Countdown of the top 10 episodes of the year

Lenny: Welcome to Lenny’s Podcast. I’m Lenny and my goal here is to help you get better at the craft of building and growing products. Normally, I interview world class product leaders and growth experts to learn from their hard won experiences building and growing today’s most successful companies. But today is going to be a very different and unique episode. I launched this podcast about six months ago. We’ve done exactly 50 episodes at this point. We’ve also done over 2 million downloads since we launched. The podcast is a top 10 technology podcast across Apple and Spotify globally. And I believe there’s about 40 to 50,000 subscribers or followers of the podcast across Apple and Spotify, which is all very exciting and kind of blows my mind.

So what I decided to do with this final episode of the year is to look back at the 10 most popular episodes that we’ve done so far. So what I’m going to do is count down from the 10th most popular episode to number one and play a clip or two from that episode that I found to be most interesting or that’s been the most popular. I’ve never done this sort of episode before. We’ll see how it goes. I think it’s going to be really interesting. If it’s not, we will never do it again. And if it is, awesome. Either way, enjoy. We’re going to get right into it after a short word from our sponsors.

Adam Grant (00:01:19): Have you ever wondered what makes great minds tick? I’m Adam Grant and on my new podcast, Rethinking, I’m trying to find the answers. Every week I interview some of my favorite thinkers to learn how we can bring out the best in ourselves and others. I talk to defying rock climbers, Oscar-winning filmmakers, creators like Lin-Manuel Miranda, entrepreneurs like Mark Cuban and thought leaders like Brene Brown. Find Rethinking on Apple Podcasts, Spotify, Amazon Music, or wherever you listen.

Welcome back and let’s kick off this countdown with the 10th most popular episode of the year, and that is with April Dunford. April is the author of obviously awesome. She, in my opinion, is the smartest person in the world on positioning and how to figure out positioning for your product. And here’s April describing the five steps to figure out your product’s positioning.

Say that you’re a PM or founder that’s ready to start figuring out their positioning for their product. What’s the first thing that you do?

April Dunford: I actually think the first step in a good positioning exercise is to really understand what do we have to position against? So put another way, it’s like saying, what do I have to beat in order to win a deal? So in positioning work we call this competitive alternatives. Now, how people mess up this first step is, I say competitive alternatives and they think competition. So things that look exactly like me. But in B2B we kind of have two sets of competitors. We have status quo, which is whatever the company is doing to attempt to solve the problem right now, even if it’s crappy and not great. And then there’s, if the company does decide they’re going to buy something different, they usually make a short list. So, it’s whoever else lands on the short list. I need to be able to put a stake in the ground and say, I got to beat all that in order to win a deal.

Now most folks will discount the status quo, but they shouldn’t because in B2B we lose about 40% of our deals to, “No decision,” which actually means we lost to the spreadsheet, we lost to pen and paper, we lost to interns. And if we’re not positioning well against that, we’re never going to get the customer to come off of that. So I got to win against status quo, but I also have to win, most of the time, if it’s B2B, you don’t just buy the first thing you come across, you make a short list of alternatives and I got to win against those as well.

So step number one, what am I positioning against? Once I have that stake in the ground, then I can start thinking about what makes us different. So the easiest way to do this is, okay, this is what I have to position against, what have I got capabilities wise that the alternatives don’t have? So feature function or even capabilities of the company, which could be pricing or professional services around other things that you’ve got, but also capabilities of the product. What have I got that the alternatives don’t have? And I can make a giant list of these things. And then I can translate that stuff into value by going down the list and saying, okay, we have this great feature, so what? Why does a customer care about it? What is the value that feature enables?

When I do that mapping over to value, what generally happens is I end up with two or three value buckets or value themes. And quite often those value buckets or value themes are different than what I would’ve gotten if I got all the smart people in my company together and said, hey, why does everybody love our stuff? When I do it this way I’m ensured that those value themes are differentiated and not just things that are generally valuable, but any alternative could get it done so why are we even talking about it? So in my mind, that’s kind of how we do it.

Once I’ve got differentiated value, then I can start thinking about, well look, I could sell this product to any company that has this problem, but not everybody cares about this value the same way. And so what are the characteristics of a target account that make them really, really care a lot about that value? If I do some deep thinking about that, that’s going to be my definition of a really best fit customer.

And then the last piece of positioning of course is market category. And so again, a lot of people will just start with market category and then try to back up, which I think is crazy ‘cause then we don’t have any way to judge the goodness of a market category. But if I’ve got, look, this is the value only I can deliver, these are the kind of people that really care a lot about that value. If I start thinking about positioning is like the context I position my product in, then the best market category is the context I position my product in such that this value is kind of obvious to these people. This is my long-winded way of doing it, but this is the only way I know how to get positioning done.

Lenny: Next up is Crystal Widjaja, who is a longtime chief product officer at Gojek. She’s currently chief product officer at Kumu, and she’s one of the smartest growth minds that you probably have not heard of. Here is Crystal talking about why most analytics efforts fail at companies.

Lenny: I want to shift a little bit to post that you wrote that maybe he’s winning more popular posts, you wrote on the Reforge blog called, Why Most Analytics Efforts Fail. I’d love to hear your broad overview of why do most analytics efforts fail and then how do teams avoid this, maybe what are two to three things they can do?

Crystal Widjaja: Yeah, I’m actually pretty surprised at how much noise that has generated because I guess it came from a place of frustration where I kept telling people like, you are doing this wrong, here’s how you should probably be doing it. But I think it resonated a lot with Foltz because they recognize all of those symptoms but they weren’t sure why it was happening. So to say, oh, this is the thing, instrumentation is what’s wrong. I think it’s a very actionable thing. It’s probably one of the most solvable problems out there. It just takes some time and mental model shifts to do it well.

So a lot of people look at tracking data as how do I track my OKR? How do I know if I’m going up or down? But they don’t use it to track or identify insights. So I will use the example of using Twitter for, “News” when in reality they’re actually using Twitter for entertainment. Do not treat metric gathering as entertainment. It’s not there for you to be like, oh, that’s interesting, how novel, and then not act on it. So real news is information that changes what you do in the real world. And if you don’t change what you’re doing, what you are doing is just getting entertainment. So let’s use that as a premise.

The next step in instrumentation is to look at the fact that measurements do not equate to insights. A measurement would be an observation, it’s a data point in your database. So the example being power users do four times more bookings is an observed fact because your transactional database obviously says that that is the case. But it’s not an insight because it doesn’t have context, it doesn’t give you information that lets you act on it and better understand the problem.

So another example would be if I see my girlfriend hanging out with a guy, I don’t know. That is an observed fact that you see in the real world. You’re a hypothesis could be that your girlfriend is cheating on you, but the insight, the actual fact might be that she’s not cheating on you, it’s her cousin. And now your insight is I am paranoid and I need to change my behavior to be less crazy. So, the insight will provide value when you have this why answered. Why is this person doing this thing? Here’s why. And then you are going to act differently.

So for our purposes, if we look at a Goodfood user will transact and is more likely to use a voucher. That’s a fact, that’s an observation. But it’s not an insight. An insight would be something like Goodfood users who are power users are more likely to use a free shipping discount on a high GMV basket versus non-power users. And that actually tells you how to change your marketing approach. It tells you in what circumstances does someone do this When it’s a high GMV basket, give power users the ability to get a free discount, but do not do this for non-powered users because they won’t convert any better than they normally would. So that helps you change your marketing spend, it helps you understand the decision points of power users versus non-power users. The insight is instrumenting properties into an event so that you can segment who is doing what behavior and make some hypotheses on that observation, test that hypothesis and then you get some causal representation of whether or not that hypothesis was right.

Lenny: The eighth most popular episode of the year is our very first episode with Julie Zhou. Julie was a longtime design leader at Facebook. She’s now the founder of a company called Sundial. She also wrote the bestseller, the Making of a Manager and her newsletter, The Looking Glass, was a huge inspiration to me that helped me start my newsletter. Here is Julie sharing her advice on getting over imposter syndrome.

Going back to your time at Facebook, you’ve made it sound like you just kind of like, ah, I joined as a designer, figured out design became a manager, and then somehow you became VP of design and it sounded too easy. That’s an insane trajectory for someone to follow. Do you have any thoughts or advice on what contributed to your success rising through the ranks that quickly for folks that are just early in their career maybe?

Julie Zhou: Absolutely. And I want to make it really clear, I would say that the first seven or eight years that I was at Facebook every single week I felt like an imposter. I had no idea really what I was doing. The constant refrain in my head is like, well, do you really deserve to be here? Do you really know what’s happening? You’re not really prepared for this job. You’ve never done this before. What do you have to be put in this situation and get to do what you do? And that was really a constant refrain in my head.

But looking back, I think it probably took me about seven or eight years until I became a little bit more comfortable with that. After seven or eight years I could look back, I could see all of the things that I got to work on, I could see all the ways that I had grown and learned in that experience. And something clicked for me where I realized it’s kind of two sides of the same coin. Being in an uncomfortable situation, being in a position where you feel like, hey, do I really know how to do this, I’m not prepared for it, kind of coincides with the fastest and most intense periods of growth in one’s career. I started to realize, well maybe it’s not so much of a bad thing. Maybe if I constantly putting myself in this situation where I haven’t seen this problem before, that’s also what’s going to push me to grow and learn.

So yes, you asked for specific advice, I think there’s two things. The first is, well, I was lucky I was in the right place at the right time. I was at a company that was scaling. And when you’re at a company that grows, there’s always a lot more opportunity to then be able to try something new, to raise their hand, to volunteer for things to be just thrown into because somebody has to do it because it’s a growing company and there aren’t a lot of other people. So the first piece of advice I would have would be like if you want those types of opportunities, sometimes you just have to be at a smaller place and you have to be at a place that is going through that rate of growth.

The second thing is embrace the fact that it’s okay to be in a position where maybe you don’t know what to do, you haven’t been trained for. It does coincide with that intense learning. Maybe approach it with that sense of curiosity and that sense of, yes, it’s hard, yes, I might be an imposter and I might feel that way for a while, but this is also what’s going to help me get there. It’s going to be what forces me to do the work and in that process learn and become better.

Lenny: It’s amazing to hear that you had imposter syndrome for such a long period of time and you basically ran design for the Facebook app, right?

Julie Zhou: Yeah.

Lenny: It’s kind of an empowering, inspiring insight that someone that at your level went through that for so long and made it through that. Do you have any other advice or thoughts on just for folks that are going through that? Because I have that to you for a number of years, just like, what the hell am I doing here? People are going to see I don’t really know what I’m doing and it’s all going to crumble as soon as I make my next mistake. Do you have any other advice there for folks going through that themselves?

Julie Zhou: I think that so much of just exactly what you said, Lenny, I think so much of it that helped me was realizing that everyone feels this way to some extent. And that’s also why I always want to talk about that. Because I feel like sometimes you can see from the outside you’re like, oh, this person has this title, they have this position, they have these responsibilities. Clearly they’ve made it, they know what they’re doing. But that’s never the case.

I mean, logically, let’s think about it. If you’re going to do anything new for the first time, how are you ever going to feel totally comfortable, totally prepared? Every time there’s something new that you hadn’t encountered before it’s always going to be a little bit rough, you’re never going to feel like perfectly at ease. It’s only upon doing something multiple times that you start to see the patterns, you start to realize, okay, it’s going to be all right. Even now, the people that I talk to, the people I really look up to, the people who I think are role models and mentors for me, I mean they regularly also share with me that it’s the same. They still encounter things that are unprecedented. If we work in tech, I mean the rate of change, the rate of the industry and companies and these new experiences that we have, that never goes away. That’s just par for the course. So I think that feeling always exists.

What I have learned is that there are better tools in your toolkit for dealing with it. One of them is of course me just reminding myself that if I feel uncomfortable, okay, other people feel that way too. Everyone does. It’s totally natural. But then to also find other pieces in that toolkit. One is I am much better at asking for help now than I was earlier in my career. I used to actually just try and hold it all in. I was like, hey, I better fake it till I make it. If everyone thinks that maybe I’m coming to the table like I know it then I can fool them.

Now I realize I was preventing myself from being able to get that support and that empathy and that camaraderie and that advice that would’ve helped me actually grow faster and maybe with a little bit less pain in the process. So one of the things I’ve learned is it’s okay to ask for help. It’s okay to reach out to people who both may be going through the same things you’re going or maybe are a step or two ahead of you in the journey, who have actually gone through that and have lived to tell the tale and can tell you it’s going to be okay. Because often that’s just what you need, you just need people to tell you it’s going to be fine. You’re fine. You’re good. You’ve got this. That’s so meaningful whenever we sometimes feel down about ourselves. So that’s another, I would say tool in the toolkit, asking for help, finding groups of support.

And then I think the third is it’s also okay to just be vulnerable and just talk to people about. I found that some of the most meaningful conversations I had, whether with people at managers or whether with my own reports is when we can be much more open about what it is that we find hard, what are we struggling with? And in that way you actually form deeper connections and people are more able to help out. We can spread the load a little bit. We can put our heads together and brainstorm a better way to solve the problem. And I find that too, even as the head of a department or a founder, it’s not going to solve everything myself. I’m never going to have all the answers. Sometimes by just sharing what the problem is by sharing the load, we’re all going to collectively come up with a better solution.

Lenny: Next up is Shishir Mehrotra, CEO of Coda, former VP of product and engineering at YouTube, PM at Microsoft. And here are two my favorite clips from Shishir. One where he shares his favorite interview question using a technique called Eigenquestions and his PHSE career growth framework.

Shishir Mehrotra: I have an interview question I ask, it’s a very simple question and it’s a coded Eigenquestions test. And the question is, a group of scientists have invented a teleportation device. They’ve hired you, Lenny, to be they’re sort of business counterpart, bring this to market, product [inaudible 00:19:50] this question actually worked well for [inaudible 00:19:52]. But say, you could be the product manager for this thing, bring it to market. What do you do? That’s the whole question. Usually people will start asking a bunch of questions and say, well, tell me more about this device. What does it do? How does it work? And is it big? Is it small? Is it fast? Does it disintegrate things or not? Does it need a receiver and a sender? Is it safe?

I’ll just let those questions come out and at some point I’ll say, okay, nice job generating all the questions. Turns out these scientists, they kind of hate talking to people and they’re kind of annoyed by all your questions. And so they’ve decided that they will answer only two of your questions and after that they expect a plan. What two questions do you ask? And interestingly, all of a sudden, like the sharp product managers, engineers, basically every role, they very quickly find what are the two, one or two eigenquestions on this topic.

There’s no right answer, but I’ll tell you one of my favorite ones is as a product manager said, okay, if I had to ask two questions, the two questions I would ask, one is it safe enough for humans or not? And that was a very crisp way to get to just safety. How reliable is it? Didn’t ask how reliable it is, how many bits in the middle of this… He’s like, just tell me it’s safe enough for humans or not. And the second one is it more expensive CapEx or OpEx? Is it more expensive to buy them or to run them?

And then he took those two questions and he said, get with those two questions, I can form these quadrants. And you can say, oh, it’s safe enough for humans and they’re very cheap to buy, but expensive to run. Then you probably run them like human fax machines. You put them everywhere you can and you say, hey look, it’s expensive to use but you’ll all have the ability to teleport anywhere you want and this is how we’re going to run it. But the other hand, they’re very expensive to buy, but cheap to run. You probably have to place them very strategically, in which case what you probably do is replace airports. Airports are pretty strategically placed in places where people are trying to get around places. If it’s not safe enough for humans, then you’ve got a whole different class of use cases where you go value what goods are transported in very costly ways. And people come up with, do you do the most expensive things? Is hell supporting people’s replacement hearts, is that a really demanding thing? But these two questions kind of get to the heart of it.

Shishir Mehrotra: The question’s totally made up, no teleportation device exists, at least not yet. I find that people’s ability to learn the method is significantly higher if it’s low stakes. That question by the way, if you ask a kid that question, hey, teleportation device, you get to ask two questions, almost every kid will quickly get to two pretty good eigenquestions. Kids are incredibly good at simplifying these things down, it’s actually a skill we remove from ourself. I’ll hear candidates tell me things, I guess I would ask them what size it is and why would you ask them what size? What decision is that going to allow you to make, to know what size? And sometimes they can explain it, sometimes not and don’t get hired. But then actually the thing I’d say about it is there are eigenquestions everywhere. I mean you can take any product out there, I’ll do it with my kids a lot, and they’ll say, I was just riding with my younger daughter and she said, how come there’s three gas stations in the same corner? Why do people do that? That’s a really insightful observation. What’s the eigenquestion? How do you place a gas station you can almost take anything and say, what is the question that really drives this answer.

It stands for problem, solution, how, execution, PSHE. So here’s how it works. So if you’re sort of a junior product manager, what happens? You get handed a problem, you get handed a solution, you get handed the how, go talk to this person, write this document, run this meeting, so on. And all you have to do is execute, run that playbook and that’s all we expect out of you. You can become a little more senior, we hand you a problem, we hand you a rough solution, you figure out the how. You figure out the how we’re going to organize this? What are the milestones? How we’re going to get it to market? How we’re going to the meetings? What are the rituals? All those things show up in the H.

At some point you become a little more senior, we hand you a problem and you come back with the solutions and we judge you on the creativity and the effectiveness of the solutions. And at some point you’re senior enough that you tell us the problems and you say, hey, I know you told me to go work on activation, but actually I think our issue is brand or I think our issue is quality or I think our issue is whatever it might be, and that’s sort of the pinnacle of this way of thinking about it.

Now just back to this picture for a moment, one of the interesting things that happened was the teams went and they evaluated their teams on these two ax axis and they end up with this sort of curved line between them. It’s not linear as you work your way through. And what happens is early in people’s career, they mostly sit at that E point, you get handed a problem and handed a solution, handed a how, and you just execute and they gradually grow in skill. Later in people’s careers, similarly, you’re at that P level, just do bigger and bigger products. And it’s like the job of being an entrepreneur or CEO or an owner or so on is just kind of do bigger and bigger projects.

But in the middle the slope changes and all of a sudden it’s not really about scope, it’s about PSHE. And there’s a circle drawn here for what I like to call the trough of dissolution. What happens in that phase, I was talking to the calibration companies about this, the reason we call the trough of dissolution [inaudible 00:25:22] is for the employee, for the person, this is a confusing time. Everything about leading up to this moment from high school and college has been about scope. And at this point you’re all of a sudden told, we’re not judging you on scope anymore, we’re judging you on this PSHE thing. That’s very confusing.

To the calibrator, to the manager, it’s also very confusing because all of a sudden the way I put it is the difference between a level three and a level seven may not be scoped. They may do the exact same job, it’s how they do the job that matters and here’s some language for how they do the job. So PSHE became a very sticky way of thinking about it. It turns out that this way of evaluating people is actually not that specific to product management. It’s really easy to see why you do the exact same thing for engineers and designers and so on. But to pick one that may not be as obvious, I’ll pick salespeople. A very common thing people do with salespeople is they evaluate them based on quota attainment. It’s like the easiest thing to do is take the salespeople and rank them by who hit their quota and who didn’t.

You go ask the sales team, who’s the best salesperson and what you’ll realize, and they’ll say, quota statement is just a signal for how good you negotiate your quota and pick the right territory. And they say, really, you want to know who’s a best salesperson. They say, well, so and so, I mean she can sell anything and she can be in the region that’s growing or the region that’s shrinking or the new product or the old product. If you think about that terminology, it’s very similar to PSHE thinking. This is the person who can come into a new space, identify the right problems and solve them. That’s what makes a really great salesperson. So it could become my framework for evaluating talent in sort of all sorts of ways. You might recognize a pattern of being a great P thinker, it’s very correlated with being good with eigenquestions. Can you spot the right problems is very similar to can you spot the right questions? Can you decide what’s important?

Lenny: Our sixth most popular episode is with Kristen Berman, founder of Irrational Labs on using behavioral science to improve your product. Here is Kristen describing the three Bs of behavioral change.

Kristen Berman: There are so many mistakes that humans make and we can call them biases, heuristics, our team uses psychologies. What are the psychologies that drive us? And so to tackle this, our team basically has created a model of behavior change we call the three Bs. And this summarizes the most important psychologies that drive user that are important to the product managers and the marketers. We’ve used this at Google, Microsoft, LinkedIn, so all the companies that we work with and they now use it.

So the first B of three Bs framework, first B is actually not a psychology, but it is the most important part of behavior change and it should kind of be obvious. If you think about behavior change, behavioral economics, it is behavior. In order to change behavior, you have to pick a behavior that you want to change. So companies are really good at outcomes, but just not as sharp at picking the behavior.

And when I say behavior, I mean action. The thing that you want someone to do, by the way, the only wrong answer here is log in. So it’s really, it’s not about logging in, it’s about what you do after you log in. And when we’re consulting teams would be like, we need to get uncomfortably specific. We say just really specific in the behavior. So example, if I’m Peloton PM and I’m working on the app, I would say something like within 7 days of somebody starting the app they do 2, 10 minute workouts with two different instructors. Now obviously that is wildly specific and you’d probably be very happy if they did one workout with one instructor, but the reality is if you don’t define that behavior, you’re going to change, you can’t actually define the psychologies that affects someone’s decision making when doing that behavior. So that’s a first B.

Kristen Berman: Second B, again, is probably pretty obvious and is very critical, it’s just barriers. So we need to reduce the barriers to doing the behavior. And there are two types of barriers we look at. One is logistical, so this is just the stuff in our way could be entering a credit card, could be any form field. And then the second is cognitive. So the cognitive barriers get in our way as well. These are things like uncertainty aversion, this is optimism bias, information aversion. Status quo, big one. It’s just you do the same thing today that you did yesterday, your job-

Lenny: Can you talk about those three you just threw out there, just briefly? I’m curious about the specific biases while were there.

Kristen Berman: Yeah, so uncertainty aversion, when something is uncertain or we’re not… So I’ll give you an example. If you’re Lift, there’s logistical friction, which is wait time. But then there’s also this uncertainty of is it going to come on time? When is it going to come? And with this uncertainty, you’re probably going to look for other options. You’re going to open up Uber and say like maybe it’ll come faster. And so when there is uncertainty in our life, we either look for other options or we just don’t make a decision at all. This is by the way, very big in healthcare where when you’re very uncertain about something, you may not even go to the doctor or you may just make the wrong decision.

Same with status quo effect. Where we kind of underlying status quo effect is this idea that we always take the path, not always but majority of… You don’t really say always when you’re talking about human behavior. Human behavior is very complex. But more often than not, we take the path of least resistant. So we do the thing that’s easiest and typically the thing that’s easiest, it’s the thing that we’ve done yesterday and the day before. So when you’re asking someone to do something different, which is what most product, especially startups, are trying to do, you actually have to increase their motivation or make it easier, reduce the barriers to get them to do that. And so status quo effect, it’s a big, big one that folks are fighting.

Lenny: Awesome, thanks for sharing this.

Kristen Berman: The third B is benefits. So this is where you want to increase the not just benefits, but the immediate benefits of doing something. So we are all present bias, which means we prioritize our present self over our future self. So there are plenty of reasons that somebody, your customer, your user should take an action, but you actually have to give them a reason to take an action today. So as an example, if you’re Asana and you’re trying to get someone to log a task, the right thing for them to do is log the task because it’s going to get their project done on time. You’re going to have a collaborative and communicative team that you’re going to want to be on. But one of the real reasons we may log a task is because of completion bias, we want to see the checkbox. We may log it because of social desirability bias, where other people see that we’re getting our work done, there’s a notification that goes to my teammate when I complete something. So these are the immediate benefits that we have to build into products and features to drive use.

Lenny: Awesome. I definitely have completion bias, I left checking those freaking check boxes.

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The fifth most popular episode of the year is with the great Elena Verna on B2B growth. Elena is currently head of growth at Amplitude. Prior to that, she was CMO at Miro, she was senior vice president of growth at SurveyMonkey and she might be the smartest person in the world on B2B growth. Just putting that out there. Here are two clips from Elena. The first on why retention is so important to your product and why it’s so important to get right. And the second on what to put into your freemium product versus your paid product.

Elena Verna: I think every single company has to first focus on being product led and retention, period. The only way that you will ever have any chance of acquisition being product led is if you nail your product led retention. Let me break it down. Retention falls into two main KPIs, which is activation and then engagement. If your product is not able to activate and more importantly engage via habitual loops and be in the habit forming zone, then you’ll have no chance to hooking an acquisition engine into your product. Because acquisition and product led means users and buy it or users refer or users create content that attracts other users.

Well, if your users are not habitually using your product, there’s less and less opportunities for you to actually create any sort of product led acquisition. So never start with product led acquisition. You first always have to start with product led retention, activation, and engagement. Then you can choose, is your product has a relationship of one to many? If it has a collaboration at its core, say Slack or Miro or even the Amplitude. Or does it have more of a single mode relationship? So let’s say Snowflake, there is not one to many relationships there between users. Well, if you have one to many relationships, product led is a fantastic way for you to prototype that model. If you don’t have them, then it becomes increasingly hard. Most of the B2B products don’t have that one to many relationship, so it’s very difficult to stand up product led acquisition. So you rely on marketing led and sales led and that’s fantastic, those are fantastic growth models as well.

The only other question becomes in the self-serve monetization, that’s product led. Otherwise you go in the sales led and you chase after those large contract values. And you can still be product led and monetization with sales team via product led sales or you can just be self-serve if you have a specific segment that is valuable for. But the question there is your use cases and your market matureness to handle self-serve or do you need that sales touch? Every industry and every sector is going through transformation at different velocities. So even if you don’t have that product like sales or self-serve in your industry now, I guarantee you it will pop up in the next 10 years. And if you are not going to introduce it, you will get disrupted by it.

Lenny: For a product leader or founder who’s thinking about what they should make free in their freemium model, do you have kind of a mental model of how you think about here’s what you should make free? Or, is that too big of a question for a quick answer?

Elena Verna: So I mean you first have to align on what your strategic value of free is. I do have a general framework of saying freemium has to check one of these boxes. Does it help my indirect monetization? So some sort of virality or network effects. If it does, I’m probably going to make it free. Does it suffice for every single user regardless of their complexity? If it does, then it’s probably commoditization of the feature anyways and I should make it free. Does it help my aha moment? If it does, then I definitely want to have a POC as part of my free and I’m going to put it in the free offering. Does it create habit loops for me? So let’s say notifications or some sort of channel communication. If it does, then I’m probably going to put it for free. So anything that actually creates friction for my growth model, I’ll probably gate it in the paid. Anything that promotes my growth model, I will put it into free. Now it is very heavily dependent on your actual monetization strategies. So it’s a little bit of over encompassing statement, but at the end of the day, I’m thinking about it very much. How does free help me achieve my growth model outcomes without sacrificing monetization potential?

Lenny: Our fourth most popular episode of the year. Just to put this out there, the next three have came in really close to each other so you can kind of mix and match them in order. But at this point, the fourth most popular episode of the year is with Ethan Smith, CEO of Graphite, and just general SEO guru. Here are two clips from Ethan, one on how people often under invest in SEO. And two, signs that SEO might be right for your product.

Ethan Smith: I think people under resource SEO a lot of times and over resource ads. So if you’re Zillow, you’re going to spend tens of millions of dollars on ads, or if you’re eBay, you’re going to spend tens of millions of dollars on ads. Why would you not have a really great SEO team? Like the amount of traffic you get is probably equal to that. So if you’re going to spend a hundred billion on ads, why would you spend $50,000 on SEO? That doesn’t make sense.

Lenny: What are just attributes of a product or a company that tell you that SEO could be a growth driver or a massive growth driver? Because I imagine SEO isn’t useful for everybody. How do you think about that?

Ethan Smith: There’s two big things. The first thing is the addressable market large, SO’S the addressable market for SEO large? And for most categories it is. The second is, do you have authority, you have existing traction? If you start from zero and you have no traction. So we talk with seed stage companies and series A companies, typically they don’t have a lot of authority and it’s too soon. And Google doesn’t want you to just be an SEO site and they want you to be a credible domain before they rank you. And if you’re starting from zero, they don’t have enough signals that you are.

So the way that we assess that is, the first signal I’ll look at is what’s your traffic? What’s your current traffic? And your non SEO traffic is actually an authority signal. So I’ll go into SimilarWeb, I’ll put the domain in, I’ll look at the total traffic and I’ll want to see at least I would say 1,000 visits a day roughly for non SEO at least, if you have five visits that that’s very little. And then the second thing I’ll look at is the number of referring domains. So I’ll go into Ahrefs or Semrush and look up the total number of referring domains. I’ll try to have at least 1,000 roughly referring domains. You could grow with less than that and less than 1,000 visits, but it’s much harder. And the more you have, the easier it is to grow and the faster you can grow and the more you can grow.

And then in terms of the addressable market, that’s a little bit more complicated, but most markets are pretty large actually in SEO, but we want it to be large. So With Power is actually an interesting example. So they’re a clinical trial lead gen site. They want acquire people to take clinical trials. How many people are typing online, I want to take a clinical trial? Not very many. But the number of people that could be taking clinical trials is very large. And so if we target the persona, what’s the key demographic of who might be a candidate for taking clinical trial? It’s very, very large. So we can then create content that targets that, like gig economy or college students or people like that. So if you think about targeting the persona, most sites have a very large addressable market.

But the way that I would think about the addressable market is that which is what product am I offering? What are the use cases for that product? What is the persona? What’s the size of that? And then I would assess that typically by looking at external benchmarks. So if I’m a shopping site and I haven’t started yet, I can look at other shopping sites, I can see how much traffic they have. So again, I can go into SimilarWeb if I’m Wish.com and I want to see what my traffic potential is, I can put in Walmart and Wayfair, put it in SimilarWeb, look at their total traffic. SimilarWeb’s free for all of this. And then I can get a sense of how big I can get.

The one other thing I’ll mention is that there are product competitors and audience competitors. So for something like, I’m at a WeWork right now. So for WeWork, I could look at the traffic for other rental office companies or I could look at companies that are ranking for the kinds of things that I would want to rank for. And they may not be direct product competitors. FinTech is interesting. So for Robinhood, Robinhood could look at other sites that allow you to sell stocks in crypto or they could look at Investipedia. Investipedia doesn’t allow you to buy stocks, but they have a bunch of traffic. It’s not a product competitor, but it’s an audience competitor. And so these competitors basically can tell you what the size of that market is. So that’s how I think about the addressable market. So ideally it’s large, it typically is. And then the more authority I have, the more I can compete. If I’m starting from zero, it’s probably too early. But once I have traction, SEO can then multiply that traction.

Lenny: We are now in the top three. Who could it be? Drum roll. The third most popular episode of the year at this point, Shreyas Doshi. Shreyas was a longtime PM at Stripe, before that he was a PM at Twitter at Google and is generally just an incredibly insightful and helpful human constantly sharing his wisdom on Twitter, and now he has his own course on Maven. Here is Shreyas describing the LNO framework, which people have brought up so many times after this episode and that I’ve personally found incredibly useful.

Shreyas Doshi: When I just joined Google as a relatively new PM, this is back in 2008, for the first three years I was overwhelmed and stressed. And that was because, one, I was a new PM in this really high performance environment. I was working on some important products and launches and I just had too much to do. And I look back at that time, and it was perhaps the most stressful time of my career. Where I would work long hours, et cetera, but even at the end of the day, I’d feel highly dissatisfied because my to-do list was endless and I wasn’t able to make a dent on it. I was also a little bit of a perfectionist. So I was like, no, no, no, I need to do this well. And yeah, I was just constantly I would come home and talk to my wife and kind of basically just complain to her about how I’m not able to make progress or as much progress as I want. That was accompanied with not being able to sleep very well because I was concerned about how much output I was producing and whatnot. So again, very stressful time in my career.

And then things changed when I discovered the ideas related to this LNO framework in a blog post. Unfortunately I can’t even find that blog post somewhere, but it had some ideas that I took and then kind of created this LNO framework on myself, which is essentially that as a product manager or as anybody in a creative high impact, high leverage role, all your tasks are not created equal. There are actually three type of tasks that you end up doing in such a role.

So there are L tasks, which are leverage tasks. And the L tasks are such that when you put in a certain amount of effort, you get 10X or 100X in return in terms of impact. So those are L tasks, leverage tasks. Then there are neutral tasks, so that’s N. And those are tasks where you basically get what you put in or just a little more than that. So you put in 1X and you get 1.1X. Those are neutral tasks. And then there are overhead tasks where you get back, again in terms of impact, you get back a lot less than you actually put in. And it turns out that many people, people who are ambitious or are perfectionists like myself, they by default treat each of these types of tasks the same way and therein lies the problem. So this was the epiphany for me back at Google when I kind of discovered some of these ideas.

What I realized that is that among the things in my to-do list, there are actually only very few L tasks. And so it made sense for me to focus a lot on those L tasks, to take on those L tasks when I was feeling most productive, most energetic during a certain time of the day. And, for the L tasks, let my inner perfectionist shine because I’m going to get so much more in return. It makes sense for me to spend that time on that PRD for instance, related to an important feature that will meaningfully impact our revenue. I’m going to spend more time on that than I ordinarily would. So now where does that more time come from? Because it cannot come from just working more hours. Well, it comes from spending less time on N tasks and O tasks. And so there are some tasks that you do, a classic example of an O task is say an expense report. It sounds silly, but I used to try to make my expense reports really good.

Lenny: Wow. That’s funny.

Shreyas Doshi: Sometimes that made no sense. But I was like, no, no, no, I need to do that. And again, this is the silliest example, but there are many examples. And something I realized is that the same type of activity can actually be either an L task or an N task or an O task. So what’s an example? So say like a classic PM activity of filing a bug report. And so many companies have these bug templates, et cetera, et cetera, like that you use to file a bug report. Well, it turns out that filing a bug report, depending on the situation, depending on what type of bug it is, can actually be an L task, high leverage task, and over there you want to file a very detailed explicit bug report. In other cases might actually be an O task, where you don’t fill out the template that diligently and you don’t add 15 screenshots with annotations, instead you just have one screenshot and you hit submit on the bug report. So that shift where usually for the same type of activity we provide the same type of engagement.

Last example I’ll use to illustrate this is taking notes. It turns out even taking notes, taking notes, synthesizing them, and then sharing them can actually be an L task, an N task or an O task depending on what type of notes they are. After I understood this, previously I would just send all notes like I tried to make them really good, which took a lot of time. But then I realized, well, this is a meeting where, yes, I need to send notes, but it’s just standard stuff. I just need to quickly list out, all people need to really know is the three action items that came out of the meetings, who owns them. That’s it. And it is not about something highly strategic or controversial. Well, in that case, I’m just going to send the notes out the moment the meeting is over, I’m just going to hit send because I’ve already taken the action items. I’m not going to try to make my notes look great so that others can appreciate, oh Shreyas always sends great notes.

On the other hand, if it was a product review with the CEO about a very contentious topic that you have gone back and forth multiple times and now you made a decision about something, you want to perfect those notes before you send them out. You want to get the language right, you want to be very clear on what the decision is so there’s no room for misinterpretation so you don’t backtrack afterwards. Or people say, well, but I thought we said this. So that’s a case where it’s an L task. And yeah, I would say just spend an hour or even two hours perfecting those notes because it’s an L task. So hopefully that helps illustrate some of the ideas behind the LNO framework.

Lenny: Runner up for the most popular episode of the year is my conversation with Marty Cagan. Marty is the legend of legend of product managers. And I’m not surprised this episode was incredibly popular. Here are two my favorite clips for my chat with Marty. One talking about why big companies are just bad at product often. And two, the four steps to be a good product manager.

Marty Cagan: Steve Jobs shared his theory from 1995 for God’s sake. His argument was, as a company gets bigger, product historically became less important. The people in a company that would be celebrated were marketing people, salespeople, finance people. Because if a company stops innovating, these are the engines for growth. Sales, marketing, or not growth with finance, but cutting cost. And his argument was this happens over time. Pretty soon, these are your leaders, they’re the ones that have been promoted. So then what happens? Good product people don’t want to work there anymore and they leave and they go to a company that values product. I think that’s a better explanation than any other that I’ve heard. And it was so prescient because when he said this, this had yet to even happen to so many other companies, but it still happens all the time.

I hate the idea those companies that have separate product owners, because product owner is just an administrative role. Product owners almost never have the skills to be a product manager, and that’s a problem. But let’s just say there’s a product manager and nobody’s ever coached this poor person and so they really don’t know much. So the first thing that product manager needs to do is get themselves prepared to contribute to their team the way they need to.

Marty Cagan: In general, that means four things. First of all, they have to really get to know the users and customers. The second thing is they have to be an expert in the data. How is your product used? How is that change over time? What’s the sales analytics? What’s the user analytics? The third thing is, and this is usually the hardest one and it’s the one that your stakeholders will judge you on, is you have to learn the different parts of the business. You have to know how it’s marketed, how it’s sold, how it’s paid for, how it monetizes. If there are any compliance, regulatory, privacy, security issues, you need to know what those are. So that you have to convince those stakeholders that you understand what the issues are and you understand what to look for and that you convince them that if there’s ever any question you will bring them a prototype that they can see and make sure it’s okay. So you need that trust with the different parts of the business. The fourth area is you have to know the competitive landscape, you have to know the industry, you have to know the trends.

Those are the four things you bring to the team. Realize the designer doesn’t have this info, the engineers don’t have this info. If the team is going to be an empowered team and they’re going to come up with solutions, they need somebody on the team that brings this knowledge, and that is you as product manager. That is the single biggest area empowered teams fall down, the product manager is ill-equipped, or a nice way of saying incompetence.

Lenny: And finally our number one most downloaded, most popular episode of the year, which raced to number one as soon as they came out, is with the one and only Matt Mochary. Matt is a full-time CEO coach. He’s worked with CEOs of companies like OpenAI, Coinbase, Notion, Rippling, Angellist, so many other amazing folks that I could just keep listing. In this episode. There are just so many nuggets of wisdom, and I could share 100 clips from just this one episode, but I’m going to choose just two. One, the power of small teams and how small teams often get more work done. And two, advice for having hard conversations with your employees and with people in general. Enjoy.

Matt Mochary: My companies have done a lot of layoffs, and here’s why, the companies that I coached. Back in March of 2020, there was a chance that the world economy was imploding. Now, of course, by April and May we realized that wasn’t the case, that the tech world kept going. In fact, it was even flourishing. But in March of 2020 we didn’t know that. And so if you were being fiscally responsible, you needed to prepare for that eventuality, so you needed pare costs. 80% of costs in any tech company is payroll, is humans. So if you’re going to pare costs, you actually have to let go of humans. So almost every one of my companies did, some on the low side of 5%, some on the high side of one company that was is a hotel company let go of 40% because that looks like their business was about to get obliterated. The results were crazy.

Within 60 days of each layoff, the CEO reported back to me, it’s insane, I don’t know how this happened, but the company’s now operating better. I’m not talking on a relative scale. I’m talking on an absolute scale. We’re putting out more features, more code, our NPS is up. Whatever it is, what whatever department is performing better. And the only answer for it was we’ve got less people. So it’s this coordination, issue is reduced with fewer people in the organization things work better. That’s the big realization that most people never discover. So they hit product market fit, they get tons of money for investors, nudged higher, higher, higher, higher. But every additional human you have in your organization causes extra overhead and geometrically so, because now that you have to keep all those people informed, give them all context, make them all feel heard. Because unless they feel like they’re contributing and you understand what they’re saying, then they feel ignored and they feel passed over and they feel disrespected and grumpy.

So there’s this morale problem that exists. So there’s this friction of information flow and a morale problem that grows and grows and grows. And really the only answer is, I mean, that’s why people bring me in because they’re growing, growing, growing, and things are breaking. So I have a system that keeps things together. But it doesn’t make it like perfect, it just makes it so that the company doesn’t fall apart. But really the ideal is just to keep the team super small. And that’s what WhatsApp did. That’s what Instagram did. That’s what Linear is doing right now. That’s what Notion has been doing for a while. And those to me are the real success stories.

Whenever I have a difficult conversation I start it off, hey, this is going to be a difficult conversation. I want you to take a few seconds and prepare yourself. You are not going to enjoy this. What I found is that the way the amygdala gets triggered is often because of surprise. So if you give someone just a few seconds to mentally prepare, then the amygdala often doesn’t get triggered nearly as hard because if they’re aware that they’re going to go into fear, if they’re going to go into anger, they’re going to go into sadness, then they can see it coming and they go, oh, that’s what it is. But if they don’t see it coming, just surprise and all of a sudden, it grips their whole brain and now they’re in it and they don’t even know they’re in it. So, that’s the first thing I do. This is going to be a difficult conversation. Are you ready? Person says yes. Then I share the news. I’m letting you go. Here’s why, da, da, da.

Then the second, I deliver the message. The third thing is now they’re feeling emotions, strong ones. Even though I warned them, they’re still feeling them. Now, you want them to be able to release those emotions. And so I say to them, my guess is you’re feeling a lot of anger right now, fear, sadness. Is that true? And if so, would you be willing to share with me what you’re feeling and what you’re thinking? And sometimes they don’t answer but many times they do and they share with me and they let it out, and that’s important to allow them to let it out. And then I make them feel heard and I actively listen, and that makes them realize that I’m not trying to run away from the pain that they’re feeling. I’m not trying to leave them alone with it. I sit with them as they have it, and then I try to help them get through it.

Lenny: And that’s our top 10. It was actually really hard to make this list because all 50 episodes have something really fascinating and interesting to share. For example, if you need help with pricing strategy, don’t miss the Modavon episode. If you want to get better at communication, don’t miss the episode of West Cow. If you’re building a marketplace, there’s the Hockenmaier episode. If you’re trying to figure out your marketing and how to build your marketing function, don’t miss the episodes with Emily Kramer and Ariel Jackson. I could keep going, but I’m just going to stop here. I encourage you to check out the full list of episodes in case you’re currently facing a problem that one of the episodes can solve.

Lenny: To close, this podcasting journey has been so much more fulfilling and exciting and interesting than I ever expected, and I’m so thankful for you for listening and for supporting this podcast, telling your friends about it. I’m also really thankful to our wonderful sponsors for supporting this work. In terms of what’s ahead, basically more the same. More amazing guests, more topics that maybe you haven’t thought about, that you need help with, maybe more amazing topics that you know need help with that I want to help you solve. I’m still learning how to interview, how to do this podcast, how to make it more amazing, and so my goal is just to continue to refine and iterate and continue making this podcast better and better.

With that, I’d love to hear from you. What do you love about this podcast? What do you hate about the podcast? What annoys you? What do you find most interesting? I’d love to hear your feedback. You can either email me at podcast@lennyrichards.com. You can also go to this episode on my newsletter, if you go to lennysnewsletter.com and find this episode, you can leave a comment at the bottom of that episode. You can also DM me on Twitter if you just want to reach out directly. Seriously, I’d love to hear from you. This is how I’m going to make this podcast better. Until then, happy holidays. Happy New Year. From the bottom of my heart, thank you for listening and for supporting this podcast. I’ll see you next year.

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