The Exchanges

Q Let's say we have three candidates that we're looking at. How do we structure that process? If you were to advise me as like an early stage founder, how would you advise me on how to structure that hiring process for product people?

A So that first call that we're going to have, you know, it's going to be talking about career, product experience, sort of a get to know you. Uh, and then we think about structuring the interviews in a few different buckets. First is around product strategy, which is talking about sort of big bets and decisions that this person has, uh, led within an organization. You have execution, which is how do you take that large strategy, translate it down into an executable roadmap. And then actually deliver on it. You have people management for, uh, you know, CPOs and product leaders, and then technical fluency, which is, you know, we do run a relatively technical product and we're selling to engineers. And so we do expect our product team to have a certain level of technical fluency.

AI assessment note: “we think about structuring the interviews in a few different buckets”

Q Let's say we have three candidates that we're looking at. How do we structure that process? If you were to advise me as like an early stage founder, how would you advise me on how to structure that hiring process for product people?

A So that first call that we're going to have, you know, it's going to be talking about career, product experience, sort of a get to know you. Uh, and then we think about structuring the interviews in a few different buckets. First is around product strategy, which is talking about sort of big bets and decisions that this person has, uh, led within an organization. You have execution, which is how do you take that large strategy, translate it down into an executable roadmap. And then actually deliver on it. You have people management for, uh, you know, CPOs and product leaders, and then technical fluency, which is, you know, we do run a relatively technical product and we're selling to engineers. And so we do expect our product team to have a certain level of technical fluency.

AI assessment note: “we think about structuring the interviews in a few different buckets”

Q What's the hardest thing about bringing in a CPO, do you think?

A I think there are really two hiring mistakes when it comes to hiring product people. The first is not really having a clear understanding of the role that you're hiring for, right? So there are a bunch of different archetypes that you can hire Some product people really spike in strategy, some really excel in culture building and team building and people management, others specialize in go to market partnership or product execution. Right. And so you really need to be crystal clear on what you are looking to hire for. And then the other, I think is really being deliberate and committed to hiring for those set of spikes. You know, I think allowing a committee to dictate a hiring decision is never good. At the end of the day, the hiring manager, the CEO in this case, needs to be empowered to make the decision, even if there isn't consensus among the hiring team.

AI assessment note: “there are really two hiring mistakes when it comes to hiring product people.”

Q What makes a good product meme versus a bad product meme?

A So I think simplicity is one, uh, really accessibility for folks and then memorability. So the fact that it is actually something that you will remember, you will walk away from that conversation remembering. So I think a few examples of this, you know, we had a big campaign, uh, for segment, which was called, you know, what good is bad data? And it's just sort of a catchy phrase, which helps you understand data quality at the end of the day is going to be really important for, uh, your data strategy. I think they can also be really small. So we had, uh, this feature, which was essentially self-healing identity graphs, obviously complex, very deep in the weeds, but we called the project project Roomba, uh, after the beloved self-driving vacuum cleaner. And, you know, that sticks with people. It allows them to understand what you're doing, even if they don't understand the specific details of it.

AI assessment note: “So I think simplicity is one, uh, really accessibility for folks and then memorability.”

Q it's so important to have that multifaceted view so you can have the empathy for each part of the organization. But before we dive into kind of product in the world of products, you're also at Bridgewater, which does shape so many people's perspectives in many ways. Calvin told me, I had to ask this one, what are one or two of your biggest takeaways from your time at Bridgewater?

A Yeah, yeah, yeah. Uh, Bridgewater is definitely, uh, Pretty special place. Uh, I don't know how many of the listeners know what Bridgewater is, one of the largest asset managers in the world. Uh, also committed to building an organization that's all about radical transparency and honesty and ruthless pursuit of the truth. So Ray Dalio as the founder has written a lot about, uh, his management principles, and those are very much embedded in the organization and the culture there. I think there were really sort of two interesting learnings here. The first is around Uh, really trying to better understand how people think around you to sharpen your decision making, especially in business conversations, uh, you know, in the workplace, people are often talking about and debating opinions, right? So, like, Harry believes option A is the best option, I believe option B, and we're going to debate option A versus option B to figure out which one is superior, but I actually think there's something more valuable and the approach that is often taken at Bridgewater is really trying to understand how Harry got to option A, right? What is the data that Harry is seeing? What is the mental model that Harry has of the world that is leading to that perspective? It's through understanding that way of thinking and processing that you can actually refine and sharpen your own decisions by really under…

AI assessment note: “I think there were really sort of two interesting learnings here.”

Q said there about kind of the specific skills. When I spoke to many of our mutual friends, they, they described you as a man of many talents, meaning that you are an all-rounder. You do lots of things well. How important do you think it is for product leaders to do a little bit of everything versus be much more specialist and work on the machine rather than in it?

A Wow. Great question. You know, I think it's tough to be a product leader in a product-led organization because You're responsible for so many different things, right? If the product doesn't sell, uh, right, you're the one who's on the hook. Uh, if your team is flooded with support requests, uh, generally product needs to go figure out what is wrong with the product. If you're misaligned on margins or the product doesn't scale, yes, that's a systems and engineering problem, but also at the end of the day, you're trying to meet your customer's needs. And so, I think the beauty and the challenge of being a product leader in a product led organization is that you're uniquely positioned to solve these issues, even if they're not traditionally product problems. But I think what that really begs is, you know, somebody who can go out and learn really quickly a bunch of different disciplines and then, you know, go solve the hardest problem within an organization, regardless of whether it fits into a product Bucket or an engineering bucket or a go to market bucket. I think a great example of this was, uh, when we introduced, uh, personas, which was a new product offering and add on to our core product within segment. We really needed to spend the next year as the product team who was closest to the discovery and the customer needs going out, pairing with our sales team and really deliver…

AI assessment note: “learn really quickly a bunch of different disciplines and then, you know, go solve”

Q For me, as an early stage founder that you're advising, what are the mistakes that you suggest I avoid when it comes to demos?

A There are sort of two pitfalls here. The first is that they become too high stakes, right? And so people feel like they need to put a lot of polish and prep into their demo. And so they spend a good chunk of their week on overhead and polish as opposed to the actual core components of the demo. And so that's why encouraging, you know, people to show docs that they've written Pull up the command line, uh, and really show off whatever that is, uh, that they've been working on in an end to end, uh, full value delivery, I think is really important. And then the other that I would say is, uh, you know, not making it too performative. It doesn't need to be a ton of people, a huge group. It can be down to your product pod or a small team that's been working together.

AI assessment note: “There are sort of two pitfalls here. The first is that they become too high stakes”

Q What makes a good product meme versus a bad product meme?

A So I think simplicity is one, uh, really accessibility for folks and then memorability. So the fact that it is actually something that you will remember, you will walk away from that conversation remembering. So I think a few examples of this, you know, we had a big campaign, uh, for segment, which was called, you know, what good is bad data? And it's just sort of a catchy phrase, which helps you understand data quality at the end of the day is going to be really important for, uh, your data strategy. I think they can also be really small. So we had, uh, this feature, which was essentially self-healing identity graphs, obviously complex, very deep in the weeds, but we called the project project Roomba, uh, after the beloved self-driving vacuum cleaner. And, you know, that sticks with people. It allows them to understand what you're doing, even if they don't understand the specific details of it.

AI assessment note: “I think simplicity is one, uh, really accessibility for folks and then memorability.”

Q agree with you there. I always also oscillate when I think about, like, actually, fuck it, I do have to ask one more thing before we dive in, but it's like, Segment was an amazing journey, yeah? Ended with an incredible exit, obviously, to Twilio, where you are now. What are one or two of your biggest takeaways from the Segment journey? That really impacted how you think about product?

A You know, I think a really important part of the segment story was that the founders, you know, before anybody joined the company had really struggled to find product market fit for a few years before landing on segment. And so there was a really high bar internally and rigorous thinking around what it takes to achieve product market fit. You know, I had the privilege of being able to introduce segments second Product. And, uh, this was really introducing sort of the first customer data platform on the market. We'd spent the first six months really sort of shaping the idea, researching this with customers, iterating on their feedback, but we were running into a ton of technical problems. Uh, we, customers weren't really ripping this thing out of our hands and Tito, who, you know, was essentially our, uh, product and engineering leader, the grownup in the room for a lot of segment story sat us down and he essentially told us we had three months to make the project work or the project was dead. And so it was the exact deadline that we needed, pressure that we needed. We ended up cutting a ton of the bells and whistles and things that we thought we needed and really simplified down to the product that customers were looking for. You know, I think there are a few takeaways from that. The first is you need to be rigorous and honest with yourself and your team. When things are workin…

AI assessment note: “The first is you need to be rigorous... more important piece is that constraints can really breed creativity”

Q said there about kind of the specific skills. When I spoke to many of our mutual friends, they, they described you as a man of many talents, meaning that you are an all-rounder. You do lots of things well. How important do you think it is for product leaders to do a little bit of everything versus be much more specialist and work on the machine rather than in it?

A Wow. Great question. You know, I think it's tough to be a product leader in a product-led organization because You're responsible for so many different things, right? If the product doesn't sell, uh, right, you're the one who's on the hook. Uh, if your team is flooded with support requests, uh, generally product needs to go figure out what is wrong with the product. If you're misaligned on margins or the product doesn't scale, yes, that's a systems and engineering problem, but also at the end of the day, you're trying to meet your customer's needs. And so, I think the beauty and the challenge of being a product leader in a product led organization is that you're uniquely positioned to solve these issues, even if they're not traditionally product problems. But I think what that really begs is, you know, somebody who can go out and learn really quickly a bunch of different disciplines and then, you know, go solve the hardest problem within an organization, regardless of whether it fits into a product Bucket or an engineering bucket or a go to market bucket. I think a great example of this was, uh, when we introduced, uh, personas, which was a new product offering and add on to our core product within segment. We really needed to spend the next year as the product team who was closest to the discovery and the customer needs going out, pairing with our sales team and really deliver…

AI assessment note: “somebody who can go out and learn really quickly a bunch of different disciplines”

Q debate or balance for me in product, which I never know the answer to, which is, is product art, or is it science? You know, again, Gustav at Spotify, he was contrarian. He said that it's 99% science, and we overestimate how much art there is. Um, others, he's the only one that says that, by the way. So my question to you is, is it more art or science?

A It's a really fun question to wrestle with. You know, I think about Product management is all about building great products that users love that are aligned with the long-term interests of the business. And so if you break that down, right, you have building great products, which I think boils down to great discovery and really understanding customer needs. And there, I do think that there is a highly scientific approach that you can take, uh, and repeated process that you can build around that. Uh, then there is building things that users love, right? Taking those prob problems and actually translating that down into creative solutions, given the technology landscape, uh, where the market is at. I think that is going to largely boil down to an art, uh, which sits somewhere between, you know, design engineering and product management disciplines. And then, uh, there's of course, making sure that where you are heading is in the long-term direction of the business. And, That requires deep market understanding, understanding where competitors are at, and where they're likely to move, and what their long-term strategy is relative to yours, and so there, I don't think you can boil that down into a formula, so I'd say mostly art.

AI assessment note: “so I'd say mostly art.”

Q agree with you there. I always also oscillate when I think about, like, actually, fuck it, I do have to ask one more thing before we dive in, but it's like, Segment was an amazing journey, yeah? Ended with an incredible exit, obviously, to Twilio, where you are now. What are one or two of your biggest takeaways from the Segment journey? That really impacted how you think about product?

A You know, I think a really important part of the segment story was that the founders, you know, before anybody joined the company had really struggled to find product market fit for a few years before landing on segment. And so there was a really high bar internally and rigorous thinking around what it takes to achieve product market fit. You know, I had the privilege of being able to introduce segments second Product. And, uh, this was really introducing sort of the first customer data platform on the market. We'd spent the first six months really sort of shaping the idea, researching this with customers, iterating on their feedback, but we were running into a ton of technical problems. Uh, we, customers weren't really ripping this thing out of our hands and Tito, who, you know, was essentially our, uh, product and engineering leader, the grownup in the room for a lot of segment story sat us down and he essentially told us we had three months to make the project work or the project was dead. And so it was the exact deadline that we needed, pressure that we needed. We ended up cutting a ton of the bells and whistles and things that we thought we needed and really simplified down to the product that customers were looking for. You know, I think there are a few takeaways from that. The first is you need to be rigorous and honest with yourself and your team. When things are workin…

AI assessment note: “constraints can really breed creativity, right? By shortening the runway”

Q Can I ask, did you find it an easy transition to make?

A Yeah. Yeah. It's a great question. I like to think analysts make incredible, uh, product managers largely because Uh, you're forced to think broadly about the business, really dive deep into data, both quantitative and qualitative and the signals that you can gather to really inform strategy. And so, you know, I felt like there was a great foundation there. I also think being, uh, you know, in the early stages of a company, you end up playing a lot of different roles, uh, and seeing a lot of different parts of the business. So analytics took on the role of growth at times of partnerships of sales ops. And so You really get a unique lens across the business sitting in analytics.

AI assessment note: “Yeah. Yeah. It's a great question. I like to think analysts make incredible”

Q I totally get that. Okay, so there we're shipping fast with low impact. Not great. Um, what's next?

A So finally, there's the good stuff, which is you're consistently shipping and you're consistently delivering high impact work. And Teams in this state are generally going to be really high context. They're going to be high trust across engineering, design, and product. They're very high talent density, right? So you have a lot of great people that are working there, and they're empowered to take risks. This is the bar that you want to set for your entire EPD org. When you have a team in this state, you want to figure out ways in which you can keep it intact and keep it going and really get the heck out of their way. But by looking at product teams through this lens, you can really think about what are the different strategies that you need to take to get them to continuously deliver and continuously deliver high impact.

AI assessment note: “So finally, there's the good stuff, which is you're consistently shipping”

Q I totally agree with you there. Can I ask, when you review your hiring mistakes, my biggest is I've overweighted brand. I've seen that they've come from a big logo, and I've gone, they must be brilliant, and they're not, ah, very often. Ah, what are your biggest hiring mistakes when you reflect on hiring for product teams?

A It's a great question. I think overweighting skills and, uh, specific domain expertise is a common one that I've fallen into specifically with hiring product people. Uh, you know, the best, uh, product leaders within our organization are generalists can, uh, apply their craft to a bunch of different domains. There are very few cases where we needed specific knowledge and skills. Uh, to bring on to the team that was really the key input into a decision. More often than not, uh, that is going to be, uh, something that somebody can learn on the job, and so, you know, you don't want to overweight skills, uh, instead really focusing on experience, the overall craft of product management, and making sure that they're at the bar there.

AI assessment note: “overweighting skills and, uh, specific domain expertise is a common one”

Q Thank you. I'm a podcaster for a living, so I mean, pretty much this is my job. I remember I'm in the arena, Kevin, okay? That's right. You said before that there's four states to product teams. I love this framing because I really find the structure quite helpful. What are the four states and how should founders think about this?

A So it's a pretty powerful model for thinking about the performance of your product teams and How you can get them to the next level. So if you just imagine this grid where you have shipping fast and slow and you have impact high and low as the other, uh, you can really think about mapping where your product teams are relative to those two dimensions. And so over time, there are really only four states that a product team can be in. You can have a team that's not shipping and there are a lot of reasons that can go into that. Uh, maybe they introduced a feature that led to an outage, and so there's a lot of fear on the team. Uh, maybe they got a lot of feedback from a last product ship, and so, uh, they're reticent to move the needle. Maybe they don't have a clear strategy, and so they're in tweaking mode. And so, essentially, they're not delivering, uh, on the roadmap. But you really need to, uh, to unlock this state, you really need to think about Uh, how can, how can you get them into shipping mode? Have them ship something really small and then celebrate the heck out of it to really encourage that feedback loop to get into the mode of delivering for customers. The second state, you can have a team that ships, but they don't, they aren't delivering impact. And so here, the pace of development is good. They're moving really quickly, but it's relatively low impact work.

AI assessment note: “if you just imagine this grid where you have shipping fast and slow”

Q For me, as an early stage founder that you're advising, what are the mistakes that you suggest I avoid when it comes to demos?

A There are sort of two pitfalls here. The first is that they become too high stakes, right? And so people feel like they need to put a lot of polish and prep into their demo. And so they spend a good chunk of their week on overhead and polish as opposed to the actual core components of the demo. And so that's why encouraging, you know, people to show docs that they've written Pull up the command line, uh, and really show off whatever that is, uh, that they've been working on in an end to end, uh, full value delivery, I think is really important. And then the other that I would say is, uh, you know, not making it too performative. It doesn't need to be a ton of people, a huge group. It can be down to your product pod or a small team that's been working together.

AI assessment note: “There are sort of two pitfalls here. The first is that they become too high stakes”

Q actually write about a competitive landscape, it really crystallizes, oh shit, this is really fucking competitive versus just thinking about it. So I totally agree with that. But if we think about writing with regards to product and prioritization, crystallizing thinking, what does that mean that we do? I'm a product manager listening. Should I write product Reviews. What can I do? Help me understand. I should write what now?

A So, you know, I think a lot of the great product thinking gets encoded into this concept of a PRD or a product requirements document. Uh, these can take multiple forms, but I really think at the end of the day, the thing that you are trying to articulate is what is the customer need? What, what have you learned through the discovery process? What are the key problems that You are looking to solve and why is your team, your organization, your product uniquely positioned to solve those problems? It's not about solutions. It's not about, uh, how you can solve them, but it's more about what and why you are solving that problem. And so this concept of the PRD is really powerful. It creates structure for product teams to really be able to articulate and synthesize everything that they've learned from going out and talking to customers. And encoding that into a packet, a document that everybody can engage with, read, give feedback on, and iterate on.

AI assessment note: “great product thinking gets encoded into this concept of a PRD”

Q sorry for you from a resource allocation perspective, because you have to, like, weigh up Product that generates revenue today. You then have to also weigh up innovation, staying ahead of the game, how to introduce AI and every other, you know, exciting new technology into the existing product suite, and then just scaling and growth. How do you balance between core product innovation and scaling as a product leader?

A I think those are the three buckets. Having that framework around the three horizons, I think is really helpful. What are you doing well today? What is emerging over the course of the next one to two years? And what do you need to do Long-term, three to five years out, uh, that's gonna set your product and org up for success. You know, I do think that the allocation across those buckets are going to swing, especially in the early days, that segment would swing pretty wildly between, you know, 90, 10, zero, really honing our, the quality of our core product in the early days to really periods of innovation where we're trying to Expand, build new products, and really solve new problems for our customers when it looked probably more like 30, 40, 30 across those different buckets, but I do think that being aligned with your founding team, uh, with your leadership team around where you want to fall across those investment areas is really key to ensuring that you're making the right decisions and allocating resources the right way.

AI assessment note: “allocation across those buckets are going to swing, especially in the early days”

Q uh, interesting lessons from, from anything, I think one that I have from this prep session that I did was around your take on memes, and Calvin also told me to ask this. He said that you said before about product memes are more important than your roadmap, and you said that before to me. What did you mean when you said product memes are more important than your roadmap?

A Yeah. So, you know, with all the talk about how important it is to write as a product leader, I think at the end of the day, most people are never going to read your PRD. Most people are not actually going to review your, you know, 20 page roadmap, no matter how well written or thought through it is. And so product memes are this concept of really simplifying your thinking down into the shortest, simplest, Most memorable perception of your product and then distributing those ideas through the meme, right? And so if you think about memes, these are generally these distillations of really complex ideas and structures. It's about compression. It's about taking these different ideas and creating knowledge shortcuts for people. And so I think a good example of this is like memes gone wrong, right? The ways in which, uh, memes can work against you. If you think about a sales team that Has lost faith in the quality of the product that they're selling. That in and of itself is a meme. It spreads at the water cooler, uh, over drinks at the end of the week. And it not only hurts your sales, but it also becomes self-fulfilling and it spreads. This is sort of the dark side of the meme. And you can, you can invert that and think about ways in which you can control the narrative and really build alignment around what you are building through exciting memes. I think, you know, we had a few cr…

AI assessment note: “product memes are this concept of really simplifying your thinking down into the shortest”

Q Two questions for you. One, I'm an early stage investment of yours. How do you advise me, a CPO or a product leader, on when's the right time to do product two?

A We, I think, waited a really long time at segment to introduce our second product, which I think was a function of our core product was, uh, growing really quickly, and we felt like we had a lot of runway. I think the key piece to keep in mind is what does that growth rate look like One to two years out. And, uh, I think that's probably the right time when you see that flattening, uh, or starting to stall out, you know, one to two years out in the future, you really need to be ahead of that. I really encourage folks to stay focused on core product as long as possible, but also knowing that you need to be thinking about the long term and new products and second products take a while to build Hone and deliver to market, and so you really probably need, you know, 12 to 24 months to make that a reality.

AI assessment note: “when you see that flattening, uh, or starting to stall out”

Q it's so important to have that multifaceted view so you can have the empathy for each part of the organization. But before we dive into kind of product in the world of products, you're also at Bridgewater, which does shape so many people's perspectives in many ways. Calvin told me, I had to ask this one, what are one or two of your biggest takeaways from your time at Bridgewater?

A Yeah, yeah, yeah. Uh, Bridgewater is definitely, uh, Pretty special place. Uh, I don't know how many of the listeners know what Bridgewater is, one of the largest asset managers in the world. Uh, also committed to building an organization that's all about radical transparency and honesty and ruthless pursuit of the truth. So Ray Dalio as the founder has written a lot about, uh, his management principles, and those are very much embedded in the organization and the culture there. I think there were really sort of two interesting learnings here. The first is around Uh, really trying to better understand how people think around you to sharpen your decision making, especially in business conversations, uh, you know, in the workplace, people are often talking about and debating opinions, right? So, like, Harry believes option A is the best option, I believe option B, and we're going to debate option A versus option B to figure out which one is superior, but I actually think there's something more valuable and the approach that is often taken at Bridgewater is really trying to understand how Harry got to option A, right? What is the data that Harry is seeing? What is the mental model that Harry has of the world that is leading to that perspective? It's through understanding that way of thinking and processing that you can actually refine and sharpen your own decisions by really under…

AI assessment note: “I think there were really sort of two interesting learnings here. The first is”

Q I totally get that. Okay, so there we're shipping fast with low impact. Not great. Um, what's next?

A So finally, there's the good stuff, which is you're consistently shipping and you're consistently delivering high impact work. And Teams in this state are generally going to be really high context. They're going to be high trust across engineering, design, and product. They're very high talent density, right? So you have a lot of great people that are working there, and they're empowered to take risks. This is the bar that you want to set for your entire EPD org. When you have a team in this state, you want to figure out ways in which you can keep it intact and keep it going and really get the heck out of their way. But by looking at product teams through this lens, you can really think about what are the different strategies that you need to take to get them to continuously deliver and continuously deliver high impact.

AI assessment note: “there's the good stuff, which is you're consistently shipping and you're consistently delivering high impact”

Q debate or balance for me in product, which I never know the answer to, which is, is product art, or is it science? You know, again, Gustav at Spotify, he was contrarian. He said that it's 99% science, and we overestimate how much art there is. Um, others, he's the only one that says that, by the way. So my question to you is, is it more art or science?

A It's a really fun question to wrestle with. You know, I think about Product management is all about building great products that users love that are aligned with the long-term interests of the business. And so if you break that down, right, you have building great products, which I think boils down to great discovery and really understanding customer needs. And there, I do think that there is a highly scientific approach that you can take, uh, and repeated process that you can build around that. Uh, then there is building things that users love, right? Taking those prob problems and actually translating that down into creative solutions, given the technology landscape, uh, where the market is at. I think that is going to largely boil down to an art, uh, which sits somewhere between, you know, design engineering and product management disciplines. And then, uh, there's of course, making sure that where you are heading is in the long-term direction of the business. And, That requires deep market understanding, understanding where competitors are at, and where they're likely to move, and what their long-term strategy is relative to yours, and so there, I don't think you can boil that down into a formula, so I'd say mostly art.

AI assessment note: “I don't think you can boil that down into a formula, so I'd say mostly art.”

Q Thank you. I'm a podcaster for a living, so I mean, pretty much this is my job. I remember I'm in the arena, Kevin, okay? That's right. You said before that there's four states to product teams. I love this framing because I really find the structure quite helpful. What are the four states and how should founders think about this?

A So it's a pretty powerful model for thinking about the performance of your product teams and How you can get them to the next level. So if you just imagine this grid where you have shipping fast and slow and you have impact high and low as the other, uh, you can really think about mapping where your product teams are relative to those two dimensions. And so over time, there are really only four states that a product team can be in. You can have a team that's not shipping and there are a lot of reasons that can go into that. Uh, maybe they introduced a feature that led to an outage, and so there's a lot of fear on the team. Uh, maybe they got a lot of feedback from a last product ship, and so, uh, they're reticent to move the needle. Maybe they don't have a clear strategy, and so they're in tweaking mode. And so, essentially, they're not delivering, uh, on the roadmap. But you really need to, uh, to unlock this state, you really need to think about Uh, how can, how can you get them into shipping mode? Have them ship something really small and then celebrate the heck out of it to really encourage that feedback loop to get into the mode of delivering for customers. The second state, you can have a team that ships, but they don't, they aren't delivering impact. And so here, the pace of development is good. They're moving really quickly, but it's relatively low impact work.

AI assessment note: “if you just imagine this grid where you have shipping fast and slow and you have impact”

Q I totally agree with you there. Can I ask, when you review your hiring mistakes, my biggest is I've overweighted brand. I've seen that they've come from a big logo, and I've gone, they must be brilliant, and they're not, ah, very often. Ah, what are your biggest hiring mistakes when you reflect on hiring for product teams?

A It's a great question. I think overweighting skills and, uh, specific domain expertise is a common one that I've fallen into specifically with hiring product people. Uh, you know, the best, uh, product leaders within our organization are generalists can, uh, apply their craft to a bunch of different domains. There are very few cases where we needed specific knowledge and skills. Uh, to bring on to the team that was really the key input into a decision. More often than not, uh, that is going to be, uh, something that somebody can learn on the job, and so, you know, you don't want to overweight skills, uh, instead really focusing on experience, the overall craft of product management, and making sure that they're at the bar there.

AI assessment note: “overweighting skills and, uh, specific domain expertise is a common one that I've fallen into”

Q Okay. Product reviews. Everyone does them very differently. How often do you do a product review?

A We've gone through a bunch of different iterations on product review over the years. At times it's been sort of wildly centralized and seen as sort of a gate to projects before they get greenlit. I think my view has evolved quite a bit here, which is product review is really an opportunity for PMs to gather additional input and drive additional alignment across the organization. And so we run product reviews on demand as product teams are at a point where they want additional input. Flexible list of attendees who can attend, uh, generally will include some folks from go to market, product leadership, uh, anybody who, design and engineering, anybody who can really weigh in and help sharpen the thinking there. I think it's really about empowering product teams to, uh, really own their own destiny.

AI assessment note: “we run product reviews on demand as product teams are at a point”

Q uh, interesting lessons from, from anything, I think one that I have from this prep session that I did was around your take on memes, and Calvin also told me to ask this. He said that you said before about product memes are more important than your roadmap, and you said that before to me. What did you mean when you said product memes are more important than your roadmap?

A Yeah. So, you know, with all the talk about how important it is to write as a product leader, I think at the end of the day, most people are never going to read your PRD. Most people are not actually going to review your, you know, 20 page roadmap, no matter how well written or thought through it is. And so product memes are this concept of really simplifying your thinking down into the shortest, simplest, Most memorable perception of your product and then distributing those ideas through the meme, right? And so if you think about memes, these are generally these distillations of really complex ideas and structures. It's about compression. It's about taking these different ideas and creating knowledge shortcuts for people. And so I think a good example of this is like memes gone wrong, right? The ways in which, uh, memes can work against you. If you think about a sales team that Has lost faith in the quality of the product that they're selling. That in and of itself is a meme. It spreads at the water cooler, uh, over drinks at the end of the week. And it not only hurts your sales, but it also becomes self-fulfilling and it spreads. This is sort of the dark side of the meme. And you can, you can invert that and think about ways in which you can control the narrative and really build alignment around what you are building through exciting memes. I think, you know, we had a few cr…

AI assessment note: “product memes are this concept of really simplifying your thinking down into the shortest, simplest”

Q sorry for you from a resource allocation perspective, because you have to, like, weigh up Product that generates revenue today. You then have to also weigh up innovation, staying ahead of the game, how to introduce AI and every other, you know, exciting new technology into the existing product suite, and then just scaling and growth. How do you balance between core product innovation and scaling as a product leader?

A I think those are the three buckets. Having that framework around the three horizons, I think is really helpful. What are you doing well today? What is emerging over the course of the next one to two years? And what do you need to do Long-term, three to five years out, uh, that's gonna set your product and org up for success. You know, I do think that the allocation across those buckets are going to swing, especially in the early days, that segment would swing pretty wildly between, you know, 90, 10, zero, really honing our, the quality of our core product in the early days to really periods of innovation where we're trying to Expand, build new products, and really solve new problems for our customers when it looked probably more like 30, 40, 30 across those different buckets, but I do think that being aligned with your founding team, uh, with your leadership team around where you want to fall across those investment areas is really key to ensuring that you're making the right decisions and allocating resources the right way.

AI assessment note: “allocation across those buckets are going to swing... 90, 10, zero... 30, 40, 30”

Q Two questions for you. One, I'm an early stage investment of yours. How do you advise me, a CPO or a product leader, on when's the right time to do product two?

A We, I think, waited a really long time at segment to introduce our second product, which I think was a function of our core product was, uh, growing really quickly, and we felt like we had a lot of runway. I think the key piece to keep in mind is what does that growth rate look like One to two years out. And, uh, I think that's probably the right time when you see that flattening, uh, or starting to stall out, you know, one to two years out in the future, you really need to be ahead of that. I really encourage folks to stay focused on core product as long as possible, but also knowing that you need to be thinking about the long term and new products and second products take a while to build Hone and deliver to market, and so you really probably need, you know, 12 to 24 months to make that a reality.

AI assessment note: “that's probably the right time when you see that flattening, uh, or starting to stall”