The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale

You've worked with many very High Performing founder CEOs Zuck, Sheryl Sandberg, Larry and Sergey at Google. Brett Taylor Google when I was there.

Felt like two PhD students. Paradise. Facebook felt like 19 year old hackers. Dorm room 80% of the culture of a company is literally defined by the personality of the founder. Our job as operators or as leaders is to help articulate the culture that they're creating.

When a lot of people think Molly Graham A lot of people think of giving away your Legos.

You have to grow as fast as your company is growing if you really want to take advantage, both learning to give away what you've gotten good at and move on to the next shiny pile of Legos.

Sarah Caldwell she told me that the framework that helped her most in her career is something that you call the J Curve versus stairs.

So Chamath, when he pitched me on this job, actually drew me a picture on a whiteboard. He said the way a lot of people do careers is a set of stairs. Just walk up the stairs and you'll get promoted every two years. But that is boring. The much more fun careers are like jumping off cliffs and you do fall, but then you climb out way beyond where the stairs could ever get you.

Today my guest is Molly Graham. Molly was an early employee at Google, also at Facebook, where she worked closely with Zuck on building the Chan Zuckerberg initiative. She also worked with Brett Taylor on Scaling Quip, which she sold a salesforce. She's also worked with hundreds of companies and founders, helping them grow into the leaders that they want to become. Today she leads Glue Club, which is a community for leaders operating in changing growing environments who want to develop themselves as quickly as their companies. Molly is maybe most known for her advice to give away your Legos, which we chat about, along with basically all of her favorite frameworks and mindsets and pieces of advice that she's developed and collected over time. For leaders who are going through rapid scale and growth and are just struggling to keep up. I think of this episode as a high growth handbook for leaders who are experiencing rapid scale. We cover the J Curves versus Stairs approach to career growth, the waterline model, and why you want to snorkel before you scuba. Her six rules for creating goals and building alignment, her rules of thumb for dealing with rapid scale and lots of change. The biggest lessons she's learned from Zuck and Sergey and Larry and Cheryl and Brett Taylor and so much more. Molly is incredible and you will be a better leader after listening to this episode. A huge thank you to Eric Antonow, Ashley Murphy, and Sarah Caldwell for suggesting topics and questions for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And if you become an annual subscriber of my newsletter, you get 19 incredible products for free for an entire year, including Lovable, Replit, Bold, Gamma, Nada and Linear Devin Post, Hog, Superhuman, Descript, Whisper Flow, Perplexity Warp, Granola, Magic Patterns, Raycast, Chapbrd, Mobin, and Stripe Atlas. Head on over to Lenny'snewsletter.com and click product Pass. With that, I bring you Molly Graham After a short word from our sponsors, today's episode is brought to you by dx, the developer intelligence platform designed by leading researchers to thrive in the AI era, organizations need to adapt quickly. But many organization leaders struggle to answer pressing questions like which tools are working? How are they being used? What's actually driving value? DX provides the data and insights that leaders need to navigate this shift. With DX, companies like Dropbox, Booking.com, adyean, and Intercom get a deep understanding of how AI is providing value to their developers and what impact AI is having on engineering productivity. To learn more, visit DX's website at getdx.com Lenny that's getdx.com Lenny if you're a founder, the hardest part of starting a company isn't having the idea, it's scaling the business without getting buried in back office work. That's where Brex comes in. Brex is the intelligent finance platform for founders. With Brex, you get high limit corporate cards, easy banking, high yield treasury, plus a team of AI agents that handle manual finance tasks for you. They'll do all the stuff that you don't want to do, like file your expenses, scour transactions for waste, and run reports all across the according to your rules. With Brexit's AI agents, you can move faster while staying in full control. One in three startups in the United States already runs on Brex. You can too@brex.com. Molly thank you so much for being here and welcome to the podcast.

Thanks Lenny. I'm excited to be here.

I feel like this conversation was an inevitability. I feel like you're the kind of guest where is like we will do this someday. I'm such a fan of your stuff. I've read all the stuff you've put out there over the years. We're going to be talking about the best frameworks and mindsets that you've developed over the years that have been really helpful to you, to founders, to companies that you've worked with, to help them with growth and scale and change and all the stuff that comes with success. The way I think about this, I want to make this the greatest hits of Molly Graham.

Love it.

And so I sourced what I think are the greatest hits from a lot of colleagues that you've worked with, a lot of people you've worked with. We've chatted about the stuff that you find other people find most helpful. So we're going to be going through all that stuff. Let's help people understand why they need, why they should listen to this advice. What's kind of the backstory on these frameworks? Where did they come from? Where did you develop them? Tell us that story.

So, first of all, Ami Vora, who you have had on your podcast, once said to me that all advice is just someone telling you what they did. And I always think about that because I really think that basically what I tell people is I've made every single mistake in the book. And then I got to the end of the book and I started inventing new mistakes. So mostly what I feel is that I like sharing my stories because I want to help people. I want to help people not make the same mistakes I did. And I also want to help people make sense of what they're experiencing. But I, I started in Tech in 2007. I actually started at Google the week the iPhone launched. And a lot of my scaling battle scars come from a couple of experiences. They come from a year and a half at Google, which is not very long. And Google was pretty big when I was there. It was thousands of employees. But my department, which was the communications department, was 25 people when I joined. And it grew in nine months to 125 people. And that was really my first experience with just all the sort of things that I still talk about today in terms of what it feels like to grow really, really fast and sort of all the tools that I started developing from there. After Google, I left and followed Sheryl Sandberg and Elliot Schrag to Facebook. And I spent five years at Facebook. And I joined Facebook in 2008. And it's important context because it was 80 million users at the time. We were smaller than MySpace. It was, you know, 270 million in revenue, 500 employees. It did not feel inevitable. Most people thought we were going to sell to Microsoft. When I told people I was going there, they were like, isn't that Place just like a site for college kids. And so I was there for five years and it was a crazy five years. When I left, it was 5,500 employees, 5 billion in revenue, over a billion users. So, you know, a huge amount of what I experienced, what I write about, what I talk about in Glue Club, which is the community that I run is, comes from, you know, sort of that, that rapid scale at Google and Facebook. But I also, I left Facebook in right after we went public, about six months after we went public. And I, I only like doing jobs that I'm highly unqualified for. I like being on learning curves so steep that I'm scared I'm going to fall off. And so I left and I wanted to learn what it took to build something from nothing. And so I joined this little startup founded by Brett Taylor, a startup called Equip. I joined a couple months before we launched and ran everything that wasn't product and engineering there for him. And that was such a valuable experience to me because the experience of building something from nothing is actually quite different than the experience of sort of holding on for dear life while things are scaling so fast around you. And it really taught me about all the tools and skills you need to go from 0 to 1 and then from 1 to 2 and how lonely it can be to build something. And we eventually sold that company to Salesforce and then again only take jobs I'm highly unqualified for. But the last really chaotic scaling experience I had was actually helping Mark Zuckerberg and Priscilla Chan start their philanthropy, the Chan Zuckerberg Initiative. And I basically helped them for the first two years of its existence or its sort of like first full existence. And it philanthropy sounds calm, you know what I mean? We're like, oh, giving money away must be so peaceful over there. And CZI grew from, I think the week I joined it was 30 people. And we like bought two companies that week. And I, it grew to 250 people that year. And it was like using every single tool in my toolkit that I had, you know, taken from every other job that I'd had. So my advice and frameworks, like I said, come from having made a lot of mistakes. But I've also sort of made a personal study over the last 18 years, believe it or not, essentially like, what does it take to thrive inside growing and changing companies? Not just to hang on for dear life, you know, what does it take to lead in the face of constant change? And really like the other piece that I find truly fascinating is what genuinely makes the difference between something that a business that grows but then plateaus versus these generational businesses, the ones that go on forever. Sort of the difference between a Twitter or MySpace and a Facebook. Billions in revenue versus hundreds of billions in revenue. So what I like to do is take my experience and use it to help other leaders. I want to give people tools that work, and I also want to be honest about how hard all of this stuff really is.

Amazing. I say this a lot on this podcast. I just love the ROI that listeners of this podcast get. You spent 20 years toiling, struggling, working so hard, learning so much, and you just hear, here's all the answers that I've learned. And obviously not all the answers, but so many things that will help people avoid the pain and suffering that you've gone through.

That's the goal.

Also, a couple quick threads I want to follow here. One is Ami Vora, who you mentioned. She's now, I think, had a product at Anthropic.

Yes.

Amazing. Former podcast guest, also speaker at the Lenny and Friends Summit last two years ago. This other point you just made about how you've always gone to places that have been way beyond kind of your. I forget how you phrased it, but just like, beyond your current capabilities almost and, like, were very difficult. I just had Matt McGinnis on the podcast. He was CEO at Rippling Now CPO at Rippling. And he was just. Just recorded an episode with him and he had this really powerful quote that if you're ever, if you're ever comfortable at work and feel like, oh, I got this, you're making a huge mistake, something's going terribly wrong, that's not where you want to be.

Yeah, I always say I get bored really easily, which is both a strength and probably my greatest weakness. So I like being scared.

Okay, so let's actually dive into some of your greatest hits of frameworks and the greatest of all greats. When a lot of people think. Molly Graham. A lot of people think of giving away your Legos. Some people haven't heard of this. Many people have. So let's cover this. What is. What is this advice of giving away your Legos?

So this definitely started in my experience at Google, and then Facebook was like, masterclass in giving away the Legos. But the way I like to talk about it is basically when I watch leaders and employees go through rapid scale, I like to think of, like, somebody putting down a giant pile of Legos in front of, like, a bunch of kindergarteners and then just being like, build something and that's sort of what it feels like when you start. It's like, well, there's so many Legos, and it's so fun. There's a lot of opportunity, but it's also kind of scary and overwhelming. And you're like, there's so many Legos. What do I do? Like, isn't there an instruction manual hidden under this pile somewhere? And. But then you, like, start building and you're like, okay. Like, you know, you build something and then you take it apart and then you put it back together. And then eventually you sort of get momentum and you're like, okay, it's like, I'm building a house. I got this. It's a house. All right, great. And then you're like, I'm good at. I'm good at building houses. Like, I was put on Earth to build houses. And almost, like, assuredly inside of scaling companies, as soon as you're like, I feel good at this, and I like, I should do this forever. Somebody's going to show up and be like. Be like, k. It's not a house, it's a neighborhood. Like, and you need to, like, take this house that's kind of half built, and you're going to pass it off to this other person that we just hired, and you are going to go build, you know, dog parks and streets and other things that are entirely unhouselike. And what happens when someone does that to you is you're like, wait a minute. First of all, I'm not done with this house, and I'm worried that this person's going to screw it up. I'm also worried that, like, building houses is actually the most fun thing, and that I'm going to give the Legos to that person and they're going to.

Have all the fun work.

And I'm going to hate building dog parks. Or, you know, the dog parks are irrelevant eventually. And it's going to turn out we're in the house building business. So you're just like, there's this, like, incredible set of emotions that come territorial paired with excitement, you know, fear paired with joy. But. But eventually you pass the house off, and then you go work on neighborhoods and you're sort of like, okay, like, dog parks. I'm good at dog parks. I got this. And then, you know, again, you get to the, like, I'm great. I was put on Earth to build neighborhoods. And immediately someone shows up and says, it's not a neighborhood. It's a country or a city or a world or. And it just Goes on and on and on. And for me, the learning, this muscle of both learning to give away what you've gotten good at and move on to the next shiny pile of legos, and learning that the emotions associated with that are inevitable, right? Like, there's no. I've been doing this for 18, 20 years. Like, I still get attacked by these emotions all the time, but that doesn't mean that you shouldn't give them away and move on to the next thing. That is both the torment of scaling companies, which is that the ground is moving under your feet, and as soon as you're comfortable, someone will make sure that you are uncomfortable. But it's also the opportunity, which is that you can go from being someone that's good at building houses to someone that knows how to build entire worlds. And that is where the Legos metaphor came from.

That is such a good metaphor. Like, if you've gone through this, you so understand what this is like and what. And also just the Legos metaphor. So good for the different things you build.

I have a very weird brain that for some odd reason, just always thinks in metaphors. So it showed up. I was at Facebook in particular. I would find that, like, every so often, I would have to have what I called a Legos talk with someone where I would just see them start to ask these questions, like, why? Why are we hiring that person? Or, like, why? What's that team even do? And I was like, okay, we need to have the chat about the Legos. And then eventually it turned into an article and a whole, whole thing.

The whole thing. And just to be clear, the advice is, give away your Legos. This is actually the path to a successful career.

You know, I have watched a lot of people over many years struggle with feeling like they, you know, they should hang on to the thing that they've been good at. And it almost always. Because, you know, essentially the nature of a scaling company is that the LEGO pile is just getting bigger and bigger and bigger. However fast that graph is going up into the right. I always say that's the graph of how fast your business is growing. It's the graph of how fast your company is expanding, and it's the graph of how fast your job is getting bigger. That means that if you actually just stay and build houses, eventually you're literally buried under a pile of Legos. Do you know what I mean? You held onto something that's down here, and the opportunity is actually to stay on top of that pile and to learn to just give away your job. Every so often at Facebook, I got to a place where I was literally giving away my job every three weeks. I was constantly rehiring myself, essentially, because you have to sort of grow as fast as your company is growing if you really want to take advantage of the opportunity that comes with companies that are growing and changing quickly.

So people are hearing this. They're like, okay, like, my rational brain's like, I should give away my Legos. It'll help me. It'll be good for my career. In real life, it's very hard to actually do, to, like, give away this empire that you've built, this team that you've built, this project that you're like, oh, this is going to be my thing. I know you have a really fun, useful tool to help people deal with that kind of irrational part of their brain. Talk about that.

So, like I said, my brain works in weird metaphors. It's a weird brain. I was raised on the Muppets, and I like to think that this one came from, I guess, growing up watching weird animals. But basically, at some point, I realized that this emotional roller coaster that comes with scaling, with growing, with going through change, any kind of change people feel, that was never going to go away. And that no matter how good I got to. Sometimes I think it gets worse the more senior you get, actually, because you sort of feel like you're supposed to know what you're doing, and then you just get attacked by this monster that's like, who even gave you this job in the first place? So basically, I externalized all these emotions that come with change into this little tiny monster. I named my monster Bob. Your monster can be named whatever you want him to be named or her or them. And Bob is, you know, Bob's job. I like to think his job is basically to make me the worst version of myself. He's the one that's like, you know, oh, that person took all the fun Legos and you should go push them over and grab them back. Bob's job is, you know, Bob's the one that wants to send the rage emails at 9pm and, you know, burn the house down. And the thing to learn about Bob is that, like I said, Bob never goes away. Bob is not. Bob is someone that you have to learn to deal with. But Bob's job is to make you the worst version of yourself. So your job is to let Bob do his thing, but not act on the emotions. Like, basically, all these emotions are normal and they are not useful. They are not the compass that should be Telling you what to do. Um, but the other rule I have for managing Bob is, you know, a lot of people are like, oh, you're feeling pissed off or tired or whatever. Like, go to bed and wake up tomorrow morning and you'll feel better. And the truth is that, like, you know, you like, I want to send the rage email at 9pm like, you still want to send it at 8am and a lot of these emotions just, like, do not go away in 24 hours. So my rule of thumb from Facebook was give it two weeks. And, you know, these. The emotional, the sort of. Bob. Bob is like these waves and they just roll through. So, you know, you made a new hire or somebody came in, or you got layered or whatever, you'll have a set of reactions. And those reactions again, they're normal, but they're not useful. They're not the ones that you should listen to. They are, Bob, and typically they go away in a couple days. You get something new, you know, some new wave. But anything that lasts longer than two weeks is actually something you should pay attention to. It's something that, you know, if it's. If it's been around for two weeks, it's something you should go talk to someone about, whether it's a manager or a friend or a coach or someone like that. That's the real stuff. Everything else is just.

Bob, is there rule of thumb for when it actually. When you shouldn't give away your Legos? When it's like, okay, maybe you should fight back on this, on this layering or, you know, whatever.

No rule of thumb in general, I would actually say embracing change is far better than fighting it. And almost invariably you cannot see what is around the corner, you know, but it is almost always the thing to focus on. Like, a lot of times, I think inside of change, we get focused on the past. And one of the most valuable things you can do as a manager and a leader is help people focus on the future. I think. I'm sure there are times when people have done it and regretted it and it has led them somewhere. You know, I think being layered, for example, you know, is one of the hardest things for people. Inside these experiences where someone brings in a manager above you, and I've also seen so many stories of that ending up being a great thing for someone, even though they couldn't see it at the time. So in general, I would just say step into the future and let the past go and see what you're going to learn. And sometimes you'll learn that, you know, it's time to leave, or that it's not. This isn't the right pile of Legos for you, but it'll end up taking you somewhere that's worth exploring. Holding onto things almost always leads us to the worst version of ourselves.

A very Buddhist way of thinking, too. Just don't cling.

There you go.

Yeah. And I think another part of this metaphor, I don't know if you think of it this way is the Legos aren't even your Legos. Right? They're like the CEOs Legos, the shareholders Legos. So you think they're your Legos, but no.

Well, it is. You know, I will say one of the hard earned things is it can feel very, like, emotional and it can feel very personal. It can feel like your work. I don't know, it can feel like your life is on the line sometimes just your work life, you know. Oh, gosh, like every. This matters so much. And one of the things that you learn as you get more senior and just have seen stuff is it's gonna be okay. You know, like a friend of mine says, careers are long, and nobody tells you that, but, like, they're long. And this moment feels so dire and it feels so hard and it feels scary and it's going to be okay. So, yeah, it is hard to know in the moment. And I think, like, the story is going to be long and this is going to be one chapter or maybe even a part of a chapter, not a whole chapter. So embrace the length to build on that point.

I've realized this is my fourth career doing what I do now, whatever the hell this is. I was an engineer, then I was a product, then I was a founder, then I was a product manager. And then what the hell I do now, whatever this is, that's a whole different path.

You don't have a name for it yet, Lonnie.

I don't. I hate all the terms people use for this world.

Somebody called me an influencer and I almost ripped their face off.

Yeah.

Yeah, man. The most interesting careers are winding and they have starts and stops and failures and successes and control. Anybody that's, you know, been through a lot of this stuff. Control is usually not the name of the game. It's usually just like, let's see what happens. You know, we're going to try this and we're going to see what happens next.

This is a great segue to another framework that I've heard from folks you've worked with that have been really impactful on them. So Sarah Caldwell, who's a big deal at OpenAI, she told me that the framework that helped her most in her career is something that you call the J Curve versus Stairs career growth framework. Talk about what that's about.

I actually gave a TED Talk about this one a couple of years ago because I am so passionate about it. But I'll tell I. That's like. You can listen to the, like, very packaged, like 8 minute version of this, but I will tell you the real story because it's very relevant to a lot of folks that listen to your podcast. So I was at Facebook for five years. Like I said, I spent two years, the first two years I was in hr and I was doing sort of employment, branding and culture work. And I was like, ready to stay there. You know, I think I had in my head I was going to stay there till we went public. Like, that was my plan. Just because I wanted to, like, help the company through that moment again in my head. So this guy that many people know, Chamath Polyabatia, came to me and Chamath ran Growth and Mobile at the time. And he came to me, we had lunch and he said in his very ch way, like, you're useless. What are you doing in hr? Like, this is stupid. Like, you should come work for me. And I. And this. Anybody that knows Chamath is like, yes, that is actually what he said. He manages to like, insult you and compliment you in one, one sentence.

So.

So he, you know, he gave me all these options on his team and then the last one he said to me was like, I'm gonna go build a mobile phone. Do you want to come? Do you want to come do that with me? And I had like four simultaneous reactions. The first was like, that is incredibly stupid. Why are we doing that? And then it was like, is that actually a thing that we're doing? And then it was like, whoa, I think that sounds kind of fun. And so I left the conversation at Chamath and I went and asked my boss, Lori Goler, who was the head of people at Facebook for a very long time, like, is this actually something we're doing? And she was like, I can't believe he offered you that. Whatever. And I. And you know, I. I basically just like, could not get it out of my head. But it was like, didn't make any sense a that Chamath had asked me because I was an hr, like, what am I doing? I know absolutely jack shit about mobile. And. But, you know, I had worked on a project with him and He, I guess, thought I was smart. And I, I talked to like Cheryl and she was like, well, that project will be dead in two months, but you can do it because you'll still have a job here. You know, a lot of my dad was like, what? Don't do that. You know, and anyway, a lot of very wise people being like, don't do that. But I kind of couldn't get out of my head. And my friend said to me, you know, you've proven you're really good at these sort of like company wide project management and hr. Why don't you go show yourself how actually good you are. Like, is this transferable? So I took the job and I spent the next six months feeling like an absolute idiot. Like I basically felt like a total jackass all the time I was sitting in rooms with these like brilliant people, you know, asking the dumbest questions of my life. And at the end of the six months, Chamath, I think, took a lot of pride in giving me like the lowest performance rating I've ever gotten in my life. Um, and you know, it just felt like falling off a cliff. And he, you know, then slowly, I remember I had been doing all these trips to Taiwan because we were actually working on hardware. And I at some point came back from Taiwan and I like drew on a whiteboard for him the layout of a mobile phone and trying to explain to him kind of like why something he wanted to do was not possible. And I so vividly remember walking out of that meeting being like, oh, like I actually know things. And slowly then over the following three years, I became an expert in mobile. And I basically, you know, the, the phone itself was a giant failure, like massive, costly failure for Facebook. But it let me, it was, it was not a failure for me. It was a huge job that taught me that I was capable of things that I never could have dreamed of if I'd stayed in hr. It set me up to be capable of taking on things that I didn't know about. And so Chamath, when he pitched me on this job, actually drew me a picture on a whiteboard. He said, you know, look, you can stay. The way a lot of people do careers is a set of stairs. You can be boring to use Jamath and stay on these stairs. Just walk up the stairs and you'll get promoted every two years and your title will change from manager to senior manager to director to senior director, whatever. And he was like, but that is boring. And he's like, the much more fun careers are like jumping off cliffs, basically, that you jump off this thing and you do fall, you know, for a period of time. I always like to say it's about six to nine months. But then this thing happens where you climb out and, you know, the picture he drew had this J curve sort of like basically leading you to places that are way beyond where the stairs could ever get you. And to be totally honest, that has been my experience, you know, that taking risks, accepting the sort of, like, terrible fall, and that experience of falling has been more than worth it. And I, you know, part of the reason why Sarah mentions it is that I do give this sort of talk to people that are inside of really fast growing companies because it's such an important place to let go of Legos and jump off cliffs because there's so much opportunity. And it is a place where if you prove to people that you're actually good, if they believe that you are the kind of person that they can use to do lots of things, you can get these opportunities that you are just so deeply unqualified for, but they can take you to places that you could never have imagined. You can come out of those companies with skills that you, you know, no one would ever have reasonably hired you to do. But I ended my time at Facebook in product and, you know, did business development and hardware and a whole bunch of stuff along the way. And again, nobody would have hired me to do that at the beginning, but it's just because I kept saying yes to things.

Molly, I got tingles listening to this story. Wow.

Does it sound familiar, Lenny?

It does. And I want to ask is, you know, jumping off a cliff, sometimes you fall and you fall and you keep falling. Are there any kind of traits of like, okay, this is one that might be a J curve and worth the risk of falling, and this is when you should probably just not. Let's not do this.

Yeah. So, you know, I just think there are different kinds of fear. And, you know, we talk a lot about this in Glue Club because one of the things, you know, there's. There is like a financial fear, right? Like leaving a job and taking a job that has financial risk associated with it, or leaving a job and taking time off, which is something I spend a lot of time talking to people about. You got to do the math, you know, and you gotta. Sometimes there is a type of fear that is telling you, like, this is not the right time, or, I don't want to be financially anxious for months and months and months. I use finances because it's the most concrete Example of, like, a type of fear that you should actually listen to. And sometimes you can do the math. And, you know, I always counsel people through that. I'm like, what is the number that you need to hit so that you're not constantly terrified financially? And that number is, you know, wildly different for people based on their background and their life. Can you do that? You know, can you consult, can you whatever in order to. To take this leap? But a lot of times, fear is just you saying, I'm scared I can't do this. I'm scared I'm not capable of it. I'm scared that I. Yeah, I'm scared I'll fail. And that's the kind of fear that I think of as, like, a flashing green light. Cause I'm like that. And it sounds like Matt McGinnis said this too, where it's like, that's the kind of fear that's saying, why don't you go prove to yourself that you are actually capable of this? Or if you fail, like, you'll have learned something, too. You know what I mean? You'll have learned, like, I took this job in product at Facebook, you know, as my last chapter there, and let me tell you things that people should never fucking hire me to do. Like, I am not a good product manager, but I would never. I'm a. I've got a great product mindset. I can sit, you know, in a bunch of chairs and. And. And hang with the product folks. But, like, I'm not the person that cares about the button. Do you know what I mean? And I would never have learned that. I wouldn't have known kind of who I was if I hadn't taken that risk and, you know, failed or. Or at least learned that it's not something I wanted to do again. So there's many different lessons that come from facing down those fears and jumping off the cliff, you know, but mostly what it is is knowing yourself better and knowing where you go next from there.

That is such helpful advice. I also love how you frame this of prove it to yourself that you can do this. It's not, I'm going to show them that I can do this. Because the way you describe this, usually it's an opportunity given to you, hey, can you do this thing? We want you to lead this new thing. And the fear is like, I don't think I can do that. And what you're saying here is, prove it to yourself that you can. Or I guess it's also, okay, maybe I can't. And then I'll learn that, and then I'll know more about myself.

Yeah, exactly. I mean, one of the greatest gifts in a career is knowing yourself, you know, and that's a. It's a lifelong journey because who you are and what you want changes. But that knowledge and that gift, like, nothing accelerates your self knowledge faster than trying to do something that you don't know how to do and that you're scared of.

There's this, probably the quote I use most on this podcast, comes up again in my mind as you talk about this. This line that the cave you fear contains the treasure you seek.

Hell. Yes, exactly. Well said.

There it is.

I haven't heard that one from you, so clearly I need to listen.

Okay, that's great. I'm glad I don't overuse it. It just feels like it comes up again and again. And I think your point about the Runway and the finances is such an important one, because that's a very real practical question. One thing I did when I took time off, I took a year off after I left my job. What helped me was I just created a Runway goal for myself. I'm just like, okay, here's what it's going to cost me for six months or a year to live without any income. Am I comfortable just burning through these tens of thousands of dollars to explore? And I see something new emerge, and so you just have to feel good. Okay, yes, I'm going to burn all that money.

That's exactly the exercise. You know, I. You're. You're saying Runway, I say burn rate. So, like, we both were raised inside of companies, inside of tech, but. But I think it is. Do the math, right? What can you afford? What? And it's both. What can you afford and still feel safe? Because sometimes, I mean, again, I think that that is different for everyone, but it is such an important set of math to do because a. A lot of times that number is smaller than you think it is. Like, than your brain makes it out to be. If you have this sort of, like, existential financial anxiety versus, like I always say, like, specific financial anxiety is much more useful than existential financial anxiety. And. And, you know, you know, some friends are leaving jobs, and I'll be like, hey, you know, Your number is 5k or 10k a month. You have to believe that you can get a consulting gig that will pay you that. Do you believe that? You know, and. And it's like, either yes or no. And then, okay, either we're doing it or we're not.

You know, the other part of this J curve that I think is really important to touch on is this idea of for the first six or nine months, you're going to be at the bottom of the J curve. Like falling, still falling. Yeah. And some projects don't last that long. And then you're like, okay, total failure. I never emerged from this fall. So is there any advice there of just like, how do you create that enough space to give you a chance to start to unfall?

I mean, the, the most valuable thing that happens as you fall is learning. And even on the other side of failure, you've learned a ton. Like I always say, like, most important thing to do in the falling phase and the risk taking land is to learn to embrace being a professional idiot. You know, basically being the one that shows up at the meeting and it's like, what are we talking about? Like, what does that word mean? Because for a bunch of reasons, number one, you can learn so much. And again, even in the face of failure, no one can take away your learning. Do you know what I mean? But the other thing is that, like, it turns out that a lot of the questions in the world that you. You're sitting in the meeting and you're like, this is a dumb question. Like, I'm gonna. Everyone's gonna think I'm an idiot. But then you get brave and you ask it, and it turns out it wasn't a dumb question. Do you know what I mean? Like, turns out that everyone had that question in their mind, but no one was brave enough to ask it. So from a skills perspective, again, regardless of outcome, being the person that sort of takes their learning in their own hands, learning no matter what, and learning to sort of like, ask those dumb questions. It's a superpower. I always say that. Like, actually my superpower is being a professional moron, because I'm the one that shows up in a room and is like, do we have goals? Like, what? What are we doing? What? Why are we talking about this? Why are we having this meeting? And most of the time, it's actually what I was hired to do, which is bring clarity.

It's so funny. I just recorded a podcast episode with a PM named Zevi who joined wix, and he had this thought. He's like a very young p. I'm just getting started. And he's like, okay, I need to be at 10xPM, because that's what they expect of me. That's what everyone. That is really good. That's how I think about 10xpm. And then he went into his first meeting and he just failed. And he just felt so bad. He's like, I guess I'm not that 10 xpm. They're all gonna see that. They're all gonna. They think I'm terrible. And then he did another presentation a little bit later, and people were so impressed with how he learned and evolved and improved. And he realized that he needs to be not a 10xPM, but a 10x learner. And that's what people actually expect from someone, especially a junior person.

Yeah, well, and I was having a conversation last night with a friend of mine who has a senior in high school, and I was like, what. What is the plan? Like, what are we telling this senior in high school like, to think about relative to their career, given everything that's going on with AI? And we talked about it a bunch, but what we both circled back to is this idea of soft skills and that. That actually, like, the only thing you can really anchor on right now is that, you know, teaching kids grit, teaching them hard work, teaching them learning. Right? Like, learning how to learn, loving, learning being able to follow in a world that's changing this fast. And I say this inside of companies too, right? I always say, like, what you know today is way less valuable than what you can learn by tomorrow. If you're inside of a company where the growth curve is like this, what you know today is, like, irrelevant. Somebody once told me they re. I'm sure this is faster now, but they rewrote the entire code base at Google every eight years, which means that, like, if you're not learning, if you're not evolving, then you become irrelevant and extinct. It's actually the whole sort of, like, underlying point of the Legos stuff is that, like, evolution is the way you stay on top. And I think that's more true today than it's ever been.

And luckily, AI is really good at helping us learn.

Totally.

So that's good. Thank you, AI. And this. This actually comes up a bunch in the podcast. I ask a lot of AI Forward people what they're teaching their kids, and curiosity is one of the main things people talk a lot about. Just, like, make them help them develop curiosity about the world and. Yeah, yeah, okay. I feel like I could be talking about this specific topic for a whole podcast episode, but I want to move on to a couple other frameworks that you've developed. One is something called a waterline model and another former colleague of yours. So this is the most impactful thing that was that they've learned from you on their career. So talk about the waterline model.

Okay, yeah, well, first of all, the waterline model is not mine. It's something, it's from some business book somewhere, but I actually learned it. So my first job out of college was leading wilderness Trips. I led 75 day wilderness trips in Patagonia and Alaska for a school called Knowles, the National Outdoor Leadership School. And Knowles basically teaches essentially leadership and communication skills to students mostly. I was mostly living like college age kids through wilderness expeditions. So by having to lead a group of your peers that you don't know. Anyway, the waterline model is something that we taught on Knowles and it's a really, really helpful model for understanding how to diagnose when something is not working on a team. And so I teach it inside of glue club and I'll just quickly explain it. So basically the way to think about the waterline model is that a team is a boat and it's a boat on an ocean trying to get somewhere. Getting somewhere is goals, right? Where what are we trying to build or ship or do? And essentially that is going to be harder, easier based on whatever the shape of the ocean is, right? If it's really choppy, it's harder. It's smooth and calm. It's going to be easy to get to your goals. So the, the water line basically asks the question, like, what is going on under the water? What is going on that's making it harder or easier to get to your goals? And there's essentially four things underneath the water and they are in a descending order. So the surface level is what's called structural things. And basically structural things are like goal setting, vision, roles, expectations, like kind of the structures you put in place to make a team and a company and a business make sense that touch every single member of the team. Right below that is something called dynamics, which is essentially like how the team works together. It's culture, it's decision making, it's how we resolve conflict. All the sort of like interwoven pieces of how teams work together. And then below that is interpersonal. So basically relationships between two people and all the things that come with us being humans. And then the bottom is intrapersonal, meaning within one person, challenges and issues there. And the interesting thing about this model is that most people, when something's going wrong on a team, a lot of times we always go to the bottom. We go to the people. We're like, the people aren't getting along, that person's having a rough moment. We go to the humans. But the rule with the waterline model, which is very memorable, is you snorkel before you scuba. So 80% of problems on teams actually happen because of structural issues or dynamics issues. So when there are problems on your team, where you start is at the top. You start structural issues. And one of my biggest things that I say all the time, over and over again, inside of Glue club is your only goal as a manager. If you do nothing else is clear roles and clear expectations. That's it. Because honestly, like, I've taken over a lot of teams in my life, and almost always I show up and it turns out that no one knows what their job is and no one knows what success looks like. And if you can make those two things clear, which again, is at the snorkel level, it will fix, you know, a huge percentage of other issues on a team. But the main thing is, like, where you start and just always sort of starting at that structural level or the dynamics level and not sort of immediately going to the people and.

And all that.

Because, yes, people cause all sorts of problems, but a lot of times they. The problems are happening because they're existing inside of a structure that's confusing.

Another very vivid metaphor. And just I love how it builds on it with the snorkeling. Okay, so just to be super clear about this, the takeaway here is you have a problem with your team, with the company. Many people think it's. They jump to, like, the people are the problem. They're not good enough, they're not working hard enough. Really, what you're saying is most often the issue is not the person, it's the situation. Whether it's the structure of how they're set up to work or the dynamics amongst the people. And specifically, what you're saying is, like, the role maybe isn't clear or what success means, and for that role is not clear.

You know, every company I've worked with or advise, like, I often start with, like, what are the goals? And usually what you get back is not clear. And that in and of itself is a structural issue. Right. How can someone show up and decide what they're going to do with their day, all day if the goals aren't clear, if they don't actually know what the priorities are? And then it goes to like, okay, role, right? Like, do I know what my job is? Do I know what number I'm was hired to own and drive? And then, like, do I know what success looks like? How does my role tie to that overall goal that the company just literally right there, you got like probably 80% of problems inside of companies because this is the hard work of company building. Like it's the stuff that's not intuitive. How do you organize a group of people to know which direction to row? You know, and that equation, again, I would say 80% of problems that I see, performance issues, like I always start with, does this person actually know what you expect of them? If not, go back to step one. Do you know what I mean? Clarify expectations. So the waterline model is just helpful for reminding us like start at the top.

So what would you do there? Say you're a manager, you're having an issue with team member. Would you go and ask, hey, let's just make sure we're aligned on goals and roles. Is that is how you approach it or is there a different approach?

So a lot of times what I do is two sided, right? So it's like, hey, tell me, here's what I'm seeing and tell me what's going on for you. Like, do you know, do you know xyz? Do you know what? Tell me what you know. When I, when I take over a team, when I'm doing my sort of like listening tour, part of what I'm asking is what do you think your job is? What do you, what number were you hired to drive? Because what you'll find is often like their picture is different than your picture. You think you've been clear. They somehow got, you know, you described an elephant and they spat out a tiger and that coming back to like, okay, no, we're building an elephant, you're in charge of the trunk. Will, you know, in some percentage of cases actually make a huge difference to the person's work and time and performance. And you know, in plenty of cases it doesn't, but that's always where I would start because it so often is just like a more fundamental problem that then would lead you to look at other things across the team. But yeah, that's, I would say two way dialogue. But re. Clarifying roles and expectations. Redescribing the elephant over and over and over again is one of the hardest parts about being a leader. Because you feel like a broken record, right? You feel like an idiot. You're like, I've said this 45 times. Turns out no one heard you the first 43. And you have to, you have to redescribe it in order for people to hear you and to re understand their sort of role and what they're doing.

I love how you reframed the way I approached it. By starting with here's what I'm seeing. What are you seeing? What, what, what do you think your role is? The very like non violent communication oriented, which is a clear pattern on this podcast. Just the power of that specific framework.

Yeah, totally. Well, like I said, work is about humans and it's the art of sort of like organizing humans to get something done and build something that's great, greater than the sum of its parts. And that is an art of sort of the humanness in all of us. How do we get people to hear us? How do we get people aligned?

Work for a lifetime. This episode is brought to you by GoFundMe giving funds the zero fee donor advice Fund did you make a New Year's resolution to give more? I want to tell you about a new product that GoFundMe has launched called Giving Funds, which is a smarter and easier way to give. GoFundMe Giving Funds is a DAC or donor advice fund from the world's number one giving platform, trusted by over 200 million people. It's basically your own mini foundation without the lawyers or admin costs. You contribute money or stock, get the tax deduction right away and then decide later where you want to donate. There are zero admin or asset fees and while the money sits there, you can invest and grow it tax free so that you can give more later. GoFundMe is a FinTech unicorn working for good. Make a Better World in 2026 and start your giving fund today at GoFundMe.com Lenny. They'll even cover your daft pay fees if you transfer your existing DA over. That's gofundme.com Lenny to start your giving fund. Okay, so let me actually follow this thread of the importance of goals and just being clear around this stuff. You have these six rules for creating clear goals and alignment on teams. Talk about these six rules.

Yeah, totally. I feel like there should be less than six, but it's where we're at. I would say at a high level. Two things before I get to the six. One is that I definitely have a bone to pick with okrs. I feel like it's, you know, it's obviously been a really helpful framework for Google and others and a lot of times when I show up inside a company or I'm talking to a leader and I'm like, you know, what are your goals? What I get back is this like spreadsheet that has like a hundred lines and is feels like it's written in Greek. And like I, when I look at It I'm like this, this doesn't create clarity for anyone. And it brings me back to sort of like what, what is the point of goals? What, why do we have them? And at the end of the day, goals are a communication tool. That's what they are. They are a communication tool designed to create clarity to help people know I'm going to show up at my desk, what should I work on? What's the most important thing? And your 100 line spreadsheet doesn't help anybody. And the second thing I would just say is like you really have to ask the question what is right for me at my this company and this stage? What is right for a seed stage company is not what is right for, you know, a company that's got an established business business and a clear go to market machine. So you know, when I'm building in seed stage, I'm setting goals every two months in a very iterative way. When I have an established business, I can actually set annual goals. But annual goals for early stage companies is just like a waste of time. So anyway, a lot of my goal setting stuff actually comes from Facebook, which I think was very, very good at this. So the first rule is that no company needs more than three company goals. And the point of company goals is to help people know what the most important things are to success. So Facebook basically had three goals for the entire time I was there. It was five years. And we did, you know, six month goal setting. I think we did annual goal setting that ended up getting reset every six months, but whatever. So the three goals were this. There was growth, which was measured as monthly active users. That was the externally reported number. Eventually maus, the second goal was engagement, meaning how often do people come back and use the site. And the third was revenue. And we literally had three goals for the five years that I was there. If you can govern that business with three goals, you can govern literally any business with three goals. So no company needs more than three goals. The second thing is that one goal needs to win in a fight. So if I'm sitting down and asking how do I prioritize my time on a given day, I need to know what is the most important thing. You know, at Facebook we had growth, right? And there's a lot of different ways you can add monthly active users to a social media site, including you can go buy a whole bunch of bots in Indonesia and that would add to your MAU number, but it would not add to your engagement number. And it was very clear for the entire Time that I was there, that engagement was the most important thing. Acquiring users that were going to use the site all the time, that's what drives revenue. It's also what drove, you know, sort of the heart of that site. Um, so if you had to prioritize something, you prioritized engagement, that goal won in the fight. The third I'll say is I call it the explain it to me like I'm five goal. But like an intern that started on Monday should be able to look at your goals and understand them. And if they can't, then you are failing because they are not a communication tool that's effective. You have to be able to understand the goals, you have to explain the acronyms, you have to have numbers that make sense to average people. Otherwise again, it fails as a communication tool. The fourth one is actually I, I stole a phrase from Claire Hughes Johnson who you've had on your podcast, but wrote a book called Scaling People. And in it she says this sentence that I love, which is strategy, strategy should hurt. And you know, I, my, my role used to be like, set non goals. Basically make it as clear what you're not going to do as what you are going to do. But strategy should hurt is a much better way to explain it to people, which is if you're not making trade offs that are painful, you are not actually helping people prioritize their time. Because the nature of work is that people will show up every day and do something and either you are very clear with them about what the priorities are or they're going to prioritize for you because they're going to choose what they work on every day. And we see this so much with founders where they can't cut things off the list. They just have to have the 10 goals. And I'm like, cool. Six of these goals are not going to get done. So either you pick which four it is or other people are going to pick for you. So strategy should hurt. If your goal setting process is not painful, then you're not prioritizing heavily enough. Okay, ready? We're on number five. This is more of an organizational point, but it's really important for the waterline model too, which is that one goal has one owner. You have a number, that number has a name next to it. If you cannot do that work, you haven't done the most important work to actually make sure that these goals get accomplished. And it's organizational work. And it's very painful because, you know, sometimes it feels like, oh, this person could own it or this. Maybe I'll just own it together. Two people owning a goal is no one owning a goal. One person owns the goal.

Who is it?

It's not you as the CEO. It's someone that works for you. So one goal, one owner, and then the last, which is the hardest, is that goals by themselves are not enough. I've spent a lot of time with founders that are like, I did it. I set the goals. Why is. Why. Why not working? I don't understand. And I'm like, what did you do after you set the goals? And they're like, I don't know. I set the goals. Goals. You know, James Clear, who wrote Atomic Habits, has this really lovely sentence which is, winners and losers have the same goal. Goals by themselves are not enough. You have to have a process by which you follow up on the goals and you hold people accountable to the goals and you learn from the goals. Because so much of goal setting, particularly, you know, if you're earlier in building your company, is about learning from trying to do something. You set a goal. Can we do it? How hard is it to move this number? You know, that is the learn. You might be wrong all the time, but you're learning what it takes to move the number. So the number setting the goal by itself, not enough. You have to build a process in the system to, like, actually learn from the goal.

Wow, this list is. There's so much power in this list. It's such too long. No, I don't think it is. Because each of these has so much depth and power to them, that saves you so much headache and. And just like wasted time and resources. Just like the idea of one owner, one goal. Something I've personally discovered to have such power because. And correct me if I'm missing something here, but just if you feel like someone else may be doing the thing or feels like it's not just fully responsibility, there's so much less energy and. And just like mental. I don't know. You just don't care as much about hitting that goal if it's you. Yeah. If it's like, Lenny, this goal is your goal, and if you hit it, it's. You've done it. If you don't, you're. You've done a bad job. Like that. Yes. Such motivating. So motivating. If it's like me and Molly. Okay, well, we'll figure it out.

It creates a flood of clarity that seeps down from the person too. And. And, you know, to go back to the waterline model, I would say so often you'll actually find companies that have set goals, but they. Everyone, no one owns the goals. Everyone owns the goals. Multiple people on the goal. And it's like that you didn't actually get all the way to the answer, you know, And I will say that the ownership thing is hard. Like, it can feel painful, but it's really important. You know, there's only one owner, and that means that that person, come hell or high water, owns that number.

Yeah. The way we. I described it, Airbnb was just like, someone asks, someone's ass has to be on the line for this. And that just works. That's such a powerful lever to drive things. To have one person responsible. The other is just this idea of, of strategy hurting. I love that. I love that phrase. I forgot, I forgot Claire had that. So true.

So good.

Because the whole idea is you need to not do things. You need to decide what you're not. Like, the whole strategy is a big part of it is what we are not doing.

Yeah, absolutely. And if you're not making painful choices, then you're not actually doing it.

And this idea of three goals. So is that just like. So do you go into a company and just like go through a checklist essentially, of. Here's the six things I look at to tell me if you. What, where there's opportunity to improve.

When I work with founders and I see their goals, what I, I use it as a way to get to know the business. And I'm just going to be like, literally like, what is this? Like, what are you trying to explain? And I can usually, through, you know, asking a lot of really dumb questions, which, like I said, one of my superpowers, get them to explain to me, you know, the one sentence and the one number that they're actually trying to get across. But it, it takes work. And that's part of, you know, it's almost like easier to write the hundred line spreadsheet than it is to say, wait, what are the three drivers of this business? Genuinely? Like, what are they and how do they relate to each other? And, and you know, there can be things underneath them, but there's three at the top that matter. So, yeah, it's, it's not a. I'm not like a scientific person about it, but a lot of it is just by asking people to explain their businesses to me. You can basically find the drivers and.

The story about Facebook having these same three goals for five years. Considering their success, you may think they're not as complicated as your business, but I Am confident they are just as, if not more complicated, their marketplace, social network, their ad business. Just there's a lot going on, and if they can work with three goals, you can do that too. And to your point, it needs, like, if it's not hurting, then you're doing something wrong.

Yeah, exactly.

I love how this is very much what I wanted this chat to be. It feels like every little segment is like its own, could be its own podcast where we could talk about this for hours. So. So I'm really excited how. How this is going. Kind of moving on to another topic. You have not necessarily rules, but rules of thumb that you find really helpful for people to have in their head as they're dealing with change and scale and growth and all that kind of stuff. So let's just walk through that.

Yeah. So for. For leaders that are, that are leading through change and growth, like, I, the list is probably long, but, you know, I always say to people, don't come to me for like, management 101. I'm not the person to ask on, like, how to run the most effective one on one that with your people. What, what I think is not talked about enough is what it takes to manage and lead through change. And that is a very particular set of feelings. And the first thing, you know, I learned when someone makes you a manager or when you take a job as a leader inside a company, you really do feel like, like, oh, like, who gave me this job? You know, and you sort of feel like you're supposed to know the answer to things. Like, people come to you and ask questions and you're like, I'm. I'm supposed to know, right? I'm a leader. I am supposed to have answers. And I think particularly inside of rapid change and, and scale and growth, it's really important to understand that your job as a manager and a leader is not to have all the answers. It is not to have all the answers. It is to get good at finding them. It is to get good at bringing people together to find the answers. And that is hard because it requires saying, I don't know, let's go figure it out a whole bunch. And it's scary as a leader to say, I don't know, because you think, oh, gosh, people are going to see through me. But, you know, again, the more you travel in life, the more you realize that the most experienced leaders are the ones that say, I don't know all the time.

I think this is a good reminder of this, Bob, the monster concept, because hearing this, okay, I don't need to have all the answers as a leader in real life, being in a meeting, people are like, hey, Molly, what do you think of this? Like, you're like, oh, shit, I should have a good answer. And so I think that's a good reminder of this idea, of this Bob the monster is going to tell you, oh, you don't know anything. You're not ready for this. You suck at this. You're going to fail everyone.

They're regretting hiring you.

Yeah, exactly.

Everyone's going to see through you. Imposter. Imposter. Imposter.

Yeah, so just remembering there's this going to be this part of your head, and that's okay, it's there, but it doesn't mean it's true.

And these things are muscles, you know, like dealing with Bob as a muscle. Right. Learning to, like, not react to all those things that attack you, but also learning, like, oh, in this moment when someone asked me a question and I'm like, oh, actually, I should be like, I don't actually know. Let's go. Who should we ask? Like, how can we learn this? How can we explore this together? What do you think? Like, those are all actually very powerful questions and they're terrifying, you know, to. Particularly earlier in your career as a leader and a manager.

Awesome. So, yeah. So the lesson there is you. No one expects you to have all the answers as a leader. No.

And. And it's particularly in this world, right? The one that's changing as fast as it is. Like, nobody. Nobody knows, you know, nobody knows what the answers are. In a lot of cases, the. The war will be won by the people that are good exploring and figuring it out.

I love that phrase.

So the second one is. And everyone that has learned this has learned it the hard way. Do not promise things that you can't control. Right. It's so tempting, like, particularly when you're hiring people to be like, oh, yeah, like, your onboarding will be smooth and calm and everything's clear. And like, we figured it. Let us tell you our vision and how obvious and clear and smart and. And then they show up and it's like, oh, shit, you know what I mean? Like, they. There's no manual. No one knows what they're doing. It's all ambiguity and chaos. Right. It's so easy when someone says, I want to know that I'm going to be your CMO forever, to be like, sure, you can be my cmo. You don't know that. Do you know what I mean? So being really Careful with promises of things that are out of your control, like stability or titles or never. Hiring over someone is like a flashing red light because there is literally no faster way to demoralize high performers than going back on a promise. Right. You, everyone that has been through it knows that feeling of like, I, they told me this when I joined. And then they don't do it. And you're like, well, this place, you know, so no faster way to demoralize people or to hire the wrong people than promising things that are actually out of your control. Being honest and upfront about who you are as a company, about what you're able to promise, like, all of that is actually, it's very hard work, but it's so important because so much is out of your control and you need to hire people that are cool with that.

Love that. Such a. I learned this the hard way once. I had one of my early projects. I. We were late and the had a product, was just so pissed. He's like, because I've been telling the CEO it's going to be on time. Because you've been telling me it's going to be on time. And then it wasn't. And why didn't you tell me that? And he's. And I was just like, okay, it'll never happen again. And he's like, you can't. Don't tell me that. Because that's not true. That may not. You can't guarantee that. And so that taught me that lesson of just like, yeah, you're right. Like, you want to say that, like, it feels so good. Okay, this will never happen again, but you just, you can't. And they know, they know you can't promise things like that.

Yeah. And sorry, I'm gonna quote Claire Hughes Johnson again, but she has this really fun phrase that she said in a talk at Glue Club that I've now latched onto and stolen from her, which is. She was like, promises like that are like letter bombs that you mail yourself that are going to explode in your face in like a year. And I was like the perfect metaphor. It's because it's like short term pain, right? Like, you want to make this person feel good right now, so you like promise them something, but in one year you're going to make them feel terrible, so don't do it.

Great advice. All right. Keep going. Yeah.

So again, could probably go on the like, topic of what it takes to manage and lead forever inside this stuff, but I'll give you two more that I yell about a lot In Glue Club, the first is that we spend huge amounts of time talking about hiring. Like, how do you get good at hiring? Like who? Like how do I. What's the right interview? How do I find the right people? Firing people is as important as hiring people. Getting good at identifying when someone does not belong or someone is not going to work out is actually a skill. And being good at it as a company and as a leader is as important as identifying the right talent. Because eventually if you're not good at firing people, what you have is essentially barnacles on a ship, really going forward with the ship metaphor anyway. But like, you know, it's drag people that are sitting around, not sort of pushing the team forward. So it's painful and it's horrible because it is humans, right? But. But when someone doesn't fit, you act. No one is right all the time when it comes to hiring. I actually say most people are wrong half the time. Like the best people in the world at hiring will tell you they have about a 50% average in terms of being right. That means half the hires don't work out. That means half the time you're going to need to fire the person. So it is, it's such an important skill to get good at, particularly when you're going through a lot of change. And the last one is humans are messy and it's very emotional. And when you're a leader, particularly if you have any kind of enneagram too, or just if you like to make people happy and you want to be liked. It can be so hard to lead teams because you get tangled in the people, right? Firing people is a painful experience. Reorganizing things, layering people, all these things are emotionally painful for the people and they're emotionally painful for you as a manager. But my mantra that almost always leads in a, in the best direction is serve the business, not the people. Meaning everyone is better off if this company is wildly successful, Everyone looks smart and, you know, makes lots of money or whatever. If this company grows and does what we all dream it can. So at the end of the day, the best decisions, the ones that are always going to be right, are the ones that are like, how do we make the. How do we do the right thing for this business? And it also helps in political situations, right? Like someone's acting weird or their Bob is raging all over the company. Like technically, everyone has the same goal. The goal is to build the biggest business possible. That's the answer. The answer is always like, what's the right thing? For the business and the people stuff can fall away when you actually focus on, like, what's the right thing for the business.

A really useful tool to do that, that I learned from my manager, is to think about when you're trying to decide, like, whether to fire someone or change a project, even though it's going to upset someone, is. Is to say, okay, if there were no emotions involved, if this person had no negative reaction to this, what would I do? Totally. And then that's the thing you should do. And then you just do it. And then the question is, how do I communicate this to them where they're least, you know, they. Their pain is lowest, essentially.

In the kindest way possible.

In the kindest way possible. And because to your point, if you optimize for the other thing, you have to make people feel good, like everything just falls apart. Like everything. They're going to suffer even more.

Absolutely. Direct is kind. And it, you know, it feels kind or really honestly easy to avoid these things or to work around them or to not. But at the end of the day, it's basically just a drag. Right. The barnacle thing. Like, it drags on your company, on your time, on your energy, et cetera.

Yeah. But again, very hard to do in real life. To do the thing that's hard and makes, you know, cause someone to be sad and upset and frustrated and.

And maybe so hard. And all these things are muscles, you know, you get better at. They don't become easy. It's not like anybody's like, oh, it's Olivia, I enjoy firing people. No, but you, you recognize it faster and you are like, oh, my, gonna need to go do this. You know, and that is actually, it's a practice and something that you need to practice to sort of become the kind of leader that leads these, like, long enduring companies.

Yeah. And this tool of thinking asking, what would I do if there were no emotions involved and this person wouldn't be upset? It helps you, like, realize. Okay, I see this actually doesn't make sense to just do it the easy way right now. Because it doesn't make sense.

Yeah, it strips away. Strips away the. The emotions.

Something else I wanted to make sure we spend a little time on is you have another tidbit along these lines, which is around putting most of your energy into high performers versus spending all your time. People that need help talk about that.

You know, as a leader, as a manager, like, you're running these teams and someone's struggling, and it's very easy to get dragged into that. And To. To sort of end up spending a huge amount of energy on it. But high performers are actually the future of your company. And if you think about it and if you've spent time on it, those are the folks where if you invest your time and energy in them, you're gonna get the sort of, like, 10x return that people talk about all the time in Silicon Valley. But what I've witnessed is that most people have, like, a high performer, and they just, like, leave them alone. They're like, that person's doing well, so I'm just gonna let them do their thing. And what. What I do when I have a high performer, that's like, my favorite thing in the world is invest time and energy in them and basically build a whole system of working with them that is designed to kind of draw out potential. And I would say there's there's two. Two things here. One is it's really important to realize that, like, our tendency is to actually spend time on low performers, and it is not a good use of our time. See the point about firing people? But the other thing is that actively investing in and developing high performers is something that's important to get good at as a leader, because that is how you kind of create these little rocket ships that end up, you know, you'll manage someone who's just like a project manager, and all of a sudden they're running a whole function inside the company eventually, but it's because you took time and energy to invest in them. And my basic way of doing that, not to, like, I could go, I could spend a long time on this. But I would just say is I run experiments. I basically develop a theory about someone. I think this person is capable of this kind of thing. And then piece by piece, it doesn't have to be like a whole job or whole project. It can just be like, you know, an incremental experiment. I'm gonna see if they can do this without, you know, with less guidance or support from me. I'm gonna give them a bigger project. I'm gonna give them something with more visibility. I'm gonna manage them less, oversee them less, whatever. All of those are experiments to basically test your theory and deepen your theory in terms of, like, this person's potential and their ability to help the company. And you're basically. For me, what I'm doing is kind of deeply getting to know that person and then trying to pair them with company needs. What do we need? What. Where. Where do we kind of like, you know, this person's Great. At zebra farming. Where do we need zebra farming? You know, so like, how do I get them working on bigger and bigger and more and more critical things? And to be honest, this is what people have done for me. Like, you know, at Facebook in particular, I benefited from people being like, ooh, like come help me with this thing. They saw potential in me and they asked me to help with something and it unlocked a huge amount for me. And so it's, it is such a powerful tool for getting more out of people that might be a little bit stuck if you leave them in this box, but if you start to expand the box, you can see you can really unlock people.

Okay, so speaking of high performers, you've worked with many very high performing founder CEOs. You worked really closely with Zuck, with Sheryl Sandberg, with Larry and Sergey Google, with Brett Taylor, who I just like, just like you try to read his resume, it's like it takes like three lines of things he's done over the course of his career. And so I just want to spend a little time on what are some things you've learned, like maybe a few things you've learned from them. That group that you find yourself sharing with other people.

Most that list is very long, but I'll give you a couple. The first one that I think is kind of counterintuitive is so I said I worked at Facebook, I worked on culture, which is one of those words that doesn't really mean anything. So I define it as sort of like the way that, the way we do things around here. And I thought my job was to like shape the culture. I thought it was to like push the culture. And the most humbling lesson I learned is 80% of the culture of a company is literally defined by the personality of the founder. Like Facebook is Mark, Google is Larry and Sergey. Like Google, when I was there, felt like it felt like a university. You know, it's where ideas are more important in a lot of ways than what's shipped. And it's like, you know, there's a campus and they basically wanted people to live there when I was there. You know, it was, it was designed to basically be a, a two PhD students paradise. Facebook felt like 19 year old hacker's dorm room when I was there, like that. And it was, you know, shipping above all and all else. And that it just, it seeped with Mark's DNA. And you know, I spent ages trying to create various changes inside the company or trying to kind of push a point. And Mark would say like literally One thing in an all hands, and it was like somebody threw a boulder into the pond. So our job as operators or as leaders around founders is to help articulate the culture that they're creating and to help, you know, extend it. My version of founder mode, which I know you've spent some time on on this podcast, is your job is to build a company that would make a decision the way the founder would when they're not in the room. Right? That is the work of building a company around a founder. But your job is not to shape culture. That is mostly defined by the literal personality, strengths and weaknesses of the person at the top. And that's been true of Mark and it's been true of Brett. Everywhere I go, that's who it is. You don't need a consulting firm to tell you just go do a personality diagnosis on your founder. And the weaknesses thing is real, you know, Like I've seen, I've seen and watched friends, like, try to ship a set of values at a company where. And it just doesn't match who the founder is. You say move fast and break things or whatever your version of that is. And your founder loves ambiguity and is perfectly happy with not making decisions. All that leads to is cultural dissonance. You know, it leads to people being like, wait, what? I thought we said, you know, we care about moving fast and making, making aggressive decisions. And it turns out, you know, so being really careful about what you say, because what people actually feel when it comes to culture is what you do and how you act every day. That is, you can never write anything down. And you will still have a culture. It will be created through the actions and the decisions that you make and that your founder makes. So that would be a huge one.

Let me spend a little more time on this because this is so good. So all this advice on culture and it's. It feels so true based on everything I've seen. So tip one, there is just you. You can't really change the culture. Maybe there's like a little bit on the edges. You could adjust. It will come down and trickle down from the founder. CEO probably mostly, but just the founders in general.

And CEO. Founder. CEO is probably the single biggest. Like co founder is like, it depends a lot on the company. Like, I think, I think stripe, you know, is probably very much like Patrick and John, you know, but it's not every co founder that has that level of power. Nuance.

Awesome. And then the. The way you describe culture, I think it's the way Seth Godin talks about it, too. Who's also been on the podcast. How cool is that? He. He said culture is. And what you said culture is the way we do things around here. Yeah, that's. That. That's what culture is, is how we is just, like, that's how people describe your cultures. The way we do things around here.

Yeah. I, you know, I, like, ran culture, whatever the hell that means, at Facebook for a hot second. I literally haven't done a values exercise since. And it sounds crazy, right? Because, like, in theory, I, like, know how to do this stuff. I don't really know how to do this stuff. But for me, the point is process and systems and how do we make decisions? Like, that's where culture actually lives. It is what you do. It's how you hire, it's how you fire. It's who you don't hire. It's all of those decisions that is culture. So whenever I'm working with a company or building a company, that's what I'm focused on. Not on, like, what's the shiny word that we're putting on the wall? You know what I mean?

Yeah. So the way you're describing is it, as you said, it's. It's what you do. It's not what you say. Yeah, awesome. Okay. Keep going.

Okay. Okay. I'll give you two more that are helpful. The. This one is marked with, like, a word. Classic. But he has this, like, very strong feeling that people don't escalate enough. And he was, like, very adamant about it at Facebook, and he brought it to czi, too, where he was like, escalation is a tool. And he's like, people get stuck. You know, they get stuck with two people with equal power trying to solve a problem. You can spend so much time bashing heads, going back and forth, and actually, what you just need to do is go up. Right? You need to go. The problem is that we think of escalation as, like, I'm. A and B and I are disagreeing. And so I'm going to go up to C and tell on B, right? Like, I'm going to go tattle to the teacher. That is not what escalation is. What escalation is is we. We disagree. Neither one of us has enough power to make this decision. Let's go to someone who does. My. My boss. My boss's boss, Whoever it is, as soon as you are stuck, escalate. Go together. Go make your case to whoever it is. Go together. Up. That is unlocking. Right. It's saving you a whole Bunch of time. And it's something that I've found as I've worked with companies and leaders include club. Like, it's not a muscle that's very comfortable for people, but it's. It's so smart. And, you know, Mark has a lot of these. But like, that one I really took away because, again, I think so many people think of escalation as bad. Like a failure. Like, I failed, so I had to escalate. No, it's a tool. It's what management is for. Like, they're there to unblock you. Let them unblock you. Stop, like, arguing over something you can't.

Decide, and they'll be so happy knowing you did not waste a week debating this and just arguing and just looking at data. It's like, okay, I can just tell you exactly what we should do. Let's go do that.

Exactly. You lack context or you lack power. And then the last one actually is from Cheryl Sandberg, who I learned an enormous amount from. Huge was like going to business school without going to business school or working with her. But I say it a lot right now, so I'm going to say it on your podcast so maybe some people will hear me. Growing more than 100% every year is a bad idea. A hundred percent. The happiest growth rate is 50%. A hundred percent is manageable. Anything more than doubling, and you are signing yourself up for a world of pain. And I have seen this over and over and over again. I had to scream way louder about it five years ago than I do now because we've been through collectively a lot of pain and a lot of layoffs. And, you know, obviously this. The combination of like, 20, 21 and then AI has led us to sort of talk about unit economics and scaling with tools, not people. But I still see companies, and I'm still talking to founders that are like, yeah, we're going to, you know, we're 50 people. We're going to be 150 people next year. And I'm like, could you possibly do that with a hundred people? You know, but here's what basically happens if you grow it more than 100%, which is you're growing too fast to de dupe all the issues. So, like, you. Somebody posts this role, it actually turns out that that role is also being hired for on this other team. So you're hiring two people who more or less have the same job description and are assigned to the same number or the same problem, but nobody talk to each other. And those two people both show up. And they're like, I am doing this. And the person's like, wait, I thought I was doing that. Anyway, so then you've got all this conf. Think about all the time and all the energy and all the money that goes into de duping that if you slow down, if you hire for quality and for real need versus sort of the panic hiring, whatever your sales model spits out or whatever, you'll actually find leverage. You find, oh, I didn't need that person, or I didn't need this whole team, or I didn't need this whole function, or I can wait for that. So slow down. And again, these are all just guidelines in terms of like the 50% is happy and 100% is manageable. But like, having seen enough of this, I can tell you like, these are good rules and you should pay attention to them. And sometimes you're like, I have to double or I have to more than double double or have to triple or whatever. I'm like, okay, just ask a whole lot of questions as you open roles. Ask a whole lot of questions as you hire because you will find duplication, you will find chaos coming in the front door. More people does not actually make you faster. Do you know what I mean? We think it does. It does not. It makes it harder. It makes it harder to get work done. It makes it slower. So you should be scared of adding people, not like, oh, this is the answer to all my problems.

Amazing. And just to be clear, you're talking about the growth of the company. So doubling in a year, bad idea. Like it. It's possible, but you're saying it's gonna be very hard and painful and, and probably a bad. A really bad idea.

Yeah. More than doubling.

More doubling, yeah. Yes, exactly. It's.

Please feel free to do whatever you want with your business.

Just advice. Uh, I just. This is top of mind. Cause I just had the interview with Matt McGinness, but so much of what he talked about is, is this resonates with what you're talking about. He talked a lot about under resourcing. Your team totally leads to much better outcomes because people don't work on the low priority stuff. They focus on only high priority stuff.

Yeah.

And the other is this idea of escalating. He talked a lot about that. Just like escalation is good. Tell me when there's something I can help with, please. I'm here waiting constantly to help.

Yeah. 100%. Yeah.

Amazing. So maybe for a final question, one of your former colleagues, Eric Antonow, who's Just like this epic dude that few people know about that I've chatted with over the last few months because he knows so many people that come on this podcast. He's a former Facebook person now at OpenAI. He asked him of what I should ask you about, and he told me something really insightful about you. He said that you had this really massive growth spurt at Facebook, which you shared and talked about. And then after you're leaving, you had this like, huge ambition to become coo, co. Become this huge, big deal boss person, just like take over the world. And then he noticed your ambitions significantly pivot to kind of working on community building and helping people with their careers. And you turned down really big C level role opportunities. And the way he described it is you. You were a dog that once thought you were a cat. And the other metaphor he uses, you change from AC Current to DC Current, which I don't know exactly what that means, but so does this resonate? And if so, just what. What happened there?

Eric is actually better at metaphors than I am, and I regularly rip his metaphors. But yes, Eric. Eric Antonov, the least well known but most brilliant person in my life. Yeah. So somebody. I gave a talk at a company recently and somebody asked the question, what's something you've changed your mind about? And I was like, woof. But I actually talked about this because so I. I'm. My brain is like developing this model that is not done yet. But it's basically this idea that, like, everybody has sort of a proving phase to their career where you're like, proving to yourself and probably to your parents and some other people, you know, that you're, like, good at stuff. You're like, I'm. I'm gonna. I'm gonna prove, you know, and. And it's an important phase because you're. You need to learn, you know, all the stuff we talked about. You need to learn what you're good at. You need to learn that you are good at things and that people should hire you for things and what are those things. But part of that phase is also kind of like doing what you think matters, like what you think you should do. You know, family programming or career books tell you this is what you should do, titles and, and all that stuff. And then I think everybody has a moment, and I think this moment varies wildly in terms of when it hits people, where you hit some sort of wall or I don't know what it is. Speed bump something, and the world forces you to say, okay, I've Proven myself, and I'm good at this thing. What do I want to do with it? You know, and for me, like, I spent, you know, 10 or 15 years proving to myself and to others that I was really good at this thing. You know, basically working with brilliant founders to help bring their vision to life. That's what you should hire me to do, right? That's what I was known for. And it turned out that that wasn't what I love doing anymore. And it was really, really hard to walk away from because there was a lot of shoulds. It was like, you should take this job with this fancy title. People are gonna think you're so cool. And, you know, you get to like, I call it a LinkedIn crush, where you're, like, really excited to post the job on LinkedIn, but you're deeply unexcited about doing the job. So you have all these LinkedIn crushes and you're like. And I sort of vividly remember this one job that I turned down where I had to go for many walks. And what I was repeating over and over again to myself was, what does this get you that you don't already have? What does this get you that you don't already have? And I think for me, it was this realization that these things that fed me early in my career just didn't feed me anymore, that I didn't get joy and excitement out of, you know, doing these jobs anymore. And I wasn't scared. Uh, so it led me to actually on a very long, windy journey, a founder journey, even though I have trouble with that title, just like the influencer title, to figure out what I wanted to build. And you know, what I would have told you I wanted to build three years ago is actually not what I'm doing today. But through a lot of really fun experiments and a journey that never ends, what I've discovered is that what I love doing is building safe spaces for leaders to learn and grow, but also to find sanity and connection in a world that's kind of insane, whether it's, you know, working in a startup or some other kind of insanity, but that, that feeds me and that there's nothing I love more than that. And I could not have told you that three years ago, but it was, to Eric's point. It really took a lot of work to switch currents or switch myself from a dog to a cat or whatever his metaphor is. And I think it's, you know, it's the work of. It's ongoing work, but it, it, it's that thing of, like, what do I want versus what do I think people expect of me?

There's so much depth there. This could be another entire podcast conversation talking through this journey. But I'm going to close with a note from your partner, Sarah. She told me that she has this sticker on her notebook with three pieces of advice that you gave her when she started at OpenAI. Get to know your customer. They have the answer. Be patient, because everything is going to change and just keep trying. So just as a final question, is there anything along those lines that you think might be helpful for people to hear, or is there anything else you want to share or leave listeners with?

Part of what I think is so important to realize inside of scaling and changing companies and, you know, the world is like, some things will always be true. And part of what I was saying to Sarah in the like, get to know the customer. They have, the answer is like, whatever bullshit is going on around you and whatever walls and ceiling are being rearranged, you know, this week, the customer is never going to change. That's a thing that will never change. And I think finding those, like, immovable objects, those compasses in the face of a storm, you know, which being inside of a scaling company in a startup, like, feels like a tornado, you know, and I think OpenAI is extra special on that front. You have to find these guiding lights that get you through that storm. And I think it's sort of the same thing as, like, serve the business, not the people. Like, what are the things that will always be true? We are here to do this. We are here to do, you know, we are here to serve the customer. And then the other piece of the sort of, like, the three things that she wrote down is like, I think that we, as humans, we seek stability, you know, like, our brains, like, would like things to stop changing. We would like things to stay the same. And that is just not a reality inside of companies that are growing and changing as fast as OpenAI or, you know, a lot of the companies today that are being built. So actually, you need to start to expect instability. You need to start to, like, just assume things are going to change. Assume you're going to have a new boss in six months. Right? I talk about this a lot when I talk to folks at OpenAI. Like, you need to stop expecting that anything's going to be the same in six months or a year. Like, like, you will have a different job, you will have a different boss. How do you prepare for that? Do you know what I mean? How do you Almost see the instability as stability because it's the only thing that is definitely going to be true. And part of that is to just keep going, you know what I mean? To just find these, these lights and these compasses or whatever metaphor sticks with you and focus on those. Because whatever is happening around you, like, you just gotta keep moving forward and keep learning as much as you can, because that's the real opportunity. Like whatever happens to the company, however successful it is, like all that you take away from it, I always say all that you take away from it is people that like working with you and want to work with you again and what you learned, that's it. You might hopefully take a bunch of money, but you might not. So like people and what you learned, that's it. Focus on that.

It's all about the friends you made along the way. That old line is true. Oh, man. Molly, I feel like we've gone for so long and we've just scratched the surface. I'd love to have you back to go deeper on a lot of this stuff. I'm going to skip the lightning round because we've gone long and I want to keep people from having to listen to more. So I'm just going to end with what are. What should people know about what you're working on? Where can people go find you online? And how can listeners be useful to you?

You can find me on LinkedIn and you can find me on Substack. I have a substack called Lessons that I'm slowly trying to turn into a community where we can talk about things, the real stuff. And you can find me at Glue Club, which, if you're a leader inside of one of these crazy companies that's changing all the time, we, we can be a great home for you.

What's the URL there? Just for folks to check.

It's glueclub.com glue.

Glue. G L U E C L U B dot com. Great.

Yeah, exactly. And in terms of people, what people can do to be useful to me, I love helping people, helping leaders with problems, like, I, I really get a lot of energy out of unsticking people and, and helping people feel supported and seen and helping them grow, I do that through Glue Club. So if you're a leader that feels like you want some sanity and some support in the face of whatever tornado you're in, that's a great place to come. But the. The same is true of Substack. So if Glue Club isn't for you, like, come on over to Substack. I've opened up a bunch of channels to just like talk about stuff, listen to people's problems, answer questions, because I love helping people and I think it's a complicated moment right now to be a leader and to figure out which way is up. So come on over.

Amazing. Molly, thank you so much for being here.

Thank you Lenny. This was really fun.

Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple, Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast. Com. See you in the next episode.