Molly Graham's Handbook for Leading Through Hypergrowth: Legos, J-Curves, and Why She Likes Being Scared
Lenny's Podcast
Molly Graham has spent roughly 18 years inside companies that were growing faster than anyone could keep up with: Google, Facebook, Quip, and the Chan Zuckerberg Initiative. She now runs Glue Club, a community for leaders in fast-changing environments. In this conversation, Lenny Rachitsky set out to collect the "greatest hits" of the frameworks Graham has developed, several of which were nominated by former colleagues. Her central argument runs through all of them. In a company that is scaling quickly, you have to grow as fast as the company does. That means repeatedly giving up what you have mastered, taking on work you are unqualified for, and building structures that stay clear while everything else keeps shifting.
Graham frames all of it as hard-won rather than prescriptive. She repeats something Ami Vora once told her, that "all advice is just someone telling you what they did," and describes her own record this way: she made every mistake in the book, got to the end of the book, and started inventing new ones.
Where the frameworks came from
Graham started in tech at Google in 2007, the week the iPhone launched. Google already had thousands of employees, but her communications department grew from 25 people to 125 in nine months. She calls that her first real experience of what extremely fast growth feels like, and the place where she started building the tools she still teaches.
She then followed Sheryl Sandberg and Elliot Schrage to Facebook in 2008. She stresses the context. Facebook had about 80 million users, roughly $270 million in revenue and 500 employees, and it was smaller than MySpace. The outcome did not feel inevitable. Many people assumed it would be sold to Microsoft, and friends asked her whether it wasn't just a site for college kids. When she left about six months after the IPO, five years later, Facebook had around 5,500 employees, $5 billion in revenue and more than a billion users.
Next she wanted to learn how to build something from nothing. She joined Bret Taylor's startup Quip a couple of months before launch and ran everything outside product and engineering. The experience taught her that going from zero to one is very different from "holding on for dear life" while a company scales around you, and it taught her how lonely building can be. Quip was eventually sold to Salesforce. Her last chaotic scaling job was helping Mark Zuckerberg and Priscilla Chan start the Chan Zuckerberg Initiative in its first two years. Philanthropy sounds calm, she jokes, but CZI had about 30 people the week she joined, bought two companies that same week, and grew to around 250 people that year. She says it required every tool she had collected.
Graham describes a personal study behind all of this. She wants to know what it takes to thrive inside changing companies rather than just hang on, and what separates a business that grows and then plateaus from a generational one. Her examples of that contrast are Twitter or MySpace versus Facebook, "billions in revenue versus hundreds of billions." A pattern she comes back to is that she only takes jobs she is "highly unqualified for." She gets bored easily, which she calls both a strength and probably her greatest weakness. "So, I like being scared."
"Give away your Legos"
Graham's best-known framework began at Google, and she calls Facebook "a masterclass" in it. She describes rapid scale as someone dumping a huge pile of Legos in front of kindergarteners and telling them to build something. The early feeling is excitement mixed with overwhelm, and people half expect to find an instruction manual under the pile. Eventually you get momentum and build a house, and you decide you were put on earth to build houses.
Inside a scaling company, she says, the moment you feel that way, "almost assuredly" someone will arrive to tell you it isn't a house, it's a neighborhood. You are asked to hand your half-built house to a new hire and go build dog parks and streets. The reaction is predictable. You aren't done with the house, you worry the new person will ruin it, you suspect houses were the fun part, and you fear dog parks will turn out to be irrelevant. She describes the mix of emotions as territorial paired with excitement and fear paired with joy. Then you get good at neighborhoods, and someone shows up to say it's a city, a country, a world.
She presents this as both the torment and the opportunity of scaling companies. The ground moves under your feet, and as soon as you get comfortable someone makes sure you aren't. But you can also go from being good at houses to knowing how to build entire worlds. Her main argument is that the company's growth curve is also the curve of how fast your job is getting bigger. If you stay and keep building houses, you end up buried under the pile. The opportunity is to stay on top of it by giving your job away regularly. At one point at Facebook she was giving her job away about every three weeks, "constantly rehiring" herself. She also recalls having regular "Legos talks" with colleagues once they started asking things like why a particular person was being hired or what some other team even did.
Bob the monster and the two-week rule
Lenny pointed out that knowing you should give away your Legos is different from being able to do it. Graham's tool for this comes from growing up on the Muppets. She realized that the emotional roller coaster of change would never go away, and that it may get worse with seniority, because you feel you are supposed to know what you're doing. So she externalized those emotions into a small monster she named Bob.
Bob's job, as she describes it, is to make you the worst version of yourself. He wants you to knock over the person who took the fun Legos, send rage emails at 9 p.m., and "burn the house down." Bob never leaves, so the skill is letting Bob do his thing without acting on it. The emotions are "normal and they are not useful." They are not a compass.
She also rejects the common advice to sleep on it. In her experience, the rage email you wanted to send at 9 p.m. is still one you want to send at 8 a.m. Her rule of thumb from Facebook is to give it two weeks. Reactions to a new hire, a reorg or getting layered tend to come in waves and pass within days. Anything that is still there after two weeks is "the real stuff," and you should raise it with a manager, friend or coach. "Everything else is just Bob."
When not to give away the Legos, and why careers are long
Asked whether there is ever a time to fight a change, Graham says she has no rule of thumb. In general, she thinks embracing change is much better than fighting it, because you can't see what is around the corner. She singles out being layered, when a manager is brought in above you, as one of the hardest experiences. She has also seen many cases where it turned out well even though the person couldn't see that at the time. Sometimes you learn it's time to leave or that this isn't the right pile of Legos for you, but in her view holding on "almost always leads us to the worst version of ourselves." Lenny called this a Buddhist way of thinking, and also noted that the Legos were never really yours. They belong to the CEO and the shareholders.
Graham adds a perspective she says comes from seniority. Work can feel as though your life is on the line, and a friend of hers points out that "careers are long" and nobody tells you that. A moment that feels dire is one chapter, or even part of a chapter. Lenny mentioned that he is on his fourth career, and Graham replied that the most interesting careers wind, with starts, stops, failures and successes, and that control is rarely what makes them work.
J-curves versus stairs
Sara Caldwell of OpenAI told Lenny that the J-curve framework was the one that helped her most in her career. Graham has given a TED talk on it but told the fuller story here.
She spent her first two years at Facebook in HR, working on employment branding and culture, and planned to stay until the IPO. Then Chamath Palihapitiya, who ran growth and mobile, took her to lunch and told her, in her paraphrase, that she was useless in HR and should come work for him. She says he has a way of insulting and complimenting you in the same sentence. The last option he offered was building a mobile phone. She had four reactions at once: this is incredibly stupid, is this actually happening, and it sounds kind of fun. Her boss, Lori Goler, was surprised he had offered it. Sheryl Sandberg told her the project would be dead in two months but that she could still take it because she would keep a job at Facebook. Her father told her not to do it. A friend asked why she didn't find out whether her skills were transferable.
She took the job and spent six months feeling "like an absolute idiot," asking the dumbest questions of her life in rooms full of brilliant people. At the end, Chamath gave her the lowest performance rating she had ever received, and she says he seemed to take some pride in it. The turn came after repeated trips to Taiwan for the hardware work. She came back and drew the layout of a mobile phone on a whiteboard to explain to him why something he wanted wasn't possible, and walked out realizing she actually knew things. Over the next three years she became an expert in mobile. She is blunt that the phone itself was a massive, costly failure for Facebook. It was not a failure for her, because it showed her she could take on things she didn't know about.
When Chamath pitched the job, he drew the framework on a whiteboard. Most people treat careers as stairs: you get promoted every two years, from manager to senior manager to director. He called that boring. The more fun careers are like jumping off cliffs. You do fall, for what Graham estimates is about six to nine months, but then you climb out on a J-curve that takes you far beyond where the stairs could have. Graham says that has been her experience. She believes fast-growing companies are especially good places to jump. Once people there believe you are capable, they will give you opportunities you are "deeply unqualified for." She ended her time at Facebook in product after also doing business development and hardware. Nobody would have hired her for those roles at the start, and she says she got them because she kept saying yes.
Which fears to listen to
Lenny asked how to tell a worthwhile J-curve from a fall that doesn't end. Graham separates kinds of fear. Financial fear is a concrete example of the kind you should listen to. She tells people to do the math. What monthly number do you need so you aren't constantly terrified, and can you cover it with consulting or other work? That number varies a lot by background and circumstances. She distinguishes "specific financial anxiety," which is useful, from "existential financial anxiety." The specific number is often smaller than your brain makes it out to be. She describes telling friends that if their number is $5,000 or $10,000 a month, the question is whether they believe they can get a consulting gig that pays that. Either they do or they don't. Lenny described his own version of this before taking a year off: he budgeted for six to twelve months of no income and decided in advance that he was comfortable spending it.
The other kind of fear, "I'm scared I can't do this, I'm scared I'll fail," Graham treats as a flashing green light. Taking the risk either proves you can do it or teaches you something about yourself. Her own example is her product role, the last chapter at Facebook. She says she is not a good product manager. She has a strong product mindset and can hold her own with product people, "but I'm not the person that cares about the button." She would not have learned that without trying. In her view, the biggest benefit is self-knowledge. Nothing accelerates it faster than trying something you don't know how to do and are scared of. Lenny quoted the line "the cave you fear contains the treasure you seek," and Graham agreed.
Being a professional idiot
On how to survive the bottom of the J-curve, especially when a project may fail before you climb out, Graham says the most valuable thing during the fall is learning, and nobody can take that away even if the project fails. She advises becoming a "professional idiot," the person who asks in meetings what everyone is talking about or what a word means. Often the question you thought was dumb turns out to be one everyone had and nobody dared ask. She calls this her superpower. She is the one who asks whether there are goals and why the meeting is happening, and she says that is usually what she was hired to do, which is to bring clarity.
Lenny compared this to Zevi Arnovitz, a young PM at Wix who first tried to be a "10x PM," flopped in an early meeting, and later impressed people with how quickly he improved. Zevi concluded that what people wanted from him was to be a 10x learner. Graham connected this to a conversation with a friend whose child is a high-school senior. Given what is happening with AI, they kept coming back to soft skills: grit, hard work, and learning how to learn. Inside companies, she says, "what you know today is way less valuable than what you can learn by tomorrow." She mentions hearing that Google rewrote its entire codebase every eight years, probably faster now, as an illustration that people who stop evolving become irrelevant. She calls evolution the underlying point of the Legos idea.
The waterline model: snorkel before you scuba
Graham is clear that the waterline model is not hers. She says it comes from "some business book somewhere." She learned it at her first job out of college, leading 75-day wilderness expeditions in Patagonia and Alaska for NOLS, the National Outdoor Leadership School, which teaches leadership and communication through expeditions. She now teaches it in Glue Club as a way to diagnose teams that aren't working.
In the model, a team is a boat trying to reach a destination, which stands for its goals. How hard that is depends on what is happening beneath the water. There are four layers from the surface down:
- Structural: goals, vision, roles and expectations, the structures that touch every member of the team.
- Dynamics: how the team works together, including culture, decision-making and conflict resolution.
- Interpersonal: relationships between two people.
- Intrapersonal: issues within a single person.
People usually dive to the bottom first and blame individuals. The rule is to "snorkel before you scuba." According to Graham, about 80% of team problems are structural or about dynamics, so you start at the top. Her most repeated advice in Glue Club is that if a manager does nothing else, their only goal should be clear roles and clear expectations. When she has taken over teams, she says, she has almost always found that no one knew what their job was or what success looked like. Fixing those two things resolves a large share of the other problems. People do cause problems, she acknowledges, but often because they are working inside a confusing structure.
When she asks founders for their goals, the answer is often unclear, and she considers that a structural problem in itself. People can't decide what to do each day without knowing the priorities, their role, the number they were hired to drive, and how that number connects to company goals. For performance issues, her first question is whether the person actually knows what is expected of them. Her approach is a two-way conversation. She says what she is seeing and asks what is going on for them. On listening tours she asks people what they think their job is and what number they were hired to drive, because their picture often differs from the manager's. "You described an elephant and they spat out a tiger." Clarifying sometimes transforms performance and sometimes doesn't, but she always starts there. She warns that you will feel like a broken record. You may have said something 45 times, and it turns out nobody heard the first 43.
Six rules for goals
Before listing her rules, Graham says she has "a bone to pick with OKRs." Founders often answer her question about goals with a spreadsheet of a hundred lines that reads like Greek. Goals, she argues, are a communication tool that tells people what to work on when they sit down each morning, and a huge spreadsheet doesn't do that. Goals should also fit the company's stage. At seed stage she sets goals every two months and iterates. An established business with a clear go-to-market machine can set annual goals, but for an early-stage company she calls annual goals a waste of time. Most of her rules come from Facebook, which she thinks was very good at this.
1. No company needs more than three goals. Facebook had the same three for the five years she was there: growth, measured as monthly active users, engagement, meaning how often people came back, and revenue. Goals were set roughly every six months. Her argument is that if Facebook could be governed with three goals, any business can.
2. One goal must win in a fight. People need to know what matters most. Her example: you could add monthly active users by buying bots in Indonesia, which would raise MAU but not engagement. At Facebook it was always clear that engagement won, because engaged users drive revenue and were "the heart" of the site.
3. Explain it like I'm five. An intern who started on Monday should be able to read the goals and understand them. That means spelling out acronyms and using numbers that make sense to ordinary people.
4. Strategy should hurt. She used to phrase this as "set non-goals," but she prefers Claire Hughes Johnson's line from Scaling People. If you aren't making painful trade-offs, you aren't helping people prioritize. People will work on something every day. Either you choose their priorities or they choose for you. When a founder insists on ten goals, she tells them six won't get done, so they can pick the four or let others pick.
5. One goal, one owner. Every number has a single name next to it, and that person is not the CEO. "Two people owning a goal is no one owning a goal." She calls this painful organizational work. Lenny said that at Airbnb they described it as needing someone's neck on the line, and that single ownership is highly motivating. Graham said it creates "a flood of clarity" that flows down from the owner.
6. Goals alone are not enough. She quotes James Clear's observation that winners and losers have the same goals. Founders tell her they set goals and nothing happened, and when she asks what they did afterward, they don't know. You need a process to follow up, hold people accountable, and learn. Early on especially, setting a goal is a way to find out how hard it is to move a number.
In practice, she says she doesn't audit goals scientifically. She asks a lot of "really dumb questions" until founders can state the one sentence and the one number they are trying to get across, and she notes that writing a hundred-line spreadsheet is easier than naming a business's three real drivers. Lenny added that Facebook's business, with its social network, marketplace and ads, was at least as complicated as most, which strengthens the case that three goals are enough.
Rules of thumb for leading through change
Graham says she isn't the person for management basics like running a good one-on-one. Her focus is leading through change, and she offered four rules.
You don't have to have all the answers. New leaders feel they are supposed to know. Graham says a leader's job, especially during rapid change, is to get good at finding answers and bringing people together to find them. That means saying "I don't know, let's go figure it out" often, which feels frightening. She has found that the most experienced leaders say it all the time. Lenny linked this back to Bob, the voice calling you an impostor. Graham called handling it a muscle and said that in a world changing this fast, "the war will be won by the people that are good at exploring and figuring it out."
Don't promise things you can't control. Recruiting tempts you to promise a smooth onboarding, a clear vision, or that someone will be CMO forever. She says promises about stability, titles, or never hiring over someone should be a flashing red light, because going back on a promise is the fastest way to demoralize high performers. It is better to be honest about what you can promise and hire people who are fine with that. She borrowed another line from Claire Hughes Johnson, who spoke at Glue Club: such promises are "letter bombs that you mail yourself" that explode about a year later. Lenny told a story from early in his career. He promised a leader who was angry about a late project that it would never happen again, and was told not to promise that because he couldn't guarantee it.
Firing is as important as hiring. Companies spend lots of time on hiring and little on recognizing when someone isn't working out. People who don't fit become "barnacles on a ship," a drag on the team. Graham says even the best hiring managers are right only about half the time, which means about half of hires will need to be let go. She calls that a critical skill during periods of change.
Serve the business, not the people. Leaders who want to be liked, and she mentions Enneagram twos specifically, get tangled up in the people during firings, reorgs and layering. Her mantra is that everyone is better off if the company is wildly successful, so the right decision is whatever is right for the business. She says this also helps when someone's "Bob is raging all over the company," because everyone officially shares the goal of building the biggest business possible. Lenny shared a tool from one of his managers: ask what you would do if the person would have no negative reaction, do that, and then figure out how to communicate it as kindly as possible. Graham summarized it as "direct is kind." These decisions never become easy, she says, but you learn to recognize them faster.
Invest in high performers
Graham argues that managers tend to spend their energy on people who are struggling and leave high performers alone because they're doing fine. She thinks that is backward. High performers are the future of the company and where the "10x return" comes from, while time spent on low performers is mostly wasted, which ties back to her point about firing.
Her method is to run experiments. She forms a theory about what a person can do, then tests and refines it step by step. She might give them less guidance, a bigger project, more visibility, or less oversight. Along the way she tries to match what she learns about the person to what the company needs: "this person's great at zebra farming. Where do we need zebra farming?" This is how, in her words, a project manager can end up running a whole function. She says people did this for her at Facebook, pulling her into projects because they saw potential, and it unlocked a great deal for her.
Lessons from Zuckerberg, Sandberg, Larry and Sergey, and Taylor
Graham chose three lessons from her list.
The founder defines most of the culture. She defines culture as "the way we do things around here," a phrase Lenny noted Seth Godin also uses. She once thought her job at Facebook was to shape the culture. The humbling lesson, as she tells it, is that about 80% of a company's culture comes from the founder's personality. When she was there, Google felt like a university, a "two PhD students' paradise" where ideas mattered as much as shipping and people were encouraged to live on campus. Facebook felt like "a 19-year-old hacker's dorm room," focused on shipping above all else. She spent ages trying to push changes, and then Mark would say one thing at an all-hands and it landed like a boulder in a pond. Operators around a founder should help articulate and extend that culture. Her version of founder mode is building a company that makes decisions the way the founder would when they aren't in the room. She says that has held true with Mark and with Bret.
She warns about value statements that don't match the founder's weaknesses. If you declare that you move fast while the founder loves ambiguity and avoids decisions, you get cultural dissonance. Culture lives in what you do: how you hire, fire, and make decisions. She says she hasn't run a values exercise since Facebook and focuses on processes and systems instead of "the shiny word that we're putting on the wall." Asked about co-founders, she said it depends. She guesses Stripe reflects both Patrick and John, but not every co-founder has that level of influence.
Escalation is a tool. She calls this a Zuckerberg classic that he pushed at Facebook and again at CZI. He felt strongly that people don't escalate enough. Two peers with equal authority can waste a lot of time arguing. People treat escalation as tattling to the teacher. The version she learned is that when neither of you has the power or context to decide, you go up together and make your case to someone who does. That is what management is for. She says it is still an uncomfortable habit for many leaders she works with.
Don't grow headcount more than 100% a year. She credits this to Sheryl Sandberg, who she says taught her as much as business school would have. Her guidelines are that 50% annual growth is the happiest rate, 100% is manageable, and more than doubling means "signing yourself up for a world of pain." She says she had to argue this much harder five years ago. After the 2021 era, the layoffs that followed, and AI, people talk more about unit economics and scaling with tools, but she still meets founders planning to go from 50 to 150 people and asks whether 100 would do. The mechanism she describes is that above doubling, you grow too fast to catch duplication. Two teams hire people for essentially the same job, both arrive believing they own it, and time and money go into sorting it out. Hiring more slowly, for quality and real need rather than "whatever your sales model spits out," reveals where you didn't need a person, a team, or even a function. If you must grow faster, she says to ask many questions every time you open a role. Her conclusion: "More people does not actually make you faster." You should be wary of adding people rather than treat it as the answer. Lenny connected this to Matt MacInnis's case for deliberately under-resourcing teams.
From proving to purpose
Lenny passed along an observation from Eric, a former Facebook colleague of Graham's now at OpenAI. After Facebook, Graham seemed intent on becoming a COO or CEO, and later turned toward community building and turned down large C-level roles. Eric had described this as going from a dog to a cat, or switching from AC to DC current.
Graham said she is working on a model that isn't finished. In her view, everyone goes through a proving phase, showing themselves, their parents and others that they're good at things and finding out what those things are. Much of that phase is also doing what you think you should do, guided by family expectations, career books and titles. At some point, and the timing varies a lot, you hit a wall or speed bump and have to ask what you want to do with what you've proven. She spent 10 to 15 years proving she was very good at helping brilliant founders bring their vision to life, and then found she no longer loved it.
Walking away was hard because of all the "shoulds." She describes "LinkedIn crushes," jobs you'd be excited to post about on LinkedIn but not excited to actually do. She remembers taking many walks over one offer she eventually declined, repeating to herself, "What does this get you that you don't already have?" The things that had fed her early in her career no longer did, and those jobs no longer scared her. That started what she calls a long, winding founder journey, though she is uncomfortable with the word "founder," just as she dislikes "influencer." What she would have said she wanted to build three years ago is not what she is doing now. Through experiments, she found that what she loves is building safe spaces for leaders to learn, grow, and find sanity and connection in a world that feels insane. She describes this as ongoing work, and at its core it means asking what she wants rather than what people expect of her.
Finding stability in instability
To close, Lenny mentioned that Sara Caldwell keeps a sticker on her notebook with three pieces of advice Graham 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.
Graham explained the reasoning. However the walls and ceiling get rearranged in a given week, the customer doesn't change. In a scaling company, which she compares to a tornado and says OpenAI is "extra special" at, you need fixed points to steer by, just as "serve the business, not the people" gives you one. People naturally want stability, but in companies growing this fast, you should expect instability. She tells people at OpenAI to assume they will have a different job and a different boss within six months and to prepare for that. The goal is to see instability itself as the stable fact, since it is the one thing guaranteed to be true.
Her final point is about what lasts. Whatever happens to the company, she says, you leave with two things: people who liked working with you and want to again, and what you learned. You might also leave with money, but you might not. "So, like people and what you learned. That's it. Focus on that."
You've worked with many very high-performing founder CEOs: Zuck, Sheryl Sandberg, Larry and Sergey at Google, Bret Taylor.
Google when I was there felt like two PhD students' paradise. Facebook felt like a 19-year-old hacker's 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.
Sara 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 2 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 Bret Taylor on scaling Quip, which he sold to 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 Sheryl and Bret 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 Antinau, Ashley Murphy, and Sara 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.
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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. Feel like you're the kind of guest where it's 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, but let's help people understand why they should listen to this advice. What's kind of the backstory on these frameworks, where do 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 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 9 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 you know, sort of all the tools that I started developing from there.
After Google I left and followed Sheryl Sandberg and Elliot Schrage to Facebook and I spent 5 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 it to Microsoft. When I told people I was going there, they were like, "Isn't that just like a site for college kids?"
And so I was there for 5 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, comes from, you know, sort of that rapid scale at Google and Facebook.
But I left Facebook right after we went public, about six months after we went public. And 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 Bret Taylor, a startup called Quip. 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, you know, sort of like 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 one and then from one to two, 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 philanthropy sounds calm, you know what I mean? We're like, "Oh, you're 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 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 of what does it take to thrive inside growing and changing companies, not just hang on for dear life. You know, what does it take to lead in the face of constant change? And really, the other piece that I find truly fascinating is what genuinely makes the difference between 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're just here: 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, head of product at Anthropic.
Yes.
Amazing. Former podcast guest, also speaker at the Lenny Friends Summit two years ago. This other point you just made about how you've always gone to places that have been way beyond, I forget how you phrased it, but just like beyond your current capabilities almost, and were very difficult. I just had Matt MacInnis on the podcast. He was COO at Rippling, now CPO at Rippling, and I just recorded an episode with him, and he had this really powerful quote that 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.
Yeah.
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 this advice of giving away your Legos?
So, this definitely started in my experience at Google. And then Facebook was like a 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 somebody putting down a giant pile of Legos in front of 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, whoa, 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? Isn't there an instruction manual hidden under this pile somewhere?
But then you start building and you're like, "Oh, okay." 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 building houses. Like, I was put on earth to build houses.
And almost assuredly inside of scaling companies, as soon as you're like, I feel good at this and I should do this forever, somebody's going to show up and be like, "Okay, it's not a house. It's a neighborhood." And you need to 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 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 that dog parks are irrelevant eventually and it's going to turn out we're in the house building business." So, there's this incredible set of emotions that come: territorial paired with excitement, you know, fear paired with joy.
But eventually you pass the house off and then you go work on neighborhoods and you're sort of like, okay, 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, and it just goes on and on and on.
And for me, 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? I've been doing this for 18, 20 years. 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. If you've gone through this, you so understand what this is like. And also just the Legos metaphor is 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 when I was at Facebook in particular. I would find that 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 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 thing,
a 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 and to 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? Held on to 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 3 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, 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 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, 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 9:00 p.m. 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 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.
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, go to bed and wake up tomorrow morning and you'll feel better. And the truth is that, you know, like I want to send the rage email at 9:00 p.m., you still want to send it at 8 a.m. And a lot of these emotions just do not go away in 24 hours. So my rule of thumb from Facebook was give it two weeks. And, you know, the sort of 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 been around for two weeks, is 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 a rule of thumb for when you actually shouldn't give away your Legos? When it's like, okay, maybe you should fight back 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, 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 this isn't the right pile of Legos for you, but it'll end up taking you somewhere that's worth exploring. Holding on to things almost always leads us to the worst version of ourselves.
It's 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 CEO's Legos, the shareholders' Legos. So, you think they're your Legos, but no, you're not.
Well, it is. You know, I will say one of the hard-earned things is it can feel very 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, 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 going to be okay. You know, like a friend of mine says, careers are long, and nobody tells you that, but 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 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, Lenny.
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.
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, Sara 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, like, you can listen to the very packaged 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, the first two years I was in HR. And I was doing sort of employment branding and culture work and I was ready to stay there, you know. I think I had in my head I was going to stay there till we went public. That was my plan, just cuz I wanted to help the company through that moment, again, in my head.
So this guy that many people know, Chamath Palihapitiya, came to me, and Chamath ran growth and mobile at the time, and he came to me and we had lunch and he said in his very way, like, you're useless, what are you doing in HR, this is stupid, you should come work for me. And anybody that knows Chamath is like, yes, that is actually what he said. He manages to insult you and compliment you in one sentence. 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 going to go build a mobile phone. 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 with Chamath and I went and asked my boss, Lori Goler, who's 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, you know, I basically just could not get it out of my head. But it didn't make any sense, A, that Chamath had asked me because I was in HR, like, what am I doing? I know absolutely jack about mobile. But, you know, I had worked on a project with him and he, I guess, thought I was smart. And I talked to Sheryl 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, 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 it out of my head. And my friend said to me, you know, you've proven you're really good at this sort of companywide 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. I basically felt like a total jackass all the time. And I was sitting in rooms with these 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 the lowest performance rating I've ever gotten in my life. And, you know, it just felt like falling off a cliff. And then slowly, I remember, I had been doing all these trips to Taiwan because we were actually working on hardware, and at some point I came back from Taiwan and I drew on a whiteboard for him the layout of a mobile phone, trying to explain to him why something he wanted to do was not possible. And I so vividly remember walking out of that meeting being like, oh, I actually know things. And slowly then over the following three years I became an expert in mobile and, you know, the phone itself was a giant failure, massive costly failure for Facebook. But 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 had 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 there. The way a lot of people do careers is a set of stairs. You can be boring, to use Chamath's word, 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 6 to 9 months, but then this thing happens where you climb out." And, you know, the picture he drew had this J-curve, 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 terrible fall and that experience of falling has been more than worth it.
And, you know, part of the reason why Sara 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 know, no one would ever have reasonably hired you to do. 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 cuz I kept saying yes to things.
Molly, I got tingles listening to this story.
Wow.
Does it sound familiar, Lenny?
It does. And what 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, no, 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 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 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 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 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 cuz I'm like that.
And it sounds like Matt MacInnis 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, you'll have learned something too. You know what I mean? You'll have learned, like, I took this job in product at Facebook, which was my last chapter there. And let me tell you things that people should never hire me to do. Like, I am not a good product manager. I've got a great product mindset. I can sit in a bunch of chairs and hang with the product folks, but 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 failed, 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, and that'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 6 months or a year to live without any income. Am I comfortable just burning through these tens of thousands of dollars to explore and 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, you're saying runway, I say burn rate. So like, we both were raised inside of companies, inside of tech. But I think it is do the math, right? What can you afford? And it's both what can you afford and still feel safe, because, again, I think that that is different for everyone. But it is such an important set of math to do, because a lot of times that number is smaller than you think it is, than your brain makes it out to be, if you have this sort of existential financial anxiety. I always say specific financial anxiety is much more useful than existential financial anxiety.
And you know, some friends are leaving jobs and I'll be like, hey, 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? And it's 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.
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 how do you create enough space to give you a chance to start to unfall?
I mean, 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, the 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 is like, what are we talking about? 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 it turns out that a lot of the questions in the world, you're sitting in the meeting and you're like, this is a dumb question, everyone's going to 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? 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 ask those dumb questions, it's a superpower. I always say that actually my superpower is being a professional, because I'm the one that shows up in a room and is like, do we have goals? What are we doing? 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 a very young PM, just getting started. And he's like, "Okay, I need to be a 10x PM, because that's what they expect of me. That's how I think of a 10x PM." 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 10x PM. They're all going to see that. 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 10x PM 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 is the plan? What are we telling this senior in high school 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 was this idea of soft skills, and that actually the only thing you can really anchor on right now is teaching kids grit, teaching them hard work, teaching them learning, right? 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 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 irrelevant. Somebody once told me, I'm sure this is faster now, but they rewrote the entire codebase at Google every eight years, which means that if you're not learning, if you're not evolving, then you become irrelevant and extinct. It's actually the whole underlying point of the Legos stuff, that 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 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 help them develop curiosity about the world.
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 the waterline model, and another former colleague of yours said this is the most impactful thing that they've learned from you in their career. So talk about the waterline model.
Okay. Yeah. Well, first of all, the waterline model is not mine. 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 NOLS, the National Outdoor Leadership School. And NOLS basically teaches essentially leadership and communication skills to students. I was mostly leading 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 NOLS, 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? What are we trying to build or ship or do? And essentially that is going to be harder or easier based on whatever the shape of the ocean is, right? If it's really choppy, it's harder. If it's smooth and calm, it's going to be easy to get to your goals. So the waterline basically asks the question, 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, 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 how the team works together. It's culture, it's decision-making, it's how we resolve conflict, all the sort of 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 with 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, 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 a huge percentage of other issues on a team. But the main thing is where you start, and just always starting at that structural level or the dynamics level and not immediately going to the people. Because yes, people cause all sorts of problems, but a lot of times the problems are happening because they're existing inside of a structure that's confusing.
Another very vivid metaphor, and 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 jump to: 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 that maybe the role isn't clear, or what success means for that role is not clear.
You know, every company I've worked with or advise, I often start with, 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, okay, role, right? Do I know what my job is? Do I know what number I was hired to own and drive? And then, do I know what success looks like? How does my role tie to that overall goal that the company has?
Just literally right there you've got probably 80% of problems inside of companies, because this is the hard work of company building. 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, 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 to start at the top.
So what would you do there? Say you're a manager, you're having an issue with a team member. Would you go and ask, hey, let's just make sure we're aligned on goals and roles? Is that 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, here's what I'm seeing, and tell me what's going on for you. Do you know XYZ? Tell me what you know. When I take over a team, when I'm doing my sort of listening tour, part of what I'm asking is, what do you think your job is? What number were you hired to drive? Because what you'll find is often 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 coming back to, okay, no, we're building an elephant, you're in charge of the trunk, will in some percentage of cases actually make a huge difference to the person's work and time and performance.
And in plenty of cases it doesn't, but that's always where I would start, because so often it's just a more fundamental problem that then would lead you to look at other things across the team. But yeah, I would say two-way dialogue. But reclarifying 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 redescribe it in order for people to hear you and to re-understand their role and what they're doing.
I love how you reframe the way I approached it, by starting with: here's what I'm seeing, what are you seeing? What do you think your role is? The very 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?
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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 feels like it's written in Greek. And when I look at it, I'm like, this doesn't create clarity for anyone.
And it brings me back to sort of like what is the point of goals? 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 you really have to ask the question, what is right for me at 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 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. 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 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 should hurt. And you know, my rule 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 it 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. 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 learning. You might be wrong all the time, but you're learning what it takes to move the number. So setting the goal by itself is not enough. You have to build a process in the system to actually learn from the goal.
Wow. There's so much power in this list. It's such a 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 just 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 if you feel like someone else may be doing the thing or feels like it's not fully your responsibility, there's so much less energy 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, you've done it. If you don't, you've done a bad job. That is 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, you know, to go back to the waterline model, I would say so often you'll actually find companies that have set goals, but no one owns the goals. Everyone owns the goals. Multiple people own the goal. And it's like you didn't actually get all the way to the answer, you know. And I will say the ownership thing is hard. 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 I described it at Airbnb was just like 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 strategy hurting. I love that. I love that phrase. 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 doing. A big part of strategy 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 do you go into a company and just go through a checklist essentially of here's the six things I look at to tell me where there's opportunity to improve?
When I work with founders and I see their goals, I use it as a way to get to know the business, and I'm just going to be like literally, what is this? What are you trying to explain? And I can usually, through, you know, asking a lot of really dumb questions, which, like I said, is one of my superpowers, get them to explain to me the one sentence and the one number that they're actually trying to get across. But it takes work. And that's part of, you know, it's almost easier to write the 100-line spreadsheet than it is to say, wait, what are the three drivers of this business, genuinely? What are they? And how do they relate to each other? And, you know, there can be things underneath them, but there's three at the top that matter. So yeah, 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, there's a lot going on. And if they can work with three goals, you can do that, too.
Yeah.
And to your point, if it's not hurting, then you're doing something wrong.
Yeah.
I love how this is very much what I wanted this chat to be. It feels like every little segment could be its own podcast where we could talk about this for hours. So I'm really excited 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 leaders that are leading through change and growth, the list is probably long, but, you know, I always say to people, don't come to me for management 101. I'm not the person to ask on how to run the most effective one-on-one with your people. 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, uh-oh, who gave me this job? You know, and you sort of feel like you're supposed to know the answer to things. People come to you and ask questions and you're like, 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 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?" You're like, "Oh, I should have a good answer." And
so I think that's a good reminder of this idea that 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. Impostor, impostor, impostor. Yeah.
Just remembering there's going to be this part of your head, and that's okay. It's there, but it doesn't mean
Absolutely. And these things are muscles, you know. Dealing with Bob is a muscle, right? Learning to not react to all those things that attack you. But also learning, oh, in this moment when someone asks me a question, actually, I should be like, I don't actually know. Let's go. Who should we ask? How can we learn this? How can we explore this together? What do you think? Those are all actually very powerful questions, and they're terrifying, you know, particularly earlier in your career as a leader and a manager.
Awesome. So, yeah. So the lesson there is no one expects you to have all the answers as a leader.
No. And it's particularly in this world, right? The one that's changing as fast as it is. Nobody knows, you know, nobody knows what the answers are. In a lot of cases, the war will be won by the people that are good at 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, particularly when you're hiring people, to be like, "Oh yeah, your onboarding will be smooth and calm and everything's clear and we figured it out. Let us tell you
our vision and how obvious and clear and smart, and then they show up and it's like, "Oh shit." You know what I mean? Like 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, cuz there is literally no faster way to demoralize high performers than going back on a promise, right? Everyone that has been through it knows that feeling of like, 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, all of that is actually 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. I learned this the hard way once. I had one of my early projects. We were late and the head of product was just so pissed. He's like, "Because I've been telling the CEO it's gonna 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 I was just like, "Okay, it'll never happen again." And he's like, "Don't tell me that, cuz that's not true. You can't guarantee that." And so that taught me that lesson of just like, yeah, you're right. You want to say that, it feels so good: "Okay, this will never happen again," but you just can't, and 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 on to 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, that is the perfect metaphor. It's cuz it's like short-term pain, right? Like you want to make this person feel good right now, so you 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 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? 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 for it with the ship metaphor, anyway. But, 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 when someone doesn't fit, 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'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 2 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 manager. But my mantra that almost always leads 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 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. 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 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 whether to fire someone or change a project even though it's going to upset someone, 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 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 of making people feel good, everything just falls apart. They're going to suffer even more down the road.
Absolutely. Direct is kind. And, you know, it feels kind, or really, honestly, easy to avoid these things or to work around them, but at the end of the day it's basically just a drag, right? The barnacle thing. It drags on your company, on your time, on your energy, etc.
Yeah. But again, very hard to do in real life, to do the thing that's hard and causes someone to be sad and upset and frustrated 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, I enjoy firing people." No, but you recognize it faster and you are like, "Oh my, I need to go do this," you know? And that is actually a practice and something that you need to practice to sort of become the kind of leader that leads these long, enduring companies.
Yeah. And this tool of asking what would I do if there were no emotions involved and this person wouldn't be upset, it helps you 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 the emotions.
Mhm. 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 with people that need help. Talk about that.
You know, as a leader, as a manager, you're running these teams and someone's struggling, and it's very easy to get dragged into that and 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 going to get the sort of 10x return that people talk about all the time in Silicon Valley.
But what I've witnessed is that most people have a high performer and they just leave them alone. They're like, that person's doing well, so I'm just going to let them do their thing. And 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 two things here. One is it's really important to realize that our tendency is to actually spend time on low performers, and it is not a good use of your 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. You'll manage someone who's just 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, 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 a whole job or whole project, it can just be an incremental experiment. I'm going to see if they can do this with less guidance or support from me. I'm going to give them a bigger project. I'm going to give them something with more visibility. I'm going to manage them less, oversee them less, whatever. All of those are experiments to basically test your theory and deepen your theory in terms of this person's potential and their ability to help the company. And 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? This person's great at zebra farming. Where do we need zebra farming? So 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. At Facebook in particular, I've benefited from people being like, "Oop, 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 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 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 at Google, with Bret Taylor, who, you try to read his resume, 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, maybe a few things you've learned from 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 the way we do things around here. And I thought my job was to shape the culture. I thought it was to 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. Facebook is Mark. Google is Larry and Sergey. Google, when I was there, felt like a university, you know, where ideas are more important in a lot of ways than what's shipped. And there's a campus and they basically wanted people to live there when I was there. It was designed to basically be a two PhD students' paradise. Facebook felt like a 19-year-old hacker's dorm room when I was there. And it was, you know, shipping above all else. And it just 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 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 Bret. 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. I've seen and watched friends try to ship a set of values at a company, 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. It leads to people being like, wait, what? I thought we said we care about moving fast and 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. 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, it feels so true based on everything I've seen. So tip one there is just you can't really change the culture. Maybe there's a little bit on the edges you can adjust. It will come down and trickle down from the founder CEO probably mostly, but just the founders in general.
The founder CEO is probably the single biggest, like
Co-founder is like
It depends a lot on the company. I think Stripe, you know, is probably very much like Patrick and John, but it's not every co-founder that has that level of power and influence.
Awesome. And then 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 said culture is, and what you said, culture is the way we do things around here.
Yeah.
That's what culture is. That's how people describe your culture: the way we do things around here.
Yeah. You know, I 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 in theory I 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. 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 what's the shiny word that we're putting on the wall. You know what I mean?
Yeah. So the way you're describing it is, as you said, 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. This one is marked with
Zuckerberg classic, but he has this very strong feeling that people don't escalate enough, and he was 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... The problem is that we think of escalation as, like, 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 disagree. Neither one of us has enough power to make this decision. Let's go to someone who does. 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 in Glue Club. Like, it's not a muscle that's very comfortable for people, but it's so smart. And, you know, Mark has a lot of these, but 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. They're there to unblock you. Let them unblock you. Stop arguing over something you can't decide.
And they'll be so happy knowing you did not waste a week debating this and then 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 Sheryl Sandberg, who I learned an enormous amount from. Huge. It was like going to business school without going to business school, 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. The happiest growth rate is 50%. 100% 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 the combination of 2021 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 50 people, we're going to be 150 people next year. And I'm like, could you possibly do that with 100 people?
But here's what basically happens if you grow more than 100%, which is you're growing too fast to dedupe all the issues. So somebody posts this role, and 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 talked 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. So then you've got all this conf... and think about all the time and all the energy and all the money that goes into deduping 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 the 50% is happy and 100% is manageable. But having seen enough of this, I can tell you 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, or I 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's possible, but you're saying it's going to be very hard and painful and probably a really bad idea.
Yeah. More than doubling head...
Head count. Yeah.
Exactly.
Please feel free to do whatever you want with your business.
Just advice. This is top of mind because I just had the interview with Matt MacInnis, and so much of what he talked about resonates with what you're talking about. He talked a lot about underresourcing your team.
Totally.
It leads to much better outcomes because people don't work on the lower 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 Antinau, who's just 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.
I asked him 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 left, you had this huge ambition to become COO, CEO, become this huge big deal boss person, just 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 were a dog, and now you're a cat. And the other metaphor he used is you changed 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 happened there?
Eric is actually better at metaphors than I am, and I regularly rip his metaphors. But yes, Eric, the least well-known but most brilliant person in my life.
Yeah. So 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 my brain is developing this model that is not done yet, but it's basically this idea that everybody has sort of a proving phase to their career, where you're proving to yourself, and probably to your parents and some other people, you know, that you're good at stuff. You're like, I'm going to prove it. And it's an important phase because 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 doing what you think matters, what you think you should do. You know, family programming or career books tell you this is what you should do, titles 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?"
And for me, I spent, you know, 10 or 15 years proving to myself and to others that I was really good at this thing, 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 loved doing anymore. And it was really, really hard to walk away from, because there were a lot of shoulds. It was like, "You should take this job with this fancy title. People are going to think you're so cool." I call it a LinkedIn crush, where you're 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 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 doing these jobs anymore, and I wasn't scared. So it led me 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 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 working in a startup or some other kind of insanity. That feeds me, and there's nothing I love more than that, and I could not have told you that three years ago. But 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 ongoing work. But it's that thing of, 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 Sara. 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 that some things will always be true. And part of what I was saying to Sara in the "get to know the customer, they have the answer" is, whatever is going on around you and whatever walls and ceilings are being rearranged this week, the customer is never going to change. That's a thing that will never change. And I think finding those immovable objects, those compasses in the face of a storm, which being inside of a scaling company and a startup 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 serve the business, not the people. What are the things that will always be true? We are here to do this. We are here to serve the customer.
And then the other piece of the three things that she wrote down is, I think that we as humans seek stability. Our brains 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 a lot of the companies today that are being built. So actually, you need to start to expect instability. You need to 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. You need to stop expecting that anything's going to be the same in six months or a year. 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 lights and these compasses, or whatever metaphor sticks with you, and focus on those, because whatever is happening around you, you just got to keep moving forward and keep learning as much as you can, because that's the real opportunity. Whatever happens to the company, however successful it is, 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 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 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 can be a great home for you.
What's the URL there, just for folks to check out?
glueclub.com.
Glue, G-L-U-E.
G-L-U-E.
C-L-U-B.com. Great.
Yeah, exactly. And in terms of what people can do to be useful to me, I love helping people, helping leaders with problems. I really get a lot of energy out of unsticking people 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 same is true of Substack. So if Glue Club isn't for you, come on over to Substack. I've opened up a bunch of channels to just 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.
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