really just fascinating to me. I think that was very interesting just because of the sheer volume of what it takes. But it also means I think all big companies are somewhat alike, though, because in order to move that many people around, the system, the process, and that's why startups can often win because the big company gets stuck in this whole largesse of moving around. I would say investment banking is a totally different thing. It's like actually entrepreneurial pods of cowboys, or at least that's the way it was when I was there, and you kind of like gun slung and did your thing to try and make money really quickly. I would say investment banking was not the finest leadership experience that I witnessed, but sometimes I think your best examples come from the worst experiences. I could not bring my whole self to work when I worked in investment banking. I muted every part of me. In fact, I joke sometimes like I became a dude because I showed up, I swore, I did what it took to be successful in that environment. And then I think you get to the smaller company, I'd say, Opendoor was about 700 people when I joined, Corel was about seven fifty people. So it's enough that I can know a lot of the employee base, and every change that you make has a big, big, big, big impact. And so I think it gets back into how you have to modulate yourself depending on the scale of the organization and frankly, the ambition that sits underneath it.

**Harry Stebbings** [9:32]:

When you think about kind of the scales that you said, that you said 700, seven fifty, and when you think about the next scale, you as the leader have to scale with every evolution of the company. How do you think about that? How do you advise also founders? I get so many founders say, I don't know if I can do it. I've never done it before. How do you think about yourself scaling and what you advise founders in terms of scaling with the company?

**Christa Quarles** [9:53]:

Yeah, it's a really interesting problem. And I've spent a lot of time thinking about it because I've been at such wildly diverse and scout companies, and what I've observed is this kind of exponential path of breakage. Companies tend to break at 50 people because it's like, you used to be able to just get everybody in the room and shout at them or put them in a Slack channel and tell them what to do, and you knew every single person and you could direct everything that they did. And then the next breakpoint is about 150 people, but curiously also Dunbar's number, so you can only hold that number of relationships in your head. And that's, I would say, the biggest breakpoint that I see most companies hit. This was exactly what happened to me at Plato. We hit 150 in all the software that's helped companies grow, but we didn't have an HRIS, so it was in somebody's spreadsheet on Excel, or we had never written a policy about anything. And so all of a sudden you have these people and you're like, Oh my God, how do you communicate to them? How do you get them aware? So 150 is a breakpoint. I see 500, 2,000, 10,000. So it's this exponential curve because essentially what happens is when you get more people, the decision trees kind of fan out and how you used to make decisions needs to change. And if the organization doesn't change with the size of it, you get stuck or mired or worse, get broken because you keep wanting to do it the way you did when you were at 50 people and you realize my message just isn't getting out. I'm not able to drive people and I'm not really inculcating a culture where people feel empowered and enabled to go forth because let me tell you, when you're at certainly 10,000 people, you can't dictate every decision. You can't drive every outcome. And so you have to build a culture, back to that Dunbar's number concept. And so culture is how people make decisions when you're not in the room. And increasingly, you're not in more rooms as the company gets bigger, and you have to really adjust and figure out how that transition is going to go.

**Harry Stebbings** [11:43]:

How do you handle what I think is the most challenging element, which is when you're not in the room and the decision is being made, how do you ensure that they're as ambitious as they should be and not go for the safe option because they don't want to get fired if it doesn't go right? How do you inspire people to be their best and not worry about downside?

**Christa Quarles** [11:59]:

Yeah, and I will say I hit that head on when I was at Opendoor. Because if you look at the history of Opendoor, it just worked. And it's not fair to just say that, but it is the power of a network effect two sided marketplace business. Essentially, we had supply, we had demand, was a scaled two sided marketplace. And the beauty of those is they do just sort of work. However, it works until it doesn't, meaning if you don't evolve the product, if you don't step into the future, eventually you will get overtaken. And so when I got into the company, we were at a point at which the software that we had inside the restaurant was an old Microsoft on prem distributed database, like not in the cloud situation, and we needed to move into the cloud and we needed to move fast and we needed to take advantage of all that that would have to offer. But you have now this company where everything just sort of worked. And so there's this like learned helplessness of like, well, if I do something, it works. If I don't do something, it works. So I'm just maybe not going to do as much, or I'm afraid to do as much. And so I did kind of hit my head against the wall, I would say for like the first year, because I was like, why can't they just, why are they ambitious? Why aren't they trying? Why aren't they going? I had hired a chief people officer and he said, well, you know, he's like, can I give you some feedback? And I was like, all right, yeah, I love feedback. And he said, you know, five of your company values are essentially move faster. It was like progress over perfection. Find the testable hypotheses. Like, I was just like, get moving! And what I realized that the only lever I had as the CEO was, What do I reward and what do I not reward? And I think what's interesting is that I had to make it unsafe not to take risk. And so if you were just going to sit in your little box and kind of like do your thing, that was going to be a risky position now. Whereas the other people who were leaning forward and trying new things, and I would evidence, frankly, grand failure in the company. I would say, Look, now obviously you don't want to have company ending failure, and hopefully you put guardrails up to evolve that, but just giving people the understanding that those people are the ones that are going to get promoted. Those are the people who are going to make go ahead. Those are the people who are getting spotlighted in the quarterly town hall or the monthly ask me anythings. And so that was the thing that I had to learn, and I learned it kind of the hard way because it wasn't intuitive to me that it was just as simple as that. Like, what are you rewarding in this organization and what reward will drive your outcome?

**Harry Stebbings** [14:19]:

How did you imbue that to the organization? Was it by someone taking a big risk and you very publicly promoting them, moving them swiftly up the hierarchy to show that you could ascend with risk? Like, How do you go from what do I reward, what do I not reward to people going, wow, that's what can happen?

**Christa Quarles** [14:36]:

Sometimes it's like as simple as just, hey, you're going to get like 10 more engineers. It's about resourcing. It's about saying, these guys are crushing it over here. Let's expand their remit. They're going to try more things. And I think to be clear, there was a point in time where we wanted to understand at OpenTable just the power of how deep the network effect could go. And so we picked a street in Palo Alto, and I said, Give it all away for free. I said, I don't care. Don't charge anything. I just want to see if we can get 100% of the restaurants on the street. And what was interesting was they came back and we literally couldn't give the product away in that instance because the restaurant would be like, Well, I'm not an OpenTable restaurant. I'm this kind of restaurant. And I was like, Okay. And so the teams that were driving that, it wasn't just me directing, obviously, but it was the team. It was a spectacular failure, but it taught us so much that, Oh my God, we're solving the wrong problem. We're solving the different problem. And I think it was just a good lesson. That team ended up, because they moved so quickly, they got to the answer so quickly, we kept evolving and iterating, and then they got more teams, then eventually their roles became bigger, and then they got promoted. And so the whole ecosystem around that swift, thoughtful risk, point of view risk, decision making, they were just much bigger and more important drivers of our overall company and organization.

**Harry Stebbings** [15:55]:

It is absolutely conversations like this, which is why I love this so much, not touching the schedule. But I'm so sorry, you said that about like, give this straight away for free. When you have a new initiative, a new plan like that, how long do you give it as a test? Like how long is enough enough before you go, cut it, guys, this is not working, all girls?

**Christa Quarles** [16:13]:

Yeah, I think it is the most important question. First of all, I always ask, what is the unscalable thing we need to do to get to scale? And so you do a lot of unscalable things. And so at some point you just start being stupid, right? You keep turning the crank and you're And I think that's what's embedded in that is this fight for product market fit. And I think when you're in a bigger company, you have product market fit over here, but if you're not looking at the adjacencies and trying to understand the tangential product market fit, if you will And I think it is an iterative process, and I think it gets back to point of view. It's like, how strong is your hypothesis? How much do you believe that this product does in fact need to exist, and therefore it's just one more tweak? And so it's really an element of, and I'm a big believer in data, right? I would trust all else bring data. It was my time at Playdoom where we were more of a data company truly than a gaming company, I would say. But there are times where your belief in what that end product state needs to be, and your belief in what that customer experience needs and could be, is what I think often propels, and you see entrepreneurs do this all the time where they're like, Add it and add it and add it. There are also externalities, I guess. Like sometimes market conditions are just not ready for the thing that you want to build, right? So we had an example of this at Opendoor where we wanted to get rid of the whole, Put your check and the whole back and forth and the dance. We had it going, but the point of sale infrastructure was not where it needed to be in order for that to ultimately be successful. And so we were just early. Had that launch now, it would be wildly successful because you see food delivery businesses and other things like that have changed the paradigm of what point of sale looks like in a restaurant, but we were just early. And so that's the other thing that Matt paid attention to is like, are there externalities that prohibit your vision from coming to reality that you don't control? And if you don't control enough of the externalities and they're not where they need to be, you could just be too early on this grand vision, I'll call it. And sometimes when you're too early, you're wrong.

**Harry Stebbings** [18:11]:

I totally agree with you in terms of the importance of market timing. A mentor told me the other day, Harry, where you're going to get undone is you have to understand the corners you can cut versus the corners you can't cut. It's a good point, and I thought about it pretty constantly through the last few days. How do you think about that question, especially in leadership and how you do things and new initiatives today?

**Christa Quarles** [18:32]:

I am a corner cutter by nature, I'd say. In fact, I've surrounded myself with iDaughters and TCrossers so that they keep me safe sometimes. I I think a lot of leadership too is just self awareness. Like, what is my temperament? What do I like to do? And I am thousand miles an hour, and I'm hopping, I'll dive into product, then I'll go into our infrastructure technology, then I'll go into marketing, and then I'll be over here in finance. And so I'm everywhere. And by definition of that, I don't know if I'm fully jack of all trades, master of none, but I'm hopefully a master of a few of them, but I know that I want people around me who are going to be obsessed about the detail. And so I think it's about finding that complementary skillset for yourself such that you can decide, okay, these are details that maybe I can't cause. And they're going to come up to you and say, Hey, time out. We got to really focus on this because if you don't fix this, this is going to be a problem. And I love people who do that because I can kind of get moving and somebody who pushes me and says, You got to pay attention here, and it's going to be real. And I think one of my favorite reference questions to ask is, Who would make a great number two for this person? And what that reference question is getting at is, of course, it's sort of quote unquote weakness, but nobody can spike along every dimension. Nobody can be amazing at every single thing that they do. They have to have an understanding of who's a great compliment for this person? Who's going do the thing that this person may not do? So I find people around me who are going to not cut corners and then tell them that they can tell me to stop.

**Harry Stebbings** [20:06]:

My personal favorite, the trouble is I work too hard. You're like, Yeah, I love that one. Brilliant. I totally love that. Can I ask you mentioned being a thousand miles an hour kind of all the time? I love that and I feel it bluntly when I interview you is why it's such a great interview. Do you ever sit back and appreciate what you've done, what you've achieved, if it was a great quarter? Do you take the time to be like, actually, we did well. I'm gonna enjoy this moment.

**Christa Quarles** [20:29]:

I've actually had to learn to do that because naturally, you know, my time equals zero is always like three months before it hits everybody else. So I have to recognize, like, they're just seeing this for the first time. You've already been processing it. So now we just did our quarterly town hall this morning, and we had great results, really, truly fantastic. And now I'm thinking, did I really stop? And I feel like I did, but I think it's important to acknowledge and to celebrate the wins along the way. I have become an AI yoga student, and I think the act of forcing myself to slow down, to take monkey mind, like when you're standing on your head, you really do have to just focus about what you're doing right in that moment. And I found it so therapeutic because people who are like, I'm constantly, I'm moving a lot, and they just literally invert, and it's a sign and signal to my body, down, take a minute. And it's in those moments that I think you have this element of refresh and creativity kind of well that you refill because you got to go at it the next day. I mean, operating is a full body contact sport, I like to say. And so you're in it and on it all the time, and so you better take care of yourself in order to be able to give back to that organization. And so that idea of take a minute, invert, slow down, figure out what's important, and then usually by the time I become right again, I know where I am, what I need to be doing.

**Harry Stebbings** [21:51]:

Can I ask a weird one? My hip is not too personal, how do you rebuild? As you said, it is a full body contact sport. It's brutal sometimes, and you just get beaten, and you're just like, I'm done. How do you rebuild when that happens?

**Christa Quarles** [22:04]:

It's a good question. I played sports in high school and college, and I think the act of losing and getting back up, like falling down and just that simple process of falling down, like, I'm down. Oh, no, that hurt. I'm down. But you've gotten up so many times. You just know, like it's just part of the process. Like you build it into the muscle memory almost where, you know, just like, This is what it feels like. Okay, I'm down. All right, here we go. Let's go get The only time that really didn't work for me was I was in a situation where I felt like I had never not been able to make it work in my life. I've always been malleable enough that, like I said, I showed up on Wall Street like, You want me to be a swearing dude? That's who I am. I'm showing up. And so I've always just modulated my behavior for environment that I was in until I got into a situation where I couldn't. And I will tell you that I got stuck for a period of time because I'd always been able to figure it out. And so what I realized was that I had to rewrite my own narrative. And I think for me, was, you can always make it work, dot, dot, dot, with good people, but if there's really bad people involved or what, you're not necessarily going to make it work. And so for me, basically prevented myself from the full fall. I kind of got stuck. And I think that's the most dangerous place for anybody to be, is the stuck state. Falling? Fine. All right. I know what I'm dealing with. You know, ugly truth? Fine. Bring it on. Let's go. Now I know what to do. It's that moment before you let yourself fall that I think is most dangerous because you're just, you're holding on. And I think when you hold on, you're not your best, you're not contributing, you're just holding on. And so I think allowing the fall, which I wasn't really wanting to do, because I success oriented, I was like, I'm at 60, I'll figure it out. But I think what you have to tell yourself too is what's on the other side is always better. And it's sometimes orders of magnitude better, and I think that fear of what could be on the other side without knowing, it's like a trapeze. It's like you have to let go to kind of catch the next one. And then there's this moment where you're like in flight. And it's scary, but I think it's the piece that I've learned. You've got to just let it go and kind of move to the next side.

**Harry Stebbings** [24:16]:

Gosh, you should be an inspirational speaker. I feel like so pumped after hearing that it was going be better on the next side. This is fantastic. Can I ask, what does being stuck look like? For people to think like, am I stuck? Is it like lack of passion and being dampened? What is stuck?

**Christa Quarles** [24:32]:

You know, for me anyway, it was showing up, I was like, kind of afraid to go in the office, but I was fearful. Like I didn't know the environment that I was in, it was uncertain. I didn't know if I was going to lose my job the next day. I didn't know if I was I think I lost the truth of myself. I didn't feel like myself. I didn't feel like the best version of myself. I didn't feel like coming in every day like, Yeah, we're going to crush it today. I felt smaller, and I felt I wasn't showing up with all of my lights lit almost. I just was like, I'm going to just come in and do my best and hope to not piss somebody off. And inevitably, because of operating at like 60% capacity, right? Like essentially what was happening, my prefrontal cortex had shut down, and I was like in the lizard brain, my amygdala back here, and we all know you lose like forty, fifty IQ points when you do that. So I was literally dumber and a worse worker, right? Like when you show up to work that way. And I think that's why I'm so obsessed about creating very inclusive environments because you're just 10 times the worker if you can show up and do the job versus worrying about like, Oh Oh my God, is my boss going yell at me today? Oh my God. I think Google has studied this where the number one factor in high performing teams is psychological safety. And so if people show up and they feel safe, then you can do your best work. And I think the thing that people forget is play is an important part of creativity, innovation. And if you kind of create this thing where it's all locked down, it's just you're not going to get the outcome you want. And so that for me was how it showed up. I was just a smaller, less happy, less bright version, not even of myself, and I felt unsafe, and I do think that my prefrontal cortex shut down. And I think I was dumber, honestly. I think I had lost the 50 IQ points because it had all shut down because I just didn't like the environment I was going into every single day.

**Harry Stebbings** [26:23]:

I think one the most important jobs of a leader is to create an environment of safety where everyone can feel like they bring their best selves to us. So I agree. I think people are such a large part of that, though. And I do wanna talk about a tweet that was sent out by Jeremy Liu, and it quoted you, and it was one of my favorite tweets. And it was a CEO has 50 spinning plates at a time, and her job is to decide which 10 to keep spinning and which 40 to let drop. Exacts are either plate adders or plate removers. Plate adders have to go. So love that one. It's practically on my wall. But if we think about fundamentally, when we look at plate removers, we want them in our team. When you think back to the best in your career, what are the clearest signs someone is a plate remover?

**Christa Quarles** [27:02]:

Well, first of all, I tried in my early career to be the plate remover. And so it comes from like, you know, I wasn't always the CEO. I wasn't always the one in charge. I mean, I literally forgot this story, but like, it goes literally back to my earliest earliest days, where I literally would remove the physical plates. I was a bus girl. I remember one of my first jobs and my job was not to remove the plates that people had finished eating on, but I was like, Oh, that needs to go. I need to get back to the kitchen and I need to run. And so there was a job that needed to be done. I saw what needed to be done And I was leaning in and figuring out where it needed to go. And I just went and did things. And so I would tell my boss, was, Hey, I thought about this and I realized that you need to be doing this, so I'm going to go take care of this and I solved this. And they would be like, Great. You know, it was almost like, Oh my God, you thought about that and then you took care of it? And it's not like you were going rogue or doing something crazy. It was these things are not obvious. But it was also not adding drama into a situation either, where you just felt like, God, you could mix it up in there. So I started out by being, I think, a plate remover myself. I think when I look at executives, it is that person. I think about my CRO at Corel right now. She's just like, Yeah, I thought about where this is gonna go, and I'm gonna pull this, and I'm gonna do this, and don't worry about this because I got it, and I'm gonna solve it. And so I was like, Great. And within ten minutes of her starting, I put customer support into her division. So she's Chief Revenue Officer, but I pulled customer support in, and I was like, I know you'll figure it out. And she was like, All right, we got this. And I think she just is leaning in, understand what the organization needs, and she's just going to deliver on where I need her to go. The other critical thing is understanding which decisions only you can make as the CEO. Many other decisions can be delegated. Many other decisions can move down the ranks. There's certain decisions that only you can make. And one of the reasons why this is important is if I'm getting distracted from the decisions that only I can make, the organization's just not going to propel itself forward because it's almost like the choke point is my ability to make those decisions. And if I'm busy over here dealing with drama that somehow somebody else could have else handled, then we are now limited by my bandwidth and my capacity, and that's the thing that's going hold the organization back.

**Harry Stebbings** [29:21]:

You teed me up so nicely there. What are the decisions that only a CEO can make?

**Christa Quarles** [29:27]:

I'll give examples. I mean, now, we're looking at our brand. If you think about, so we've got a lot of different software brands underneath Corel. So we've got Parallels, so like running Windows on a Mac or our remote application. We've got all these sub brands. I've got WinZip. And so this idea of what do we call ourselves? What is the narrative of our organization? I don't think anybody else in the organization can do that work. I have to craft the mission of where we are, the purpose of why we are here, how we call ourselves. Now I can have help on writing the elements of it, but it's really my decision to guide that next three, four, five, six, ten years of this company. And how do I go do that? It's crafting where the narrative comes. The other key things that only a CEO can do is put the CEO team in place too. When I left OpenTable and I was looking at president jobs, I was like, Well, it's just a two variable equation. I have to like the people and the company, whereas here I just had to like the company because I've got to put the team in place to go make that company successful. And so I think it's really about getting the right people in the organization to lead and drive. And the third thing, so like, would say brand mission, kind of purpose of the company, the people of the company. And then really the third thing would really be, you know, kind of how we interface with our board. How are we driving forward that conversation? You know, I can't put my, you know, Chief People Officer in that role. I have to do that role. That is my position. It's our fiduciary duty to communicate and drive and make sure that the board is feeling satisfied that we are on the right path. And if I'm focused over here on, I don't know, HR issue number 72, I'm just distracted and I'm not going to be putting my time and energy in where it best would land. It's funny because before I became a CEO, I'd hear all these CEOs going, Gosh, I just need time to think. I was like, Who are these people? Who needs That seems such a dilettante ish kind of response to the role. And then I got to be a CEO and I was like, Gosh, I just need time to think. I think it's because of this, you get weighed down by all of these potentially unnecessary, not game changing, not company ending, not company making decisions. And you are not spending your time on the things that are like Right now, we have a key tech decision to be making on our Parallels business. I need to go make that. We need to go drive that. And that needs to be my priority, not whether or not how we insource or outsource our customer support. Like my CRO, she can actually manage and drive that decision. And I think that's important one.

**Harry Stebbings** [32:01]:

You said about the CEO team that I have to dig in on that. The hardest one for me, and I'm asking the easiest of questions today, my word. But it's like, how do you know when a stretch exec or a stretch VP, is a stretch too far? And how long do you give them?

**Christa Quarles** [32:14]:

It is the really hard question because I think, you know, I'm a big believer in driving the personality, but I also think if I wasn't a CEO, I would either be hopefully a stand up comedian on my good days, but I would be a psychologist. Understand what are you really good at doing? You know, what do you love to do? What does the company need you to do? And oftentimes where this all gets out of balance is I'm asking somebody to do something they either aren't very good at, and we're all spiky in different dimensions, so understanding where is this person really awesome, where are they maybe not? Or they like, they hate doing the thing, or they're just not into it. And their attitude is like, I don't want to do this thing. In fact, we promoted a guy the other day, and one of the questions I asked the manager, I said, How ambitious is he? And he was like, Oh, he's very ambitious. I was like, Great. I was like, Because his desire to do these things is going to be higher. He's going to want to lean in. He's going to want to try these things. And so I think you have to kind of ask those questions and say, Are all those pieces in alignment? Because it could be that what you're And this is, by the way, this evidences a lot in these scale problems. So the person who is amazing from zero to 50 often can't take the next leap. Some people can. Some people are purple unicorns and they can ride the ride. Like an early salesperson would be a great example where that first wave through, they're like the lone wolf. They're figuring out how to sell. They're figuring out what the words are. And then once they figure it out and you get into like lather, rinse, repeat, they either get bored or they're just not that organized because they're super creative people. And so they're just not going to be able to make that leap. So they're like, okay, could we put them on another mission? Could we put them over in this other thing where we can take advantage of this incredible ability they have? Because if it just gets into lather, rinse, repeat, they might put a bullet in their heads. They just don't want to do it. And I think that's the key thing is like, you're always looking across the organization and trying to find out where people are out of alignment. And so it does take time to figure that out though. And I think I spent a lot of time asking an executive, When do your eyes light up when you talk about your job? And there's these moments where you can just see that part of their job just brings them immense amount of joy. And I was like, Okay, we're going to find you an opportunity to do that. And if we can do that, then this is going to be good. Now, it may not be what we need you to do. So like I both said, was like, if you're an apple and I need an orange, I can't make you become an orange. I can make you a juicier apple, that's great, but I can't actually make you be an orange. And so it's not personal. And so the kind thing is to say, Hey, let's go find you a job where everybody needs, like, they need an apple desperately, and I'm going crush it with you, and let's go do that. Let's go figure that out. That's the part where you, as an executive, can waste vast amount of emotional energy trying to convert somebody to being something that they're actually not. Now, this is more of a comment about people later on in their career. If you're like 22, people can become anything.

**Harry Stebbings** [35:10]:

The final element I do want to touch on before the quickfire is you mentioned the third element of only CEOs can make that decision being board engagement, board interaction. You have this incredible purview, obviously, running the board that you do today, but then also sitting on Kimberly Clark, Affirm, among others you have done before. So a question that I have is, how has sitting on other boards, as you have done, impacted how you think about great leadership of your own board today? Everything.

**Christa Quarles** [35:35]:

I will say, so the very first board meeting I ever attended, I came back and my next presentation to my own board changed radically. I realized these people show up five times a year, or maybe more often in some VC board, that they just simply don't have the context. In fact, somebody gave me this advice early on. They said, Don't underestimate how little your board retains. And I was like, Oh my God. Right? So you realize they're coming in, they're having to reshift their own context. They're having to understand the problem that's in front of them. I was way, not too in the weeds, but I presumed too much context that the board had. And what I really needed was the board to give, I like to say, the provocation. You're there to stimulate thought and idea around something by virtue of my diverse set of experiences. I'm going to stimulate that with the team around me and say, Oh, have you thought about this? Have you thought about that? So I both have radically changed how I present to my board and how I communicate. And then I understand sort of the limitations between what it means to be on a board and what it means to be an operator. And you don't want those lines to cross because then it gets not as effective.

**Harry Stebbings** [36:49]:

Okay, given the limits of their knowledge retention, how does that change how you engage with them and extract the most value from them? Is it coming with very strategic direct questions? How does it change?

**Christa Quarles** [36:59]:

Yeah, I think the key thing is, so a board's gonna ask, say they ask 10 things, but they don't have data on all those things. And so my job is to go back to the board and say, Look, I've looked at each of these questions you've asked. I prioritize them relative to their impact on the business. And these four things you guys were asking about, honestly, like these are 1% movers, so they're not really gonna change. So it's really about assessing magnitude of how big could that idea be inside my organization. There's no way the board's gonna know or be able to size those opportunities. So it's my job to go, Hey, we've sized these, we've now prioritized them. And these two things we talked about, I think are critical and foundational for the center and future of our company. These eight things, honestly, they're gonna be a distraction. And usually the board's like, Great! I mean, every now and then you get a board member who has a pet peeve about something, and that's an interesting one to handle. And maybe I've been that to other people, I hope I haven't, but I like to hope that I'm just trying to understand better, but that can happen occasionally where that line does get blurred.

**Harry Stebbings** [38:04]:

How do you handle that? Because every founder, I'm sure, has a VC mostly with a pet peeve and they just keep on drilling. What is the right way to approach In

**Christa Quarles** [38:13]:

my view, like, you feel like it is just not the right path, it's just to bring them in and say like, all right, let's go deep. Let's spend an hour on this. You and me, let's just go deep and let's understand. We might also just be talking past each other. Cause on the one hand, I'm a big believer in there's usually a kernel of truth, even if I disagree with 90%, like I'm staunch disagreement with you on 99%. There's like that 1% that I have to say, how can that be true? I just try to flip it and say, Even if I don't want to do it and I don't think it, how could it be true? And then I usually do a curiosity session where we just like, Let's go deep, let's understand, and maybe I'm missing something. I think being defensive and saying, I know it all, how dare you? That's obviously not going to be great. And it's certainly not a place of curiosity either. Like, I think you want to lean in and be like, let me understand this better. Like, why are you obsessed about it? Give me your data. Maybe they have data you've not seen around a market externality that's really important back to the prior part of the conversation. So I think all of that's really important to lean in with curiosity and then to not let it repeat, though. I think that it's kind of like a stuck state, back to that other part, is if you just let them keep asking every meeting and you just don't hit it on the head, you're are going to be frustrated, they are going to be frustrated. I would just say, don't let it continue if it is continuing. Just take some time and knock it down.

**Harry Stebbings** [39:32]:

I do want to move into my favorite though, which is a quick fire answer. I say a short statement and then you give me your immediate thoughts. Does that sound okay? That sounds great. Okay, so what's the favorite book and why?

**Christa Quarles** [39:42]:

I love so many books. The one that I read that I was really just eye opened was Caste by Isabel Wilkerson. And it reflects essentially race relations in America, but also India and other parts of the world. They go through Nazi Germany. And to me, I look at caste as just a great limiter of humanity. Think it's like we are not taking advantage of every human being's right to contribute. I just opened my eyes on so much structural sclerotic, frankly, ways that we do things. I think about it in the microcosm of my own company, and it's like, how are we limiting our ability to kind of lean in? So for me, it was just this really eye opening and groundbreaking from that dimension, and I think everybody should read it.

**Harry Stebbings** [40:29]:

What do you know now that you wish you'd known at the start of your career in tech?

**Christa Quarles** [40:33]:

It's all going be okay. Chill out a little. I think I was so amped and eager and ambitious, and I wanted the outcomes. Sometimes didn't slow down and stop and celebrate enough along the way, and I think I was just onto the next thing, onto the treadmill. I mean, I would regularly take the weekend off between jobs. I thought that was a good idea. And I think the idea is like, take a minute, you'll actually be better, you'll be more creative, you'll be fresher, you'll be able to give more if you can take that time in between things and to take a pause.

**Harry Stebbings** [41:09]:

What's the biggest lie that rich people tell themselves?

**Christa Quarles** [41:13]:

Oh my God, they're just so much more capable. It's not luck that I'm just really that much better than everyone else. I think that's a lie. I think understanding the importance of preparation meeting opportunity, I. E. Luck, that's an important thing. Like where you are born, the time you are born. I think all of that leads into how people are successful and how money comes to be. What

**Harry Stebbings** [41:37]:

advice do you often give but find hard to take?

**Christa Quarles** [41:41]:

I think put your own oxygen mask on first. One of the things I say in my company, it'll often happen like somebody's going to a funeral or somebody's mom gets cancer or a kid gets sick, and I will say to them, self, family, company, always in that order, because if you can't take care of yourself, you can't give oxygen to the next person, and I find that sometimes I run a little too hard.

**Harry Stebbings** [42:03]:

If you could change one thing with the wave of a wand, what would it be?

**Christa Quarles** [42:08]:

You know, I used to say I'd like to be able to tele transport, but I think we've done this in the age of Zoom. The superpower I always wanted was that. Honestly, it's climate. I mean, it's 108 in Seattle and my team's there today. I was just in Southern California, was 100 degrees. Climate change is upon us. We saw this whole red dawn in San Francisco last September, and so I would heal this planet, full stop.

**Harry Stebbings** [42:34]:

An ultimate one. What three traits would you most like your children to adopt?

**Christa Quarles** [42:38]:

I would hope that they are kind, curious. You know, I'd say the third one is still just joyful. You know, I think life is harder when you don't bring joy to the equation. One of our sayings is joy and laughter belong here. So I think that's an important one as well.

**Harry Stebbings** [42:56]:

Final one for you. If we sat down in five years' time and everything has gone to plan, as we said, I wish you had known it would go to plan, where would we be then?

**Christa Quarles** [43:04]:

Well, for me and my company, I mean, I think we're kind of an underdog story. I think we have old software here and there, we're rewriting the future, and we're rebuilding it from the inside out. So I think it's people, I hope, look at me and go, how on earth did she do that? I never would have thought she could have taken that set of assets and it became that thing. And, you know, I look at people like Lisa Su at AMD and what she started with and where she is right now, and it's just like nobody would have looked at that at that time and thought that that could have happened. So a story like that would be just remarkable.

**Harry Stebbings** [43:40]:

Listen, Christa, this has been so much fun to do. I can't thank you enough for joining me today. And it's been such a pleasure.

**Christa Quarles** [43:45]:

I loved it. Thanks so much. Bye, Harry.

**Harry Stebbings** [43:50]:

My word. If that wasn't a master class in leadership, I do not know what is. Christa was just incredible, and I wanna say huge thank you to her for being so open and willing to move away from schedule as easily as she did that. If you'd like to see more from us, of course, you can on the twenty minutevc.com. But before we leave you today,

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