Lenny's Podcast: Product | Career | Growth - Linear’s secret to building beloved B2B products | Nan Yu (Head of Product)

Episode Date: January 30, 2025

Nan Yu is the head of product at Linear, one of the most beloved and fastest-growing B2B SaaS products out there today, and the gold standard for high-performing tech teams. In our conversation, we discuss:• Why speed and quality aren’t actually at odds• Linear’s unique approach to product development• Nan’s systematic approach to creativity• Linear’s philosophy on deadlines• The “double triangle” framework for product management• Nan’s approach to landing his dream product roles• Much more—Brought to you by:• Sinch—Build messaging, email, and calling into your product• Paragon—Ship every SaaS integration your customers want• Wix Studio—The web creation platform built for agencies—Find the transcript at: https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu—Where to find Nan Yu:• X: https://x.com/thenanyu• LinkedIn: https://www.linkedin.com/in/thenanyu/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Nan Yu and Linear(04:54) Survey insights: Linear vs. Jira(07:51) The speed vs. quality myth(09:24) Building and iterating quickly(15:31) Avoiding bloat in enterprise software(23:57) Understanding user needs deeply(30:09) How to approach customer calls(34:10) Creating strong emotional hooks(40:31) Managing the product backlog(44:46) Systemizing creativity(48:16) Demo: Saving drafts in Linear(51:38) Breaking constraints and building at extremes(54:15) Adopting new tools(58:22) The “double triangle” framework for product management(01:04:23) Effective job-hunting strategies for PMs(01:09:15) Thoughts on deadlines(01:14:15) Lightning round—Referenced:• Jira: https://www.atlassian.com/software/jira• Linear: https://linear.app/• Patrick Collison’s post on X: https://x.com/patrickc/status/1869422495985750459• Magnus Carlsen on X: https://x.com/magnuscarlsen• Hikaru Nakamura on X: https://x.com/gmhikaru• Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead• Customer Request feature on Linear: https://linear.app/customer-requests• Everlane: https://www.everlane.com/• Schlep Blindness: https://paulgraham.com/schlep.html• Linear’s triage tool: https://linear.app/docs/triage• Patrick Collison’s post about mental models on X: https://x.com/patrickc/status/1443215022029619200• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of• Mode: https://mode.com/• The Diplomat on Netflix: https://www.netflix.com/title/81288983• Sakura Micron pens: https://www.amazon.com/SAKURA-PIGMA-MICRON-ESSENTIAL-COLORS/dp/B07VJFXT3C/—Recommended books:• Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986• The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [e-mail].—Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

I think you see in 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. 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 pinnacle of their craft, you can basically tell how good the output is going to be of their work product by how fast they're going. What does speed look like when you say it can be done quickly and high-quality? What it really looks like is, you know, you have some rough time budget for how long you think something's going to 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.

Imagine a criticism you all get. Over time, you'll probably become a bloated piece of software as well. When we examine this problem, we kind of look at, well, 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 the, this bloatedness that makes I sees kind of hate their lives. Something that your head of sale 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.

My goal is to feel bad in the same way that customers feel bad. Today, my guest is Non You. Non 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 Non, 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 non- You. This episode is brought to you by Cynch, 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 Cynch comes in. Over 150,000 businesses, including eight of the top 10 largest tech companies globally,

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Learn more and get started at cinch.com slash Lenny. That's s-in-c-h.com slash Lenny. This episode is brought to you by Paragon, the integration infrastructure for B-2B SaaS companies. Is AI on your 2025 product roadmap? Whether you need to enable rag with your user's external data, like Google Drive files, Gong transcripts, or dear tickets, or build AI agents that can automate work across your user's 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.

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are already shipping new integration seven times faster with Paragon, keeping their engineers focused on core product development. Ready to accelerate your AI roadmap this year, visit useparagon.com slash Lenny to get a free MVP of your next product integration. Nan, thank you so much for being here and welcome to the podcast. Thanks for having me. I'm a long-time listener and reader, so it's really a treat to be here. 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 up, 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. Wow, I mean, hopefully that means we're doing a good job. I think 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 they 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. I mean, it's really good to hear that because, you know, 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 in these places and just, you know, watching everyone around him struggle using the tools that they had available and, like, always 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 technology and design and engineering, all this kind of stuff because it was fun, right? All of us started off, like, building stupid Myspace pages and all of these, like, side projects when we were young. and it started off as this fun thing that we do and we're like, wow, we're going to do this for a career. And then to have all of this kind of stuff put these big speed bumps into our day-to-day workflow. It just was really sad. So that's what, you know, that's why we started linear to sort of really bust their role of that. What I love about linear, I feel like it's an inspirational business because many people want to, I'm going to 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 or 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 you 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 enterprise software, especially. So let's get into it. The first question I want to

get into is something that I think you see in the team at linearcies 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 just an innate fact, and something I've heard you talk about is that's not actually true. And I actually saw Patrick Olson tweet this exact point that I'll read after you, I want to hear your thoughts. But talk about what you've learned about how there's maybe not actually this trade-off between speed and quality. 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 over-index on is, is like, rushing or

being sloppy. And what they should be indexing on is being really competent or being like an expert. So if you look at, if you look at people who are like at the pinnacle 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 going to be of their work product by how fast they're going. They're going really fast and they're obviously not like being sloppy and then leaving a mess all over the place. It's like, yeah, well, 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 try stuff. And when we're building software, 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 going to get a bunch of iterations done and try different things and really feel out these different variations is by just going very fast. 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? What it really looks like is, you know, you have some rough time budget for how long you think something is going to 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 panning out the way we expect it to or that we have some crazy incorrect assumption. And, you know, you don't want to wait until you're 80% done to be able to make that kind of judgment because then it's just too late. Then you're pushing deadlines out and you're, uh, you're making your marketing team very sad. Amazing. Okay. So the way you think is we're going to 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. Yes. Yeah. Yeah. I guess how can you do that? Because most teams can't do that. Most teams need to research, design, build. Okay, cool.

We have something and it's a month later. What allows you to do that? I mean, there's a lot of components of it. I think having really good talent really helps, right? Having engineers who don't get blocked by every single little design choice, you know, they're happy to just make something workable, even if they don't feel comfortable with that particular solution,

they'll just bust through it 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 going to be great. Right? That is not in the cards, right? 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. Some of it was, wow, this first version was pretty good. Let's make some minor adjustments 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 really, you know, really in tip-top shape, right? It just has to work and get the job done and, you know, kind of validate or invalidate our major assumptions.

I'll read this quote from Patrick Halston. He tweeted this today as I was preparing for this interview. And he's the CEO and founder of Stripe. you're not familiar. His tweet was, I increasingly believe that good, cheap, fast, choose to, Maximus devious misinformation spread by the slow. In my experience, slow and expensive usually go together. Yeah, exactly. I mean, use the contractor kind of an example. Like, if someone's making a modification to your house and it's taking forever, like, one, you're in a hotel and also the bills are adding up. The other example I used when we were chatting about this earlier is

chess players. I'm thinking of Magnus Carlson 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. Yeah, I think that's the same of the case and like, you know, Magnus and Hikaru and all those guys who are at the

top of their game, you know, they can go unbelievably fast. In fact, that's the usual, I mean, I don't want to get too out of my depth with chess, but the usual way you try to make the game fair, you give them much, much less time, right, than someone who's not quite a strong of a player. and they'll still win a lot of time too. So maybe just to close out this point

to 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? I think it's really that

that sort of attitude and point of view question, right? To sort of understand and take the sort of almost like controlled risk that the first version of this is not going to be perfect. So it actually makes it a lot cheaper in many ways. It means you don't need a 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? 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 is facing our users? You can take it back to users. You can even let them into an early beta or something like that and get real validation there. And the sort of really focus on getting the smallest kind of just shippable element. Not shippable in the sense of like I can actually put out the production, but in the sense of I can, you know, start learning from here. Just a question I imagine as in everyone's mind is,

what do you do with this first very ugly V1? Not ugly, not fully ready. First version. Is this something you're using internally to see if it's something? Is it something you have beta and design partners with? We have a sort of gradually increasing sort of

circle of users that use every single feature. So by the time it hits GA, by the time it gets released, it's been used by a lot of different users to that point. So the first circle is just internal users. We use linear every single day to write software and do our own work. So 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, 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 release it to sort of early access customers who can give us good feedback and

also just try to solve their problems with it. If no one engages with it, if no one's using it, then 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 GA where everyone gets it. That's an amazing answer. Okay, so secret number one to linear success. I'm going to take some notes here is get new feature product ideas out to people as early as possible, say in the first 10% of the amount of time you've allotted, and then release it kind of increasingly to more and more people to get feedback.

Like, I think the 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 all go. Yeah, totally. I imagine a criticism you all get. 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 checkboxes. 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 spent 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, I need single sign on with this thing in 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? This question actually comes to us a lot from candidates that are interviewing with us. When you go like, hey, do you have any questions for us? Like, this is the question that we're going to get. Right. So we hear quite a lot.

And it's very sensible for them to ask it, right? Because they see sort of history being kind of littered with the corpses of startups trying to compete in the space and not making it. And I think when we 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 stuff that we absolutely have to say no to

is also the exact kind of thing that leads to this kind of like bloatedness that makes ICs kind of hate their lives. And 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 no debate because we've already thought about it. And this is the thing that we can't, we can't take a single step down this path.

So I think that's like, honestly, one of the core promises of linear is that we will not make this particular tradeoff. So when you see people saying like, wow, you know, linear is so much faster, it's so much easier to use that it makes my work so much more enjoyable. Like this is the reason because we have not taken a single step in this direction. It's very easy for a PM to say yes to this kind of request, right? Because they're talking with, often they're talking with buyers, right, any kind of like B2B type of space. They're talking with whoever the gatekeeper is and sales is putting pressure on them. And they're saying like, hey, we really want this one feature. It's going to make our reporting nicer, so, like, you know, the director is going to be really excited by 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 whole premise is wrong because the moment you start going down this path and you make the IC user experience worse, they're just going to 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 going to do that.

part or I'm going to do it very sporadically. And then, you know, I'm going to just focus on my actual job. And then all your reporting is wrong because all the data is wrong and it's like sparse. And you get, you get situations where people will, you know, they'll say like, well, here's a drop-down field that someone put in here that's required. There's nine choices. I don't know what any of them meet. So I'm just going to pick one at random.

I'm just all I'm going to pick the first one. Also, I'm going to pray that my boss is not actually using this data to do any kind of reporting. that has consequence because the data can't possibly be correct. So I think for us, it's a very easy decision when it comes to that particular category of feature request. I love how simple and clear that is. Basically, you all have a policy.

We will prioritize ICs over middle managers, especially. I love that it's around reporting almost always. It sounds like, I want to track what's happening. Yeah, exactly. I want to track what's happening. Well, what do you want to track? Well, I want to track which, you know, which version of the product. this thing's tied to, you know, based on 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 going to do that, man. 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 adding that one feature that will close a massive million dollar sale. 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 holding the line on this. Is that right?

So it is, but I also think that there's not as much pressure as you would expect, right, to do these kinds of things. There are basic scaling things. Like, you know, we had to make like Samo and skim and that kind of stuff. It's like, yeah, sure, we're going to 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 the apps like value proposition, What buyers care about is, is this going to 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, especially with larger companies, right? The current situation where it 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. 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. Yeah. And the thing is, it's not everything you want, right?

Because people come with a laundry list. And it's like, laundry list, here's 10 things I want. You know, like, do you want all of those 10 things equally? They're like, no, actually, I don't. The first three are the things that really matter to us. 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. going to get to the quality level and the depth that we're able to offer by offering those as native features. It's interesting thinking back to that survey I shared where like the tool people want to switch to if IT allowed them was linear. And on the one hand, you could argue, well, okay, IT's not letting them use linear for all these reasons. On the other hand, you guys are growing really quickly within enterprise.

Like you're not, you're a new business. You started, I think, mid-market startups and now you're working where you up. And so I think it's, it's not fair to say it's not going to work in enterprise. It's clearly working really well. I don't know if there's any stats. You can share anything of that, but it seems to be going well, expanding a market. Yeah, I mean, growth has been good. Growth in enterprise has been, you know, leading the other segments because I think we,

this year especially, we reached a tipping point where, you know, I think with software, so much of the buying decision is based on almost like a brand thing. Or like, is this for us, right? It's like, you know, a lot of times people pick, you know, like, quote, enterprise software. It's like, why? You know everyone doesn't want this. And they're like, yeah, but it's like, it's for us. You won't get fired for buying Microsoft or whatever.

Yeah, exactly. And I think that we're starting to have enough brand penetration amongst enterprises where people can can have that feeling. Right. Hey, like, linear is for us. 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 want to go fast? Yeah. I had Jeffrey Moore in the podcast, and this is exactly what causing 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, I love new stuff. And I'm going to, an early adopter kind of evangelist, 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. I also think that with this kind of this particular category of tool, 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 exact that's really wedded to 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 where, you know, we make sure we follow up. And, you know, we've had a lot of these where, you know, we've been said no to. two years ago, and now we have some new features, and go like, oh, yeah, it seems like, it seems like you're ready for our scale or whatever. You mentioned that when you have these debates and questions that come at,

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 I see wants to be more productive and successful in here. Give us a little sense of some of the more complicated debates that aren't necessarily, in that bucket. I think 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 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. Like a specific person. Like you have a specific person. Okay. Yeah. Yeah, exactly. Not a hypothetical person, right? Not one that you made up, like, you know, Alice Bob or whatever is like, no, I, like, here's the 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 reality in that way is, you know, is a big part of how we really think about and discuss these things. This connects the way I think

about my newsletter is 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. Yeah. I think, I think a trap that a lot of times PMs will fall into is they will make something and they'll make some choices in it because, you know, maybe it's beautiful or it's elegant, but they don't go the step of like, is reality also beautiful and elegant? Because reality is kind of ugly sometimes. And if you have a beautiful, ugly solution, it doesn't match with reality. It doesn't

really matter. People can look at it and they can, they can, they can, ooh and awe. But if they don't use it to get their work done, it's never going to have, like, long-term staying power. Do you have a heuristic of how often you need to hear something for you to, could be convinced this is worth investing? And, you know, people may hear this. Oh, when Bob, Bob wants us featured. That doesn't make sense. It's just one guy. How do you know when it's like, Okay, we should really invest in this. Part of it is you hear something and you're like, gosh, that actually is, no one's 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 a kneeling, right, where like you have a thing and it's not quite the right shape and you put it out into the wild. So this happens like way in the 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 it doesn't quite fit reality. 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 you didn't, then it's like, 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 right or wrong? That's one sort of category. Another category is just you're getting, you know, you're getting requests for maybe a very big feature or a 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. how you're trying to use this. And there's like a hundred different use cases. So you have choices

here, right? You can either build the big feature that covers all the long tail use cases, or you can try to see if there's like really concentrated pools of use cases for this that really make a lot of sense to kind of adopt as a sort of first order type of feature. So I think those are the two sort of strategies that we 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 for this big general feature that people are asking for, are there actually more specific

kind of use cases that we should be solving and we should be solving really, really well. A thread that's coming through so far across a lot of these examples is getting to the person, the specific person using the thing

and making them happy and making sure the ask is going to solve their actual problem. 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,

and not, there's like 100 people generally asking for this thing and let's build what we think is a general solution. Yeah. Like, I'll give you an example of all of these things, right, which we just launched a feature called customer requests. And basically what this does, right, it brings, it adds a new concept to linear, which is like a customer, right? For B2B companies, this is very relevant.

And the reason we did this is because we kept getting this request for, you know, for like fully customized fields. right? And we would be like, well, what is it that you want with your custom fields? Because the problem is you add 100 custom fields and all your IC start hitting it. Right. So like, 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? Walmart asked for this feature and it's really important. I need everyone to know that Walmart needs this. I need to track in. I need to see like how have we, you know, report, we can report on like,

what have we done for Walmart over the past year so that when we're, my CSM has a one-on-one conversation with a rep, they can have some kind of evidence that we've been doing stuff for them, like all those kind of stuff. We're like, okay, cool. Like, that sounds like a very useful and powerful thing you want to do. How do you expect people to, like, tag these things? Well, manually, because that's how we did in our spreadsheets.

It's like, okay, instead of that, we're going to hook up with your customer support tools. We're going to hook up with your CRMs. We're going to automatically bring in, like, feedback from these companies. We're going to analyze the emails where they're coming from. And then we're just, if someone, request a feature that gets escalated into engineering, it'll just be tagged with whoever asked for it. But you don't have to do anything, right? But you will know, and you can still report on this stuff. But there's nothing about this that makes I see's 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 and exactly what the email said. So when they get all the, when they're doing the design or the or the details, they can actually see the real life use cases that are present and solve for those directly. As I'm hearing this, it's like, okay, obviously this seems like an obvious solution. of course. 40% of people telling me they have customers. 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're another. Most of the time you're going to build this custom field. Something that your head of sale 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 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 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. You know, it's funny because I think from the outside, right, I'm on these sales calls and then the AE or someone's like, watch me ask these questions. And I think often they're like, what are you doing? Like, you're just,

you're just like asking questions from angles that 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 can do the normal analytical thing and be like, ask five Y's and like try to figure out like, well, what are your goals? And, you know, as a persona X, I want to achieve this outcome. You can do it that way.

But 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 going to get promoted at work. Like, okay, great. I understand the severity of your problem at this point, right? Like, what is the actual sort of emotional valence that is motivating whatever you're telling me? And it takes a little while to get there, right?

Like, you can ask people directly, like, how do you feel? And, like, they're not necessarily going to 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 open up to you and, like, tell you like,

honestly, like, you know, I had this thing happen where 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 my marketing team lost their mind because they're like, we can't ship something at December 30th.

Everyone's on vacation, right? And you're like, and then they're like, yeah, this made me feel really bad. So I don't ever want to put dates on things ever again. Right? So like, okay, cool, we can help you deal with that, right? Like, if that's what you're feeling, then I can, you know, kind of start building stuff to make sure that you never have to have that bad feeling again.

People talk about empathy. Like, you need to have empathy as a PM. You need to build empathy. The best product leaders have empathy. And 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 of the deadline. Yeah. And it's, you know, if you, if you ask somebody in that last story, like, like, 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? But it tells you is like you had this terrible moment of communication. That was just, it felt like miscommunicated and you're, you know, like, it's just going to keep happening over and over again. And so, you know, the thing that we did specifically to solve this, was we, you know, on projects in linear, you can just specify of 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 sense of like false precision so that, you know, it ends up with a whole bunch of miscommunication down the line. I could see why people love linear is it just makes them feel less bad, less often. Yeah. There's a lot of. connection here. I know this idea of emotions and feeling bad as 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? So I just sort of set the background of this, right? I worked in very, very competitive industries. I worked at Everlane, which was like a direct-to-consumer clothing brand. I worked mode, which is like BI tools and there's like so many BI tools out there. And then obviously linear, like we're, you know, we're project management. There's a lot of project management tools. And I think the more competitive your, your industry is the, the more the sort of like low hang 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, like, what's your goal? Like, what is your job

to be done and all this kind of stuff? And so you have to kind of look at things from an angle that other people might not have seen. And for me, right, and for us, it's, it's the, the angle of, of, like, where are the emotional hooks that, you know, that you're experiencing, you know, as you go through your work day, as you use our product, as you use, like, competitors' products. And I think it's probably under-explored because, I don't know, I feel like, I feel like, we're, like, very thinky people. We don't really, you know, we, like, kind of avoid the touchy-feely stuff. And so, like, I think that's the opportunity, right? you can sort of see, where are you feeling back to a day where you don't even know, right?

You might think, I hate Mondays, right? Like, 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 gave you a button that made the report, that helps, like, yeah, yeah, then I might not hate Mondays so much. And so, like, I think Paul Graham has a word for this. He calls it, he calls it, he calls it, shlep blindness, right?

Like, I'm like schlepping through life and I'm just completely blind to it. And it's true, right? You kind of have to 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 kind of note the spots where, you know, you could really use a lot of improvement. Is there an example? I'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 an example of the dates. I guess is there anything else? A big sort of feature that people love about linear is we have this thing called triage management. And what it does is it sort of systemizes this thing where like if I put a issue into 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, you know, like people will, you know, people will be able to kind of respond to it and in a sort of organized

manner, right? And I think this, you know, this kind of automation, this feature, it came out of two different feelings people were happening. One, people were trying to implement this stuff by hand. And it was just a lot of touches. And they were doing it, but they felt like,

oh, I'm totally underwater. Why you're underwater? Well, I have to like manage all these, throw all these tickets around and route them correctly and stuff like that. 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, because they were managing by hand, 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 then there's the, you know, the folks who didn't do that. that 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 going to respond to them. So, like, there's all of these, like, bad view that people are having. They're all kind of the same group cause, which is like there wasn't a very automated, organized way to deal with your triage queue. Marketers, I know that you love TLDEARS, so let me get right to the point. Wick Studio gives you everything you need to cater to any client at any scale, all in one place. Here's how your workflow could look. Scale content with dynamic pages and

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And when you're ready for more, Wix Studio grows with you. Add your own code, create custom integrations with Wix-made APIs, or leverage robust native business solutions. Drive real client growth with Wix Studio. Go to wix studio.com. I'm going to try to summarize some of the secrets of a linear success 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 they're using early stuff. Two is prioritize the IC and the user basically versus the buyer or the middle manager that wants reporting and all these custom features. So it's basically focused on the user, 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 a hundred times, find the person that actually needs this thing and understand what's going on. And then four is look for bad, feel 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? You know, the part ways to like focus on user, I think it's maybe a little bit more subtle than that. 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 an 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, they're just very misaligned. And you have to find those situations and be pretty judicious about how you make those tradeoffs and where you can really find kind of like win-win outcomes there. That's a really important nuance. something else that's come through a couple times as you've been talking is also something Patrick Cawson 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 going to figure out what to build. We're going to 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 you do a bunch of research, look at data, talk to people, that informs your mental model of what the customer needs. 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 imagine. 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. Yeah, I mean, 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 areas to, you know, 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 think it's like something that people sort of struggle with is like they might have this model in their head. Like a PM might have this model in their head about how user behaves. But it's just like very hard to share that with someone else. 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 the 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.

Is there an example of something that's sitting here, Roadmap? I don't know if you can share these sort of things. that just, I'm sorry, sitting in the backlog of just like, we're not quite ready to tackle this yet, but here's something we're inkling on. Yeah, sure. Capacity planning is a thing that's been sitting in our, in our backlog. And it's something that 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 some infra thing. And that's the thing people struggle with all the time. All the solutions out there are bad, right? Like the best solution is a very, very custom spreadsheet that someone would make. And it's a lot about keep. So we have some ideas about how we might automate this, how we might use existing, you know, data within linear to really help out with this problem. But I don't think we've 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 sit down with them and talk through it. 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 elegant way. Yeah. And I want to really stress a, like a nuance here, which is like, it's, it's not that we want to solve the entire problem.

The entire problem is, like, quite big, right? but there's something that's like really right for linear to do without like help people, you know, sort of have a have a good starting point for them to sort of like reason about it. And so I think a lot of like building conviction around stuff 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 overpromising and not being able to deliver on it.

And I think what's also useful here is you all keep your team very small intentionally and being constrained keeps you from taking on these things too early because you don't have the engineers to build new designers. Yeah, that's true. I actually hadn't really put that part together, but I think that's, you know, I think some of the reason we've done it this way is because we don't have the bandwidth,

action, everything. So we kind of like, you know, have this backlog that we maintain to make sure that we, when we do take it on, we're pretty set up for success. 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 fewer teams. I want to move in a different direction and talk a bit about how you actually think about building new products, something that I've heard from you is that you have a systemized way of being creative, which I think is kind of a dream for a lot of people. It's 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. Can you talk about it? Yeah, totally. I think, you know, when people talk about like being creative, a lot of times the, what they have a problem with is extrapolating. Right. 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 extreme can you take it? Like, you're designing 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 trait? I think, like, I don't know you guys did this at Airbnb, but I think Brian Chesky talks about like, like, what's the 11 star experience? Is that a thing you guys did? It was the thing he talked about.

There's always a, yeah, there's always a push of what's like the 10x version of some idea. When you think in that way, right, when you're saying like, hey, what's the, you know, what's the 11-star experience? 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 experience we can give people? And you throw away things like, I don't know, like, like cost. You throw away things like practicality, right?

Because that's not what's interesting. What's interesting is I want to. to actually explore the possibility space. And I think this is really important to do because the goal is to get you to see beyond, like, 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 just, like, don't even realize we have them.

So just to break past all of them. And then you can really see what your office are. Because, you know, we talk about like, we talk about product decisions. It's like, oh, yeah, you have like these choices. Like, what are you going to decide? And there's all this decision-making kind of, you know, I'm a theory, right? But like 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 so I think the whole goal of this is to try to, you know, expand the search space, right, of what you're trying to do. So what you're saying is people often don't think 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. And there's this process of breaking out of that. And 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? But you're saying that actually is what you do and that actually works really well. Yeah. And, you know, you actually build it, right? You can think of a very extreme version of a product thing.

like, hey, like, let's actually, for the first version, you know, we talked about, like, the first version you know it's 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 going to 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. Awesome. Let's talk about an example of this because this feels awesome. Yeah, I can, I can talk to an example. Is it okay if I demo something? Absolutely. Let's do it. Yeah, let me show and tell. do that right now.

Here we go. We're going to share a screen. All right. So this is just like a demo space instead of linear. So the feature where we did this that I remember very clearly because it was kind of recent is we built this feature to save drafts for your issues. Right. So linear, you know, as hard as an issue tracker, if I make a new issue, and let's say I'm,

trying to report a bug or something, right? So it's like I make a bug report. Then, 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 someone distracts you. Someone pings you on Slack or you have to go to a meeting or something like that. You're like, I got to put this away for a second.

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 problem. And the first version of this, right, we're like, the most, what do we want to do? Like, linear is 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 want to throw it away, you don't want it. Just hit the X button and we'll just throw it away. Right. We're not going to interrupt you with a pop up that says, like, do you want to 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? If you close this and we don't like ask you if you want to save change, you might feel like, oh, I just lost my changes on accident. We knew that going in, right? We built us anyway. And, yeah, it felt super unsafe, right?

It turns out that that sort of inkling that we had was true, right? But when we really felt exactly how unsafe it was. 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 a new, you know, a new issue and then you start typing some stuff. And it's just like auto saving as soon as you type a single character.

And that did feel quite safe. So cool. But it also ended up like leaving behind like a whole. a whole bunch of, you know, like a paper trail of things you change your mind about, right? You've probably had this happen in like document tools where you have a whole bunch of things in your space called like untitled document or like new document or stuff like that. So many untitled folders. Yeah, so many untitle folders, right?

It's because, yeah, because the moment you like said new folder, it like starts saving it and then you don't actually mean for that to happen. So, you know, we had those two sorts of variations that we built and we felt through. and where we ended up was like a sort of balance between those two, right? And so what happens is if I, if I'm creating a new issue like I am here and I close it out, it'll interrupt me. We have to interrupt you. Otherwise, it feels too unsafe.

So I can save the draft, right? I can go to my draft. 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 going to keep working on it. But then I get interrupted again, then I'm just going to auto-save for you. There's no point. I'm not going to ask you again. I'm always going to auto-save because I'm not going to create.

a new 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 an existing draft that you're messing around with, we're just going to auto-save everything. And someone doing a sort of analysis, right, if they did like a detailed tear down of these decisions, they might, they might say, like, wow, 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 finally where they really meet. Such a good example.

The way that you described is you went, like, here's the safest route. Here's the fastest version. 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 going to be very fast? Is this like the way you think most companies

should operate these sorts of attributes? Do you think it's specific to what makes their product different? How do you think about that? I think for a lot of companies, you have to ask, like, what is the promise 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 going to have to implement search pricing to make that happen, right?

Like, it's always going to be available. So here's the tradeoff 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 kind of have to sort of decide like where in that spectrum does it make sense, you know, based on the promise of your company. A lot of people talk about this idea of working backwards.

Francesc Interbemby is a big concept. Working backwards from the ideal, let's design the best possible scenario and work backwards. I love that this is even more tactical, which is just pick the extreme version of very specific attributes. Probably 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.

Yeah, exactly. I did this a lot, actually, Airbnb just like testing the extreme. So it super resonates this idea. And 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? Yeah, we roll out some of these versions to people.

So the super fast version that was unsafe, that only went internal and everyone felt it was too unsafe. But then we like, okay, let's go to a super safe version. And then we roll that out. and everyone started having a whole bunch of, and we did the, like, how many drafts are people making? Like, this is too many. Like, the people are leaking behind, like, this crazy paper trail.

Okay, we got to figure out some, some difference here. Awesome. So this very much connects to your first point of get things out really quick. And in this case, it's like extreme versions. You're probably not going to, that are not going to work long term, but it will teach you. Yeah, exactly. Amazing.

Okay. And seeing it in action, I'm like, okay, obviously this is the solution. That's how the way the shit feel. Yeah. And to your point, it was not an obvious solution when you start. to thinking about it. Yeah, I mean, the best solutions are always obvious in hindsight, right? And it's just like you have to develop a process internally to eventually find your way there. Hmm. 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. Talk about that because I thought that was really fascinating. You know, 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 on buttons and good things happen. And then they turn that process and that tool, you know, they spin it off into a startup and they, like, make it start.

This process repeats thousands of times. So when you adopt that tool, you're not just adopting the actual software. You're adopting the idea that this is a practice that you ought to be doing in the first place. So if you're a marketing person, right, and you adopt some marketing software, you're not just saying like, okay, now I can, you know, kind of write emails and send to the people. There's all sorts of process around that. Like you're organizing stuff in the campaigns.

You're measuring click-through rates. You're like calculating, you know, cost of acquisition. And all that stuff probably comes equipped with a tool because those are the right practices to do when you're doing this sort of marketing exercise. And whether you knew about it before, right, or you learned it from the tool, like, as a buyer for this kind of product, what I'm doing is I'm saying, like, hey, I'm going to 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. Interesting. So it's, you're basically buying into a way of working when you're adopting a piece of software, not just have this problem and he's solved. Yeah, exactly. And I think the most, the most salient example of this is if you've ever seen 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 redo all of their internal processes and the way they've managed 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're actually doing good, like, management of resources. So they're like, 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 is best to do.

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 going to avoid letting people customize too much because we know they'll have a bad time. And then two is just this idea of we are opinionated about the way you should work in linear. And it's like you have a 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. Yeah, yeah. It's definitely connected in a way. And I think sometimes when people talk about 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, in my opinion, they're just two opinions, man. Like, like, you know, neither is right or wrong. What we try to do is find where there's actual consensus, right, amongst a lot of different 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 a company, we see companies like doing a really good job of managing their triage queue. But 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 don't know this is what they need. Can we just give them a button to activate this? And now they have the practice within their or two. So I think a takeaway here is when you choose a tool, recognize it's going to change the way you operate and be thoughtful about,

is this the way we want to work versus just we just have a problem we want solved. Yeah, exactly. I want to come back to something, kind of a thread that's come up a couple times in our chat, is the way you collaborate internally. It feels like there's a pretty unique way. 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? Yes, something that's worked really, really well for us is we think of product management as partially like a go-to-market discipline in the same way that sales and marketing are. 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 how they, they interact and collaborate. And we all kind of understand why that's useful, why it's helpful. But this sort of other form of collaboration between product management, sales and marketing, I think it's something that's like

probably really under examined. And often, you know, often I feel like, in organizations, you actually see kind of like some antagonism between product and like sales and marketing. And I think that's kind of a shame, right? Because, you know, when, when we, kind of come together, the way we think about, you know, the, the way that we think about selling is a matter of like, especially because 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, like a big part of what we try to do is we try to help them pick. which I 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 talking about engineers is my sense, right? Yeah, like engineers is a big one, but even product managers, right? Like product managers kind of know when, you know, like 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 this thing guy. Don't call them project managers. Yeah, exactly.

Like for example. So I think that's a big part of, you know, what we have to do. So like we, you know, 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 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, 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. And then, you know, with sales. is like they're validating all that message like in the field, right? They're saying 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 between those three disciplines.

What I've seen you refer to this way of working as is a double triangle, which is, I think, a compliment to like the PM engineer designer. You talk about that and give us this visual what that looks like. Yeah. I know, I think PMs, right, like product managers, we often have a tough time like trying to explain, like, what is your job, right? like, you know, it's like a little bit of everything. And I think the, you know, the job that I sort of do, right,

and that we see it as is you're taking the sort of building side of the organization and the selling side of the organization and bring it together. That's, you know, you're taking all of the commercial, like, motivations and goals of the company and making sure that what you build actually solves for those goals. And, you know, you're sort of tempering that with like what's, you know, possible and sort of where the opportunities are. to actually build stuff.

So to me, it's the PM in the middle, and then you have engineering product design and then sales marketing product management on the other side. PM was always in the middle. Indeed. But I think that's true from the perspective of PM.

And I love this 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 Brian Juski's whole thing about how PMs are should be doing marketing. And so the way they changed at Airbnb, every PM is also PMM and there's no more. They're product marketers now. That's their title. And that's like the extreme version of what you're describing. Yeah, yeah, it is. And I think Apple's been doing that way for forever too.

Got it. So the advice here is if you're a PM at a B2B business, lean into the sales and marketing side of it, lean into the go-to-market. Yeah. And in fact, if you're leaving something on the table, right, in terms of like the kind of impact that you're 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 have more impact. Just to make it even more concrete for PMs that are like, okay, I want to do this. I want to, I want to do what linear's doing. I'm going to get more sales.

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? 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're 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 where the emphasis is, like, you should understand the customer at a pretty deep level, probably deeper than any other, like, group at the company, because the kinds of requirements gathering discovery that you're doing. So you're going to find, you're going to know the native language that your customer speak a lot better and help your marketing team originate those words.

Got it. So basically be really involved in the product marketing, the writing, the emails, the headlines, the website. Yeah, yeah, exactly. And I know the word product marketing is also so overloaded. They do so many different things. But if that sort of like content, you know, kind of creation piece, that's that you really have an opportunity that contribute to.

Yeah, I love how concrete that is. It's like, don't think about this concept product marketing. Just think about the words that your potential customers and customers see. Okay. Final area I want to spend a little time on is totally different. It's around getting a job. Oh, yeah, okay. You have a pretty unique approach to finding a gig.

I heard from the founder of Mode about the very unique way you approached getting a job there. I imagine linear is a similar boat. What advice can you share with folks that are looking for a job may be struggling that work for you when you were looking for your next gig? product management is a kind of a unique role, right? Like, because we do just about everything, you don't really get pigeonholed into, you know, being sort of compared along a single dimension with everyone else. And everyone who's hiring PMs,

just like when they're hiring execs, they're kind of hoping that they bring them on to solve some burning problem that they have. And so it's your job when you're in the interview process to figure out what that burning problem is. Right? of like put on 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 I think what ends up happening a lot is when you're in an interview process you're just like trying to put your best foot forward trying to say that 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 going to say that so you're just like one of in people and you want to 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 rule of advice so the way you're describing it is The company has a job to be done. Say it's drive growth of some feature. In this case, it's like for linear, just building a killer,

a successful B2B product. I don't know. That's a broad one. Usually you're not interviewing for head of product role, so that's maybe too broad. So it's like, what is this PM role's job to be done at the company and then help convince them you who are the best person to solve, to do that job and solve this problem for them. Yeah.

And a lot of times when you take that approach, it'll feel like. you already work there. And like the way that I did this, I got advice from my friend. He said, like, I was interviewing for this job at Moe that you referenced. And I'm like, how should I approach it? He's like, just aptly he already worked there. What would you do?

And then it's like, okay, I could do that. So then when you're in this interview process and someone, you know, someone's asking you a question, they goes, you have any questions for me? Like, you can ask them, like, what are your okays this quarter? How can someone help you achieve those? Right? You can, like, be that specific about it.

And like, oh, yeah. Sure, I can tell you about the exact thing that I'm doing this quarter. And then you'll have some level of intelligence about what's, you know, what people are actually trying to solve. Because I think often we just like get stuck like in these very high level of general types of questions. Like, what are, you know, what's the company goal of all that kind of stuff? And it's like, no, you can get really specific.

Like, if you were collaborating with that person in your job, like, what would you say to them? I love how actionable this advice is. There's obviously an element of like this takes work and time. a lot of people are interviewing at a lot of companies trying to find a job. Is part of your advice, like pick the ones you're most excited about invest a lot of time in this way of interviewing? You know, you can invest a lot in the ones where you know that you're going to be able to overdeliver on. If you understand what they're actually trying to solve, then you know where you're going to have both the highest chance of success of getting hired, but also like doing a really great job on the other end of it.

And you talk about how you're like, pretend you have the job, pretend you actually have this job as part of the interview process. Oftentimes as an outsider, you don't have enough information to like have a really good thought on what the solution is and maybe part of it is going to be so, like, wrong because you're like, I don't know, actually no, I don't know the data. Do you actually try to reach out to the engineers and designers on the team to try to understand things? How far do you go to try to solve these problems and show what you can do? Yeah, I mean, you know, you're in the interview loop, right?

These are people that you're going to be working closely with. So start there, right? do your discovery questions. And if there's an area that you think you want to dig, you can ask. There's no harm asking, hey, can you put me in touch with an engineering manager who's working on the same problem? And, you know, if no one else is asking, again, you're going to have an extra piece of feedback from that inch manager.

So, yeah, like, this guy asks, like, really good questions. And it seems like they're, you know, they're really with it. Like, no one else is going to have that piece of feedback. So during the, during the debrief process. And just asking that question alone will show them how deeply you're thinking about this already. Yeah. Amazing.

Nan, is there anything else that we have not covered that you want to touch on or share or you think might be helpful to listeners before we get to a very exciting lightning room? You know, I have a very specific point of view on deadlines. I don't know if that's a let's do it. Fire away. I think like what often happens is people get depressed about deadlines, right? they're like, hey, here's the, here's the ship date, and then you never make it.

You know, I don't know if you've had this feeling before. Absolutely. You were an engineer before too, right? So it's just like, engineers is better like, oh, yeah, yeah, yeah. Deadlines are just, they're complete fabrications. And the only way to make deadlines real is to take them so seriously that they are basically like a P0 problem. And like everything else has to not matter in comparison to the deadline because that's the, that's the only way you're going to be able to signal to the team and also to all the stakeholders

is that you're actually taking it seriously. So, you know, my feeling on deadlines is don't have too many of them, right? And when you do, it's a P0. So the engineers are working on it. They don't get the work on anything else. Like someone's, oh, I need them for this. Like, don't, nope, you're not pulling them off of anything. We're doing this. As a PM, your job is to just cut as much scope as possible to make it possible to hit that deadline. Right. Like, what are the things actually blocking us from doing it because what you want to do is at the moment where you have to make the go-no-go call on whether the ship, you want to be able to actually have a product that you can say yes to, right? It might not have all the features you had wanted or whatever it is. And you can say no,

right? You can make that choice, but you want to set yourself up to be in a position where you can actually say yes to know as something. Because like what often happens is like, oh, we want this thing. Well, it's not even close to being done yet. So there's no possible way we can say yes. Right. I can't ship it. It's just, it's like half broken. It's like, no, no, no, you want to get to a point where it works, right? It might not be the product that you want, but it is an actual real product that you can conceive ofly shit. So you said that don't have too many deadlines, but when you do, make sure you, everyone understands these are actual deadlines. When do you decide it's worth having a deadline?

Is it like a marketing launch or a thing? What's worthy of a deadline in your experience? Yeah, it's usually having to do with some kind of external marketing type of exercise that you're trying to try to hit. Got it. And I think that that's like the other thing that I think as builders, we can often look at like launch dates and stuff like that. It's like, oh, you know, who cares if it's a little bit later or we skip this change log or whatever it is? And I think that that's, you know, that's really, I don't know, it makes me go crazy when I hear people say that in all honesty. You know, with marketing communication customers, you basically have a limited amount of opportunities to do so, right?

A year is 365 days. There are 12 months, right? Each of those months has about four weeks. Like, there's some rhythm where you get to have 50-ish weeks to say something to your audience, you know, once a week. Or you get to have 12 months to say something really big or four quarters to say something huge. If you miss one of the opportunities, you don't get it back again. You can't like time travel back and say like, okay, actually, let's redo first quarter and like say this message that we wish we could have gotten out into the field.

that is such a powerful point I could see the sales marketing go-to-market element of your job coming out there I imagine everyone that's in that feels like yes this is exactly right maybe just the last question along this line so I love this idea of taking deadlines

very seriously when you commit to a deadline at the same time as you pointed it out it creates a lot of stress knowing there's a deadline we have to hit so one lever you mentioned is cutting scope another is just people spending more time estimating to have more accurate deadlines, you invest in that? How do you think about just like for an engineering team to come into a deadline? How much to spend on like derisking and estimating versus just let's just do our best and then we'll cut and adjust. You know, this might be my hot

take, but we do almost no estimating in order to hit deadlines. What we do, right, is we ship as early as we can. So if, you know, the thing we talked about earlier, where like if by the time that 10% of the time has elaps, you have a working thing. you can now spend the rest of the time deciding whether or not you want to do another iteration or you want to polish that thing and get it to be a shibble state. Right. So you're you're, kind of setting up your future self to be able to make that decision. So none of this is, you know, you can't, you can't go into this at the very last moment say like, okay, now we have to take the deadline seriously, right? You kind of have to do it from the beginning and commit to the process

of going very fast, iterating early, and then putting yourself in a position where you can say yes or no to a product. so interesting and so different from the way most companies operate. This was everything I was hoping would be. I think this is going to help a lot of people build much better product, which would be good for the world if more products are like linear. With that, we reached a very exciting lightning round. Are you ready?

Yeah, let's do it. Okay, let's do it. Okay, first question, what are two or three books that you have recommended most to other people? I think the one book that I recommend the most is the design of Everyday Things by Don Norman. I read it originally in college for an HCI class I was taking. And I think of everything I've ever read, it's the thing that sort of caused me to see the world from the perspective of everything you interact with as a product.

Right. Every single, you know, every pencil that you use, every door that you open is a product that somebody designed. And is that the big takeaway from that book? Because it comes up a lot. And I think it's such an old book. And so I guess for someone that hasn't read or maybe doesn't have time to read it is the big takeaway for you.

Someone designed everything. There's a reason things aren't great and they can be improved. Yeah. I mean, I saw this the other day. I was at a cafe in my neighborhood and I saw a kid rip a handle off the door, like of the cafe. He like pulled it so hard it came right off because it was a push door, but it had a handle that looked like you could pull it. And that's like one of the canonical examples of the book.

Yeah, the Norman doors are just mysteries. Yeah. Awesome. Next question. Do you have a favorite recent movie or TV show you've really enjoyed? I've, I watched The Diplomat on Netflix, I think it was. Terrific. You know, it's really fun.

Easy, watch. It has, like, some, like, West Wing vibes if you were into that back in the day. Yeah. Have you seen the second season? Yeah, I finished the second season. I wasn't as excited about the second season just to put that out there. The first season was really good and then just kind of went off a little, like, okay, I guess. I guess it's cool.

But, yeah, it got a little, like, spy thrillery, I think. Yeah, yeah. Okay, cool. But still really good. And on Netflix. Okay, cool. Do you have a favorite product you recently discovered that you really like? I didn't discover it, but I discovered a version of it that was really interesting.

There's a pen. Actually, I have one on my desk. It's called like the Sakura Micron. I don't know if you use these. It's like a felt-tip pen. It's really great, right? Like, you know, it was originally invented like in Japan for like artists to like, draw like comic books and stuff.

And, you know, you can use it for anything. I use it for journaling or whatever. But I was on Amazon. I was looking, you know, I was trying to buy more. And I found a package that said, like, a Bible study kit. I was like, why is this labeled Bible study kit? And it was literally just the pen in like four different colors. And it was because like the thing doesn't bleed through pages.

So if you have like a Bible, which they often have these kind of like really flimsy kind of newsprint pages, it's not going to bleed through. And it's just really interesting to me that someone marketed like a normal package of these pens as a Bible study kit. And for people who like we're looking for that key. And it's like, it was like official too. It was not some something hacked together. It was actually like an official packaging of this. Amazing. What a unique pen choice.

Two more questions. Do you have a favorite life motto that you often come back to and find useful in work or in life? The correct amount is too much minus one. And I think this kind of ties into like to try the extreme version of it of a thing where I don't know, like a stupid example. Like how much pizza do you want to eat? It's like, well, five slices was too many. I feel bad. Then four was probably the right number.

Right. And then if you want to find the right number, sometimes you just have to like really shoot for the edge and then find out what's too much. And then you'll find out exactly what the right amount is. I love how tactical that is. Makes me think about Elon Musk's thing about cutting things. Like one of his formulas for just getting stuff done.

One of them is just like cut stuff before trying to optimize it and, and automate it. And his advice is if you don't bring back 10% of things you cut, you're not cutting enough. Yeah. Exactly. Final question. You worked at Everlane for a number of years,

and you shared the rough idea of a story around a shirt, maybe our bestseller that they have now and how you helped create a bestselling women's shirt. Do you show that story? Yeah. So, I mean, to be clear, I witnessed the creation. I don't think I had a direct hand in it. But, yeah, so, you know, I saw this advertisement the other day on Instagram

for it's called a women's box cut tea. And it's a, it's a t-shirt that's like kind of wide and short, right, for women. And I looked and they had like 20 colors of it. And it's, it sells super well. And I remember when we, when we created this thing. And it was because there was a batch of defective men's t-shirts.

They all came in like an inch and a half too short. And so, like, we couldn't sell them, right? You would have your belly button sticking out. Like, no one wants to wear that. And then so what we did was like, well, we have to salvage the image. because we were a very small company and we had to make cash flow and, you know, we couldn't just damage it out. So, so, you know, the design team and the marketing team kind of came together and

they said, okay, here's what we're going to do. We're going to cut another two inches off of this and make it really cropped, right, and market it towards women as like a cropped, boxy silhouette. And we, and we did that. We're like, okay, hopefully, you know, hopefully we can salvage this, this inventory and not have to, like, take a ride down. It sold out in like a week. And we're like, oh, okay, I guess we just made a hit product. And it's like one of these things where, uh, it's very hard to know what this was, right? Was this like a marketing thing? Was this a design thing? I don't know. But we just, kind of come together and you, you, you find like the right product market fit in like the weirdest way. I love that it's still going. Yeah, it's still going. Like originally it was just white. Now there's

like 20 colors. Oh, man. I love how many industries you have worked in. Fashion, data analytics, project management. I don't know what's next. There's more, I imagine. Non, this was incredible. I really appreciate making time for this. Like I said, I think we're going to have helped a lot of people build better products. Two final questions. Where can folks find you line if they want to reach out and learn more? And how can listeners be useful to you?

Yeah, I'm on X slash Twitter as the non-you. It's T-H-E and then my name. And, you know, if they have any feedback about linear, you know, we're very happy to take it, especially, you know, for people who kind of like use it in their day-to-day. We really want to hear from users. What's the best way for them to share that? Is it tweet at you?

Is it go to the website? What do you recommend? Oh, yeah, you can tweet at us. You can, you can DM me on Twitter. My DMs are open, so it's all good. Amazing. Nan, thank you so much for being here. Yeah, of course.

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

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