The Exchanges

Q Now we're going to kick off the show today with Shreyas Doshi. Shreyas is an all-round product OG. Most recently, Shreyas spent over five years at Stripe, where he was Stripe's first PM manager and helped grow the PM function from five to more than 50 people. What are the three different product leader personas that I should know about when entering this hiring process?

A One of the patterns is the three types of product leaders, and they are the operator, The craftsperson and the visionary. What is really important is there is no one right answer. First of all, it really depends. But the second thing is that it's important to recognize that it's not like a certain person can only be an operator. They can wear each of these hats. So you can think about them as hats, but still people have a primary hat and that's the hat that makes them most comfortable. That's the hat they would rather wear. But the operator is excellent at scaling teams. Driving cross-org alignment and unblocking execution. And the operator superpower is communication. On the other hand, one of their challenges is actually original product insight. So this is very important to remember. There are oftentimes, there are operators who just, like, have amazing resumes. They've scaled companies and products extremely well, whether it's larger companies or mid-sized companies. But despite all that experience, they do not have the ability to come up with really original Product insights. This is where often things go wrong with a CPO hiring or VP product hiring. Sometimes your situation is such that you don't, do not yet need an operator. Eventually almost everybody starts needing an operator in their head of product role, but you don't yet need one, but you bring somebody on with the…

AI assessment note: “they are the operator, The craftsperson and the visionary.”

Q Absolutely. So this is always what frustrates me when they give me that output matrix and it's like, no, no, I want input match. I want number of tasks created in notion, number of new projects. Number of net new additions to each project in terms of sharing capabilities. What was health metrics, Shreyas?

A Yeah, health metrics are, you know, another way to define it is like their hygiene metrics, and the key, the way I like to describe a metric is like, what key question is this category of metric answering, right? So with health metrics, the key question that it's answering is, is this product available and performing in the manner that users would reasonably expect? Right? So users are not using your product in isolation. They use many different products, and human beings compare how your product does compared to other things that they are used to using. And so, you know, users implicitly tend to have a certain type of expectation for the, for the type of product you are. And those expectations vary. If I'm using an e-commerce product, my expectations are very different. And I'm using a social product versus if I'm using some internal, uh, you know, enterprise product as just an example. Um, so is this product available and performing in the manner that users would reasonably expect is the key question. And some examples of health metrics are latency, uh, initial load time, uh, data loss rate, errors that you see. So these are things that are really important for you to, uh, uh, keep track of because oftentimes, you know, we, we fixate on Sort of the, the growth funnel and all of those things. And if we lose sight of like basics that we're not getting right in the product, uh, …

AI assessment note: “with health metrics, the key question that it's answering is, is this product available”

Q If I'm hiring my first CPO head of product, whatever we want to name it, a senior product hire, is that profile the profile I want to go for, being the craftsperson?

A That is a reasonable default, especially if you're early stage, uh, startup, uh, uh, and say perhaps, uh, you know, pre-PMF or just about reaching PMF, then craftsperson is a fairly good default. Uh, but there again, it, uh, depends on, uh, your competence as a founder. Uh, and so particularly, again, when I go through these kinds of sessions with founders, Uh, one of the core things I asked them is like, why do you want to hire a product manager? Whether, whether it's at any level, an individual contributor or a leader, what is it that you want this person to do that you are doing right now? Uh, because presumably you want to kind of like delegate certain responsibilities. So what is it? Uh, and is it the right thing to delegate? Sometimes Harry, uh, the answer is, oh, I want to delegate a lot of the operational work. I want to delegate, uh, you know, the, the, the, uh, figuring out like how the sprints are going to work or figuring out, uh, you know, how customer support is going to get impacted by this new product feature that we are launching. Those types of things I want to delegate, uh, but I still feel like I need to own, uh, the core kind of, you know, customer insight, the core product insights, uh, and some of the definition of the product. In those cases, uh, you may want to bring a sort of like a mid-level or a junior operator type personal person, uh, and kind of d…

AI assessment note: “That is a reasonable default, especially if you're early stage”

Q Absolutely. So this is always what frustrates me when they give me that output matrix and it's like, no, no, I want input match. I want number of tasks created in notion, number of new projects. Number of net new additions to each project in terms of sharing capabilities. What was health metrics, Shreyas?

A Yeah, health metrics are, you know, another way to define it is like their hygiene metrics, and the key, the way I like to describe a metric is like, what key question is this category of metric answering, right? So with health metrics, the key question that it's answering is, is this product available and performing in the manner that users would reasonably expect? Right? So users are not using your product in isolation. They use many different products, and human beings compare how your product does compared to other things that they are used to using. And so, you know, users implicitly tend to have a certain type of expectation for the, for the type of product you are. And those expectations vary. If I'm using an e-commerce product, my expectations are very different. And I'm using a social product versus if I'm using some internal, uh, you know, enterprise product as just an example. Um, so is this product available and performing in the manner that users would reasonably expect is the key question. And some examples of health metrics are latency, uh, initial load time, uh, data loss rate, errors that you see. So these are things that are really important for you to, uh, uh, keep track of because oftentimes, you know, we, we fixate on Sort of the, the growth funnel and all of those things. And if we lose sight of like basics that we're not getting right in the product, uh, …

AI assessment note: “health metrics are, you know, another way to define it is like their hygiene metrics”

Q Can you help me out? What's the craftsperson in terms of like that profile then? Walk me through that one.

A Yes. Uh, so the craftsperson is excellent at defining products and strategy and mentoring other product people. Uh, and, and their superpower is product insight. So if the craftsperson is able to translate an extremely ambiguous goal or an extremely ambiguous vision into concrete product that has a very high chance of winning. Uh, and that skill of translating something high level and ambiguous to actual product, uh, actual user experience, the pixels, uh, the customer support experience, the interplay of the various things that need to happen to make a product and a business successful, they are able to translate that, uh, really well. Uh, and so again, their superpower is product insight, but they're not excellent at, uh, dealing with large orgs and its taxes. Right. Because any larger comes with all sorts of taxes that you have to deal with. They just don't enjoy that. Right. Um, uh, over my career, I, I started off as a visionary, which we can talk about later. Uh, but then I morphed myself into being a craftsperson. And so like, you know, as organizations started getting large, I was just like uncomfortable with managing that. Like I said, I found that boring. Uh, they love spending time with the team, uh, and, and users. Okay. So now it's interesting operators. They love spending time with their peers. So other kind of other functional heads and company execs and the boar…

AI assessment note: “the craftsperson is excellent at defining products and strategy and mentoring other product people”

Q Now we're going to kick off the show today with Shreyas Doshi. Shreyas is an all-round product OG. Most recently, Shreyas spent over five years at Stripe, where he was Stripe's first PM manager and helped grow the PM function from five to more than 50 people. What are the three different product leader personas that I should know about when entering this hiring process?

A One of the patterns is the three types of product leaders, and they are the operator, The craftsperson and the visionary. What is really important is there is no one right answer. First of all, it really depends. But the second thing is that it's important to recognize that it's not like a certain person can only be an operator. They can wear each of these hats. So you can think about them as hats, but still people have a primary hat and that's the hat that makes them most comfortable. That's the hat they would rather wear. But the operator is excellent at scaling teams. Driving cross-org alignment and unblocking execution. And the operator superpower is communication. On the other hand, one of their challenges is actually original product insight. So this is very important to remember. There are oftentimes, there are operators who just, like, have amazing resumes. They've scaled companies and products extremely well, whether it's larger companies or mid-sized companies. But despite all that experience, they do not have the ability to come up with really original Product insights. This is where often things go wrong with a CPO hiring or VP product hiring. Sometimes your situation is such that you don't, do not yet need an operator. Eventually almost everybody starts needing an operator in their head of product role, but you don't yet need one, but you bring somebody on with the…

AI assessment note: “they are the operator, The craftsperson and the visionary.”

Q What's the craftsperson in terms of like that profile then? Walk me through that one.

A So the craftsperson is excellent at defining products and strategy and mentoring other product people, and their superpower is product insight. The crafts This person is able to translate an extremely ambiguous goal or an extremely ambiguous vision into concrete product that has a very high chance of winning. That skill of translating something high level and ambiguous to actual product, the pixels, the customer support experience, the interplay of the various things that need to happen to make a product and a business successful, they are able to translate that really well. Again, their superpower is product insight, but they're not excellent at dealing with large orgs and its taxes. Right? Because any large org comes with all sorts of taxes that you have to deal with. They just don't enjoy that. They love spending time with the team and users. It's interesting. Operators, they love spending time with their peers, other functional heads and company execs and the board. Whereas a scraps people absolutely love spending time with users and customers and the team. And they get really excited about product deep dives and, oh, let's walk through this flow and how can we make it better? So that's the craps person. It's a very essential ingredient in any team. Whether it's a product leader or even individual product managers, you need these people so that you can translate something a…

AI assessment note: “So the craftsperson is excellent at defining products and strategy and mentoring other product people”

Q Should the founder not be the visionary, and the CPO not be the craftsperson?

A It's usually one of the founders that's the visionary. Perhaps, you know, there's another founder that's more like an operator, and maybe even a third that's more like a craftsperson. But typically, there's one founder who's the core visionary, who then takes ownership of the product, and sometimes wears the crafts And like I said, they can be fairly good at it to kind of translate that vision into certain kind of product manifestations, but at some point it becomes harder for them. Like, because once you start getting users, and once you start getting usage, what ends up happening is users are pulling you in many different directions. The visionary has a very clear view of the future, but being responsible people, they also now take into account user and customer feedback, and that can get confusing at times. Even if it's not confusing for them, they may find it hard to kind of like Bring the team along on like, okay, given all this kind of conflicting feedback and this plethora of ways in which we can take the product, here's what we're going to do as step one, step two, step three. Here's how we're going to actually build out the product. These are the flows that matter. These are the flows that don't matter. That's when, whether it's a CPO or a VP product or even a director of product or an individual product manager, craftsperson becomes a great asset for a visionary.

AI assessment note: “craftsperson becomes a great asset for a visionary”

Q What's the craftsperson in terms of like that profile then? Walk me through that one.

A So the craftsperson is excellent at defining products and strategy and mentoring other product people, and their superpower is product insight. The crafts This person is able to translate an extremely ambiguous goal or an extremely ambiguous vision into concrete product that has a very high chance of winning. That skill of translating something high level and ambiguous to actual product, the pixels, the customer support experience, the interplay of the various things that need to happen to make a product and a business successful, they are able to translate that really well. Again, their superpower is product insight, but they're not excellent at dealing with large orgs and its taxes. Right? Because any large org comes with all sorts of taxes that you have to deal with. They just don't enjoy that. They love spending time with the team and users. It's interesting. Operators, they love spending time with their peers, other functional heads and company execs and the board. Whereas a scraps people absolutely love spending time with users and customers and the team. And they get really excited about product deep dives and, oh, let's walk through this flow and how can we make it better? So that's the craps person. It's a very essential ingredient in any team. Whether it's a product leader or even individual product managers, you need these people so that you can translate something a…

AI assessment note: “the craftsperson is excellent at defining products and strategy and mentoring other product people”

Q Should the founder not be the visionary, and the CPO not be the craftsperson?

A It's usually one of the founders that's the visionary. Perhaps, you know, there's another founder that's more like an operator, and maybe even a third that's more like a craftsperson. But typically, there's one founder who's the core visionary, who then takes ownership of the product, and sometimes wears the crafts And like I said, they can be fairly good at it to kind of translate that vision into certain kind of product manifestations, but at some point it becomes harder for them. Like, because once you start getting users, and once you start getting usage, what ends up happening is users are pulling you in many different directions. The visionary has a very clear view of the future, but being responsible people, they also now take into account user and customer feedback, and that can get confusing at times. Even if it's not confusing for them, they may find it hard to kind of like Bring the team along on like, okay, given all this kind of conflicting feedback and this plethora of ways in which we can take the product, here's what we're going to do as step one, step two, step three. Here's how we're going to actually build out the product. These are the flows that matter. These are the flows that don't matter. That's when, whether it's a CPO or a VP product or even a director of product or an individual product manager, craftsperson becomes a great asset for a visionary.

AI assessment note: “craftsperson becomes a great asset for a visionary.”

Q Not at all. As I said, I've loved some of your Twitter threads, and they've been pretty informative to me. Uh, but let's start with a little bit on you. So you've been part of some of the most incredible orgs from Stripe, Twitter, Google. How did you make your way into the world of product first? And let's start there.

A Yeah. So I started my career, uh, back in, uh, the difficult, tough days, uh, of the Valley. Uh, this was 2001, uh, as an engineer and as an engineer here in California who needed a visa, uh, it was very difficult to get jobs back then. It was like drastically different environment than the one we found ourselves in over the last decade. Uh, and so I was lucky enough though to, uh, you know, join some Really great teams, uh, early on in my career as an engineer. And, uh, I moved to Silicon Valley in 2003, uh, to join, uh, a team that used to formally be loud cloud, uh, the Marc Andreessen Ben Horowitz company. Uh, and, uh, when I was there, I got introduced to product management, uh, mainly because, uh, uh, I found myself, uh, Getting sent to customer interviews and customer meetings and whatnot by my manager, and I didn't quite understand why, because I was just an engineer, very early career, but I think my managers back then saw in something in me that I did not, uh, yet, uh, so, uh, and, and I found myself getting very interested in, um, uh, learning about what customers are doing with the product, and, And particularly coming up with, you know, more creative solutions, uh, about, uh, you know, to solve the customer problems. And that's when I realized that, uh, you know, maybe I should try this product management thing. And so, uh, traditionally back then, most people woul…

AI assessment note: “I got introduced to product management, mainly because I found myself getting sent to customer interviews”

Q If I'm hiring my first CPO head of product, whatever we want to name it, a senior product hire, is that profile the profile I want to go for, being the craftsperson?

A That is a reasonable default, especially if you're early stage, uh, startup, uh, uh, and say perhaps, uh, you know, pre-PMF or just about reaching PMF, then craftsperson is a fairly good default. Uh, but there again, it, uh, depends on, uh, your competence as a founder. Uh, and so particularly, again, when I go through these kinds of sessions with founders, Uh, one of the core things I asked them is like, why do you want to hire a product manager? Whether, whether it's at any level, an individual contributor or a leader, what is it that you want this person to do that you are doing right now? Uh, because presumably you want to kind of like delegate certain responsibilities. So what is it? Uh, and is it the right thing to delegate? Sometimes Harry, uh, the answer is, oh, I want to delegate a lot of the operational work. I want to delegate, uh, you know, the, the, the, uh, figuring out like how the sprints are going to work or figuring out, uh, you know, how customer support is going to get impacted by this new product feature that we are launching. Those types of things I want to delegate, uh, but I still feel like I need to own, uh, the core kind of, you know, customer insight, the core product insights, uh, and some of the definition of the product. In those cases, uh, you may want to bring a sort of like a mid-level or a junior operator type personal person, uh, and kind of d…

AI assessment note: “That is a reasonable default, especially if you're early stage”

Q There's a lot that I would just want to unpack. I want to start with just some nomenclature. Product management is thrown about quite a lot as a term. When I say product management to you Shreyas, how do you define it?

A Yeah. I love that question because, um, um, there are many definitions of product management. And, uh, so my definition is product management is the art science and practice of making successful products and making products successful. Okay. So there are two aspects here and it's not just a play on words. Both are very important. Making successful products, uh, means that you often have to start with, uh, nothing and then make a successful product. And so that's kind of the early stage to reaching product market fit and beyond scaling. Uh, so, uh, Uh, so, so that's one aspect of it. The other aspect, which is making products successful, uh, is when say there is a product, uh, that already exists and maybe, you know, you weren't there at the beginning, uh, but it's, uh, at a stage where it's either poised for a lot of growth or, or it's not, uh, maybe it's even a turnaround story. Uh, and, uh, uh, product management again is the art, science and practice of, uh, Actually making that happen. Right. And, um, you know, when I, when I share this, Harry, a lot of times people will, uh, ask me, oh, but wait, what is success? Can you define success for me? Uh, and so my view of success is it's not complicated product success. Uh, you need to start with three things to begin evaluating product success, which is, uh, user adoption, customer satisfaction, and business impact. Right. Ultim…

AI assessment note: “product management is the art science and practice of making successful products”

Q Before we move into the visionary, you mentioned like the, the craftsperson struggles with the scaling product team. What are the first things to break Shreyas in a scaling product team? What are the first signs of things breaking?

A Yeah. So there are two, uh, two core things that, um, tend to break across most situations. Uh, one is, uh, within the team. Uh, and that is that, uh, as a team grows, a large part of your role as a leader becomes one, uh, you're basically a repeater. You just have to keep repeating the same thing. Uh, and, uh, you may repeat it in different ways. But you're effectively repeating the same message. Um, and so, so you can imagine, like, if you're managing a team of 20, uh, or 25 people, uh, you can, like, have a, sort of, you know, personal, uh, relationship, some amount of trust, some amount of, like, just mind meld with, uh, a group that's, say, 20 or 25. Um, but now your team is 50 people, uh, including engineers, designers, et cetera, or, like, The team is 80 people, right? Like, there's a team that's kind of building a product that has 80 people. It's impossible. It's impossible, uh, to, To create that mind meld. Right. So you need to change your approach, which is now, instead of relying on one to one or one to few, uh, interactions, you have to rely on one to many interactions. Right. Uh, but people don't remember as much as we, uh, think they remember. Right. So, so you have to keep repeating the vision, the goals, the strategy, et cetera, et cetera. And like that becomes a really important part of your role. Uh, and. You know, a craftsperson can do this, but as the team …

AI assessment note: “there are two, uh, two core things that, um, tend to break across most situations.”

Q Uh, so if you, if you look back at the Colossons in particular, can I ask what profile would you put them in, in terms of craftsperson, visionary, or operator? They're different, very different people.

A So yeah. So, uh, I mean, uh, they're both brilliant people. So It is a tough question. It's hard to kind of like, you know, put them in one box, and not that these archetypes are about boxes, but my assessment would be that Patrick is very much a visionary craftsperson type person, so, you know, every time I've interacted with him, and I learned a lot from, you know, about product from interacting with him. That's been the conversation is, is the visionary craftsperson, uh, mindset, uh, which is, what is the big idea here, right? Like, and how are we gonna differentiate? Uh, and, uh, how, how are we gonna get user adoption? Uh, and also, uh, you know, how do we get, like, the, the product details right? Uh, how do we surprise users? Uh, how do we make, uh, you know, how do we further the brand? Uh, you know, how is this brand aligned? Those types of things. Um, uh, were, uh, a constant kind of, you know, um, aspect of, uh, my interactions with Patrick. Uh, so he would be that visionary, uh, craftsperson archetype. Uh, John is interesting, uh, in that, like, uh, you know, he is He's one of the rare people who can do, I think, who kind of can do, and I've seen him do all three really well. Uh, in fact, there were many times when like John was managing certain teams on an interim basis, uh, at Stripe that like, you know, he clearly had never managed that type of team, whether it's…

AI assessment note: “Patrick is very much a visionary craftsperson type person”

Q There's a lot that I would just want to unpack. I want to start with just some nomenclature. Product management is thrown about quite a lot as a term. When I say product management to you Shreyas, how do you define it?

A Yeah. I love that question because, um, um, there are many definitions of product management. And, uh, so my definition is product management is the art science and practice of making successful products and making products successful. Okay. So there are two aspects here and it's not just a play on words. Both are very important. Making successful products, uh, means that you often have to start with, uh, nothing and then make a successful product. And so that's kind of the early stage to reaching product market fit and beyond scaling. Uh, so, uh, Uh, so, so that's one aspect of it. The other aspect, which is making products successful, uh, is when say there is a product, uh, that already exists and maybe, you know, you weren't there at the beginning, uh, but it's, uh, at a stage where it's either poised for a lot of growth or, or it's not, uh, maybe it's even a turnaround story. Uh, and, uh, uh, product management again is the art, science and practice of, uh, Actually making that happen. Right. And, um, you know, when I, when I share this, Harry, a lot of times people will, uh, ask me, oh, but wait, what is success? Can you define success for me? Uh, and so my view of success is it's not complicated product success. Uh, you need to start with three things to begin evaluating product success, which is, uh, user adoption, customer satisfaction, and business impact. Right. Ultim…

AI assessment note: “my definition is product management is the art science and practice of making successful products”

Q ah, we need to reduce the time to value. It needs to be quicker. It needs to be more, uh, kind of emotive and valuable faster. And sometimes I think yes, and sometimes I think you have to go slow to go fast, and you do need to connect your data sources, your different accounts, whatever the, Processes. How do you think about time to value when advising companies today?

A Yeah, I, I think, uh, it goes back to what is the core customer motivation and how strong is that core customer motivation? Okay, so, and I think this is something that, uh, very few teams do on a consistent basis. Um, and in fact, some of the companies I advise, like, I, I love to see after I've advised them for a while, where, like, they'll run some products by me, uh, and, uh, they will actually start with, uh, okay, so the core customer motivation or the core user motivation we think is X, and so in order to help the customer fulfill that motivation, here's the product. So they lead with the motivation rather than leading With, um, uh, the, the actual product experience. And so I love that. Now, just expanding on that a bit, when the core customer motivation is extremely high, you can afford to lengthen that time to value. Right? Uh, but when the core customer motivation is not that high, eh, and, and particularly, um, you have to remember, it's not just about what they hope to accomplish, it's also about what alternatives they have. So the alternatives factor into the degree of motivation, uh, around fulfilling, uh, that motivation with your product. So if I have a lot of alternatives, including the alternative of continuing with the tool, uh, or the app that I already use, uh, Uh, that I'm used to using, uh, which may be suboptimal. Um, then my core customer, my core moti…

AI assessment note: “when the core customer motivation is extremely high, you can afford to lengthen that time to value.”

Q Totally with you. A leaky bucket is never a good bucket to have. Um, tell us, you know, when you speak and you advise incredible companies, I spoke to many of the founders that you advise, um, when you speak to founders and work with founders today, what do you think is the most misunderstood metric category? And, and why do you think that is?

A Um, I think one category that is highly misunderstood is, well, it's not so much a category as it is a type, which is, you know, these days a lot of people talk about the North star metric, the NSM. What's your North star metric? And, um, I'll tell you, I get a lot of emails and, um, messages, overall DMs from folks who, who ask me, you know, Hey, I'm, I have this product, I have this startup and, um, Uh, you know, have some, some ideas on what my North Star metric should be. And, uh, and here it is. And so what do you think? And, and the reason I say this concept is misunderstood is that the North Star metric is not a panacea. Uh, and, you know, there are some, you know, some people who want to train you on North Star metrics may make it seem that way. Uh, but the north star metric is not a panacea. Uh, just defining, finding the perfect metric, uh, as your NSM, um, is actually not necessary, right? Like you, uh, when you're, when you're, especially when you're early stage, uh, what you're mainly looking for is, is my product resonating, right? And so what I often advise founders is, you know, It's classic. Like, don't try for perfection with your North Star metric. If you found something that generally works and is measurable, just pick it as your North Star metric. Uh, you don't have to try to tweak it and, you know, get into immeasurable categories, because oftentimes what …

AI assessment note: “I think one category that is highly misunderstood is... the North star metric”

Q Before we get into the different types of product leaders, speaking of that North Star metric, and you're advising me in my hypothetical startup journey, should I, the founder and CEO, be the one to determine the North Star metric and prioritize product metrics, or should that be the responsibility of my CPO head of product?

A Oh, bye. Um, The, the answer to that is, do you, do you feel competent enough to do it? That's the main question. Uh, and, uh, if you do as a founder, uh, then, um, by all means, uh, define it, uh, yourself. And, you know, of course, nobody really does it on their own. Like you're in a real work setting, you're getting feedback from folks anyway. Uh, but yeah, it would be your responsibility if you are fairly competent in this area. If you're not very competent in the area, uh, it is still ultimately your responsibility. Now you might delegate aspects of it, uh, to somebody else on your team, whether it's the chief product officer or somebody else. Uh, but ultimately because this is such a, you know, top level metric that you're gonna try to create targets against, That you're going to hopefully track on a regular basis. You have to be deeply involved. Uh, and so, you know, in either case, whether you're competent, uh, with it, uh, or you don't feel highly competent with it, uh, your involvement as a founder is extremely necessary, especially for an early stage product.

AI assessment note: “it is still ultimately your responsibility. Now you might delegate aspects of it”

Q Before we move into the visionary, you mentioned like the, the craftsperson struggles with the scaling product team. What are the first things to break Shreyas in a scaling product team? What are the first signs of things breaking?

A Yeah. So there are two, uh, two core things that, um, tend to break across most situations. Uh, one is, uh, within the team. Uh, and that is that, uh, as a team grows, a large part of your role as a leader becomes one, uh, you're basically a repeater. You just have to keep repeating the same thing. Uh, and, uh, you may repeat it in different ways. But you're effectively repeating the same message. Um, and so, so you can imagine, like, if you're managing a team of 20, uh, or 25 people, uh, you can, like, have a, sort of, you know, personal, uh, relationship, some amount of trust, some amount of, like, just mind meld with, uh, a group that's, say, 20 or 25. Um, but now your team is 50 people, uh, including engineers, designers, et cetera, or, like, The team is 80 people, right? Like, there's a team that's kind of building a product that has 80 people. It's impossible. It's impossible, uh, to, To create that mind meld. Right. So you need to change your approach, which is now, instead of relying on one to one or one to few, uh, interactions, you have to rely on one to many interactions. Right. Uh, but people don't remember as much as we, uh, think they remember. Right. So, so you have to keep repeating the vision, the goals, the strategy, et cetera, et cetera. And like that becomes a really important part of your role. Uh, and. You know, a craftsperson can do this, but as the team …

AI assessment note: “there are two, uh, two core things that, um, tend to break across most situations”

Q How do you determine when to listen to customer feedback versus when to progress with expected and planned roadmap and ignore it? Tough question.

A Oh boy. That's, uh, you know, the, the perennial question of product management. Uh, and look, my view on this is, um, There are Some teams that say that, um, they are, uh, highly customer driven, uh, and that's seen kind of as a virtue, which is like, oh, we are very customer driven. Um, but in reality, what ends up happening when you kind of label yourself that way, that you're customer driven is, uh, you end up just following what customers are telling you. Uh, and, and sometimes that can be the right answer, uh, especially. You know, once your product has already, uh, sort of, like, reached a certain scale, uh, you can be customer-driven, uh, and build, uh, you know, what they ask you to build, and because you already have some assets, some differentiation, uh, and so, so that works. Uh, but I have found that it's very important, uh, to, you know, ground what you do, uh, in terms of a core strategy. So the strategy becomes a, the piece, uh, the artifact, uh, the guideline, uh, for when you listen to customers and when you don't listen to customers. Um, so, and this is best explained, uh, perhaps, uh, via an example. Um, so, uh, you know, one of the products I managed at Stripe, uh, was, uh, Stripe terminal, which is an in-person kind of point of sale payment solution. Uh, and Uh, point of sale, uh, payments have been around for a really long time, and Stripe was creating it…

AI assessment note: “the strategy becomes a, the piece, uh, the artifact, uh, the guideline”

Q features, but fuck it. We're gonna make this feature that plays Iron Maiden when you buy anything, um, and it's going to be a wow consumer experience. So we're going to come in like above, but kind of except below in other areas. Do you see what I mean? Do you have a preference on your investing for where they insert themselves on that feature insertion point or product insertion?

A You know, uh, what I, what I've found, uh, uh, most interesting is, and I think this generally works for most products and, uh, new products and, uh, new startups. Is, uh, when you are entering a fairly crowded space where maybe there's a very powerful incumbent, um, the customer segment you target becomes really important because what you wanna do is you wanna target, uh, a kind of customer, a segment of customer, uh, that the incumbent is not doing a very good job of, uh, satisfying. Uh, and for that target customer, then you determine, uh, okay, what are their unfulfilled needs? Right? So yes, the incumbent has a bunch of like features and like they're doing well, et cetera, but you will find pockets of customers and segments, these segments that are highly dissatisfied. Uh, and, and so that's a good strategy, uh, for a new product where you find those pockets of, uh, the customer segments that are highly dissatisfied. Uh, with certain features because they're not important for the incumbent across its customer base, but they're very important for this specific segment. And that's where I like companies that are, that are very clear on targeting certain segments and then creating highly differentiated experiences for them. Uh, and when you do that, and this is essentially what we did at, uh, with Stripe terminal is when you target a specific segment, Uh, and meet their unful…

AI assessment note: “I like companies that are, that are very clear on targeting certain segments”

Q Totally with you. A leaky bucket is never a good bucket to have. Um, tell us, you know, when you speak and you advise incredible companies, I spoke to many of the founders that you advise, um, when you speak to founders and work with founders today, what do you think is the most misunderstood metric category? And, and why do you think that is?

A Um, I think one category that is highly misunderstood is, well, it's not so much a category as it is a type, which is, you know, these days a lot of people talk about the North star metric, the NSM. What's your North star metric? And, um, I'll tell you, I get a lot of emails and, um, messages, overall DMs from folks who, who ask me, you know, Hey, I'm, I have this product, I have this startup and, um, Uh, you know, have some, some ideas on what my North Star metric should be. And, uh, and here it is. And so what do you think? And, and the reason I say this concept is misunderstood is that the North Star metric is not a panacea. Uh, and, you know, there are some, you know, some people who want to train you on North Star metrics may make it seem that way. Uh, but the north star metric is not a panacea. Uh, just defining, finding the perfect metric, uh, as your NSM, um, is actually not necessary, right? Like you, uh, when you're, when you're, especially when you're early stage, uh, what you're mainly looking for is, is my product resonating, right? And so what I often advise founders is, you know, It's classic. Like, don't try for perfection with your North Star metric. If you found something that generally works and is measurable, just pick it as your North Star metric. Uh, you don't have to try to tweak it and, you know, get into immeasurable categories, because oftentimes what …

AI assessment note: “the reason I say this concept is misunderstood is that the North Star metric is not a panacea”

Q Can I ask, should the founder not be the visionary and the CPO not be the craftsperson?

A That is often the case. Again, it's by definition that, like, you need to have a Big vision for something, something that does not exist or is highly suboptimal in the world, uh, that you want to, uh, you want to fix. And so, so oftentimes, uh, founders end up being, uh, that kind of visionary archetype. Uh, and on founding teams, I've found that it's, it's usually, you know, one of the founders that's the visionary. Uh, and perhaps, you know, there's another founder that's more like an operator, uh, and maybe even a third that's more like a craftsperson. Uh, and I'm not saying it has to be that kind of composition, uh, but typically, you know, like this point I've kind of advised, uh, you know, a hundred plus companies just in the past two years on various topics. Uh, and, uh, I found that like, usually there's one founder who's the core visionary, who, who then takes ownership of the product, uh, early on naturally. Uh, and kind of like, you know, sometimes wears the craftsperson hat, and like I said, they can be fairly good at it to kind of translate that vision into certain kind of product, uh, manifestations. Uh, but at some point, uh, it becomes harder for them, like, because once you start getting users and once you start getting usage, what ends up happening is users are pulling you in many different directions, right? The visionary has a very clear view of the future, …

AI assessment note: “That is often the case.”

Q Can you help me out? What's the craftsperson in terms of like that profile then? Walk me through that one.

A Yes. Uh, so the craftsperson is excellent at defining products and strategy and mentoring other product people. Uh, and, and their superpower is product insight. So if the craftsperson is able to translate an extremely ambiguous goal or an extremely ambiguous vision into concrete product that has a very high chance of winning. Uh, and that skill of translating something high level and ambiguous to actual product, uh, actual user experience, the pixels, uh, the customer support experience, the interplay of the various things that need to happen to make a product and a business successful, they are able to translate that, uh, really well. Uh, and so again, their superpower is product insight, but they're not excellent at, uh, dealing with large orgs and its taxes. Right. Because any larger comes with all sorts of taxes that you have to deal with. They just don't enjoy that. Right. Um, uh, over my career, I, I started off as a visionary, which we can talk about later. Uh, but then I morphed myself into being a craftsperson. And so like, you know, as organizations started getting large, I was just like uncomfortable with managing that. Like I said, I found that boring. Uh, they love spending time with the team, uh, and, and users. Okay. So now it's interesting operators. They love spending time with their peers. So other kind of other functional heads and company execs and the boar…

AI assessment note: “the craftsperson is excellent at defining products and strategy and mentoring other product people”

Q Final one. What recent company product strategy have you been most impressed by?

A Hmm. You know, there's a company, uh, that's based out of India. It's called Lead School, and I've been advising them for more than a year, and, um, their, uh, their product strategy, um, is, uh, is just really exciting for me, uh, because, um, uh, what they're doing is they're, uh, bringing high quality, really high quality school K through K through two or 12 education, uh, Uh, to smaller towns and smaller cities. So not the big metropolitan areas in India, but the smaller towns and smaller cities in India, uh, where what they want to do is they want to create greater parity of the quality of education you can get, uh, being part, uh, you know, living in a smaller town as a child in India, in India, uh, and kind of, uh, and they're doing that via a combination of curriculum, uh, technology, uh, and, uh, uh, operations to support the curriculum and technology. And so it's been great to sort of like watch them kind of not just formulate that strategy, but also execute on it for the last year.

AI assessment note: “It's called Lead School, and... their product strategy, is just really exciting”

Q Before we get into the different types of product leaders, speaking of that North Star metric, and you're advising me in my hypothetical startup journey, should I, the founder and CEO, be the one to determine the North Star metric and prioritize product metrics, or should that be the responsibility of my CPO head of product?

A Oh, bye. Um, The, the answer to that is, do you, do you feel competent enough to do it? That's the main question. Uh, and, uh, if you do as a founder, uh, then, um, by all means, uh, define it, uh, yourself. And, you know, of course, nobody really does it on their own. Like you're in a real work setting, you're getting feedback from folks anyway. Uh, but yeah, it would be your responsibility if you are fairly competent in this area. If you're not very competent in the area, uh, it is still ultimately your responsibility. Now you might delegate aspects of it, uh, to somebody else on your team, whether it's the chief product officer or somebody else. Uh, but ultimately because this is such a, you know, top level metric that you're gonna try to create targets against, That you're going to hopefully track on a regular basis. You have to be deeply involved. Uh, and so, you know, in either case, whether you're competent, uh, with it, uh, or you don't feel highly competent with it, uh, your involvement as a founder is extremely necessary, especially for an early stage product.

AI assessment note: “it is still ultimately your responsibility. Now you might delegate aspects of it”

Q Um, and so what's the difference between a competent and an incompetent visionary given so much of their beliefs of future held? What's the difference?

A Yeah. So it is, uh, you, you cannot define it, uh, looking forward, uh, simply because ultimately, and there's not going to be a satisfying answer, but this is, True. Uh, as far as I've seen is you're just more right about where the world is headed. Uh, and, and there are people, uh, you know, clearly there are people who are more right than others. This is actually why I love Amazon's one of Amazon's leadership principles is, uh, leaders are right a lot. Uh, and, and it's my favorite of their, they have really great leadership principles. This one's my favorite. Because, uh, this is so misunderstood because, you know, there are many people who say, well, like, you know, there is no such thing as being visionary, as being right a lot. Like you just, you know, you, but you, you, you, you follow a process and, uh, make sure it's a good process. Make sure you set OKRs, make sure you, uh, execute, uh, well and success will be yours. No, that is not how anything works in the real world. Right? That is actually the operator speaking when that operator has taken a product from say, 20 to 60, or 60 to a hundred, and it's easy to say that, oh, success is all about just following processes, setting structures, setting goals, and diligently following them, and all of that is very important, but they forget that it's actually A high degree of creativity and instinct that gave you the luxur…

AI assessment note: “you're just more right about where the world is headed”

Q features, but fuck it. We're gonna make this feature that plays Iron Maiden when you buy anything, um, and it's going to be a wow consumer experience. So we're going to come in like above, but kind of except below in other areas. Do you see what I mean? Do you have a preference on your investing for where they insert themselves on that feature insertion point or product insertion?

A You know, uh, what I, what I've found, uh, uh, most interesting is, and I think this generally works for most products and, uh, new products and, uh, new startups. Is, uh, when you are entering a fairly crowded space where maybe there's a very powerful incumbent, um, the customer segment you target becomes really important because what you wanna do is you wanna target, uh, a kind of customer, a segment of customer, uh, that the incumbent is not doing a very good job of, uh, satisfying. Uh, and for that target customer, then you determine, uh, okay, what are their unfulfilled needs? Right? So yes, the incumbent has a bunch of like features and like they're doing well, et cetera, but you will find pockets of customers and segments, these segments that are highly dissatisfied. Uh, and, and so that's a good strategy, uh, for a new product where you find those pockets of, uh, the customer segments that are highly dissatisfied. Uh, with certain features because they're not important for the incumbent across its customer base, but they're very important for this specific segment. And that's where I like companies that are, that are very clear on targeting certain segments and then creating highly differentiated experiences for them. Uh, and when you do that, and this is essentially what we did at, uh, with Stripe terminal is when you target a specific segment, Uh, and meet their unful…

AI assessment note: “that's where I like companies that are very clear on targeting certain segments”

Q ah, we need to reduce the time to value. It needs to be quicker. It needs to be more, uh, kind of emotive and valuable faster. And sometimes I think yes, and sometimes I think you have to go slow to go fast, and you do need to connect your data sources, your different accounts, whatever the, Processes. How do you think about time to value when advising companies today?

A Yeah, I, I think, uh, it goes back to what is the core customer motivation and how strong is that core customer motivation? Okay, so, and I think this is something that, uh, very few teams do on a consistent basis. Um, and in fact, some of the companies I advise, like, I, I love to see after I've advised them for a while, where, like, they'll run some products by me, uh, and, uh, they will actually start with, uh, okay, so the core customer motivation or the core user motivation we think is X, and so in order to help the customer fulfill that motivation, here's the product. So they lead with the motivation rather than leading With, um, uh, the, the actual product experience. And so I love that. Now, just expanding on that a bit, when the core customer motivation is extremely high, you can afford to lengthen that time to value. Right? Uh, but when the core customer motivation is not that high, eh, and, and particularly, um, you have to remember, it's not just about what they hope to accomplish, it's also about what alternatives they have. So the alternatives factor into the degree of motivation, uh, around fulfilling, uh, that motivation with your product. So if I have a lot of alternatives, including the alternative of continuing with the tool, uh, or the app that I already use, uh, Uh, that I'm used to using, uh, which may be suboptimal. Um, then my core customer, my core moti…

AI assessment note: “when the core customer motivation is extremely high, you can afford to lengthen that time to value.”