Linear’s secret to building beloved B2B products | Nan Yu (Head of Product)
en
January 30, 2025
TLDR: Nan Yu, head of product at Linear, discusses their unique approach to developing quality SaaS products quickly, debunking the speed vs. quality myth, diving into user needs deeply, managing product backlogs systematically, and more.

In this insightful episode, Nan Yu, the Head of Product at Linear, shares golden strategies behind creating fast, high-quality products that teams love. He discusses themes such as managing speed versus quality, understanding user needs, and the value of creativity in product development.
Key Takeaways from the Conversation
Speed and Quality: Debunking the Myth
- The misconception that speed compromises quality is widespread. Nan argues that true speed stems from competence and expertise rather than rushing or sloppiness.
- Successful professionals are often faster because they have refined their craft, leading to productive iterations.
- The approach – By the time 10% of the scheduled time has elapsed, a functional prototype should emerge to test key hypotheses.
Unique Product Development Philosophy
- Avoiding Bloat: A significant challenge in B2B software is the tendency toward feature bloat. Nan emphasizes that requests from middle management often lead to complex features that disrupt the user experience for individual contributors (ICs).
- Creative Solutioning: Nan employs a systematic approach for creativity by challenging the team to think about extreme versions of product features, allowing them to explore innovative solutions beyond the obvious.
Empathy in Customer Interaction
- Understanding customer emotions is key. Nan trains himself and the team to explore the underlying feelings behind customer feedback rather than just relying on surface requests. This depth of understanding influences product direction and fosters loyalty.
- Customer Calls: Engaging deeply in customer conversations enables product managers to align their products closely with user needs and avoid assumptions.
The Double Triangle Framework
Nan introduced the Double Triangle framework in product management that integrates:
- Engineering and Design teams with Sales and Marketing.
- This model enhances communication, aligning product features with market demand while keeping the user experience at the forefront.
Recommendations for Aspiring Product Managers
- Seek User Insights: Focus on gathering individual user stories rather than generic feedback. Strive to connect with actual users to gain firsthand insights.
- Rapid Prototyping: Dare to release early versions of products to internal users to gauge reactions and make adjustments.
- Prioritize ICs: When addressing feature requests, prioritize the needs and experiences of individual contributors over middle management demands.
- Deadlines as P0 Problems: Treat deadlines seriously and ensure that projects remain focused on key features, trimming scope as necessary without compromising quality.
Job Hunting Advice
Nan shares a "discovery approach" for job hunting:
- Identify Problems: Research the company to understand their burning challenges and position yourself as the solution.
- Engage with Team Members: Seek to connect with potential colleagues to gather insights into their work, strengthening your case during interviews.
Conclusion
Nan's insights into product management reflect a fresh and engaging outlook on building beloved B2B products. By embracing speed without sacrificing quality, focusing deeply on user needs, and integrating various functions of a company, product managers can create tools that teams genuinely appreciate.
Valuable Resources:
- Books Recommended by Nan: The Design of Everyday Things by Don Norman, emphasizes understanding design across everyday products.
- Tips to Enhance Creativity: Examples like challenge ideas to the extreme can unlock innovative solutions.
This episode of Lenny's Podcast encapsulates key lessons and practical tips for anyone looking to navigate the world of product management effectively.
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I think you see on the team at linear that a lot of people don't see, which is that there's not actually a trade-off between speed and quality. 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 what future requests can we debate and what kind of future requests do we absolutely have to say no to. The stuff that we absolutely have to say no to is the exact kind of thing that leads to this bloatedness that makes ICs kind of hate their lives.
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 Nan Yu. Nan is head of product at linear, which is one of the most beloved, most beautifully designed, and also the fastest growing B2B SaaS product out there today. You rarely see the kind of love that people have for linear for any enterprise B2B SaaS product, and so there is a lot that we can learn from how linear operates and how they build product.
In my conversation with 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-
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Non, 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've been 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 I interact with my engineering teams and I find inspiration in its design.
Linear is simple to use yet powerful. Linear's design is obviously an industry benchmark, but moreover, the performance and speed is a massive productivity boost.
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 get 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 just was really sad. So that's what we started linear, to sort of really bust through all of that.
What I love about linear, I feel like it's a 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 to something that's better.
And linear is an amazing example of building an excellent product and actually succeeding. And there's a lot more to it than maybe than just building an awesome product. So that's what I'm excited to dig into and understand how 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. First question I want to get into is something that
I think you see in the team at linear C's 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 a innate fact. And something I've heard you talk about is that's not actually true. And actually saw Patrick Hall's and 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 a naive way. Because when they think about speed, the thing they over index on is rushing or being sloppy. And what they should be indexing on is being really competent or being an expert. So if you look at people who are at the pinnacle of their craft, it could be anything. It could be a chef or a programmer or 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 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 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? 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 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.
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. 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 expected you? Or did we have some crazy incorrect assumption? And 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 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 in a month later.
Well, it 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 intense. You know, we don't have any expectation that the first version of it is going to be great.
That is not in the cards. 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. 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 all sanded down and really into top shape. It just has to work and get the job done and validate or invalidate our major assumptions.
I'll read this quote from Patrick Holson. He tweeted this today as I was preparing for this interview, and he's the CEO and founder of Stripe, if you're not familiar. His tweet was, I increasingly believe that good, cheap, fast, choose to maximize 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 you saw us making a modification to your house and it's taking forever, like one, you're in a hotel and also that the bills are adding up.
The other example is when we were chatting about this earlier is chess players. I'm thinking of Magnus Carlsen watching him. I think he was like number one in speed chess in addition to just regular chess and what a microcosm of this point.
Yeah, I think that's the sort of the case in 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 and give someone something concrete they can do with this information, say they want to start moving faster while not cutting quality, what do you think they can do? It's one thing they can start trying to work on and improving in the way they operate. I think it's really that 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 I can actually put on the production, but in the sense of I can start learning from here.
Just a question I imagine, as 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 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, right?
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, 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 an implication here is just most wasted time is on building things nobody actually ends up wanting or using. And so the sooner you at least get directional sense of already heading in a good direction, the faster it all goes.
Yeah, totally. 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 spend a lot of time thinking about. Maybe give us a glimpse into some of the conversations you have internally when there are these feature requests like, oh, I need single sign-on with this thing and this button here. How do you think about what to add, what not to add, and how to add these features to not make it bloated?
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? This is the question that we're going to get. We hear quite a lot. It's very sensible for them to ask it because they see history being littered with the corpses of startups trying to compete in this space and not making it.
And I think when we examine this problem, we kind of look at what kind of future 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 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 icy workflows worse, right? Like it's like, if it fits that description, we're just saying no.
There's no debate because we've already thought about it. And this is the thing that we can't take a single step down this path. So I think that's honestly one of the core promises of linear, is that we will not make this particular tradeoff. So when you see people saying, wow, linear is so much faster, it's so much easier to use, that it makes my work so much more enjoyable. 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? And 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, hey, we really want this one feature. It's going to make our reporting nicer. So 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 fall straight off.
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. No one has to do this. If I'm an engineer, I get paid to write code. My performance review is based on my code contribution. It's not based on that I fill in all the tickets.
So I'm just not going to do that part, or I'm going to do it very sporadically. And then 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 situations where people will say, well, here's a dropdown field that someone put in here that's required. There's nine choices.
I don't know what any of them means. So I'm just going to pick one at random. I'm still 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 like it's a very easy decision when it comes to that particular category feature request.
I love how simple and clear that it's 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. So when I track what's happening. Yeah, exactly. So I want to track what's happening. Well, what do you want to track? Well, I want to track which, you know, like, which version of the product this thing 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-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. Imagine it helps a lot that imagine the CEO is very bought into this, and 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, as you would expect, right? To do these kinds of things. There, there are basic scaling things like, you know, we had to make like, sample 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 and type of work. But when it comes to work that's related to the actual, you know, the actual business logic of, of the apps, like value proposition,
What buyers care about is, is this going to make their team more effective? That's the reason that they're making this buying decision in the first place, is that they're like, well, the current situation we're in, especially with larger companies, the current situation we're in is kind of a mess. And if we can convince them that these types of things are actually the reason that it's a mess, then 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 it's not everything you want, right? Because people come with a laundry list.
And it's like, here's 10 things I want. You're 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'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 is not letting them use linear for all these reasons. On the other hand, you guys are growing really quickly within enterprise. Like you are not.
You're a new business. You started, I think, mid-market startups, and now you're working right up. And so I think 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 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, well, 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 have that feeling, right? They're like, hey, like linear is for us. They're like, who are we? Well, we are a large company that wants to act like a startup. Right. It's like, who doesn't want that? Right. Who doesn't want to go fast? Yeah.
I had Jeffrey Moore on the podcast and this is exactly what crossing the chasm looks like. He talked about basically you need someone that's across the chasm like a later adopter that isn't the person that's 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 particular category of tool, and with a lot of other B2B software, no means not now. Not right now because it doesn't fit our budget. It doesn't fit our change management situation. We have this exact that's really wedded to this other tool. But those things change. So we keep in contact with them. They're in our CRM, where we make sure we follow up. And we've had a lot of these where
We've been said no to two years ago. And now we have some new features and go like, oh, yeah, 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, 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 than you.
Give us a little sense of some of the more complicated debates that aren't necessarily in that bucket. I think that the complicated debates are often, you know, when we do add a new native feature, do we extend an existing feature and make it more powerful or do we add a new sort of service?
And a big part of that is trying to figure out exactly who's going to use it, what are the actual real-life use cases that we know about? 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. So tying it all the way back to real people is a specific person. Yeah, exactly.
Not 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 time here's their email you can ask them and I think that being able to tie it all way back to to reality in that way is You know as a big part of how we really think about and discuss these things this connects It's 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 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 maybe it's beautiful or it's elegant, but they don't go the step of like, is reality also beautiful and elegant? Cause reality is kind of ugly sometimes.
And if you have a beautiful August solution that doesn't match with reality, it doesn't really matter, right? People can like look at it and they can, they can do an odd, 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 be convinced this is worth investing in? You know, people may hear this. Oh, one Bob wants this featured. That doesn't make sense. Just one guy. How do you know when it's like, okay, we should really invest in this? Part of the issue here is something and you're like, gosh, that actually is not, not one's that true. It means that the way we thought about this was a little bit raw.
And I call this process, I don't know if it's the right way to describe it, I call it a kneeling, where you have a thing and it's not quite the right shape and you put it out into the wild. So this happens way in the first bit of the life of a particular feature. You release a thing and then you start getting feedback about it, but it doesn't quite fit reality.
And then you kind of ask yourself, did we test that aspect of it? Did we actually match that part to reality? And if you didn't, then that's the part where you don't actually need that many pieces of feedback against it. It's not a 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 requests for maybe a very big feature or feature set from a lot of different people. But then you dig in and you try to say like, OK, well, tell me about how you're trying to use this. And there's like 100 different use cases.
So you have choices here. You can either build the big feature that covers all the long tail use cases, or you can try to see if there's really concentrated pools of use cases for this that really make a lot of sense to adopt as a 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, you know, 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. There's like 100 people generally asking for this thing. Let's build what we think is a general solution.
Yeah. I'll give you an example of all of these things, which we just launched a feature called customer requests. And basically, what this does, it adds a new concept to linear, which is a customer. For B2B companies, this is very relevant. And the reason we did this is because we kept getting this request for fully customized fields.
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 ICs start hitting it. So we don't want to go down that path, but what is it actually you're trying to do? And 40% of them were because, well, I have a customer, Walmart or whatever. Walmart asks for this feature, and it's really important. I need everyone to know that Walmart needs this.
I need to track it. I need to say, how can we report on what have we done for Walmart over the past year, so that when 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. All those kinds of stuff. Cool. That sounds like a very useful and powerful thing you want to do.
Uh, how do you expect people to like tag these things? Well, manually. Cause 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 CRM's. 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, if someone requests 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 ICs lives harder. In fact, it makes them feel more confident because when they're building the thing, they actually understand like who's asking for it and exactly what the email said. So when they get all the, when they're doing the design or the, or the, or the details, they can actually see the real life use cases that are present and solve for those directly.
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 hear 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 what's just built 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, 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. Great. I understand the severity of your problem at this point. What is the actual emotional valence that is motivating whatever you're telling me? And it takes a little while to get there. You can ask people directly, how do you feel? And 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 like open up to you and like tell you like honestly like you know I had this thing happen where I marked 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 in mind.
because they're like, we can't ship something at December 30th. Everyone's on vacation, right? And they're like, and then they're like, yeah, this may feel really bad. So I don't ever want to put dates on things ever again. Right. So like, okay, cool. We can, we can help you, we can help you deal with that, right? Like if that's, if that's what you're feeling, then I can, you know, kind of start building stuff to, to make sure that you never have to have that bad feeling in it.
People talk about empathy, like you need to have empathy as a PM and you need to build empathy. The best product leaders have empathy in this. I think it's such a succinct and powerful way of describing what empathy actually looks like as a product leader, which is I want to feel as bad as they feel in hearing the story they tell.
And it sounds like the way you do that is you keep asking questions to understand what the moment they felt bad about something, in this case, the deadline. Yeah. And if you ask somebody in that last story, what kind of issue do you have? You're like, oh, marketing and I would just never align on anything. It's like, that doesn't really tell you what's going on. But it tells you it's like, you had this terrible moment of communication that felt like Mr. Meghan. And you're like, it's just going to keep happening over and over again.
And so the thing that we did specifically to solve this was on projects in linear, you can just specify of target date at whatever level of granularity you want. 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. Whatever you're happy promising, you can just put it on there. And that way, you never feel like you have to give this sense of false precision so that it ends up with a whole bunch of miscommunication down the line.
I could see why people love linear as it just makes them feel less bad less often. There's a lot of connection here. I know this idea of emotions and feeling bad is a core part of how you think about building product, looking for moments people feel bad. There's 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. It's sort of set the background of this, right? I've worked in very, very competitive industries.
I worked at Everlane, which was a direct-to-consumer clothing brand. I worked at Mode, which is BI tools, and there's so many BI tools out there. And then obviously at Linear, we're project management. There's a lot of project management tools. And I think the more competitive your industry is, the more the low-hanging goal-oriented stuff is already picked. Because every PM from every one of these companies has been asking, well, what's your goal? What has your job been done? 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, and for us, it's the angle of where are the emotional hooks that you're experiencing as you go through your workday, as you use our product, as you use competitor's products. And I think it's probably under explored because
I don't know. I feel like PMs and engineers were 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 through a day where you don't even know, right? You might think I hate Mondays, right? Like, why do you hate Mondays? Well, Mondays 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 and that helps, like, yeah, yeah, then I might not hate Mondays so much.
And so like, I mean, Paul Graham has a word for this. He calls it, he calls it schlep blindness, right? Like, I'm like schlep in their life and I'm just completely blind to it. And it's true, right? You kind of have to have an outsider come in and sort of see, you know, what the rhythm of your feelings are throughout the day, throughout the week. And you're like, 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 solve, 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 if I put an issue into a different team, if I'm asking them to do something or I'm reporting a bug to them, it sticks it in a special zone where it'll notify the right people. They're on a rotation and people will be able to kind of respond to it in a sort of organized manner. And I think this kind of automation, this feature,
It came out of two different fields people were having. One, people were trying to implement this stuff by hand, and it was just a lot of touches, right? And they were doing it, but they felt like, oh, I'm totally underwater. Why are you underwater? Well, I have to manage all these, you know, throw 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 spent so much attention doing this.
And then there's the folks who didn't do that. The feeling was just like, well, it's totally uncontrolled. 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. And then the people on the other side are like, I throw tickets over the wall. I have no idea what happens to them. I have no expectation that people are ever going to respond to them. So there's all of these bad views 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.
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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 data users and people that are aware of they're using early stuff. Two is purgeize the IC in the user basically versus the buyer or the middle manager that wants reporting and
in all these custom features. So it's basically focus 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 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, 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, the, the, the part where you sit like focus on, uh, focus on the user. I, I think it's, it's maybe a little bit more subtle than that. There's, there's a nuance which is like find where the incentives are really misaligned amongst your user base. Right. There's a middle manager that wants, you know, really detailed reporting.
And there's 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 trade-offs 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 Hall since we did 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 and their life.
And then that informs what you build. And so that anytime you do more research, talk to customers, it's informing your view of the person. And then you're like, oh, this was different from what I imagined. Or oh, wow, this is exactly what we've been thinking and let's build that. Anything along those lines that you might want to share. 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 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 reevaluate, okay, what is our current understanding of how we might best approach this thing?
And I think something that people struggle with is 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 very hard to share that with someone else. You have to telepathically throw it into their brain, which is hard. So what we try to do is identify areas that we might attack with a product, but also keep an up-to-date analysis of each of those areas so that everyone can 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. I'm sorry, he's sitting in the backlog. 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 backlog.
It's something we see managers struggle with all the time, which is I have a limited amount of personnel and resources, and I need to deploy them in such a way where we can theoretically accomplish our roadmap, but also we don't get blocked by some bottleneck, that we don't end up blocking all of the projects because this one engineer is stuck on some info thing. And that's a thing people struggle with all the time. All the solutions out there are bad.
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 data within linear to really help out with this problem. But I don't think we've quite cracked it yet. I think there's some nuances that we have to really explore a little bit further. So we're kind of continuously developing this. And as we hear from users that are struggling with this problem, we will get on a call with them and sit down with them and talk through.
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 like a nuance here, which is like, 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 good starting point for them to sort of like reason about it.
And so I think a lot of 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 end up over promising and not being able to deliver on it. And I think what's also useful here is you'll 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 their designers.
Yeah, that's true. I actually hadn't really put that part together, but I think that's, I think some of the reason we've done it this way is because we don't have the bandwidth to action everything. So we kind of have this backlog that we maintain to make sure that 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 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 when people talk about being creative, a lot of times what they have a problem with is extrapolating. They can kind of see the stuff that's right in front of them, but 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 what direction to go.
So the way that we try to do it is we ask a question, which is like, okay, how, how extreme can you take it? Like you're 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, some trait? Um, I think like, I don't know if 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 a 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 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 cost, you throw away things like practicality, right? Because that's not what's interesting. What's interesting is I want 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 your defaults. We have all of these constraints that we're operating under that we kind of psychically have in the back of our heads that we just don't even realize we have them. So just to break past all of them. And then you can really see what your options are.
Because we talk about product decisions. It's like, oh, yeah, you have these choices. What are you going to decide? There's all this decision-making kind of a theory. But the biggest risk is you didn't see the right choice to begin with. You have these three choices and none of them were right. It's this fourth one that was over in this corner. But you didn't look at that corner, so you never found it. And so I think the whole goal of this is to expand the search space 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 choice is they're deciding between or just like, oh, man, 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, yeah, what's the craziest? Yeah. But you're saying that actually is what you do. And that actually works really well.
Yeah, and you actually build it, right? You can think of a very extreme version of a product and it's like, hey, like, let's actually, for the first version, you know, we talked about like the first version, you know, 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 what the right actual answer is because we 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 talk to an example. Actually, is it OK if I demo something? Absolutely. Let's do it. Let me show and tell you 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. So linear, 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, so it's like I make a bug report,
Then I might start thinking through like, OK, 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 of someone who pings you on Slack, or you have to go to a meeting or something like that. You're like, I've got to put this away for a second. I'll come back to it later. Note to self. 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, OK, this is the this is the problem. And the first version of this, right? We're like, OK, 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 like interrupt you with a pop up that says, like, do you want to save your changes or any of that kind of stuff? Right. Well, we'll just.
absolutely get out of your way as fast as possible. So we're like, what's the risk? Well, it might feel really unsafe. If you close this and we don't ask if you want to save change, you might feel like, well, I just lost my changes on accident. We knew that going in. We built this anyway. And yeah, it felt super unsafe. It turns out that that sort of inkling that we had was true. But we really felt exactly how unsafe it was. So then we were like, OK, well, what's the
What's the safest thing we could possibly do? The safest thing is just to auto-save everything. You start 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. That did feel quite safe.
cool, but it also ended up leaving behind a whole bunch of paper trail of things you change your mind about, right? You've probably had this happen in document tools where you have a whole bunch of things in your space called untitled document or new document and stuff like that. So many untitled folders. Yeah, so many untitled folders, right? It's because the moment you say new folder, it starts saving it and then you don't actually need 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'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 drafts, right? I can go to my drafts. And then if I'm in this sort of draft I've already made and I go in there and I, you know, and I start to say like, okay, I'm going to keep working on it, but then I get interrupted again, then I'm just going to auto save it for you.
There's no point. I'm not going to ask you again. I'm always going to ask you because I'm not going to create like 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 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 find where they really meet. Such a good example. The way that you described it 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? Because these are linear principles, we're going to be very fast. Is this 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, 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 just, it's always going to be available. So here's, 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. Francesca intervened to use a big concept of 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 thing, 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 at 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 rolled out some of these versions to the super fast version that was unsafe. That only went internal. Everyone felt it was too unsafe. But then we thought, let's go to the super safe version, and then we roll that out, and everyone started having a whole bunch of... We did the... How many drafts are people making? This is too many. The people are leaking behind this crazy paper trail. We got to figure out some difference here.
Awesome. So this very much connects to your first point of get something, get things out really quick. And in this case, it's like extreme versions. You're probably not 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. And that's how the way this should feel. Yeah. And to your point, it was not an obvious solution when you started 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 that 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.
I think 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 all of their colleagues can now 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 make a 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, and you adopt some marketing software, you're not just saying, OK, now I can write emails instead of the people. There's all sorts of process around that. You're organizing some of the campaigns. You're measuring click-through rates. You're calculating costs 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, or you learned it from the tool as a buyer for this kind of product, what I'm doing is I'm saying, hey, I'm going to bring in this baseline level of marketing competency into my organization. That 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 I need solved.
Yeah, exactly. And I think that the most salient example of this is if you've ever seen a company adopt an ERP product, it's the most painful thing you can imagine. It's doing deep surgery. They have to redo all of their internal processes in the way they manage inventory and all this kind of stuff. But they're willing to do it because they know that this is a battle-tested way of making sure that you're actually doing good 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 a couple of things I know about linear. One is what you've shared of just avoiding these customizations requests from people. You have a very opinionated way of, here's how you should operate in order to build a great functioning product organ company in general. I'm just connecting threads here. One is, we're going to avoid letting people customize too much because we know they will 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 little linear method. I think it's called of just like here's how a product team should operate based on everything we've seen be successful.
Yeah, yeah, it's definitely kicked 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, you know, neither is right or wrong. What we try to do is find where there's actual consensus.
amongst a lot of different high-performing teams. Then we can take those practices and say, okay, for a team that isn't already practicing this, can we give them a button so that they can start practicing this? When a company, we see companies doing a really good job of managing their triage queue, but it's very manual. Can we automate this? Then for this other company that really needs it, they don't know this is what they need. Can we just give them a button to activate this and now they have to practice within 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 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 of 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, right? When you talk to people and like, hey, 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 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 we kind of come together, the way we think about, you know, 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, um, which I help a 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 talk about engineers is my, is my, my sensor.
Yeah, engineers is a big one, but even product managers. Product managers know what the job is like, so when you come in, you say the wrong words, people give this thing down. Don't call them project managers. Yeah, exactly, for example. I think that's a big part of what we have to do. On our PM team, we actually have a full-time product marketer, and her job is to
Technically, 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 we're building and you know working with directly with the teams and try to figure out how to talk about it And then when 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 with sales, they're validating all that message in the field. They're saying the words to customers directly and telling you if it's sticking or not, and then you can 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, compliment the PM engineer designer. Talk about that and give us this visual that that looks like.
Yeah, I think PMs, product managers, we often have a tough time trying to explain what is your job. It's a little bit of everything. And I think the job that I do, that we see it as you're taking the building side of the organization and the selling side of the organization and bringing it together.
You're taking all of the commercial motivations and goals of the company and making sure that what you build actually solves for those goals. And you're sort of tempering that with what's 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 a 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 Jesky's whole thing about how PMs should be doing marketing. And so the way they changed it or B&B, 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, in fact, if you're leaving something on the table in terms of the kind of impact that you are having at your job, that's probably the thing that you're leaving on the table. You're probably already doing a good job of collaborating with engineering and design. It's probably the sort of sell side that there's an opportunity for you to have more impact.
Just to make it even more concrete for PMs that are like, OK, I want to do this. I want to do what linear is doing. I'm going to get more sales. What does it look like when someone is more is in this double triangle working more closely with sales? You talked about being on sales calls. What else there? Can you share it just like here? Try these things.
I think originate the message that you sense your audience. There's a lot of things that marketing does which you're never going to necessarily touch. There's always like demand gen and figuring out channel strategy and all this kind of stuff. Sure. That's a pure marketing concern. But actually picking the words and where the emphasis is.
You should understand the customer at a pretty deep level, probably deeper than any other group at the company because the kinds of requirements gather and discovery that you're doing. You're going to know the native language that your customers speak a lot better and help your marketing team originate those words. Got it. So basically be really involved in the
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 some of the different things. But it's that sort of content, you know, kind of creation piece that you really have an opportunity to contribute to. Yeah, I love how Cargree that is. It's like, don't think about this concept of product marketing. Just think about the words that your potential customers and customers seek.
Okay. Uh, 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, uh, approach to finding a gig. Uh, I heard from the founder of mode about the very unique approach, uh, way you approached getting a job there. I imagine linear is a similar boat. Uh, what, what advice can you share with folks that are looking for a job? Maybe struggling. That worked for you when you were looking for your next gig.
probably management is kind of a unique role, right? Because we do just about everything, you don't really get pigeonholed into 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. So put on your discovery hat. And you go figure out what is the actual job to be done of the hiring manager when they're bringing on a new PM on to their team. And if you can do that, 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 we're in an interview process, you're just trying to put your best foot forward, trying to say that you're great at everything, you have very few weaknesses, maybe you try too hard, whatever it is. But everyone's going to say that. So you're just one of in people. And you want to make yourself a little bit of just you versus the field. You are the solution to a problem, and then everyone else is 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 successful B2B product. I don't know. That's a broad one. Like usually you're not interviewing for a head of product roles. So that's maybe too broad. So it's like, what is this?
PMroll's job to be done at the company and then help convince them you are the best person 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, right? And like the way that I did this, like I got advice from a friend. He said, like, I was interviewing for this job in mode that you referenced. And I'm like, how should I approach it? He's like, just apply your work 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's asking you a question that goes, you have any questions for me, you can ask them, what are your OKRs this quarter?
How can someone help you achieve those? You could be that specific about it. I'm 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 people are actually trying to solve. Because I think often we just get stuck in these very high level of general types of questions. So like, what's the company goal of all that kind of stuff? And it's like, no, you can get really specific. If you were collaborating with that person in your job, 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 and 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 over deliver on, right? 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 pretend you have the job, because then you actually have this job as part of the interview process. Oftentimes as an outsider, you don't have enough information to have a really good thought on what the solution is and maybe part of it is gonna be so wrong, because you're like, I don't know, actually, no, I don't have the data. Do you actually try to reach out to the engineers and designers on a team to try to understand things? How far do you go to try to solve these problems and show them what you can do?
Yeah, I mean, you're in the interview loop. These are people that you're going to be working closely with. So start there. 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 if no one else is asking, again, you're going to have an extra piece of feedback from that inch manager. So yeah, the sky asks really good questions. And it seems like they're really with it. 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 we're thinking about this already. Yeah. Amazing. None. 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? Uh, you know,
I have a very specific point of view on deadlines. I don't know if that's a fire away. I think what often happens is people get depressed about deadlines. Hey, 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, deadlines. They're just they're they're complete fabrications. And the only way to make deadlines real is to take them so seriously that they are basically like a P zero 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 that you're actually taking seriously. So, you know, my, my feeling on deadlines is don't have too many of them, right? And when you do, uh, it's a P zero.
So the engineer is working on it. They don't get the work on anything else. Like someone's, oh, I need them for this. Like, don't, no, 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 sit yes to.
It might not have all the features you had wanted or whatever it is, and you can say no. You can make that choice, but you want to set yourself up to be in a position where you can actually say yes or no to something. Because 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. I can't ship it. It's like half broken. It's like, no, no, you want to get to a point where it works. It might not be the product that you want, but it is an actual real product that you can conceivably ship.
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 sort of 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. 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
It makes me go crazy when I hear people say that in all honesty. With marketing and communication with customers, you basically have a limited amount of opportunities to do so. A year is 365 days. There are 12 months. 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 out, it creates a lot of stress knowing there's a deadline we have to hit. So one lever you've mentioned is cutting scope. Another is just people spending the more time estimating to have more accurate deadlines. You invest in that. How do you think about just like for an engineering team to commit to a deadline? How much to span on like de-risking 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 elapsed, 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 shipable state.
right? So you're, 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, you can't, you can't go into this at the, at the very last moment and say, 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. Non, this was everything I was hoping it'd 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. Every single pencil that you use, every door that you open is a product that somebody designed.
And is that the big takeaway for that book? Because it comes up a lot. And I think in 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 and 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. And because it was a push door, but it had a handle that looked like you could pull it. And that's, that's like one of the canonical examples of the book. Yeah. Some of those are just mysteries. Yeah. Awesome. Next question. Do you have a favorite recent movie or TV show? You really enjoyed it.
I've watched the diplomat on Netflix, I think it was. Terrific. It's really fun. Easy watch. It has some West Wing vibes if you were into that back in the day. 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, yes, it's cool. But yeah, it got a little like spy thriller-y, I think. Yeah. Yeah. Okay. Cool. But still really good in our 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 the Sakura Micron. I don't know if you use these. It's like a felt it pen. It's really great. It was originally invented in Japan for artists to draw comic books and stuff.
And, you know, you can use it for anything, you gotta 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, Bible study kit.
I was like, why is this labeled Bible study kit? And it was, 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, 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 were looking for that keyword. And it's like, it was like official too. It was not something hacked together. It was like 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 the 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.
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. It 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 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 your bestseller that they have now, and how you helped create a best-selling women's shirt. Do you share that story? Yeah, so to be clear, I witnessed the creation. I don't think I had a direct hand in it.
Yeah, so I saw this advertisement the other day on Instagram for, it's called the women's box cut tea. And it's a t-shirt that's kind of wide and short for women. And I looked and they had 20 colors of it. And it's like, it sells super well. And I remember when we created this thing.
It was because there was a batch of defective men's t-shirts. They all came in an inch and a half too short. We couldn't sell them. You would have your belly button sticking out. No one wants to wear that. What we did was we had to salvage the inventory because we were a very small company and we had to make cash flow. We couldn't just damage it out.
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 did that. We're like, okay, hopefully, you know, hopefully we can salvage this inventory and not have to like take a ride down.
It's so 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 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 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.
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 a 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-U, it's THE, and then my name. And if they have any feedback about linear, we're very happy to take it, especially for people who 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 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.
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Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify)

Lenny's Podcast: Product | Growth | Career
Tobi Lütke is the founder and CEO of Shopify, a $130 billion business that powers over 10% of all U.S. e-commerce. Starting as a snowboard shop in 2004, Shopify has become the leading commerce platform by consistently approaching problems differently. Tobi remains deeply technical, frequently coding alongside his team, and is known for his unique approach to leadership, product development, and company building. In our conversation, we discuss:• Why complexity kills entrepreneurship• How to develop and leverage your unique talent stack• How specifically Tobi approaches thinking from first principles• The importance of focusing on unquantifiable qualities like joy and delight• Why Tobi works backward from a 100-year vision• Why metrics should support decisions, not make them• The power of following your curiosity• What Tobi believes it takes to be a great product leader• Much more—Brought to you by:• Sinch—Build messaging, email, and calling into your product• Liveblocks—Ready-made collaborative features to drop into your product• Loom—The easiest screen recorder you’ll ever use—Find the transcript at: https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook—Where to find Tobi Lütke:• X: https://x.com/tobi• LinkedIn: https://www.linkedin.com/in/tobiaslutke/• Website: https://tobi.lutke.com/—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) Welcome and introduction(04:17) The Tobi tornado(07:10) Maximizing human potential(11:05) Education and personal growth(16:47) Operating without KPIs(25:00) First-principles thinking(40:04) Remote work(45:59) Why Tobi never stopped coding(54:46) Embracing disagreement(01:01:27) The 100-year vision(01:09:29) Balancing tactics and positioning(01:17:15) Encouraging entrepreneurship(01:19:34) The power of good UX(01:28:42) The talent stack and unique opportunities(01:34:30) The role of passion in product development(01:36:39) Final thoughts and farewell—Referenced:• How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng): https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawar• Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams• The ultimate guide to performance marketing | Timothy Davis (Shopify): https://www.lennysnewsletter.com/p/performance-marketing-timothy-davis• Brandon Chu on building product at Shopify, how writing changed the trajectory of his career, the habits that make you a great PM, pros and cons of being a platform PM, how Shopify got through Covid: https://www.lennysnewsletter.com/p/brandon-chu-on-what-its-like-to-build• IRC: https://en.wikipedia.org/wiki/IRC• Goodhart’s law: https://en.wikipedia.org/wiki/Goodhart%27s_law• Glen Coates on LinkedIn: https://www.linkedin.com/in/glcoates/• How Shopify builds product: https://www.lennysnewsletter.com/p/how-shopify-builds-product• The Last Dance on Netflix: https://www.netflix.com/title/80203144• Autoregressive Models for Natural Language Processing: https://medium.com/@zaiinn440/autoregressive-models-for-natural-language-processing-b95e5f933e1f• Archimedean property: https://en.wikipedia.org/wiki/Archimedean_property• Tabula rasa: https://en.wikipedia.org/wiki/Tabula_rasa• Daniel Weinand on LinkedIn: https://www.linkedin.com/in/danielweinand/• World of Warcraft: https://worldofwarcraft.blizzard.com• Harley Finkelstein on LinkedIn: https://www.linkedin.com/in/harleyf/• Monorepo: https://en.wikipedia.org/wiki/Monorepo• The Sarbanes Oxley Act: https://sarbanes-oxley-act.com/• Shopify builds Shopify Balance with Stripe to give small businesses an easier way to manage money: https://stripe.com/customers/shopify• Stanford marshmallow experiment: https://en.wikipedia.org/wiki/Stanford_marshmallow_experiment• Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong/• We are the Web: https://link.wired.com/public/32945405—Recommended books:• Finite and Infinite Games: https://www.amazon.com/Finite-Infinite-Games-James-Carse/dp/1476731713• The Infinite Game: https://www.amazon.com/Infinite-Game-Simon-Sinek/dp/073521350X/—Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.—Lenny may be an investor in the companies discussed. Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe
February 02, 2025
An operator’s guide to product strategy | Chandra Janakiraman (CPO at VRChat, ex-Meta, Headspace, Zynga)

Lenny's Podcast: Product | Growth | Career
Chandra Janakiraman shares insights on his product strategy playbook, defining and developing a winning strategy, the importance of preparation and strategy sprints, common pitfalls in strategy development, role of AI in future strategy, and lessons from Zynga & Meta.
January 26, 2025
10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey)

Lenny's Podcast: Product | Growth | Career
Elena Verna discusses 10 growth tactics that never work like color optimizations, third-party signups, and removing friction; her favorite growth frameworks; and increasing career optionality.
January 19, 2025

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