The Exchanges

Q Do you have favorite questions that you do like to ask in product interviews?

A Um, I like the really open-ended questions that will solicit the stories, right? Like asking folks to describe something they've worked on in their last role or in any role that they're most proud of. Um, something that they, you know, what's something you took, like completely whiffed and failed at. You thought it was totally going to work, but it didn't. And like, what did you learn from that experience? Um, Um, I, I think it's important to hear about interpersonal challenges too, like what's, you know, what's an area of conflict you had, especially for larger, um, folks that are coming into a larger environment or larger team, like, Walk me through a really gnarly interpersonal conflict you had and like, how did you, how did you navigate it? Um, I think open-ended product ones. I love asking folks, um, what is your, like, what is one product that you use every day, but can't stand using? Like you wish you didn't have to use it every day, but you do. Um, and then also like, what's, what's a product or, or service that you adore and love, however big or small it might be like, why, you know, why do you love it? I think just getting people to talk about the things they enjoy and the things they don't enjoy and why, um, is, is helpful. You learn a lot about them, and it's less about judging the thing itself and more about just hearing, um, you know, hearing how they, how they th…

AI assessment note: “asking folks to describe something they've worked on in their last role”

Q Can I ask, you mentioned before when we were chatting that actually some of his lessons really impacted you and how you thought. When you think back to the discussions in the early days, are there any that stand out in terms of really impacting your product thinking?

A I think one of the things that's always stood out to me about Scott is he's, he's, he's a really powerful storyteller. Um, and you know, the, the, It's really important to turn tangible product ideas into dreams and be able to interpolate between the two. Like, here's an example of what I mean, right? Like mechanically speaking, Periscope is a live, Periscope was a live streaming platform, right? You start a live stream, anyone can watch it. And that's, that's great. It's like very descriptive to just to describe things that way. Right. But that's one way of describing things. It's another way to describe it, to say, you know, Periscope is the closest thing to teleportation. Periscope can help bring truth and empathy to, um, to communication, right? Truth because it's live. It's undisputed. You can't debate what's happening. It's like literally unfolding in front of you. There's no filters. There's no editing and empathy because if you can step in someone's shoes and hear their perspective and hear the intonation in their voice, that's really powerful. And like, that's a total reframing of what is otherwise a very mechanical feature. And I think Scott really influenced how we thought about that just because his brain works that way, right? Like one of the reasons he was attracted to this idea was this metaphor of teleportation. And so I think it's probably a very subtle thing t…

AI assessment note: “It's really important to turn tangible product ideas into dreams and be able to interpolate”

Q Do you have favorite questions that you do like to ask in product interviews?

A Um, I like the really open-ended questions that will solicit the stories, right? Like asking folks to describe something they've worked on in their last role or in any role that they're most proud of. Um, something that they, you know, what's something you took, like completely whiffed and failed at. You thought it was totally going to work, but it didn't. And like, what did you learn from that experience? Um, Um, I, I think it's important to hear about interpersonal challenges too, like what's, you know, what's an area of conflict you had, especially for larger, um, folks that are coming into a larger environment or larger team, like, Walk me through a really gnarly interpersonal conflict you had and like, how did you, how did you navigate it? Um, I think open-ended product ones. I love asking folks, um, what is your, like, what is one product that you use every day, but can't stand using? Like you wish you didn't have to use it every day, but you do. Um, and then also like, what's, what's a product or, or service that you adore and love, however big or small it might be like, why, you know, why do you love it? I think just getting people to talk about the things they enjoy and the things they don't enjoy and why, um, is, is helpful. You learn a lot about them, and it's less about judging the thing itself and more about just hearing, um, you know, hearing how they, how they th…

AI assessment note: “I like the really open-ended questions that will solicit the stories, right?”

Q decisively enough and moving with speed and, and executing well there. I, I do want to ask you, I find product reviews fascinating, uh, especially looking in from the outside. When you think about product reviews for you, how do you do product reviews? How often do you do them? Who's invited to them? Can you take me inside the world of how you structure them and, and organize them?

A Sure. Um, so I'll, I'll first give you the what, and then I'll give you the why. So in terms of like the what, um, we have product reviews on a week or I, I host product reviews on a weekly basis. Um, and the reason I say I is like cascading down our product organization. Some of our product leads have their own cadences around product reviews as well, but sort of at the leadership level, we have weekly product reviews, um, where we have three slots a week and, um, Each of those slots are 45 minutes, um, followed by a 15 minute debrief, which is just for like the leadership team to kind of get our thoughts together. Um, so we end up at most, um, we typically try and get an average of three of these reviews in a week. Um, and, um, uh, sort of mechanically, like team, team comes in, they share some, um, You know, the product review is either like a early hypothesis stage. Like we're sort of like forming the strategy. Here's kind of where we think this is going. And we want to get feedback and input on the strategy, the success, success criteria, and maybe some early thoughts on the experience, or it's more of an experiential product review. Like this product is actively being built or exists and it's pre-launched. Like, here's how we're thinking about the go to market. Um, here's what the actual product looks like. We'll do a live demo, or it's usually a post launch review. Um, w…

AI assessment note: “we have weekly product reviews, um, where we have three slots a week”

Q Final one for the quickfire, I promise. You said that about mistakes. Can you take me to a product decision that you made that was a mistake? What did you learn and how did it impact your thinking?

A I think one of the biggest mistakes we made with Periscope Is we, um, we changed the default, um, Sort of data retention to persist indefinitely. What I mean by that is like, for the first six months or so, maybe even longer of Periscope, you would start a live broadcast and when it ended, it would go away after an hour, right? We had like an hour long recording window so folks could watch it if they missed the live notification or whatever, but like Periscope broadcasts were essentially ephemeral in nature. And, um, we ended up kind of swinging the other way. And I was like the chief proponent of this, by the way. Um, Which I regret now in retrospect. Um, and the reason why we were like, oh my God, we need to make sure periscopes can last forever is because we saw so many incredible broadcasts, right? So many iconic moments being captured live, and they just felt like a, a grave injustice to society and the world for this, like, incredible content to go away, right? Like, why is this recording being deleted an hour from now? We had this, like, incredible celebration or this breaking news event that was captured live on, on video, on our platform, and it's, like, being deleted. What is that all about? Um, And, um, and so our solution to this, um, which we sprinted really hard on was we, um, we made recordings, um, we made it so that recordings could persist forever. And we made…

AI assessment note: “one of the biggest mistakes we made with Periscope Is we... changed the default”

Q What are the signs that it's not working well? If it's not working well, what do you do?

A Signs that it's not working well. Slow velocity. If the team is just treading water and spinning their wheels, and week after week, or product review after product review, it just seems like displacement is zero. That's never a good sign. Another sign is If the team doesn't convey strong conviction, like oftentimes teams make the mistake of assuming that they just need to share what they think leadership wants to hear. And that's actually far from the case. Like what I care about is like the team has a very strong point of view and it's very easy to kind of smell test whether they do or they don't and whether they are just kind of either they're genuinely lost or they're lost and they're just trying to, you know, share a plan that they think will Be blessed by leadership. And that's like, I think very corrosive to progress and ultimately the likelihood of like solving the customer problem. And so I think that's a sign that we try and look for. It's like, and the way you, you really tease that out is really pushing the team. Like, why do you feel this way? Like, why is this the hypothesis? Why is this the solution to the problem that you pushed on? And like, why not this hypothetically? And what we like to hear in those situations is the team standing up for their perspective and really articulating the With conviction, why approach X is the right approach, and I think some of m…

AI assessment note: “Signs that it's not working well. Slow velocity. If the team is just treading water”

Q What are the signs that it's not working well? If it's not working well, what do you do?

A Signs that it's not working well. Slow velocity. If the team is just treading water and spinning their wheels, and week after week, or product review after product review, it just seems like displacement is zero. That's never a good sign. Another sign is If the team doesn't convey strong conviction, like oftentimes teams make the mistake of assuming that they just need to share what they think leadership wants to hear. And that's actually far from the case. Like what I care about is like the team has a very strong point of view and it's very easy to kind of smell test whether they do or they don't and whether they are just kind of either they're genuinely lost or they're lost and they're just trying to, you know, share a plan that they think will Be blessed by leadership. And that's like, I think very corrosive to progress and ultimately the likelihood of like solving the customer problem. And so I think that's a sign that we try and look for. It's like, and the way you, you really tease that out is really pushing the team. Like, why do you feel this way? Like, why is this the hypothesis? Why is this the solution to the problem that you pushed on? And like, why not this hypothetically? And what we like to hear in those situations is the team standing up for their perspective and really articulating the With conviction, why approach X is the right approach, and I think some of m…

AI assessment note: “Signs that it's not working well. Slow velocity. If the team is just treading water”

Q Can I ask, you mentioned before when we were chatting that actually some of his lessons really impacted you and how you thought. When you think back to the discussions in the early days, are there any that stand out in terms of really impacting your product thinking?

A I think one of the things that's always stood out to me about Scott is he's, he's, he's a really powerful storyteller. Um, and you know, the, the, It's really important to turn tangible product ideas into dreams and be able to interpolate between the two. Like, here's an example of what I mean, right? Like mechanically speaking, Periscope is a live, Periscope was a live streaming platform, right? You start a live stream, anyone can watch it. And that's, that's great. It's like very descriptive to just to describe things that way. Right. But that's one way of describing things. It's another way to describe it, to say, you know, Periscope is the closest thing to teleportation. Periscope can help bring truth and empathy to, um, to communication, right? Truth because it's live. It's undisputed. You can't debate what's happening. It's like literally unfolding in front of you. There's no filters. There's no editing and empathy because if you can step in someone's shoes and hear their perspective and hear the intonation in their voice, that's really powerful. And like, that's a total reframing of what is otherwise a very mechanical feature. And I think Scott really influenced how we thought about that just because his brain works that way, right? Like one of the reasons he was attracted to this idea was this metaphor of teleportation. And so I think it's probably a very subtle thing t…

AI assessment note: “this metaphor of teleportation... really influenced how we thought about the product.”

Q moment for sure. We mentioned the art of storytelling. In terms of art and applying it to product, you know, we see kind of this very data-centric, metric-driven approach to product today as well. I'm super interested. How do you think about product? Is it more art or science? What would you say? 80, 20? 20, 80? How do you think about product as more art or more science today?

A It's hard to put numbers to these things. Um, I certainly think that, um, it's a combination of both. There's a lot of science involved, right? Like, um, You need to be really good at understanding customer needs. You need to be good at understanding data. Um, you need to be good at, um, it also depends on what we're talking about product generally, or whether we're talking about product management, but Certainly as far as product management is concerned, like being able to, um, communicate clearly around, um, roadmaps and strategies and tactics and sequencing when you're trying to coordinate a bunch amongst a large group of people that have to collaborate together to make something happen. Like there's a lot of science involved there. Um, I think that art is frankly the most underappreciated part of it, like the art of storytelling and, um, the sort of passion and emotion That should go into building products. I have never, I cannot think of a single product that I love that, that, um, wasn't built with a high degree of emotion involved. Like if you think of like the most iconic products and the teams that built them, I would suspect that they were like deeply emotional, um, in, in not a pejorative way and like in, in a, um, really valuable way about what they were doing, why they were doing it, why it was important for the world. And so I think to me, that's like, Where a lot…

AI assessment note: “It's hard to put numbers to these things. Um, I certainly think that, um, it's a combination of both.”

Q Kayvon, you're gonna help me here. I'm a first-time founder. I am building my team, and you are my brilliant advisor. Uh, I, I think I need to hire my first PM, but I'm not sure that now's the right time. When do you think is the right time to hire your first PM? What are signals that would suggest now is the right time?

A Well, I think one signal is if, um, if the team is constantly reacting to, um, Um, what the product needs. Like if you're constantly underwater and the things you end up prioritizing are the things that you learn really late are broken. Um, and you're, you're not feeling like you can be proactive around identifying where the product is going. Then that means that the team is collectively, whatever the current recipe of folks on the team are, doesn't have the right balance of, um, being able to think proactively versus just reacting to things that are happening. And so that might be a one good signal of like, well, the division of labor and the time allocation right now just isn't right. So you either need to hire a PM to help think about that stuff or hire a PM to help take on a lot of the work that's happening so that the, the right subset of people at the The founders or the head of product or design or engineering or whatever can start to think more about that stuff proactively because that can be a very dangerous slippery slope if the team collectively ends up just being reactive rather than thinking about where the, where the product should be going. Um, so that's one. Two, I think another signal is if the team is getting large enough that there's a lot of, um, Um, sort of communication lossiness around, all right, like we're, we're doing a lot of stuff now, but not everyo…

AI assessment note: “Well, I think one signal is if, um, if the team is constantly reacting”

Q decisively enough and moving with speed and, and executing well there. I, I do want to ask you, I find product reviews fascinating, uh, especially looking in from the outside. When you think about product reviews for you, how do you do product reviews? How often do you do them? Who's invited to them? Can you take me inside the world of how you structure them and, and organize them?

A Sure. Um, so I'll, I'll first give you the what, and then I'll give you the why. So in terms of like the what, um, we have product reviews on a week or I, I host product reviews on a weekly basis. Um, and the reason I say I is like cascading down our product organization. Some of our product leads have their own cadences around product reviews as well, but sort of at the leadership level, we have weekly product reviews, um, where we have three slots a week and, um, Each of those slots are 45 minutes, um, followed by a 15 minute debrief, which is just for like the leadership team to kind of get our thoughts together. Um, so we end up at most, um, we typically try and get an average of three of these reviews in a week. Um, and, um, uh, sort of mechanically, like team, team comes in, they share some, um, You know, the product review is either like a early hypothesis stage. Like we're sort of like forming the strategy. Here's kind of where we think this is going. And we want to get feedback and input on the strategy, the success, success criteria, and maybe some early thoughts on the experience, or it's more of an experiential product review. Like this product is actively being built or exists and it's pre-launched. Like, here's how we're thinking about the go to market. Um, here's what the actual product looks like. We'll do a live demo, or it's usually a post launch review. Um, w…

AI assessment note: “we have weekly product reviews, um, where we have three slots a week”

Q How do you do that? Is it asking questions, not telling? Is it tone? How's your communication style changed to make that transition?

A I think there's a lot of basic stuff, like asking questions rather than telling and tone and all of that. But above and beyond the basic stuff, what I've learned is, and it's feels very unnatural, but, but I think it's important to do nonetheless, um, is just repeating to the point of like utter repetition and seemingly like, I feel like I'm a broken record, but like, just to be clear, this is me not conveying a decision. This is me just asking the question or, um, Hey, like, please don't take this as a directive, but I'm curious if, and like sort of that, that prefix of making clear that, Conviction that is about to come out of my mouth is purely A conversation starter. Um, like that, I end up almost trying to almost preface every statement I make with that, um, for fear of it not being misconstrued. Um, the other thing that I've learned is important is just, um, regularly communicating with our teams and other forums, like what is the purpose of product review and how, how should you interpret feedback? So like literally just recently, like three weeks ago, I sent an update to the whole team. Saying like, Hey, we've been doing product reviews this way for some time. Now here's some like observations and here's some changes that we're making. And on the observation side, one of the things we made very clear, like it, I think it was, we said something along the lines of. Assume…

AI assessment note: “preface every statement I make with that, um, for fear of it not being misconstrued.”

Q Final one for the quickfire, I promise. You said that about mistakes. Can you take me to a product decision that you made that was a mistake? What did you learn and how did it impact your thinking?

A I think one of the biggest mistakes we made with Periscope Is we, um, we changed the default, um, Sort of data retention to persist indefinitely. What I mean by that is like, for the first six months or so, maybe even longer of Periscope, you would start a live broadcast and when it ended, it would go away after an hour, right? We had like an hour long recording window so folks could watch it if they missed the live notification or whatever, but like Periscope broadcasts were essentially ephemeral in nature. And, um, we ended up kind of swinging the other way. And I was like the chief proponent of this, by the way. Um, Which I regret now in retrospect. Um, and the reason why we were like, oh my God, we need to make sure periscopes can last forever is because we saw so many incredible broadcasts, right? So many iconic moments being captured live, and they just felt like a, a grave injustice to society and the world for this, like, incredible content to go away, right? Like, why is this recording being deleted an hour from now? We had this, like, incredible celebration or this breaking news event that was captured live on, on video, on our platform, and it's, like, being deleted. What is that all about? Um, And, um, and so our solution to this, um, which we sprinted really hard on was we, um, we made recordings, um, we made it so that recordings could persist forever. And we made…

AI assessment note: “one of the biggest mistakes we made with Periscope Is we, um, we changed the default”

Q moment for sure. We mentioned the art of storytelling. In terms of art and applying it to product, you know, we see kind of this very data-centric, metric-driven approach to product today as well. I'm super interested. How do you think about product? Is it more art or science? What would you say? 80, 20? 20, 80? How do you think about product as more art or more science today?

A It's hard to put numbers to these things. Um, I certainly think that, um, it's a combination of both. There's a lot of science involved, right? Like, um, You need to be really good at understanding customer needs. You need to be good at understanding data. Um, you need to be good at, um, it also depends on what we're talking about product generally, or whether we're talking about product management, but Certainly as far as product management is concerned, like being able to, um, communicate clearly around, um, roadmaps and strategies and tactics and sequencing when you're trying to coordinate a bunch amongst a large group of people that have to collaborate together to make something happen. Like there's a lot of science involved there. Um, I think that art is frankly the most underappreciated part of it, like the art of storytelling and, um, the sort of passion and emotion That should go into building products. I have never, I cannot think of a single product that I love that, that, um, wasn't built with a high degree of emotion involved. Like if you think of like the most iconic products and the teams that built them, I would suspect that they were like deeply emotional, um, in, in not a pejorative way and like in, in a, um, really valuable way about what they were doing, why they were doing it, why it was important for the world. And so I think to me, that's like, Where a lot…

AI assessment note: “I certainly think that, um, it's a combination of both.”

Q You mentioned kind of the difference product and product management. I find product management kind of term thrown around today with actually little thought about real definition. I think it means different things to different people. How do you think about the definition of what product management really means to you?

A Well, maybe it's more helpful starting first with like, what, what is the role of a product manager? And then we can expand out to like product management more generally. I think, I think in its simplest form, like the role, um, the distinct role of a product manager. And I say distinct because on small teams, like everyone needs to shoulder all the responsibilities, or at least I think that can be very powerful for small teams. But I think the distinct role of a product manager is they are the person who should be defining Um, the vision and mission and purpose and strategy of a, of a product and why it matters for the customer and, and why and how it can be impactful for the business. Like the, the why of the product, um, and the, how we will measure its success. I think typically we expect product managers to be able to like be chiefly responsible for, um, coming up with that definition and making sure everyone on the team understands it. Right. Cause if we're swimming in the wrong direction, or if we're all optimizing for different outcomes, that's not helping anyone. It's not helping the customer. It's not helping the team. And I think a product manager can, can, can be like the quarterback that, um, is responsible for making sure there's at all times clarity around like, what are we building? Why, how do we measure its success? Um, so that's like one piece of it. And the …

AI assessment note: “defining Um, the vision and mission and purpose and strategy of a, of a product”

Q Kayvon, you're gonna help me here. I'm a first-time founder. I am building my team, and you are my brilliant advisor. Uh, I, I think I need to hire my first PM, but I'm not sure that now's the right time. When do you think is the right time to hire your first PM? What are signals that would suggest now is the right time?

A Well, I think one signal is if, um, if the team is constantly reacting to, um, Um, what the product needs. Like if you're constantly underwater and the things you end up prioritizing are the things that you learn really late are broken. Um, and you're, you're not feeling like you can be proactive around identifying where the product is going. Then that means that the team is collectively, whatever the current recipe of folks on the team are, doesn't have the right balance of, um, being able to think proactively versus just reacting to things that are happening. And so that might be a one good signal of like, well, the division of labor and the time allocation right now just isn't right. So you either need to hire a PM to help think about that stuff or hire a PM to help take on a lot of the work that's happening so that the, the right subset of people at the The founders or the head of product or design or engineering or whatever can start to think more about that stuff proactively because that can be a very dangerous slippery slope if the team collectively ends up just being reactive rather than thinking about where the, where the product should be going. Um, so that's one. Two, I think another signal is if the team is getting large enough that there's a lot of, um, Um, sort of communication lossiness around, all right, like we're, we're doing a lot of stuff now, but not everyo…

AI assessment note: “one signal is if, um, if the team is constantly reacting”

Q What questions or signs would suggest to you that someone is comfortable? Because they'll say, yep, I'm super comfortable, very flexible, always happy to move with times, but actually they're not. What are signs or questions that would tease out or suggest someone does actually have that?

A I think hearing about their experience, right? Like I think hearing stories of what folks have done in their prior roles and what the, what, what challenges they overcame or what, you know, even just like asking very high level prompts, like what's the gnarliest, most frustrating thing you've had to deal with in your last role, either some customer problem you had to solve or some team dynamic that was really, um, really stressful and how did you navigate it? Um, and I think just hearing people talk about, um, Like every, people will direct you in very helpful ways if you give them prompts about their own experience. Um, and that in itself can be very illuminating, right? Hearing them share their recollection of something that they perceived to be challenging for them and how they overcame it, how they navigated it. And I think in those stories, you can learn a lot around A, what they've experienced and B, how they, how they think about these, these, these challenges. So it's always imperfect. Like you won't really know until you work with someone, but I think, um, soliciting these anecdotes of their experience, um, can be far more helpful than that sort of cookie cutter interview questions that are easy for folks to have good prepared answers to.

AI assessment note: “asking very high level prompts, like what's the gnarliest, most frustrating thing”

Q Where do you think many founders go wrong or make mistakes when it comes to hiring their first product people? Could be PMs, could be more general product team.

A I think the most classical mistake is actually not in Making hiring mistakes, but in making, in making the mistake of waiting too long to realize you made a mistake, right? Like that's in my experience, the way harder thing. Um, like you can, you can get really good and you should get really good screening, um, for the right candidates for the right roles at your company, but there's always a certain element of, um, unpredictability or the certain chance that someone ends up not being the right role for the right job. And I think all too often, I've made this mistake plenty of times myself. You just realize that too late and it takes too, too long to, um, It takes too long to transition that person out. Um, and that is really, really expensive. It's expensive for the, um, the hiring manager. It's not, you know, doing any favors to the, to the candidate who will likely have a better chance of succeeding somewhere else. And it's not great for the team, right? The team ultimately, um, teams who work on really hard problems can either be incredibly inspired by the strength and quality and camaraderie of their teammates, or can be incredibly demoralized By a teammate who's just not the right person for the right role. Uh, and that I think is the far more common mistake of just taking too long to figure that out.

AI assessment note: “making the mistake of waiting too long to realize you made a mistake”

Q What are the signs that it's not working well? If it's not working well, what do you do?

A Um, signs that are, that it's not working well, um, Uh, slow velocity, right? Like if, if the team is just, um, treading water and spinning their wheels and week after week or product review after product review, it just seems like displacement is zero. That's never a good sign. Um, another sign is, um, if the team doesn't convey strong conviction, like oftentimes teams make the mistake of assuming that, um, Um, they just need to share what they think leadership wants to hear. And that's actually far from the case. Like what we actually care about, what I care about is like the team has a very strong point of view. Right. And, and it's very easy to kind of smell test whether they do or they don't and whether they are just kind of either they're genuinely lost or they're lost and they're just trying to, you know, share a plan that they think will, you know, be blessed by leadership. And that that's like, I think very corrosive to, um, progress and ultimately the, um, likelihood of like solving the customer problem. And so I think Um, that's a sign that we, we try and look for. It's like, and the way you, you really tease that out is really pushing the team. Like, why, why do you, why do you feel this way? Like, why is this the hypothesis? Why, why is this the solution to the problem that you pushed on? And like, why not this hypothetically? Um, and what we like to hear in those …

AI assessment note: “signs that are, that it's not working well, um, Uh, slow velocity”

Q How do you do that? Is it asking questions, not telling? Is it tone? How's your communication style changed to make that transition?

A I think there's a lot of basic stuff, like asking questions rather than telling and tone and all of that. But above and beyond the basic stuff, what I've learned is, and it's feels very unnatural, but, but I think it's important to do nonetheless, um, is just repeating to the point of like utter repetition and seemingly like, I feel like I'm a broken record, but like, just to be clear, this is me not conveying a decision. This is me just asking the question or, um, Hey, like, please don't take this as a directive, but I'm curious if, and like sort of that, that prefix of making clear that, Conviction that is about to come out of my mouth is purely A conversation starter. Um, like that, I end up almost trying to almost preface every statement I make with that, um, for fear of it not being misconstrued. Um, the other thing that I've learned is important is just, um, regularly communicating with our teams and other forums, like what is the purpose of product review and how, how should you interpret feedback? So like literally just recently, like three weeks ago, I sent an update to the whole team. Saying like, Hey, we've been doing product reviews this way for some time. Now here's some like observations and here's some changes that we're making. And on the observation side, one of the things we made very clear, like it, I think it was, we said something along the lines of. Assume…

AI assessment note: “above and beyond the basic stuff, what I've learned is... utter repetition”

Q But you mentioned the sheer inbound that you get, and you also mentioned kind of listening to people earlier in the Periscope journey versus not listening. Final question before we do a quick fire, but just simply, how do you think about when to listen to customer feedback versus when to go on product gut intuition?

A I think, well, listening to customers is always important. I think that the, um, that The mistake sometimes people make is listening to their solutions rather than listening to their problems. I think there's always truth and, um, clarity in the problems that people are experiencing. But, um, you know, sometimes the, you know, sometimes that can blend into like, and you should just do this to solve my problem. And I think that can sometimes be a slippery slope where, um, You know, it's, it behooves a team to like really absorb and think about the underlying problem and be expansive and creative about the possible solutions, even if those solutions, um, are not, you know, even on the minds of, of the customer or the, you know, might be different from what the customer might have suggested. Um, and, um, So this is like the, the Henry Ford quote, right? Like faster horse versus a car type thing. Um, there's an underlying problem there that is important, but the solution may not be what might be on the, the, the minds of the customer. Um, I think in terms of the intuition question, I believe that a healthy dose of intuition is always valuable, right? And I think you have to balance intuition with data and insights. Um, but intuition can be the difference between, um, You know, uh, just choice paralysis and needing and requiring an exhaustive amount of data and validation before you…

AI assessment note: “mistake sometimes people make is listening to their solutions rather than listening to their problems”

Q What questions or signs would suggest to you that someone is comfortable? Because they'll say, yep, I'm super comfortable, very flexible, always happy to move with times, but actually they're not. What are signs or questions that would tease out or suggest someone does actually have that?

A I think hearing about their experience, right? Like I think hearing stories of what folks have done in their prior roles and what the, what, what challenges they overcame or what, you know, even just like asking very high level prompts, like what's the gnarliest, most frustrating thing you've had to deal with in your last role, either some customer problem you had to solve or some team dynamic that was really, um, really stressful and how did you navigate it? Um, and I think just hearing people talk about, um, Like every, people will direct you in very helpful ways if you give them prompts about their own experience. Um, and that in itself can be very illuminating, right? Hearing them share their recollection of something that they perceived to be challenging for them and how they overcame it, how they navigated it. And I think in those stories, you can learn a lot around A, what they've experienced and B, how they, how they think about these, these, these challenges. So it's always imperfect. Like you won't really know until you work with someone, but I think, um, soliciting these anecdotes of their experience, um, can be far more helpful than that sort of cookie cutter interview questions that are easy for folks to have good prepared answers to.

AI assessment note: “asking very high level prompts, like what's the gnarliest, most frustrating thing”

Q What one piece of advice would you give to a product leader today starting a new role?

A Don't work on a product that you are not insanely, irrationally passionate about. Like if you don't go to bed and wake up in the morning dreaming of and thinking about that product, um, life's too short. There's other products that you should work on. Um, cause I think that that's what it takes to build something great. The difference between something great and something meh and good is like, you have to have An irrational amount of passion and conviction about that product needing to exist in the world and being the best that it can be. And by the way, this is not just true for product managers. It's true for the designers and engineers and, you know, the best things are built from those who really were passionate about them.

AI assessment note: “Don't work on a product that you are not insanely, irrationally passionate about.”

Q What's been your biggest takeaway now from also angel investing?

A Angel investing as someone who's very, who, who has strong opinions and convictions around Building product is, is, is always tricky business. Cause you have to know that you're, um, you're so far from the details and you're, you shouldn't necessarily volunteer your perspective unless it's, um, asked for. Like I can't, Treat one of my angel investments like a product review, you know, like I have even less context for what those teams are going through as, um, a team that's coming to a product review. And I think with the right level of context and, um, and, uh, And, and prompting. I, I would hope that an angel investor could be very, very valuable, as Scott was to us, um, in the early days of Periscope, but you have to be very, I think, conscious of, um, when that's useful, and when that's solicited, um, and when it's, when it's not, when like, when, when, when the startup and the, and your, Portfolio company when what they need from you is actually something else. Right. Um, and so I think that's usually the way that manifests for me is like, um, just being, trying to be incredibly supportive when called upon and when asked, um, and not trying to like step on toes, you know.

AI assessment note: “you shouldn't necessarily volunteer your perspective unless it's, um, asked for.”

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

A Um, uh, I mean, macro, I meant what I said about Adobe. I think the transfer fundamental transformation in Navigated is really impressive. The other one on a totally different, um, totally different token is I am awestruck and inspired by what SpaceX is doing. Very different type of product than a social media technology company. Um, but I think that there's so much that's fascinating about SpaceX. One, I think that is one of the most ambitious products and teams on the planet, literally seem to be not just this planet. Um, and just that level of ambition, right? Like making life multi-planetary, um, is insane. Like most people hear about it and they're just like, what? Um, and it's, it's truly ambitious, um, in a way that I think is Incredibly inspiring to the speed at which that the team is working, right? Just like, you know, with something so sophisticated and challenging, both technologically and financially and operationally, the speed at which they're literally building rockets is, um, it's really puts a lot of things in perspective, right? When like some feature that we are working on is like going really slowly, it's like kind of helpful to ask the question, like, SpaceX kind of built a rocket in less time than we're saying this will take. Um, so I think that's inspiring. And then third, you know, they're, they're building in public in a way that is incredible. Right. …

AI assessment note: “I am awestruck and inspired by what SpaceX is doing.”

Q You mentioned kind of the difference product and product management. I find product management kind of term thrown around today with actually little thought about real definition. I think it means different things to different people. How do you think about the definition of what product management really means to you?

A Well, maybe it's more helpful starting first with like, what, what is the role of a product manager? And then we can expand out to like product management more generally. I think, I think in its simplest form, like the role, um, the distinct role of a product manager. And I say distinct because on small teams, like everyone needs to shoulder all the responsibilities, or at least I think that can be very powerful for small teams. But I think the distinct role of a product manager is they are the person who should be defining Um, the vision and mission and purpose and strategy of a, of a product and why it matters for the customer and, and why and how it can be impactful for the business. Like the, the why of the product, um, and the, how we will measure its success. I think typically we expect product managers to be able to like be chiefly responsible for, um, coming up with that definition and making sure everyone on the team understands it. Right. Cause if we're swimming in the wrong direction, or if we're all optimizing for different outcomes, that's not helping anyone. It's not helping the customer. It's not helping the team. And I think a product manager can, can, can be like the quarterback that, um, is responsible for making sure there's at all times clarity around like, what are we building? Why, how do we measure its success? Um, so that's like one piece of it. And the …

AI assessment note: “the distinct role of a product manager is they are the person who should be defining”

Q But you mentioned the sheer inbound that you get, and you also mentioned kind of listening to people earlier in the Periscope journey versus not listening. Final question before we do a quick fire, but just simply, how do you think about when to listen to customer feedback versus when to go on product gut intuition?

A I think, well, listening to customers is always important. I think that the, um, that The mistake sometimes people make is listening to their solutions rather than listening to their problems. I think there's always truth and, um, clarity in the problems that people are experiencing. But, um, you know, sometimes the, you know, sometimes that can blend into like, and you should just do this to solve my problem. And I think that can sometimes be a slippery slope where, um, You know, it's, it behooves a team to like really absorb and think about the underlying problem and be expansive and creative about the possible solutions, even if those solutions, um, are not, you know, even on the minds of, of the customer or the, you know, might be different from what the customer might have suggested. Um, and, um, So this is like the, the Henry Ford quote, right? Like faster horse versus a car type thing. Um, there's an underlying problem there that is important, but the solution may not be what might be on the, the, the minds of the customer. Um, I think in terms of the intuition question, I believe that a healthy dose of intuition is always valuable, right? And I think you have to balance intuition with data and insights. Um, but intuition can be the difference between, um, You know, uh, just choice paralysis and needing and requiring an exhaustive amount of data and validation before you…

AI assessment note: “balance intuition with data and insights”

Q What's been your biggest takeaway now from also angel investing?

A Angel investing as someone who's very, who, who has strong opinions and convictions around Building product is, is, is always tricky business. Cause you have to know that you're, um, you're so far from the details and you're, you shouldn't necessarily volunteer your perspective unless it's, um, asked for. Like I can't, Treat one of my angel investments like a product review, you know, like I have even less context for what those teams are going through as, um, a team that's coming to a product review. And I think with the right level of context and, um, and, uh, And, and prompting. I, I would hope that an angel investor could be very, very valuable, as Scott was to us, um, in the early days of Periscope, but you have to be very, I think, conscious of, um, when that's useful, and when that's solicited, um, and when it's, when it's not, when like, when, when, when the startup and the, and your, Portfolio company when what they need from you is actually something else. Right. Um, and so I think that's usually the way that manifests for me is like, um, just being, trying to be incredibly supportive when called upon and when asked, um, and not trying to like step on toes, you know.

AI assessment note: “trying to be incredibly supportive when called upon and when asked”

Q What are the signs that it's not working well? If it's not working well, what do you do?

A Um, signs that are, that it's not working well, um, Uh, slow velocity, right? Like if, if the team is just, um, treading water and spinning their wheels and week after week or product review after product review, it just seems like displacement is zero. That's never a good sign. Um, another sign is, um, if the team doesn't convey strong conviction, like oftentimes teams make the mistake of assuming that, um, Um, they just need to share what they think leadership wants to hear. And that's actually far from the case. Like what we actually care about, what I care about is like the team has a very strong point of view. Right. And, and it's very easy to kind of smell test whether they do or they don't and whether they are just kind of either they're genuinely lost or they're lost and they're just trying to, you know, share a plan that they think will, you know, be blessed by leadership. And that that's like, I think very corrosive to, um, progress and ultimately the, um, likelihood of like solving the customer problem. And so I think Um, that's a sign that we, we try and look for. It's like, and the way you, you really tease that out is really pushing the team. Like, why, why do you, why do you feel this way? Like, why is this the hypothesis? Why, why is this the solution to the problem that you pushed on? And like, why not this hypothetically? Um, and what we like to hear in those …

AI assessment note: “signs that are, that it's not working well, um, Uh, slow velocity”

Q Before we dive into the show, I do have to ask you, I was a big fan of Periscope. When you look back at that time and that journey, what were some of the biggest takeaways from that experience, particularly from a product perspective that impacted your view on product today and, and how you kind of approach that with Twitter?

A Um, some important takeaways. Um, well, I'll, I'll give you one that's, um, not so much about the product, but about the process of starting a company and building something like here is the interesting thing about the idea behind Periscope. Mechanically speaking, You know, back in 2014, when we were building periscope, the idea of like a live streaming app was not new or, or like rocket science, right? Like there was a graveyard of consumer live streaming apps that have been, that have been tried for five years before. And then you had apps like, you know, YouTube and live stream. And I think Vimeo at the time might've had live streaming as well, or maybe this is before they acquired, but anyway, like there's a bunch of these tools out there. So, you know, everyone's first thought when they When they hear about a new live streaming app is like, okay, another, another fucking one of these, like what, why do we need this? And, and by the way, like no one uses this on mobile devices. Cause you had apps like Justin TV that, you know, didn't quite get go anywhere in terms of the consumer live streaming angle, right? They pivoted into more specialized use cases like, like Twitch. Um, and so, um, one of the most like painful takeaways of that era for me was just how many people thought this was a terrible idea. And how frustrating that was for a group of, you know, people, um, on our…

AI assessment note: “not so much about the product, but about the process of starting a company”