The Exchanges

Q it and the people that you add to the team. When we spoke before, you said that there were maybe challenges to hiring someone to solve a specific problem. That seems kind of counter to the point of hiring in a way to solve for that role or for that position. So how do you feel about hiring someone to solve a problem? And what are your thoughts on this?

A Well, ultimately, you want to hire people who can help you solve your problems. But I think hiring people to solve a problem that you don't know how to solve yourself is a little bit of a red herring. I think it is wishful thinking that you will be able to find the right person if you don't know what you're looking for. And for example, a lot of founders out there will say, I need to find someone who can build my app. Because I don't know how to code. Well, if you don't know how to code, how do you know if that code or that person will be good at coding? How do you know that code will handle the right edge cases? How do you know if it will scale? How do you know if they're even writing it in the right languages, right? And so we did this a lot early at exec. We tried to hire someone who knew more about growth and customer acquisition, which ultimately we needed, but we should have spent more time, in my opinion, learning what we needed, figuring out how to make it work, then finding the right person who could take it to the next level. So I don't think it's necessarily wrong to say, hey, I need to hire out of my role, something I'd try and do a lot. But what I try and do first is to really understand what I'm looking for, because that way I'll be able to set better criteria during the hiring process, understand what candidates should come and represent, and then ultimately pass…

AI assessment note: “hiring people to solve a problem that you don't know how to solve yourself”

Q have these amazing achievements as a team, should one really celebrate them, really embrace them, and be grateful and appreciate that moment, or is it always a case of, you've got to go for the next one? I'm always concerned about getting apathetic when you celebrate successes, but then also conscious that one needs How do you think about kind of celebrating internal successes and whether one should or shouldn't?

A Well, it's always a balance, and I probably erred on the side of not celebrating enough, but ultimately, humans are humans. They want to be praised for the things that they do well, self-included, and we want to know where we can improve, and so you do have to balance that, I think. You want to take time to congratulate people, call people out on the job that they've been doing, and celebrate as a team on the wins. But then one of the things I think we've done particularly well at Cruise is, is we've gotten back to work. I always think about the time when we announced that we were, we were being acquired by General Motors, which by all means is, you know, a great feat for such a small company at the time. And Sam Altman came into our office to celebrate and he brought a bottle of whiskey and it was probably an hour or two after all the media came out and he comes in and everyone's just sitting at their desk working. And he was like, what happened to the celebration? And what happened was, you know, we, we got up, we, we made the announcement. Everyone had a glass of champagne and then we said, Hey, we're going to celebrate later tonight. And everyone just kind of went back to work and it was just another day. And then I think that was a nice balance of, Hey, we're, we're not done because we've been acquired. We still have a long ways to go and we want to do this right. And we w…

AI assessment note: “Well, it's always a balance, and I probably erred on the side of not celebrating enough”

Q have these amazing achievements as a team, should one really celebrate them, really embrace them, and be grateful and appreciate that moment, or is it always a case of, you've got to go for the next one? I'm always concerned about getting apathetic when you celebrate successes, but then also conscious that one needs How do you think about kind of celebrating internal successes and whether one should or shouldn't?

A Well, it's always a balance, and I probably erred on the side of not celebrating enough, but ultimately, humans are humans. They want to be praised for the things that they do well, self-included, and we want to know where we can improve, and so you do have to balance that, I think. You want to take time to congratulate people, call people out on the job that they've been doing, and celebrate as a team on the wins. But then one of the things I think we've done particularly well at Cruise is, is we've gotten back to work. I always think about the time when we announced that we were, we were being acquired by General Motors, which by all means is, you know, a great feat for such a small company at the time. And Sam Altman came into our office to celebrate and he brought a bottle of whiskey and it was probably an hour or two after all the media came out and he comes in and everyone's just sitting at their desk working. And he was like, what happened to the celebration? And what happened was, you know, we, we got up, we, we made the announcement. Everyone had a glass of champagne and then we said, Hey, we're going to celebrate later tonight. And everyone just kind of went back to work and it was just another day. And then I think that was a nice balance of, Hey, we're, we're not done because we've been acquired. We still have a long ways to go and we want to do this right. And we w…

AI assessment note: “Well, it's always a balance, and I probably erred on the side of not celebrating”

Q it and the people that you add to the team. When we spoke before, you said that there were maybe challenges to hiring someone to solve a specific problem. That seems kind of counter to the point of hiring in a way to solve for that role or for that position. So how do you feel about hiring someone to solve a problem? And what are your thoughts on this?

A Well, ultimately, you want to hire people who can help you solve your problems. But I think hiring people to solve a problem that you don't know how to solve yourself is a little bit of a red herring. I think it is wishful thinking that you will be able to find the right person if you don't know what you're looking for. And for example, a lot of founders out there will say, I need to find someone who can build my app. Because I don't know how to code. Well, if you don't know how to code, how do you know if that code or that person will be good at coding? How do you know that code will handle the right edge cases? How do you know if it will scale? How do you know if they're even writing it in the right languages, right? And so we did this a lot early at exec. We tried to hire someone who knew more about growth and customer acquisition, which ultimately we needed, but we should have spent more time, in my opinion, learning what we needed, figuring out how to make it work, then finding the right person who could take it to the next level. So I don't think it's necessarily wrong to say, hey, I need to hire out of my role, something I'd try and do a lot. But what I try and do first is to really understand what I'm looking for, because that way I'll be able to set better criteria during the hiring process, understand what candidates should come and represent, and then ultimately pass…

AI assessment note: “hiring people to solve a problem that you don't know how to solve yourself”

Q there, and it brings me to the conversation I want to start on, which is you've got to delegate To someone, and that's the team itself. And when we chatted before, you said you're only as good as your team. I also know that you believe kind of achieving a self-sufficient team should be a leader's number one priority. Why do you think it should be the number one priority?

A Uh, Well, I think it's really because as a leader, it's about scaling yourself. You have to scale yourself. You have to be able to do more. Is to trust other people to do those things. There's only 24 hours in a day. You cannot work all 24 hours of those, and so you have to be able to hire people who you can delegate and give them direction to say, hey, this is how we work, this is how you should do things here, and then you have to trust them to do so. And that's the only way you can grow a company beyond a lifestyle business or a small business that gets run by one or two, three people.

AI assessment note: “because as a leader, it's about scaling yourself.”

Q I totally agree in terms of placing that trust in them in the beginning. In terms of kind of setting benchmarks, How do you think about kind of team and maybe individual KPI setting for you kind of setting the benchmark as the leader of that kind of team and function?

A Yeah, that's a great question. I think the way that we've thought about it here is we've done a lot of KPI setting these OKRs for constantly adapting. There's no real silver bullet for motivation, right? KPIs are just a way to hold yourself accountable and keep the team motivated to do the work that they need to do. And if you set the goals too easy, you know, people will take it easy. But if you set them too hard, it will be very demotivating, and it'll feel like it's impossible, and people will get burned out. So for us, it's kind of trying to strike that middle balance of something that is a stretch goal, but not necessarily unobtainable, based off of everything we know today, and then also listening to the team and feeling how they react to the goal, and making sure that we are reactive and can make changes appropriately. That's not to say that we're going to change the goals as soon as we run into a problem, but as things progress, you have to be able to adapt And then the last thing I think is, is really making sure that people are bought into the goals. And so for us, it's establishing them together, making sure the leadership all understands this is what we're working towards and that they're spreading that down to their teams and that the ultimately the teams are bought into those goals.

AI assessment note: “trying to strike that middle balance of something that is a stretch goal”

Q Not at all. The pleasure's all mine. But I wanted to ask, with this incredible success that we see today with Cruise and all that you've achieved today, it all has to start somewhere, though. So let's take it back a little bit at the beginning. How did you make your way into the world of startups? And then what was that founding moment for you with Cruise?

A Yeah, that's a great question. You know what, what's funny is I actually never intended to be in startups, really. If I go all the way back to when I was graduating from college, I applied to like 30 banking jobs, but it was in 2009, and so I didn't get any jobs. I got, I think, two jobs. One was at a startup in San Francisco, and the other was to teach English in Korea. I decided that I would join the startup because I didn't really want to go on the job hunt again in a year. And that brought me to the Valley and into startups and kind of into this world. And my brother actually has told this story as he advises people on how to get into startups, but he says, you're the product of your closest friends. And so when I saw other people doing this, I decided over time that I should try this out. I should try and start a company. It doesn't seem that crazy. And ultimately dove into startups a couple of years after moving to the Bay and started a company there and started executives. When it comes to Cruise, this was all my co-founder Kyle's idea. He's a CTO now, and I was wrapping up my last startup, and it seemed like a great idea, or at the very least, a really interesting story, and it turns out it was.

AI assessment note: “this was all my co-founder Kyle's idea. He's a CTO now”

Q how to do the work. Cause I spoke to someone the other day and they said that micromanagement is the biggest sign that you have a stretch VP in the role and a case where it's a stretch too far. How do you think about that balance between a stretch VP, which is sometimes necessary and sometimes beneficial versus a stretch too far where actually they maybe can't fulfill it?

A Well, I always, you know, I love to give people the benefit of the doubt and to give them the opportunity because I think that being at a startup, it's an opportunity to grow yourself as well. And if you hire someone who's already done the job, then they're not necessarily growing in the role. You're not fulfilling their personal goals of like learning or, you know, becoming a better manager or otherwise. And so for me, micromanagement is really a sign that you're not happy with how things are going. And there's kind of two ways that I think about how to fix that. One is to provide them better guidance and clear instruction on what you expect. And the other is kind of what you're alluding to is that maybe they're not able or capable to do that role, in which case you need to either scope it back To a scope that they can manage or get them the proper training to do so.

AI assessment note: “maybe they're not able or capable to do that role, in which case”

Q trust of the employees. I do have to also, I think trust is always built in like increments. So when adding people to the team, does one kind of inherently trust them and their ability to really own the role? Or do you think that, like I said, trust is built in increments? How do you think about that and kind of creating that ownership of role within that employee?

A Well, I think there's two ways to look at that, right? If you're optimistic, you think of it as glass half full and people lose trust over time. If you're not, you think of it as kind of glass half empty and you have to fill that glass. And for me, I try and rely on the fact that we have clear hiring practices, clear criteria for bringing people on, and giving people as much responsibility as I think they can take on, and seeing how they do. And over time, you adjust, you either give them more, you give them less, you give them a better direction, a clearer direction. But I think that it is something that is built over time, but if you inherently believe that you, in yourself, and your hiring practices, you should be willing to give people a lot of trust in the beginning.

AI assessment note: “you should be willing to give people a lot of trust in the beginning”

Q I totally agree with you in terms of being bought in, but in terms of that kind of relationship between kind of the leader and the team and spreading it down, as you said, the common thing that I see within teams is essentially micromanagement from leadership on employees within specific functions. How do you feel about micromanagement? Is there ever a time for it?

A Well, I think micromanagement is the easiest way to make everyone miserable. And I've done it before, right? And actually, Justin gave me the feedback. We were at exec, like, hey, you know, you are doing this, and this is a problem. And it was someone who, you know, I've actually developed a lot of trust with now and actually works with me today, but, you know, started with me at exec. At the time, I didn't like what he was doing. I can't remember what it was. I thought he was going about it wrong. And I was like, kind of telling him, Hey, you should do this. You should do this. You should do this. And, you know, Justin told me I should either do the work or let him do the work. But what I'm doing right now is making us both super pissed and maybe he does it right. Maybe he doesn't, but ultimately you have to give him the chance because you trust him to do it, or you should take over that role and he should do something else. And I take that to heart. I think about that every day. I, whenever I'm having a conversation with someone and then I I don't necessarily like what's going on, and I think that has really changed my view on how to manage people, because ultimately people who you hire fail, or they will succeed, but hopefully they will learn from that failure, and then will not fail on that task again. So I don't, I think micromanagement is really a sign that you have not n…

AI assessment note: “micromanagement is the easiest way to make everyone miserable”

Q trust of the employees. I do have to also, I think trust is always built in like increments. So when adding people to the team, does one kind of inherently trust them and their ability to really own the role? Or do you think that, like I said, trust is built in increments? How do you think about that and kind of creating that ownership of role within that employee?

A Well, I think there's two ways to look at that, right? If you're optimistic, you think of it as glass half full and people lose trust over time. If you're not, you think of it as kind of glass half empty and you have to fill that glass. And for me, I try and rely on the fact that we have clear hiring practices, clear criteria for bringing people on, and giving people as much responsibility as I think they can take on, and seeing how they do. And over time, you adjust, you either give them more, you give them less, you give them a better direction, a clearer direction. But I think that it is something that is built over time, but if you inherently believe that you, in yourself, and your hiring practices, you should be willing to give people a lot of trust in the beginning.

AI assessment note: “you should be willing to give people a lot of trust in the beginning.”

Q I totally agree with you in terms of being bought in, but in terms of that kind of relationship between kind of the leader and the team and spreading it down, as you said, the common thing that I see within teams is essentially micromanagement from leadership on employees within specific functions. How do you feel about micromanagement? Is there ever a time for it?

A Well, I think micromanagement is the easiest way to make everyone miserable. And I've done it before, right? And actually, Justin gave me the feedback. We were at exec, like, hey, you know, you are doing this, and this is a problem. And it was someone who, you know, I've actually developed a lot of trust with now and actually works with me today, but, you know, started with me at exec. At the time, I didn't like what he was doing. I can't remember what it was. I thought he was going about it wrong. And I was like, kind of telling him, Hey, you should do this. You should do this. You should do this. And, you know, Justin told me I should either do the work or let him do the work. But what I'm doing right now is making us both super pissed and maybe he does it right. Maybe he doesn't, but ultimately you have to give him the chance because you trust him to do it, or you should take over that role and he should do something else. And I take that to heart. I think about that every day. I, whenever I'm having a conversation with someone and then I I don't necessarily like what's going on, and I think that has really changed my view on how to manage people, because ultimately people who you hire fail, or they will succeed, but hopefully they will learn from that failure, and then will not fail on that task again. So I don't, I think micromanagement is really a sign that you have not n…

AI assessment note: “I think micromanagement is the easiest way to make everyone miserable.”

Q Not at all. The pleasure's all mine. But I wanted to ask, with this incredible success that we see today with Cruise and all that you've achieved today, it all has to start somewhere, though. So let's take it back a little bit at the beginning. How did you make your way into the world of startups? And then what was that founding moment for you with Cruise?

A Yeah, that's a great question. You know what, what's funny is I actually never intended to be in startups, really. If I go all the way back to when I was graduating from college, I applied to like 30 banking jobs, but it was in 2009, and so I didn't get any jobs. I got, I think, two jobs. One was at a startup in San Francisco, and the other was to teach English in Korea. I decided that I would join the startup because I didn't really want to go on the job hunt again in a year. And that brought me to the Valley and into startups and kind of into this world. And my brother actually has told this story as he advises people on how to get into startups, but he says, you're the product of your closest friends. And so when I saw other people doing this, I decided over time that I should try this out. I should try and start a company. It doesn't seem that crazy. And ultimately dove into startups a couple of years after moving to the Bay and started a company there and started executives. When it comes to Cruise, this was all my co-founder Kyle's idea. He's a CTO now, and I was wrapping up my last startup, and it seemed like a great idea, or at the very least, a really interesting story, and it turns out it was.

AI assessment note: “When it comes to Cruise, this was all my co-founder Kyle's idea.”

Q there, and it brings me to the conversation I want to start on, which is you've got to delegate To someone, and that's the team itself. And when we chatted before, you said you're only as good as your team. I also know that you believe kind of achieving a self-sufficient team should be a leader's number one priority. Why do you think it should be the number one priority?

A Uh, Well, I think it's really because as a leader, it's about scaling yourself. You have to scale yourself. You have to be able to do more. Is to trust other people to do those things. There's only 24 hours in a day. You cannot work all 24 hours of those, and so you have to be able to hire people who you can delegate and give them direction to say, hey, this is how we work, this is how you should do things here, and then you have to trust them to do so. And that's the only way you can grow a company beyond a lifestyle business or a small business that gets run by one or two, three people.

AI assessment note: “I think it's really because as a leader, it's about scaling yourself.”

Q how to do the work. Cause I spoke to someone the other day and they said that micromanagement is the biggest sign that you have a stretch VP in the role and a case where it's a stretch too far. How do you think about that balance between a stretch VP, which is sometimes necessary and sometimes beneficial versus a stretch too far where actually they maybe can't fulfill it?

A Well, I always, you know, I love to give people the benefit of the doubt and to give them the opportunity because I think that being at a startup, it's an opportunity to grow yourself as well. And if you hire someone who's already done the job, then they're not necessarily growing in the role. You're not fulfilling their personal goals of like learning or, you know, becoming a better manager or otherwise. And so for me, micromanagement is really a sign that you're not happy with how things are going. And there's kind of two ways that I think about how to fix that. One is to provide them better guidance and clear instruction on what you expect. And the other is kind of what you're alluding to is that maybe they're not able or capable to do that role, in which case you need to either scope it back To a scope that they can manage or get them the proper training to do so.

AI assessment note: “maybe they're not able or capable to do that role, in which case”

Q I totally agree in terms of placing that trust in them in the beginning. In terms of kind of setting benchmarks, How do you think about kind of team and maybe individual KPI setting for you kind of setting the benchmark as the leader of that kind of team and function?

A Yeah, that's a great question. I think the way that we've thought about it here is we've done a lot of KPI setting these OKRs for constantly adapting. There's no real silver bullet for motivation, right? KPIs are just a way to hold yourself accountable and keep the team motivated to do the work that they need to do. And if you set the goals too easy, you know, people will take it easy. But if you set them too hard, it will be very demotivating, and it'll feel like it's impossible, and people will get burned out. So for us, it's kind of trying to strike that middle balance of something that is a stretch goal, but not necessarily unobtainable, based off of everything we know today, and then also listening to the team and feeling how they react to the goal, and making sure that we are reactive and can make changes appropriately. That's not to say that we're going to change the goals as soon as we run into a problem, but as things progress, you have to be able to adapt And then the last thing I think is, is really making sure that people are bought into the goals. And so for us, it's establishing them together, making sure the leadership all understands this is what we're working towards and that they're spreading that down to their teams and that the ultimately the teams are bought into those goals.

AI assessment note: “trying to strike that middle balance of something that is a stretch goal”

Q Totally agree with you. You have to create though an organism and a company that really ingests those learnings and is reset What do you think can be done in terms of kind of organizational building and structure to ensure that you're really kind of maximizing information ingestion and learning opportunity as a structure and as a team?

A Honestly, I think it's really adopting the right attitude, right? I think, and this goes back to culture, and I know that's something we've talked a lot about on the show with other founders. At Cruise, one of our core values is be humble, and humility for us is that there's always something to learn out of every experience. Whether you succeed or fail, there's always a way to execute better. And so whenever we think about how we got into a situation to promote this culture, we always ask ourselves, how are we going to get out of this? Not necessarily dwelling on, okay, how do we get into this situation and what's the problem? And Kyle is actually really good at this. Uh, and I think that's one of the things that, that separates him and other founders is that he's really always focused on what do we need to do to get to the next step? Not necessarily how, what problems or whose fault it was that we're in this situation to begin with. And it's understanding that dwelling in the past, you are not really thinking about the product or, or the future and kind of what you really need to do. It's not to say that you shouldn't think about the problem so that you don't repeat it, but there's a time and place for retros and kind of understanding, okay, this is what we need to do better in the future. And I think that is really what has promoted a culture of learning and adapting at cruis…

AI assessment note: “Honestly, I think it's really adopting the right attitude, right? I think, and this goes back to culture”

Q Totally agree with you. You have to create though an organism and a company that really ingests those learnings and is reset What do you think can be done in terms of kind of organizational building and structure to ensure that you're really kind of maximizing information ingestion and learning opportunity as a structure and as a team?

A Honestly, I think it's really adopting the right attitude, right? I think, and this goes back to culture, and I know that's something we've talked a lot about on the show with other founders. At Cruise, one of our core values is be humble, and humility for us is that there's always something to learn out of every experience. Whether you succeed or fail, there's always a way to execute better. And so whenever we think about how we got into a situation to promote this culture, we always ask ourselves, how are we going to get out of this? Not necessarily dwelling on, okay, how do we get into this situation and what's the problem? And Kyle is actually really good at this. Uh, and I think that's one of the things that, that separates him and other founders is that he's really always focused on what do we need to do to get to the next step? Not necessarily how, what problems or whose fault it was that we're in this situation to begin with. And it's understanding that dwelling in the past, you are not really thinking about the product or, or the future and kind of what you really need to do. It's not to say that you shouldn't think about the problem so that you don't repeat it, but there's a time and place for retros and kind of understanding, okay, this is what we need to do better in the future. And I think that is really what has promoted a culture of learning and adapting at cruis…

AI assessment note: “Honestly, I think it's really adopting the right attitude, right?”