Nan Yu: How Linear ships beloved B2B software at speed

1. 0:00 – 4:54

   Introduction to Nan Yu and Linear

   1. LRLenny Rachitsky0:00

      (instrumental music plays) I think you see on the team at Linear that a lot of people don't see, which is that there's not actually a trade-off between speed and quality.

   2. NYNan Yu0:06

      People talk about this as if there were a trade-off because when they think about speed, the thing they over-index on is, like, rushing or being sloppy. What they should be indexing on is being really competent. If you look at people who are, like, at the, the pinnacle of their craft, you can basically tell how good the output is gonna be of their work product by how fast they're going.

   3. LRLenny Rachitsky0:26

      What does speed look like when you say it can be done quickly and high-quality?

   4. NYNan Yu0:30

      What it really looks like is, you know, you have some rough time budget for how long you think something's gonna take. By the time 10% of it has passed, after week one, you have something that works, that tests some kind of key hypothesis internally.

   5. LRLenny Rachitsky0:42

      I imagine a criticism you all get. Over time, you will probably become a bloated piece of software as well.

   6. NYNan Yu0:47

      When we examine this problem, we kind of look at, w- what feature requests can we debate and what kind of feature requests do we absolutely have to say no to? The stuff that we absolutely have to say no to is the exact kind of thing that leads to this bloatedness that makes ICs kind of hate their lives.

   7. LRLenny Rachitsky1:02

      Something that your head of sales shared with me is how impressed he is with the way you ask questions on customer calls and just keep digging and digging until you get to something.

   8. NYNan Yu1:10

      My goal is to feel bad in the same way that customers feel bad.

   9. LRLenny Rachitsky1:16

      (intro music plays) Today my guest is Nan Yu. Nan is head of product at Linear, which is one of the most beloved, most beautifully designed, and also the fastest growing B2B SaaS product out there today. You rarely see the kind of love that people have for Linear for any enterprise B2B SaaS product, and so there is a lot that we can learn from how Linear operates and how they build product. In my conversation with Nan, he shares a system that he uses for being creative and coming up with non-obvious solutions to customer problems, why it's a red flag to him when PMs tell him there's a trade-off between speed and quality, how he talks to customers in order to figure out the emotion that they want to avoid and then figure out the solution to avoiding that emotion, plus some killer advice on how to land a job, including how he landed his job at Linear and his previous role at Mode, and so much more. If you have a desire to build a company or a product that's as beloved as Linear, this episode will give you a ton of tactics and ways to change how you and your team operate. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes and it helps the podcast tremendously. With that, I bring you Nan Yu. This episode is brought to you by Cinch, the customer communications cloud. Here's the thing about digital customer communications. Whether you're sending marketing campaigns, verification codes, or account alerts, you need them to reach users reliably. That's where Cinch comes in. Over 150,000 businesses, including eight of the top 10 largest tech companies globally, use Cinch's API to build messaging, email, and calling into their products. And there's something big happening in messaging that product teams need to know about: rich communication services, or RCS. Think of RCS as SMS 2.0. Instead of getting texts from a random number, your users will see your verified company name and logo without needing to download anything new. It's a more secure and branded experience. Plus you get features like interactive carousels and suggested replies. And here's why this matters. US carriers are starting to adopt RCS. Cinch is already helping major brands send RCS messages around the world, and they're helping Lenny's Podcast listeners get registered first before the rush hits the US market. Learn more and get started at cinch.com/lenny. That's S-I-N-C-H dot com slash Lenny. This episode is brought to you by Paragon, the integration infrastructure for B2B SaaS companies. Is AI on your 2025 product roadmap? Whether you need to enable RAG with your users' external data like Google Drive files, Gong transcripts, or Jira tickets, or build AI agents that can automate work across your users' other tools, integrations are the foundation. But building all these integrations in-house will cost you years of engineering, time you don't have given the fast pace of AI. That's where Paragon's all-in-one integration platform comes in. Build scalable workflows to ingest all of your users' external data into your RAG pipelines and leverage Action Kit, their latest product, to instantly give your AI agents access to over 100 integrations and thousands of third-party actions with a single API call. Leading AI companies like AI21, You.com, 11X, and Coffee.ai are already shipping new integrations seven times faster with Paragon, keeping their engineers focused on core product development. Ready to accelerate your AI roadmap this year? Visit useparagon.com/lenny to get a free MVP of your next product integration.

2. 4:54 – 7:51

   Survey insights: Linear vs. Jira

   1. LRLenny Rachitsky4:54

      (instrumental music plays) Nan, thank you so much for being here and welcome to the podcast.

   2. NYNan Yu4:59

      Thanks for having me. I'm a longtime listener and, and reader, so it's, uh, really a treat to be here.

   3. LRLenny Rachitsky5:05

      I want to share something with you to kick off that I haven't shared with you yet, that I haven't shared with anyone. These results might have come out by the time this podcast comes out, but I'm running a survey right now that I'm calling "What's in your stack?" where all my subscribers are asked, "What tools do you use most day-to-day? What tools do you love most? What tools do you hate?" And one of the questions asked was, "What tool do you wish you could switch to if your IT department allowed you to?" The number one answer by far is people want to switch from Jira to Linear.

   4. NYNan Yu5:38

      Wow. I mean, th- hopefully that means we're doing a good job.

   5. LRLenny Rachitsky5:41

      I think (laughs) that's exactly what that means. I'll read a couple quotes to give you a sense of what people are saying about Linear. I doubt these are surprising to you, but this gives people a sense of why you're here and why I'm excited to extract as much wisdom as I can from you. So a couple quotes here. "Linear is a joy to use as I interact with my engineering teams and I find inspiration in its design."Linear is simple to use, yet powerful. Linear's design is obviously an industry benchmark, but moreover, the performance and speed is a massive productivity boost.

   6. NYNan Yu6:12

      I mean, it's really good to hear that because, you know, in, in a lot of ways that's what we're trying to do. You know, if you think about, like, the entire impetus behind why Linear was started, it's because, you know, Kari was kind of, like, sitting at, like, Coinbase and Airbnb and these places and just, you know, watching everyone around him struggle using the tools that, uh, they had available and, like, all these kind of incumbent tools, and just, you know, like, seeing that it kind of made people, like, kind of hate their day-to-day a little bit. And we all got into, uh, technology and, and design and engineering, all this kind of stuff, uh, because it was fun, right? All of us started off, like, building stupid MySpace pages and, and all of this, these, like, side projects when, when we were young. Uh, and it started off as this fun thing that we do and we're like, wow, we get to do this for a career. And then to have all of this kind of stuff, uh, put these big speed bumps into, uh, into our day-to-day workflow just, uh, was really, was really sad, so that's what, you know, that's why we started Linear, to sort of really bust through all of that.

   7. LRLenny Rachitsky7:11

      What I love about Linear, I feel like it's an inspirational business because many people want to, "I'm gonna build just a much better version of something," and often that doesn't actually work out. Often nobody cares enough, there's all these barriers and reasons people don't switch to something that's better. And Linear is an amazing example of building an excellent product and actually succeeding, and there's a lot more to it than, maybe than just building an awesome product. So that's what I'm excited to dig into and understand how y'all operate. And I guess just based on these results, to me this is the ultimate sign of product market fit. People like being sad they can't use a product in B2B-

   8. NYNan Yu7:47

      (laughs) Yeah.

   9. LRLenny Rachitsky7:47

      ... enterprise software especially. So let's get

3. 7:51 – 9:24

   The speed vs. quality myth

   1. LRLenny Rachitsky7:51

      into it. First question I want to get into is something that I think you see and the team at Linear sees that a lot of people don't see, which is that there's not actually a trade-off between speed and quality. I think a lot of people think this is, uh, just an innate fact, and something I've heard you talk about is that's not actually true. And I actually saw Patrick Carlson tweet this exact point that I'll read, after you, I wanna hear your thoughts. But talk about what you've learned about how there's maybe not actually this trade-off between speed and quality.

   2. NYNan Yu8:20

      Uh, people talk about this as if there were a trade-off almost in kind of, like, a naive way because when they think about speed, the thing they overindex on is, is like rushing or being sloppy, and what they should be indexing on is being really competent or being, uh, like an expert. So if you look at, um, if you look at people who are, like, at the, the pinnacle of their, of their craft, right? It could be anything. It could be like a chef or a programmer or, you know, someone building houses or something. You can basically tell how good the output is gonna be of their work product by how fast they're going, right? If they're going really fast and it's, like, they're obviously not, like, being sloppy and then leaving a mess all over the place, it's like yeah, well they, they got there because this is just second nature to them and they're able to kind of go at a really rapid pace and, you know, try stuff. Uh, and when we're building software, that's, that's such a big component of how good the product is on the other side of it, which is like, how many iterations were you able to do? So the only way you're gonna get a bunch of iterations done and try different things and really feel out, uh, these different variations is by just

4. 9:24 – 15:31

   Building and iterating quickly

   1. NYNan Yu9:24

      going very fast.

   2. LRLenny Rachitsky9:25

      In terms of speed, is the speed there moving quickly on each of those iterations? Like what does speed look like when you say it can be done quickly and high quality? What does speed look like?

   3. NYNan Yu9:35

      Uh, speed, what it really looks like is, uh, you know, you have some rough time budget for how long you think something's gonna take, and by the time 10% of it has passed, you have a workable solution, right? It's not like, "Oh, at the halfway point we have something that is maybe a candidate that we can play around with." It's like no, no, no. Like after week one you have something that works, that tests some kind of key hypothesis internally so that you can feel, like, is this thing actually, uh, panning out the way we expect it to or is, did we have some crazy incorrect assumption? And you know, you don't want (laughs) to wait till you're 80% done to be able to make that kind of judgment because then it's just too late. Then you're, you're pushing deadlines out and you're, uh, you know, you're making your marketing team very sad.

   4. LRLenny Rachitsky10:18

      Amazing. Okay. So the way you think is, "We're gonna spend a month on this feature. Let's get something workable we can start testing with potential users even internally in the first few days, essentially in the first week."

   5. NYNan Yu10:31

      Yes. Yeah.

   6. LRLenny Rachitsky10:32

      Yeah. I guess how, how can you do that? 'Cause most teams can't do that. Most teams need to research, design, build. "Okay, cool. We have something and, and it's a month later." What allows you to, to do that?

   7. NYNan Yu10:43

      Yeah. I mean, there's a lot of components of it. I think having really good talent really helps, right? Having engineers who, uh, don't get blocked by every single little design choice. You know, they, they're, they're happy to just make something workable. Even if they don't feel comfortable with that particular solution, they'll, they'll just bust through it and, uh, and make something happen there. Part of it is intent. You know, we don't have any expectation that the first version of it is gonna be great, right? That's just, that's just, that is not in the cards, right? Like look, the first version of it is our best guess in the general direction of what we want to actually ship in the end. And sometimes it works out. Sometimes they're like, "Wow, this first version was pretty good. Let's make some minor adjustments and we're, and we're good to go." But there's no expectation there. So no one feels like they have to be a perfectionist and get everything, like, all sanded down and, and, and really, uh, you know, really in tip-top shape, right? It just has to work and get the job done and, and, you know, kind of validate or invalidate our, our major assumptions.

   8. LRLenny Rachitsky11:38

      I'll read this quote from Patrick Carlson. He tweeted this today as I was preparing for this interview, and he's the CEO and founder of Stripe if you're not familiar. Uh, his tweet was, "I increasingly believe that good, cheap, fast choose to maximized devious misinformation spread by the slow."

   9. NYNan Yu11:52

      (laughs)

   10. LRLenny Rachitsky11:54

       "In my experience, slow and expensive usually go together."

   11. NYNan Yu11:57

       Yeah, exactly. I mean, use the, the, the contractor kind of a example. Like if someone's making modifications to your house and they're taking forever, like one, you're, you're in a hotel and also the, the, the bills are adding up.

   12. LRLenny Rachitsky12:08

       (laughs) The other example you used when we were chatting about this earlier is chess, chess players. Uh, I'm thinking of Magnus Carlsen, watching him. I think he was like number one in speed chess, in addition to just regular chess, and what a microcosm of this point.

   13. NYNan Yu12:22

       Yeah. I, I think that's, uh, that's sort of the case in like, you know, Magnus and Hikaru and all those, all those guys who are at the, at the top of their game. You know, they can, they can go unbelievably fast. In fact, that's the, that's the usual... I mean, I, I don't want to get too out of my depth with, with chess, but the usual way you, you, uh, try to make the game fair is you give them much, much less time, right, than someone who's, uh, not quite as strong of a player. And, and they'll, they'll still win a lot of the time too.

   14. LRLenny Rachitsky12:43

       So maybe just to close out this point and give someone something concrete they can do with this information, say they want to start moving faster while not cutting quality, what do you think they can do? What's one thing they can start trying to work on and improving in the way they operate?

   15. NYNan Yu12:58

       I think it's really that, um, that sort of attitude and point of view question, right? Just sort of understand and, uh, take the sort of almost like controlled risk that the first version of this is not gonna be perfect. So it actually makes it a lot cheaper in many ways. It means you don't need a per- pixel-perfect design, it means you don't need to make sure that all of the little UI bugs and stuff like that are solved, because none of that really matters, right? It has... What matters is you have working software that you can interact with and you can see if it feels good. Does it actually solve the core problem that, uh, is facing our users? You can take it back to users, you can even like let them into an early beta or something like that and get real, um, you know, validation there, and, uh, and to sort of really focus on getting the, the smallest kind of shippable element. And like not, not shippable in the sense of like I can actually put it out into production, but in the sense of like I can, you know, start learning from here.

   16. LRLenny Rachitsky13:50

       Just a question I imagine is in everyone's mind is what do you do with this first very ugly V1... Not ugly, not, not fully ready (laughs) uh, first version? Is this something you're using internally to see if it's something? Is it something you have beta design partners with?

   17. NYNan Yu14:04

       We have, uh, a sort of gradually increasing sort of circle of users that use every single feature. So by the time it hits, uh, GA, by the time it gets released, it's been used by a lot of different users up to that point, right? So the first circle is just internal users. We use Linear every single day to, you know, to write software and do our own work, so you know, we have that kind of advantage. And then once we feel like it's good enough, we'll put it into some beta customer group, y- again, as early as we can in the process, right? We have to make sure that we don't end up corrupting people's data and it doesn't look hideous and that kind of stuff. But as long as it reaches that level of quality, we can, uh, we can release it to, to sort of early access customers who can give us good feedback and also just try to solve their problems with it, right? If no one engages with it, if no one's using it, then, you know, that's a pretty good signal that we didn't really hit the mark. And then we have a couple of different beta audiences that we grow, and then the ultimate release obviously is for, uh, for GA where everyone gets it.

   18. LRLenny Rachitsky14:59

       That's an amazing answer. Okay, so secret number one to Linear success, I'm gonna take some notes here, is get, uh, new feature product ideas out to people as early as possible, say in the t- first 10% of the amount of time you've allotted, and then, uh, release it kind of increasingly to more and more people, uh, to get feedback. Uh, like I think an implication here is just most wasted time is on building things nobody actually ends up wanting or using, and so the sooner you at least get directional sense of are you heading in a good direction, the faster it'll all go.

   19. NYNan Yu15:30

       Yeah, totally.

5. 15:31 – 23:57

   Avoiding bloat in enterprise software

   1. NYNan Yu15:31

   2. LRLenny Rachitsky15:31

      I imagine a criticism you all get, uh, people are like, "Yes, Linear is so great, so beautiful, so much better than what's been out there for decades, but over time you'll probably become a bloated piece of software as well. That's just the fate of enterprise software. You have to check all these check boxes, IT teams need all these features," and so there's always this like, "Oh yeah, sure, you guys can operate this way for now. You have an amazing product for now, but it'll get ugly and bloated." How do you think about avoiding that? I know it's something you spend a lot of time thinking about. Maybe give us a glimpse into some of the conversations you have internally when there's these feature requests like, "Oh, we need single sign-on with this thing and this button here." How do you think about what to add, what not to add, and how to add these features to not make it bloated?

   3. NYNan Yu16:14

      This question actually comes to us a lot from candidates that are interviewing with us, right? Like when you go like, "Hey, like do you have any questions for us?" Like this is the question that we're gonna get, right? So, um, we hear it quite a lot and, uh, and I... It's very sensible for them to ask it, right? Because they, they see, you know, sort of history being kind of like (laughs) littered with the corpses of startups trying to compete in this space and, and n- not making it. And I, I think when we, uh, examine this problem, we kind of look at, well, what kind of feature requests can we debate and what kind of feature requests do we absolutely have to say no to? And the, the stuff that we absolutely have to say no to is, uh, also the, the exact kind of thing that leads to this kind of like bloatedness that, you know, makes ICs kind of hate their lives. Uh, and it's, it's very specific. It's customization features requested by middle managers in order to make reporting a little bit easier at the cost of making IC workflows worse, right? Like it's like if it fits that description, we're just saying no. There's, there's like, there's no debate because we've already thought about it and th- this is, this is the thing that we can't, we can't take a single step down this path. So I, I think that's like honestly one of the core promises of Linear is that we will not make this particular trade-off, right? So when you, when you see people saying like, "Wow, you know, Linear is so much, uh, faster, it's so much easier to use, uh, it makes my, my work so much more enjoyable," like this is the reason, because we have not taken a single step in this direction. Uh, it's very easy for a PM to say yes to this kind of request, right? Because they're talking with, oft- often they're talking with buyers, right, in a kind of like B2B, uh, type of space. They're talking with whoever the gatekeeper is and sales is putting pressure on them, uh, and they're saying like, "Hey, we really want this, this one feature. It's gonna make our reporting, like, nicer so like, you know, the, the, uh, you know, the director's gonna be really excited about this and we'll definitely make a buying decision based off of this." And we have to kind of convince them that this is a false trade-off.... right? The, the whole premise is wrong because the moment you start going down this path and you make, um, you make the IC user experience worse, they're just gonna disengage, right? No one has to do this. Like if I'm an engineer, I get paid to write code. My performance review is based on my, like, code contribution. It's not based on, like, did I fill in all the tickets right? So I'm just not gonna do that part or I'm gonna do it very sporadically. And, uh, and then, you know, I'm gonna just focus on, on my actual job. And then all your reporting is wrong because all the data is wrong and it's, like, sparse and... You know, you, you get, you get situations where people will, um, you know, they'll, they'll say like, "Well this, here's a dropdown field that someone put in here that's required. There's nine choices. I don't know what any of them mean, so I'm just gonna pick one at random. I'm just always gonna pick the first one. Also, I'm gonna pray that my boss is not actually using this data to do any kind of, uh, reporting, and that, that has consequence because the data can't possibly be correct." So I, I think for us it's like, it's a very easy decision when it comes to that particular, uh, category or feature request.

   4. LRLenny Rachitsky19:12

      I love how simple and clear that is. Basically, you all have a policy. We will prioritize ICs over middle managers especially. (laughs) I love, I love that it's around reporting almost always, it sounds like. Just wanna track what's happening.

   5. NYNan Yu19:23

      Yeah, exactly. It's always, "I wanna track what's happening." "Well, what do you wanna track?" "Well, I wanna track uh, which, you know, like, uh, which, uh, version of the product this thing's, uh, tied to, you know, based on some, you know, some field information." It's like, okay, like, how is the person working on this supposed to even know that information? Well, it takes a five, it takes like a five-minute scavenger hunt every single time. It's like, I don't think they're gonna do that, man.

   6. LRLenny Rachitsky19:43

      What I imagine happens, and I think why this is hard for most companies, is there's an implication that you're turning down deals. You're not, uh, adding that one feature that will close a massive million dollar sale. Uh, very difficult to do. I imagine it helps a lot that I imagine the CEO is very bought into this and there's this, we will win long term, uh, holding the line on this. Is that right?

   7. NYNan Yu20:05

      So it is, but I also think that there's not as much pressure as, as you would expect, right? To do these kinds of things. There, there are basic scaling things like, you know, we had to make like SAML and SCIM and that kind of stuff. It's like yeah, sure, we're gonna do those sorts of, like, keep the lights on type of work. But when it comes to work that's related to the actual, you know, the actual business logic of, of, you know, the, the app's, like, value proposition, what buyers care about is, is this gonna make their team more effective, right? That's the reason that they're making this buying decision in the first place, is that they're like, "Well, you know, the current situation we're in..." And especially with large companies, right? "The current situation we're in is kind of a mess. And if we can convince them that these types of things are actually the reason that it's a mess, then, like, we can really kind of navigate them out of wanting them in the first place."

   8. LRLenny Rachitsky20:57

      Got it. So there's an element of you think you need this, but it turns out you'll be more successful and get everything you want not getting this.

   9. NYNan Yu21:04

      Yeah. And it, and maybe, and the thing is, it's not everything you want, right? 'cause like ev- c- people come up with a laundry list. And it's like, "Laundry list, here's, here's ten things I want." You're like, "Do you want all of those ten things equally?" They're like, "No, actually I don't. The first three are the things that really matter to us."

   10. LRLenny Rachitsky21:16

       Mm-hmm.

   11. NYNan Yu21:16

       "If we solve the first three, then the other stuff we can negotiate on." So our job is to solve the first three way better than anybody else, that if they got through the first three through some kind of, like, visual programming, customization type of thing, that it was, it's never gonna get to the quality level and the depth that we're able to offer by offering those as native features.

   12. LRLenny Rachitsky21:37

       It's interesting thinking back to that survey c- I shared where, like, the n- the tool people want to switch to if IT allowed them was Linear. And on the one hand you could argue, well, okay, IT is not letting them use Linear for all these reasons.

   13. NYNan Yu21:49

       (laughs)

   14. LRLenny Rachitsky21:50

       On the other hand, you guys are growing really quickly within enterprise. Like, you are not, you're a new business. You started, I think, mid-market startups and now you're working your way up. And so, uh, I think it's, it's not fair to say it's not gonna work in enterprise. It's clearly working really well. I don't know if there's any stats you sh- you can share or anything like that, but it seems to be going well, expanding up market.

   15. NYNan Yu22:10

       Uh, yeah, I mean, growth has been good. Growth in enterprise has been, you know, leading the other segments, uh, because I think we've... This year especially, we reached a, a tipping point where... You know, I, I think with, with software so much of, of the buying decision is, is based on, uh, almost like a brand thing or, like, "Is this for us?" Right? It's like, you know, a lot of times people, people pick, you know, like, quote, "enterprise software." It's like, "W- why? You know everyone doesn't want this." And they're like, "Yeah, but it's like, it's for us," right? It's for-

   16. LRLenny Rachitsky22:36

       You won't get fired for-

   17. NYNan Yu22:37

       Yeah, you ne-

   18. LRLenny Rachitsky22:38

       ... buying Microsoft or whatever.

   19. NYNan Yu22:39

       Yeah, exactly. And I think that we're starting to have enough brand penetration amongst enterprises where people can, can have that feeling, right? That, that, "Hey, like, Linear is for us." They're like, "Who are we?" "Well, we are a large company that wants to act like a startup." Right? It's like, who doesn't want that, right? Who doesn't wanna go fast?

   20. LRLenny Rachitsky22:58

       Yeah. I had, uh, Geoffrey Moore on the podcast and this is exactly what crossing the chasm looks like. He talked about basically you need someone that's across the chasm, like a later adopter, that isn't the person that's, uh, I love new stuff and I'm gonna, an early adopter kind of evangelist. But you need someone that's, like, traditional, old school, takes their time to start to adopt it for you to be like, "Oh, okay, now maybe I should really take it seriously."

   21. NYNan Yu23:21

       I also think that with this kind of, this particular category of tool, uh, and with a lot of other B2B software, not, like, no means not now, right? Not right now because it doesn't fit our budget, it doesn't fit our change management situation. Oh, we have this exec that's really wedded to this, um, this, you know, this other, this other tool. But those things change, right? So we keep in contact with them. They're in our CRM or, you know, we're, we make sure we follow up and, and all. We've had a lot of these where, uh, you know, we've been said no to and when that was two years ago, and now, like, we have some new features and they go like, "Oh yeah, it seems like, seems like you're ready for, uh, you know,

6. 23:57 – 30:09

   Understanding user needs deeply

   1. NYNan Yu23:57

      for our scale or, or whatever."

   2. LRLenny Rachitsky23:59

      You mention that when you have these debates and questions that come out, you have features, say, a big company wants, there's this category of, "We know we will not build things for middle managers that want reporting and custom stuff just to track what's happening," versus, "Something that I see once b- to be more productive and successful with Linear."Give us a little sense of some of the more complicated debates that aren't necessarily in that bucket.

   3. NYNan Yu24:22

      I, I think that the complicated debates are often, you know, when we do add a new native feature, do we extend an existing feature and make it more powerful or do we add a new sort of service? And a, a big part of that is, you know, kind of trying to figure out exactly who's going to use it, what are the actual, like, real life use cases that we know about. You know, like that, I know that Bob from Company X has this workflow, and this is how it would work for him, here are the different variations where it would work, right? So like, tying it all the way back to, like, real people-

   4. LRLenny Rachitsky24:51

      Like a specific person?

   5. NYNan Yu24:53

      ... is, yes-

   6. LRLenny Rachitsky24:53

      Like you have a specific person in mind?

   7. NYNan Yu24:54

      ... a specific person.

   8. LRLenny Rachitsky24:54

      Okay.

   9. NYNan Yu24:55

      Yeah. Yeah, exactly. Um, n- not, not a hypothetical person, right? Not one that you made up, like, you know, Alice, Bob or whatever. It's like, no I... Like here's their first name, last name, here's their email, you can ask them. And I think that being able to tie it all the way back to, uh, to reality in that way is, um, you know, is a big part of how we really think about and discuss these things.

   10. LRLenny Rachitsky25:13

       This connects with the way I think about my newsletter, is, uh, I always try to answer the question a very specific, like, a person actually asked, not a general sense of something people may be interested in. And that very specific question, like it implies there's a need. Like, not implies, it proves there's at least one person who needs this thing, versus you have this idea of somebody that may want this thing.

   11. NYNan Yu25:36

       Yeah. I think, I think a trap that a lot of times PMs will fall into is they will make something bec- and they'll, they'll make some choices, and, because, you know, maybe it's beautiful or it's elegant, but they don't go the, the step of, like, is reality also beautiful or elegant? 'cause reality is kind of ugly sometimes. And if you have a beautiful, elegant solution that doesn't match with reality, it doesn't really matter, right? People can, like, look at it and they can, they can ooh and ah, but if they don't use it to get their work done, it's never gonna have, like, long-term staying power.

   12. LRLenny Rachitsky26:01

       Do you, do you have a heuristic of how often you need to hear something for you to s- could be dis- convinced this is worth investing in? You know, people may hear this, "Oh, one Bob, Bob wants this feature." That doesn't make sense, it's just one guy. Uh, how do you know when it's like, okay, we should really s- invest in this?

   13. NYNan Yu26:17

       Part of it is you, you hear something and you're like, gosh that actually is... N- not only is that true, it means that the way we thought about this was a little bit wrong. And like, I call this process, I don't know if it's the right way to describe it, I call it annealing, right? Where like you have a thing and it's, it's not quite the right shape and you put it out into the wild. So this happens like way in the, um, in the, uh, sort of first, you know, kind of bit of the life of a particular feature, right? You release a thing and then you start getting feedback about it, about hey, it doesn't quite fit reality and, uh, and then you kind of ask yourself like, did I, did we test that aspect of it? Like did we actually match that part to reality? And if we didn't, then it's like that's the, that's the part where you don't actually need that many pieces of feedback against it, right? It's not really a volume thing, it's like did we think about this, uh, right or wrong? There, that's one sort of category. Another category is just y- you know, you're getting, um, you know, you're getting requests for maybe a very big feature, uh, or feature set from a lot of different people. But then you dig in and you try to say like, "Okay, well tell me about how you're trying to use this." And there's like a hundred different use cases. So th- you have choices here, right? You can either build a big feature that covers all the long tail use cases, or you can try to see if there's like really concentrated pools of, uh, of use cases for this, um, that really make a lot of sense to kind of adopt as a, as a sort of first order, uh, type of feature. Um, so I think those are the two sort of strategies that we, um, employ the most, right? It's like did we think about this wrong and now we're just learning something about how it matches reality? Or, you know, for this big general feature that people are asking for, are there actually more specific, uh, kind of use cases that we should be solving and we should be solving really, really well?

   14. LRLenny Rachitsky27:52

       A thread that's coming through so far across a lot of these examples is getting to the, uh, the person, the specific person using the thing and making them happy and making sure the ask is gonna solve their actual problem. Uh, in the case of looking at the IC versus the middle manager, in this case it's like let's talk to the person actually asking for this thing, not there's like a hundred people generally asking for this thing and let's build what we think is a general solution.

   15. NYNan Yu28:18

       Yeah. Like, like, uh, I'll, I'll give you an example of-

   16. LRLenny Rachitsky28:20

       Great.

   17. NYNan Yu28:20

       ... of, you know, all of these things, right? Which we just launched a feature called customer requests, and basically what this does, right, it, it brings, i- it adds a new concept to Linear which is like a customer, right? For B2B companies this is very relevant. And the reason we, uh, we did this is because we kept getting this request for, uh, you know, for like fully customized fields. Right? And, and we would be like, "Well what, what is it that you want with your custom fields?" Because, you know, the problem is you add a hundred custom fields and all your ICs start hating it, right? So it's like w- we don't want to go down that path, but like what is it actually you're trying to do? And like 40% of them were because, "Well, I have a customer, you know, like, you know, Walmart or whatever, right? And Walmart asked for this feature and it's really important. I need everyone to know that Walmart needs this. And I need to track in, I need to see like how, however we, you know, report, we can report on like what have we done for Walmart over the past year so that when my CSM has a, has a one-on-one conversation with a rep they can like have some kind of evidence that we've been doing stuff for them." Like all this kind of stuff. We're like, "Okay, cool." Like that's, that sounds like a very useful and powerful thing you want to do. Uh, how do you expect people to like tag these things? "Well, manually, because that's how we did it in our spreadsheets." It's like, okay, how... Well, instead of that we're gonna hook up with your customer support tools, we're gonna hook up with your CRMs, we're gonna automatically bring in like feedback from these companies, we're gonna analyze the emails and where they're coming from, and then we're just... If, if someone requests a feature that gets escalated into engineering, it'll just be tagged with whoever asked for it. Like you don't have to do anything, right? You, but you will know, and you can still report on this stuff, but there's nothing about this that makes ICs' lives harder. In fact it makes them feel more confident because when they're building the thing they actually understand like who's asking for it and exactly what the email said so when they, they get all the, when they're doing the design or the, or the, or the details, they can actually see the real life use cases that are present and solve for those directly.

7. 30:09 – 34:10

   How to approach customer calls

   1. NYNan Yu30:09

   2. LRLenny Rachitsky30:09

      As I'm hearing this it's like, okay obviously this like seems like an obvious solution. Of course, 40% of people are telling me, their customer, uh, in reality most of the time if you hear from a bunch of your customers, "Hey, I need this custom field."And sometimes you hear one thing, sometimes you hear another. Most of the time you're gonna build this custom field. Something that your head of sales shared with me is how impressed he is with the way you ask questions on customer calls and just keep digging and digging until you get to something that is, is an insight for you, and then you start to try to solve the problem for them and think about what the product might be. And I think this is such a, a- an important and underappreciated skill for PMs. Is there any advice you could share of just like how you approach this, how you ask questions, how you think about these customer calls to get to, "Okay, now I see what we need to build," versus, "We'll just build what they're asking for"?

   3. NYNan Yu30:58

      You know, it- it's- it's funny because I think from the outside, right, I'm- I'm on these sales calls and then the, the AE or someone's like wa- watching me ask these questions, and I think often they're like, "What are you doing?" Like, "You're- you're- you're just- you're just like asking questions from angles that I- I don't even know what your goal is here." And my goal is to feel bad in the same way that customers feel bad, right? They come to us with a request, "Hey, we want X," and it's like there's something motivating it. And it's not... You- you can do the normal analytical thing and be like ask five whys and like try to figure out like, "Well, what are your goals?" And, you know, as a, as a persona X, I want to achieve this outcome. You can do it that way, but y- y- you might miss the reason that they actually feel bad for not having this, this thing. Like, "I can't accomplish this goal." "So what?" "So I'm not gonna get promoted at work." Like, "Okay, great. I understand the severity of your problem at this point," right? Like, like, "What is the actual sort of emotional valence that is motivating whatever you're telling me?" And it takes a little while to, to get there, right? Like you can ask people directly like, "How do you feel?" And like they're not necessarily gonna tell you, but if you have a long enough and deep enough conversation with them, you start to sort of level with them and you're like starting to see stuff from their perspective, and the more you see it from their perspective and the more they know that, the more they're willing to kind of like open up to you and like tell you, like, "Okay, like honestly, like..." You know, I- I had this thing happen where, uh, I marked the, the ship date of this project as December 30th because it's a Q4 project and I wanted to put it at the, you know, very end, and then, uh, my marketing team lost their mind because they're like, "We can't ship something on December 30th. Everyone's on vacation." Right? And you're like... And then they're like, "Yeah, this has made me feel really bad. So I don't ever want to put dates on things ever again." Right? And so like, "Okay, cool. We- we can- we can help you- we can help you deal with that," right? Like, "If that's- if that's what you're feeling, then I can, you know, kind of start building stuff to, um, to make sure that you never have to have that bad feeling again."

   4. LRLenny Rachitsky32:50

      People talk about empathy, like you need to have empathy as a PM, you need to build empathy, the best product leaders have empathy in this. I think it's such a succinct and powerful way of describing what empathy actually looks like as a product leader, which is, "I want to feel as bad as they feel in hearing the story they tell." And it sounds like the way you do that is you get- you keep asking questions to understand what it... Like the moment they felt bad about something, in this case, the deadline.

   5. NYNan Yu33:16

      Yeah. And it's... You know, and if you- if you ask someone in that- in that last story, like- like, you know, "What- what, you know, what kind of issue do you have?" You're like, "Oh, like, you know, marketing and I would just never align on anything." It's like that doesn't really tell you what's going on, right? They- What it tells you is like you had this terrible moment of communication that was just it felt like miscommunicated and you're- and you're like, "It's just gonna keep happening over and over again." And, uh, so, you know, the thing that we did specifically to solve this, uh, was we... You know, on projects in Linear, you can just specify, um, a target date at whatever level of granularity you want, right? You can say it's a December project, you can say it's a Q4 project, you can say it's a second half of 2024 project. Like, whatever you're happy promising, you can just put it on there, and that way you never feel- you never feel like you have to like give this, this, uh, sense of like false precision, so that, you know, it ends up with like a whole bunch of miscommunication down the line.

   6. LRLenny Rachitsky34:04

      I could see why people love Linear, is it just makes them feel less bad less often. (laughs)

   7. NYNan Yu34:08

      (laughs) Yeah.

   8. LRLenny Rachitsky34:08

      There's a lot of connection

8. 34:10 – 40:31

   Creating strong emotional hooks

   1. LRLenny Rachitsky34:10

      here. I know this idea of emotions and feeling bad is a core part of how you think about building product, looking for moments people feel bad. Is there anything more you could share there to share how you think about this idea of emotional hooks, emotional moments, and how you decide what to build?

   2. NYNan Yu34:27

      So- So I- To sort of set the- the background of this, right, I've worked in very, very competitive industries, you know. I- I worked at Everlane, which was like a direct-to-consumer clothing brand. Uh, I worked at Mode, which is like BI tools and there's like so many BI tools out there. And then, obviously with Linear, like we're- you know, we're project management. There's a lot of project management tools. And I- I think the more competitive your- your industry is, the- the more the sort of like low-hanging goal oriented stuff is- is already picked, right? Because every PM from every one of these companies has been asking like, "Well, like, you know, what's- what's your goal? Like what is your job to be done?" And all this kind of stuff. And, uh, so you have to kind of look at things from, uh, an angle that other people might not have seen. And for- for me, right, and for us, it's- it's the- the angle of- of like where are the emotional hooks, uh, that, you know, that- that you're experiencing, you know, as you go through your workday, as you use our product, as you use like competitors' products? And then I think it's probably underexplored because, um, I don't know, I- I feel like PMs and engineers were like very thinky people. We don't really... You know, we- we like kind of avoid the touchy feely stuff. And, uh, so like I think that's the opportunity, right? You can sort of see, where are you feeling bad throughout your day where you don't even know, right? You might think, "I hate Mondays," right? Like, "Why do you- why do you hate Mondays?" "Well, on Mondays I have to go out and like gather a whole bunch of stuff to write this report that it's really annoying." Oh, so if I give you a button that made the report, would that help? It's like, "Oh, yeah, then I might not hate Mondays so much." And, uh, so like, uh, I think Paul- Paul Graham has a word for this. Um, he calls it- he calls it schlep blindness, right? It's like- I'm like schleping through life and I'm just completely blind through it- blind to it. And- and it's true, right? You ha- you kind of have to have an outsider come in and sort of see, you know, what the rhythm of your feelings are throughout the day, throughout the week, and- and like kind of note the spots where, you know, you could really use a lot of improvement.

   3. LRLenny Rachitsky36:14

      Is there an example? Uh, I know you've shared a couple, but just where you've noticed this in someone using maybe a competitor or even Linear that you solved. I know you gave the example of the dates. I guess is there anything else?

   4. NYNan Yu36:26

      ... a, a big sort of, uh, feature that people love about Linear is, um, we have this, uh, this thing called triage management. And, uh, what it does is it sort of systemizes this thing where like if I put an issue into a, a di- a different team, right? If I'm asking them to do something or I'm reporting a bug to them, it sticks in a special zone where it'll notify the right people, they're on a rotation and, and, you know, like people will, um, you know, people will, uh, be able to kind of respond to it and, uh, in a, in a sort of organized, you knows, uh, manner, right? And I, I think this, you know, this kind of automation, this, this feature, it came out of two different fields people were having. Like one, people were trying to implement this stuff by hand and it was just a lot of touches, right? And they were doing it, but they, you know, they felt like, "Oh, I'm totally underwater." Why are you underwater? "Well, I have to like manage all these, you know, throw all these tickets around and route them correctly," and stuff like that. Um, and they didn't sort of see this as like an opportunity to have a tool, you know, specialize in managing their triage queue. They just, like, the- because they were managing by hand, and they were on top of it, right? But it just felt really bad because they just had to spend so much attention doing this. And, uh, and then there's the, you know, the folks who didn't do that. Like, the feeling was just like, "Well, it's totally out of control. People are just throwing tickets over the wall and I don't know what to do with them. I don't know where they are. They end up in all these holes," right? And then the people on the other side are like, "I throw tickets over the wall, I have no idea what happens to them. Like, I have no expectation that people are ever gonna respond to them." So like there's all of these like bad feelings that people are having that are all kind of the same root cause, which is like there wasn't a very automated organized way to deal with your triage queue.

   5. LRLenny Rachitsky37:54

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   6. NYNan Yu38:59

      Right. (laughs)

   7. LRLenny Rachitsky38:59

      ... so far. So the first is get something out as quickly as possible, say in the first 10% of the time that you have to build this thing, and get it out to internal users and then maybe a growing list of beta users and people that are aware, that are using early stuff. Two is prioritize the IC and the user basically versus the buyer or the middle manager that wants reporting and, and all these custom features. So it's basically focus on the user, uh, which I think you hear a lot, but I love this very specific example. Three is get very... When you hear asks for features and requests, get to, like, the specific person using the thing, not just general, "Okay, cool. I've heard it 100 times." Find the person that actually needs this thing and understand what's going on. And then four is look for bad fee- people feeling bad in a moment working in the product. Is there anything else that I'm missing that's important or any nuance you want to add?

   8. NYNan Yu39:53

      You know, the, the, the part where you said like focus on, uh, focus on the user, I, I think it's, it's maybe a little bit more subtle than that. There's, there's a nuance which is like find where the incentives are really misaligned amongst your user base, right? There's a middle manager that wants, you know, really detailed reporting, and there's a IC who just really doesn't want to go through all those extra steps, and the incentives for what they want are just like very... Uh, they're just very misaligned. And you have to find those, um, situations and be, uh, pretty judicious about how you make those trade-offs and where you can really find kind of like win-win outcomes there.

   9. LRLenny Rachitsky40:30

      That's a really important

9. 40:31 – 44:46

   Managing the product backlog

   1. LRLenny Rachitsky40:31

      nuance. Something else that's come through a couple times as you've been talking is also something Patrick Collison tweeted once that has stuck with me, which is this idea of having a mental model in your head of the user. So the way he described it and the way you've described it is oftentimes people are like, "Cool, we're gonna figure out what to build. We're gonna do a bunch of research, talk to users, that'll inform what we build, and we build it," versus what you've been saying and what he said is, uh, you do a bunch of research, look at data, talk to people. That informs your mental model of what the customer needs in their life, and then that informs what you build. And so that anytime you do more research, talk to customers, it's informing your view of the person and then you're like, "Oh, this was different from what I imagined," or, "Oh wow, this is exactly what we've been thinking and let's build that." Anything along those lines that you might want to share?

   2. NYNan Yu41:19

      Yeah, I mean, I, I can tell you a little bit about how we manage our backlog, which I think actually ties directly into this. We, at any given moment, we have probably like 20 or 30, like, opportunities that we could possibly explore, right? Just product opportunities, right? Like, problems to solve, uh, areas to, you know, sorta- to kind of improve for our users. But they're not, they're not, like, ready yet, right? They're like, "We don't have enough conviction around how we might approach it," so we kind of just accumulate understanding of this stuff and sort of periodically we accumulate some more stuff and then we, like, re-evaluate, "Okay, what is our current understanding of how we might best approach this thing?" And I, I think like something that people sort of struggle with is that they might have this model in their head. Like, a PM might have this model in their head about how a user behaves, but it's just, like, very hard to share that with someone else. You, you have to, you know, you have to, like, telepathically throw it into their brain, which is hard, right? So what we try to do is kind of identify, you know, areas that we might, you know, attack with a product, but also sort of keep an up-to-date analysis of each of those areas so that everyone can kind of, like, engage with it and also contribute.

   3. LRLenny Rachitsky42:22

      Is there an example of something that's sitting in your road map? I don't know if you can share these sort of things that just- I saw where you're sitting in the backlog of just like, "We're not quite ready to tackle this yet, but here's something we're in- inkling on."

   4. NYNan Yu42:31

      Yeah, sure. Um, capacity planning is a, is a thing that's been sitting in our-

   5. LRLenny Rachitsky42:34

      Hmm.

   6. NYNan Yu42:34

      ... in our backlog. And, uh, it's, it's something we see managers struggle with all the time, right? Which is like, I have a limited amount of, you know, personnel and resources, and I need to deploy them in such a way where we can, you know, theoretically accomplish our roadmap, but also we don't get blocked by some bottleneck, that we don't end up, like, blocking all of the projects because this one engineer is stuck on, uh, some infra thing. And, you know, tha- that's a thing people struggle with all the time. All the solutions out there are bad, right? Like the, the best solution is a very, very custom, uh, spreadsheet that someone would make, and it's a lot of upkeep. Uh, so we have some ideas about how we might automate this, how we might use existing, you know, data within Linear to, to really help out with this problem. And, uh, but I don't think we've quite, quite cracked it yet, right? I think there's some nuances that we have to really explore a little bit further, so we're kind of, you know, continuously developing this. And as we hear from, as we hear from users that are struggling with this problem, we will, like, you know, get on a call with them and, and sit down with them and, and talk through it.

   7. LRLenny Rachitsky43:31

      And the idea there is keep informing this mental model, keep informing what this could be, until you get to a place of like, "Okay, cool. I think we figured out what will really solve this problem in an elega- in an elegant way."

   8. NYNan Yu43:42

      Yeah. And I, I, I wanna like really stress a, a, like a nuance here, which is like, it's, it's not that we wanna solve the entire problem, 'cause the entire problem's like, quite big, right? But there, there's something that's like, really right for Linear to do that would like, help people, you know, sort of have a, have a good starting point for them to sort of like reason about it. And, uh, and so I, I think a lot of, like, building conviction around stuff is, is not even, like, do we have a workable solution? It's like, how much of the problem should we actually take on? Because if we take on too much of the problem, then we'll, like, end up over-promising and not being able to deliver on it.

   9. LRLenny Rachitsky44:13

      And I think what's also useful here is you all keep your team very small intentionally, and being constrained, uh, keeps you from taking on these things too early because, uh, you don't have the engineers to build them, or designers.

   10. NYNan Yu44:24

       Yeah, that's, uh, that's true. I, I actually hadn't really, uh, put that part together, but I think that's, you know... I think, I think, um, some of the reason we, we, we've done it this way is because we, we, you know, we don't have the bandwidth to action everything. So we, we kind of like, you know, have this, uh, this backlog that we maintain to make sure that we, when we do, uh, take it on, we're, we're, we're pretty set up for success.

   11. LRLenny Rachitsky44:41

       Yeah. It's interesting. I think a lot of companies are starting to realize that, that they can build better products and move faster with

10. 44:46 – 48:16

    Systemizing creativity

    1. LRLenny Rachitsky44:46

       fewer teams. I wanna move in a different direction and talk a bit about how you actually think about building new products. Something that, uh, I've heard from you is that you have a, uh, systematized way of being creative-

    2. NYNan Yu44:58

       (laughs)

    3. LRLenny Rachitsky44:59

       ... which I think is kind of a dream for a lot of people is like, "How do I be more creative? How do I think of new innovative concepts?" You have a really interesting process for how you do this. Uh, can you talk about it?

    4. NYNan Yu45:09

       Yeah, totally. I, I, I think, you know, when, when people talk about, like, being creative, a lot of times, uh, the, what they have a problem with is extrapolating, right? They, they can kind of see the stuff that's right in front of them, but like, what about two or three steps down the line? And then it's just like, well, there's just so much possibility. I don't know which, you know, what direction to go. So, the way that we try to do it is we ask a question which is like, okay, how, how extreme can you take it? Like, you're, you're designing a, a, a product. You're trying to come up with a solution. Like, what's the most outrageous version of this along some, you know, some, some trait? Um, I, I think, like, I don't know if you guys did this at Airbnb, but I think Brian Chesky talks about, like, like, what, like, what's the 11-star experience? Is that, is that a thing you guys did?

    5. LRLenny Rachitsky45:51

       That, it was a thing he talked about. (laughs) There's always a, yeah, there's always a push of what's, like, the 10X version of some idea.

    6. NYNan Yu45:57

       When you, when you think in that way, right? When you're saying like, "Hey, what's the, you know, what's the 11-star experience?" Uh, what you're, what you're really asking is like, "Hey, what's, like, the most luxurious version of this, this, like, hotel stay?" Or, like, "What's the most unforgettable, you know, kind of, uh, experience we can give people?" And you, you throw away things like, I don't know, like, uh, like, like cost. You throw away things like practicality, right? Because that, that, that's not what's interesting. What's interesting is I, I want to actually explore the possibility space. And I think this is really important to do, because the, the goal is to get you to see beyond, like, your, your defaults, right? We have all of these constraints that we're operating under that we, like, kind of psychically have in the back of our heads that we, we just, like, don't even realize we have them, so just, uh, break past all of them. And, and then you can really see what your options are. Because, you know, we talk about, like, um, we talk about, like, product decisions as like, oh yeah, you have like, these choices. Like, what, what are you gonna decide? And there's, there's all this decision-making kind of, uh, uh, you know, I don't know, theory, right? But like, the, the biggest risk is you didn't see the right choice to begin with, right? You have these three choices and like, none of them were right. It's this fourth one that was like over in this corner, but you didn't look in that corner so you never found it. And, uh, so I, I think the, the whole, the goal of this is to try to, you know, expand the, the search space, right? Of what, of what you're trying to do.

    7. LRLenny Rachitsky47:09

       So, what you're saying is people often, uh, don't think, uh, out, out of the box enough by kind of not thinking too radically enough, and so the choices they're deciding between are just like, oh, meh options.

    8. NYNan Yu47:23

       Yeah. Yeah.

    9. LRLenny Rachitsky47:23

       And there's this process of breaking out of that, and, uh, I think there's like... I think you could hear this and be like, yeah, sure. Like, I could spend like 10 minutes being like, oh, hey, what's the craziest idea? But you're saying that actually is what you do and that actually works really well.

    10. NYNan Yu47:39

        Uh, yeah, and, you know, you do it and you, you actually build it, right? You, you can think of a, a, a very extreme version of a product and it's like, hey, like, let's actually... For the first version, you know, we talked about like, the first version you know is not really the right answer. Sometimes you know it's so hard because you know it like, this is the most extreme version of the answer. So let's build that as fast as we can, and see how it feels. And then we're gonna learn so much about, like, what the right actual answer is because we will have seen this area of the product space and really felt it.

    11. LRLenny Rachitsky48:05

        Awesome. Let's, uh, let's talk about an example of this, 'cause this feels awesome. Uh-

    12. NYNan Yu48:09

        Yeah, I, I can, I can talk through an example. Actually, I, is it okay if I, I demo something?

    13. LRLenny Rachitsky48:13

        Absolutely. Let's do it.

    14. NYNan Yu48:14

        Yeah, let me-

    15. LRLenny Rachitsky48:14

        Show and tell.

    16. NYNan Yu48:15

        Let me do that right now.

    17. LRLenny Rachitsky48:15

        Here we go.

11. 48:16 – 51:38

    Demo: Saving drafts in Linear

    1. LRLenny Rachitsky48:16

       We're gonna share a screen.

    2. NYNan Yu48:18

       All right. Um, so this is just like a, like a demo space, uh, inside of Linear. So the, the, the feature where we did this that I, I remember very clearly, 'cause it was kind of recent, um, is we built this, uh, this feature to save drafts for your issues, right? So Linear, you know, at its heart is an issue tracker. If I, if I make a new issue...... uh, and let's say, I- I'm, you know, trying to report a bug or something, right? So it's like, I make a bug report. Then, uh, you know, I might start thinking through like, okay, what are the repro steps? And then I start typing them. And this happens all the time, right? When you're at work, you're doing this, and then someone distracts you. Someone pings you on Slack, or you have to go to a meeting, or something like that. You're like, "I gotta put this away for a second. Uh, I'll come back to it later." Like, you know, note to self, you know, figure out the actual repro steps and do it. So, like what can you do? Like, well, you want to save it as a draft. So we're like, okay, this is the, this is the problem. And the first, uh, version of this, right? We're like, okay, the most, wh- what do we wanna do? Like, Linear's about being fast, so we don't want to get in your way. We want to say, like, what is the fastest draft saving experience possible? Right? So if you save it as draft, you can save it as draft. If you decide to not, you wanna throw it away, you don't want it, uh, just hit the X button and we'll, we'll just throw it away. Right? We're not gonna like interrupt you with a pop-up that says like, "Do you wanna save your changes?" Or any of that kind of stuff. Right? We'll just absolutely get out of your way, fast as possible. So we're like, what's the risk here? Well, it might feel really unsafe, right? (laughs) If we, if y- if you close this, and we do- we don't, like, ask if you want to save your changes, you might be like, "Oh, I just lost my changes on accident." We knew that going in. Right? We built this anyway. And, uh, yeah. It felt super unsafe, right? (laughs) It turns out that, you know, that- that- that sort of inkling that we had was true, right? But we- and we really felt exactly how- how unsafe it was. Uh, so then we were like, okay, well, what's the, what's the safest thing we could possibly do? Right? The safest thing is just auto save everything, right? So you start, you start a new, you know, a- a new, uh, issue, and then you start typing some stuff, and it's just like auto saving as soon as you type a single character. And, uh, that- that did feel quite safe. So, cool. Um, but (laughs) it also ended up, like, leaving behind, like, a whole bunch of, you know, uh, like a paper trail of things you change your mind about, right? You know, like, you've probably had this happen in, like, uh, document tools where you have a whole bunch of things in your, in your space called, like, untitled document or, like, new document, or stuff like that, and it's just like-

    3. LRLenny Rachitsky50:24

       (laughs) So many untitled folders.

    4. NYNan Yu50:25

       ... leading... Yeah. So many untitled folders, right? It's 'cause, yeah, 'cause the moment you, like, say it's a new folder, it, like, starts saving it, and then you don't actually mean for that to happen. So, uh, so, you know, we, what we... We had those two sorts of variations that we built and w- we felt through. And, uh, where we ended up was, like, a sort of balance between those two, right? And so wha- what happens is if I, uh, if I'm creating a new issue, like I am here, uh, and I close it out, it'll, it'll interrupt me. Or like, it'll, "We have to interrupt you. Otherwise, it feels too unsafe." So I can save the drafts, right? I can go to my drafts. And then if I'm in this sort of draft I've already made, and I go in there and I, you know, and I start to say, like, "Okay, I'm gonna keep working on it," but then I get interrupted again, then I'm just gonna auto save it for you. There's no, there's no point. I'm not gonna ask you again. I'm always gonna auto save, because I'm not gonna create a n- like, a new o- object. I'm just making modifications in place. So we made this sort of very specific choice of, like, on a brand new issue, we will interrupt you, and then on a existing draft that you're messing around with, we're just gonna auto save everything. And someone doing a, uh, a sort of analysis, right? If they did, like, a detailed tear down of th- of these decisions, they might we- they might say, like, "Wow, they- they made very specific choices here." But the path to get there is to do something totally extreme in one direction and then totally extreme in another direction, and then find

12. 51:38 – 54:15

    Breaking constraints and building at extremes

    1. NYNan Yu51:38

       where they- they really meet up.

    2. LRLenny Rachitsky51:39

       Such a good example. The way that you described it is you went, like, "Here's the safest route. Here's the fastest version." Uh, where did you come up with these list of options? And for folks that are trying to do this for their company, are these, like, because these are Linear principles, like, we're gonna be very fast?

    3. NYNan Yu51:57

       Yeah.

    4. LRLenny Rachitsky51:57

       Uh, is this, like, the way you think most companies should operate, these sorts of attributes? Do you think it's, like, specific to what makes their product different? How do you think about that?

    5. NYNan Yu52:04

       I- I think for a lot of companies, it's y- you have to, you know, ask, like, "What is the, what is the promise that your, that your product or your business is making people?" You know, it might be you always have a car available if you need it. And if you do that, then, like, maybe we're gonna have to implement surge pricing to make that happen, right? Like, it's just, it's always gonna be available, so here's- here's the trade-off that we have to make. It's, like, a very extreme point of view to do that. Or you might say, like, "The price is always predictable, but sometimes you can't have a car in the first place." Like, those are all sort of choices that you get to make, and you- you kind of have to sort of decide, like, where on that spectrum does it make sense, you know, b- based on the promise of your company.

    6. LRLenny Rachitsky52:40

       A lot of people talk about this idea of working backwards, Francesc. Airbnb was a big concept of working backwards from the ideal. Let's design the best possible scenario and work backwards. Uh, I love that this is even more tactical, which is just pick the extreme version of very specific attributes. Probably not the s- not the ideal, but it'll give us insight into a version of the ideal, and an element that works well, and then what doesn't.

    7. NYNan Yu53:05

       Yeah. Exactly.

    8. LRLenny Rachitsky53:06

       I- I did this a lot, actually, at Airbnb, just, like, testing the extreme. Uh, so it super resonates, this idea. And w- when you say test, so was it, like, you build it and play with it? Do you roll it out to, like, some of these circles of users? Or is it often just internal and then you, like, learn, and then iterate?

    9. NYNan Yu53:23

       Yeah. We- we- we rolled out some of these versions to- to people.

    10. LRLenny Rachitsky53:25

        Oh, wow. Okay.

    11. NYNan Yu53:25

        So the- the- the s- the super fast version that was l- that was unsafe, w- that only went internal. E- everyone felt it was too unsafe.

    12. LRLenny Rachitsky53:33

        Mm-hmm.

    13. NYNan Yu53:33

        But then, then we're like, "Okay, let's go to the super safe version." And then we rolled that out, and everyone started having a whole bunch of... You know, we did the, like, how- how- how many drafts are people making? Like, this is too many. Like, the people are leaving behind, like, this crazy paper trail. Okay, we gotta- we gotta figure out some- some- some difference here.

    14. LRLenny Rachitsky53:46

        Awesome. So this very much connects to your first point of get something, get things out really quick. And in this case, it's, like, extreme versions you're probably not gonna, that are not gonna work long term, but it will teach you.

    15. NYNan Yu53:56

        Yeah. Exactly.

    16. LRLenny Rachitsky53:58

        Amazing. Okay. And seeing it in action, I'm like, okay, obviously this is the solution. That's how the way this should feel. (laughs)

    17. NYNan Yu54:04

        Yeah.

    18. LRLenny Rachitsky54:04

        And to your point, it was not an obvious solution when you started thinking about it.

    19. NYNan Yu54:08

        Yeah. I mean, the best solutions are always obvious in hindsight, right? And it's just like, you have to develop a, a process internally that, to eventually find your way there.

    20. LRLenny Rachitsky54:14

        Mm.

13. 54:15 – 58:22

    Adopting new tools

    1. LRLenny Rachitsky54:16

       Something else that you've mentioned when we were chatting that connects to some of the things we've been talking about is you have this perspective that B2B software isn't just solving people's problems, it's also teaching them how to work. And it's kind of this, like, accumulation of information. Could you talk about that? 'Cause I thought that was really fascinating.

    2. NYNan Yu54:36

       You know, I, I, I think, like, if you think about how a lot of B2B software gets created, it's because there was some person in the middle of some giant company who implemented some kind of process, and they're like, "Wow, this process is really working for us. Maybe we should make it easier." And they build a little tool internally, and then, like, all of their, you know, colleagues can now, like, press some buttons and good things happen. A- and then they turn that process and that tool, you know, they spin it off into a startup, and they, like, make a start, right? Th- this, this process repeats thousands of times. So when you adopt that tool, you're not just adopting, like, the, the actual software. You're adopting the idea that this is a practice that you ought to be doing in the first place. So, I, you know, like, if you're, if you're a marketing person, right, and you, like, you adopt some marketing software, you're not just saying, like, "Okay, now I can, you know, kind of write emails and send them to people." There's all sorts of process around that. Like, you h- you're organizing something in the campaigns. You're measuring click-through rates. You're, like, calculating, you know, uh, cost of acquisition. And all that stuff probably comes equipped with a tool, because those are the right practices to do when you're, when you're doing this sort of, uh, marketing exercise. And, you know, whe- whether you knew about it before, right, or you learned it from, uh, from the tool, like, as a, as a buyer for, uh, for this kind of product, what I'm doing is I'm saying like, "Hey, I'm gonna bring in this baseline level of marketing competency into my organization," right? That, like, this is the worst we can do is whatever the tool defaults are.

    3. LRLenny Rachitsky55:57

       Interesting. So it's ... You're basically buying into a way of working when you're adopting a piece of software, not just, "I have this problem I need solved."

    4. NYNan Yu56:06

       Yeah. Exactly. And I, I think the, the most, um, the most, like, salient example of this is, if you've ever seen, uh, like a, like a company adopts, like, an ERP product, it's the most painful thing you can imagine, right? They have to, they have to, you know ... It's doing deep surgery. They have to re- redo all of their, uh, internal processes and the way they manage inventory and all this kind of stuff. But they're willing to do it because they know that this is a battle-tested way of making sure that, you know, you, you are actually doing good, um, like, management of, of, uh, of resources. So they're like, "Look. We're growing up now. It's time for us to adopt these best practices. In order to do that, we have to adopt this tool, and we will conform to whatever the tool expects us to do."

    5. LRLenny Rachitsky56:44

       This connects to a couple things I know about Linear. One is what you've shared of just avoiding these customizations requests from people. Like, you have a very opinionated way of, "Here's why we ... Here's how you should operate in order to build a great functioning product org and company in general." So I think, like, I'm just connecting threads here. One is, like, "We're gonna avoid letting people customize too much 'cause it, we know they will have a bad time." And then two is, yeah, just this idea of, uh, we are opinionated about the way you should work in Linear. And it's like, you have the Linear method, I think it's called, of just like, "Here's how product team should operate based on everything we've seen be successful."

    6. NYNan Yu57:19

       Yeah. Yeah. It, it's, it's definitely connected in a way. And I, I, I think sometimes when, when people talk about, um ... You mentioned, like, being opinionated. And I think sometimes when people talk about being opinionated, it can feel like they're almost saying like, "Hey, this is, like, kind of arbitrary," right? Like, "Your opinion and my opinion, they're just two opinions, man." Like, like, you know, w- w- neither is right or wrong. What we try to do is find where there's actual consensus, right, amongst a lot of different, uh, high-performing teams. And then we can, you know, take those practices and say like, "Okay, for a team that isn't, you know, already practicing this, can we give them a button so that they can start practicing this?" Right? When, when, when a company, we see companies, like, doing really good job of managing their triage queue, and, but it, you know, it's like, you know, it's very manual. We're like, "Okay. Can we automate this?" And then for this other company that really needs it, that they, they don't know this is what they need, can we just give them a button to activate this? And now they have to practice within there or two.

    7. LRLenny Rachitsky58:10

       So I think a takeaway here is when you choose a tool, uh, recognize that it's gonna change the way you operate and be thoughtful about, is this the way we wanna work?

    8. NYNan Yu58:19

       Yeah.

    9. LRLenny Rachitsky58:19

       Versus just, we just have a problem we want solved.

    10. NYNan Yu58:21

        Yeah, exactly.

14. 58:22 – 1:04:23

    The “double triangle” framework for product management

    1. NYNan Yu58:22

    2. LRLenny Rachitsky58:22

       I wanna come back to something, kind of a thread that's come up a couple times in our chat, is the way you collaborate, uh, internally. It feels like there's a pretty unique way ... You, you said you're on all the sales calls. Is there anything that you can share about how you collaborate internally, how the different functions collaborate that may be unlike how other companies operate that might be helpful for them to learn from?

    3. NYNan Yu58:44

       Yes. Something that's worked really, really well for us is, uh, we think of product management as, as partially like a go-to-market discipline in the same way that sales and, and marketing are, right? Like, when y- when you talk to people and like, "Hey, like, tell me how product management works in your company," they'll probably say something about like, "Well, there's engineering, product, and design. They work in this triad, and here's, you know, here's how they, they interact and, and collaborate." And we all kind of understand why that's useful, why that's helpful. Uh, but this sort of other form of collaboration between product management, uh, sales, and marketing, I think it's something that's, like, probably, um, really under-examined. And often ... You know, often, I, I feel like in organizations, you actually see kind of, like, some antagonism between product and, and, like, sales and marketing. Uh, and I think that's kind of a shame, right? Because, you know, when, when we, uh, come- kind of come together, the way we think about, um, you know, the, the way that we think about selling is a matter of, like, especially 'cause we sell to ... We sell the very sort of expert practitioners, and they have, like, a, they have a very sensitive BS detector, right? So, like, we h- like, a big part of what we try to do is we try to help them pick, um, we're trying to help our marketing team, like, pick exactly, like, the right word and the right phrasing to make us sound, like, native to the language that our customers speak, and also give us a lot of-

    4. LRLenny Rachitsky1:00:04

       You're talking about engineers, is my, is my, I ... my sense, right?

    5. NYNan Yu1:00:07

       Yeah. Like, engineers is a, is a big one, but even product managers, right?

    6. LRLenny Rachitsky1:00:10

       Mm-hmm.

    7. NYNan Yu1:00:10

       Like, product managers kind of know when, you know, like, they, they know what the job is like, so when you kind of come in, you say the wrong words, people kind of like give you a, give you the stink eye.

    8. LRLenny Rachitsky1:00:17

       Don't call them project managers.

    9. NYNan Yu1:00:19

       Yeah. Exactly. Like, for, for example. So I, I, I think that's a, that's a big part of, uh, you know, what we have to do, right? So like we, you know, on the, on our, on our PM team, we actually have a full-time product marketer, right? And her job is to, like, you know, like, tactically it's like all the change logs come from her, all the release notes, right? And also, like, the, you know, she's, she's always crafting the language for whatever upcoming release that we're, uh, we're building and, you know, working with, directly with the teams and trying to figure out how to talk about it.And then once we, you know, go out and build the campaigns, um, build assets and things like that, like that's where, that's where a lot of the language is coming from. It's coming from the work that she's doing. Uh, and then, you know, with sales, like they're validating all that message like in the field, right? They're, they're saying (laughs) the words to customers directly and telling you if it's like sticking or not. And then you can kind of like, you know, have a really good feedback cycle, uh, between those three disciplines.

    10. LRLenny Rachitsky1:01:05

        What I've seen you, uh, refer to this way of working as, is a double triangle, which is, I think, a compliment to like the PM engineer designer. Talk about that and give us a s- visual of what that looks like.

    11. NYNan Yu1:01:15

        Yeah. You know, I, I think, (laughs) W- uh, W- PMs, right, like product managers, we, w- we often have a, a tough time like trying to explain like what i- what is your job, right? Like, you know, oh, it's like a little bit of everything. And I, I think the, you know, the job that I sort of, uh, do, right, and that we see it as is, uh, you're taking the sort of building side of the organization, and the, the selling side of the organization, and bringing it together. That's, you know, you're, you're taking all of the commercial like motivations and goals of the company and making sure that what you build, it actually solves for those, uh, those goals. And, you know, you're, you're sort of tempering that with like what's, you know, possible, and, uh, and sort of where the opportunities are to, to actually build stuff. So, I, uh, like to me, like it's, it's the PM in the middle, and then you have, uh, engineering product design, and then sales marketing product management on the other side.

    12. LRLenny Rachitsky1:02:03

        PM was always in the middle.

    13. NYNan Yu1:02:05

        Indeed.

    14. LRLenny Rachitsky1:02:05

        Uh, but I think that's true from the perspective of PM. Uh, and I, I love, I love this, uh, visual of just like the PM is connecting the builders to the sellers, and you're involved in both worlds. This connects very directly to the Brian Chesky's whole thing about how PMs are, are... should be doing marketing. And so the way they changed at Airbnb, every PM is also a PMM and there's no more... Uh, they're product marketers now. That's their title. And they, that's like the extreme version of what you're describing.

    15. NYNan Yu1:02:33

        Yeah. Yeah. It is. And I think Apple's been doing that way for forever too.

    16. LRLenny Rachitsky1:02:37

        Mm-hmm. Got it. So the advice here is if you're a PM at a B2B business, uh, lean into the sales and marketing side of it. Lean into the go-to-market.

    17. NYNan Yu1:02:45

        Yeah. And in fact, if, if you're, if you're leaving something on the table, right, in terms of like w- the kind of impact that you are having at your job, that's probably the thing that you're leaving on the table. You're probably already doing a good job of, you know, collaborating with engineering and, uh, and design, right? It's probably the sort of sell side that you're, that you're, uh, you know, kind of there's an opportunity for you to, to have more impact.

    18. LRLenny Rachitsky1:03:05

        Just to make it even more concrete, for PMs that are like, "Okay, I wanna do this. I wanna, I wanna do what Linear's doing. I'm gonna get more salesy," what does it look like when someone is more, uh, is in this double triangle working more closely with sales? You talked about being on sales calls. What else there can you share of just like, "Here, try these things"?

    19. NYNan Yu1:03:20

        I, I think originate the message that you, uh, that you send to your audience, right? Like there's a lot of things that marketing does, which you are never going to necessarily touch, right? There's always like demand gen, and figuring out channel strategy, and all this kind of stuff. Like sure, right? That's a pure marketing concern. But actually picking the words and w- where the emphasis is, like you should understand the customer at a pretty deep level, probably deeper than any other, uh, like group at the company, 'cause you know, 'cause of the, the kinds of requirements gathering discovery that you're doing. So you're gonna fi- you're gonna know the native language that your customers speak a lot better, and, uh, you know, help your marketing team originate those words.

    20. LRLenny Rachitsky1:03:58

        Got it. So basically be really involved in the, in the mo- product marketing, the writing, the, the emails, the headlines, the website.

    21. NYNan Yu1:04:06

        Yeah. Yeah. Exactly. And it's like, I know, I know like the word product marketing is also so overloaded.

    22. LRLenny Rachitsky1:04:09

        Yeah.

    23. NYNan Yu1:04:09

        They do so many different things and it... But it's that, it's that sort of like content, you know, kind of creation piece that's, uh, that you really have an opportunity to contribute to.

    24. LRLenny Rachitsky1:04:16

        Yeah. I love how concrete that is. It's like, don't think about this concept of product marketing. Just think about the words that your potential customers and customers see.

15. 1:04:23 – 1:09:15

    Effective job-hunting strategies for PMs

    1. LRLenny Rachitsky1:04:24

       Okay. Uh, final area I wanna spend a little time on is totally different. It's around getting a job.

    2. NYNan Yu1:04:31

       Oh yeah. Okay.

    3. LRLenny Rachitsky1:04:32

       You have a pretty unique, uh, approach to finding a gig. Uh, I heard from the founder of Mode about the very unique apro- uh, way you approached getting a job there. I imagine Linear is a similar boat. Uh, what h- what advice can you share with folks that are looking for a job, maybe struggling, that worked for you when you were looking for your next gig?

    4. NYNan Yu1:04:51

       Th- product management is, uh, kind of a unique role, right? Like because we do just about everything, they're... N- you don't really get pigeonholed into, you know, being sort of compared along a single dimension, uh, with everyone else. And everyone who's hiring PMs, just like when they're hiring execs, they're, they're, they're kind of hoping that they bring them on to solve some burning problem that they, they have. And, uh, so it's your job when you're in the ev- in the interview process to figure out what that burning problem is, right? So like put on your, your dis- your discovery hat, right? And you go figure out like what is the actual sort of like job to be done of the hiring manager when they're bringing on a new PM onto their team. And if you can do that, right, and then make a good case that you are the person to solve that problem, then hiring you becomes a sort of like binary choice between do I hire the solution to my problem or do I hire someone else? And, and I think what, what ends up happening a lot is when we're in, you know, when you're in a, a interview process, you're just like trying to put your best foot forward, trying to say that you're, you're great at everything. You have like very few weaknesses. Maybe you try too hard. Like whatever it is, right? And, and then you... But everyone's gonna say that. So you're just like one of N people, and you wanna make yourself a little bit of like just you versus the field, right? Like you are the solution to a problem, and then everyone else is a, you know, sort of like a, uh, uh, a roll of the dice.

Episode duration: 1:21:07