The Exchanges

Q How do you do that? Is that with mirror boards? Is that with, what does that look like?

A Yeah Uh,, I mean I,, I'll hate to confess, but obviously, you know, we use Slack for a lot of these things, but what I would say is the most typical flow would be someone will write a doc that kind of frames what the discussion is, the key context decisions, you know, whether they use Google Docs or uh, Notion or Canvas, which Slack just released, but I think the big thing that's actually happened is Designers and engineers now will record clips with screen sharing in Slack, and it'll be a quick three or five minute clip. And if it's a designer, they'll be like walking through a prototype and stigma, or if it's an engineer, they'll be doing the same, but with a real life code. And they'll actually show you the thing instead of say, Hey, let me, you know, the classic meeting. Otherwise there's a 20 minute presentation. Everyone's sitting there being like, okay, I wish I could just go through this quickly on my own. Now it's Everyone pre-watch this thing and then come in with your perspective, your ideas, your feedback, so you can get straight into the discussion instead of having half the meeting via presentation. Um, so I think that's made a big difference, honestly.

AI assessment note: “the most typical flow would be someone will write a doc that kind of frames”

Q Love that one. Is product more art or science? What's the ratio? And if you were to put a number on it, what would it be?

A Here's my somewhat equivocating answer, which is Out of a really mature feature area, it's more science than art, because it's about optimization, and you have so much data on the scale. So there, I would say, 80, 20, science, art. I think, if you're at an early stage company, or at a really early, you know, part of the product development life cycle for a new feature or new product capability, I would say it's like, 75% art, 25% science, and you can be informed by the science and the measurement, but there's so much art In the curation, the editing, the creative approach, the vision that you have to focus on before you have enough scale to get it to optimization mode.

AI assessment note: “So there, I would say, 80, 20, science, art.”

Q How do you do that? Is that with mirror boards? Is that with, what does that look like?

A Yeah Uh,, I mean I,, I'll hate to confess, but obviously, you know, we use Slack for a lot of these things, but what I would say is the most typical flow would be someone will write a doc that kind of frames what the discussion is, the key context decisions, you know, whether they use Google Docs or uh, Notion or Canvas, which Slack just released, but I think the big thing that's actually happened is Designers and engineers now will record clips with screen sharing in Slack, and it'll be a quick three or five minute clip. And if it's a designer, they'll be like walking through a prototype and stigma, or if it's an engineer, they'll be doing the same, but with a real life code. And they'll actually show you the thing instead of say, Hey, let me, you know, the classic meeting. Otherwise there's a 20 minute presentation. Everyone's sitting there being like, okay, I wish I could just go through this quickly on my own. Now it's Everyone pre-watch this thing and then come in with your perspective, your ideas, your feedback, so you can get straight into the discussion instead of having half the meeting via presentation. Um, so I think that's made a big difference, honestly.

AI assessment note: “Designers and engineers now will record clips with screen sharing in Slack”

Q Can I, I, I totally agree with you in terms of like the, the need to renew product market fit with the changing of company scale. What are the biggest challenges to doing that?

A You know, I think if you look earlier stage, I think the, the single biggest challenge, because I think the first time you had product market fit, almost every company They're designing for themselves in some way. I think if you look at the founder story, you know, when people talk about, like, what's the founder's right to compete in this market? What's their founder, you know, market story? It's almost always, I have this problem in my personal life, or I see this problem in my work life, and I want to solve it for me, and hopefully other people want it too. And so, if I look at Foursquare, that was definitely a case with Dennis. His DNA was, I want to try going to every single place in New York City. I want to have this map of the world and my friends all superimposed together, and I hope other people want it. And it turned out, at peak, fifty million people in the world wanted this too. Uh, Slack, obviously, was, was two stories of that. You know, the first was trying to build for this game that they wanted. That didn't take off. The second version was, hey, we built this amazing tool eternally. Uh, maybe other people might want it too. Let's hope that there's a big enough market. Once you saturate that market, if you are lucky enough to saturate it and that other people do want the thing, I think the biggest first leap is how do you have The self-awareness, the humility, a…

AI assessment note: “how do you have The self-awareness, the humility, and then the intellectual curiosity”

Q Can I, I, I totally agree with you in terms of like the, the need to renew product market fit with the changing of company scale. What are the biggest challenges to doing that?

A You know, I think if you look earlier stage, I think the, the single biggest challenge, because I think the first time you had product market fit, almost every company They're designing for themselves in some way. I think if you look at the founder story, you know, when people talk about, like, what's the founder's right to compete in this market? What's their founder, you know, market story? It's almost always, I have this problem in my personal life, or I see this problem in my work life, and I want to solve it for me, and hopefully other people want it too. And so, if I look at Foursquare, that was definitely a case with Dennis. His DNA was, I want to try going to every single place in New York City. I want to have this map of the world and my friends all superimposed together, and I hope other people want it. And it turned out, at peak, fifty million people in the world wanted this too. Uh, Slack, obviously, was, was two stories of that. You know, the first was trying to build for this game that they wanted. That didn't take off. The second version was, hey, we built this amazing tool eternally. Uh, maybe other people might want it too. Let's hope that there's a big enough market. Once you saturate that market, if you are lucky enough to saturate it and that other people do want the thing, I think the biggest first leap is how do you have The self-awareness, the humility, a…

AI assessment note: “the biggest first leap is how do you have The self-awareness, the humility”

Q How do you do that? And how much do you listen to your customers versus independently progress on your own research and thought processes?

A I think the easy answer or the straightforward answer is, I think you have to get even deeper into your customers' lives and better understand by, by customing the next set of customers who aren't using your product. Uh, so, you know, in the case of Slack, I think it was initially, if you read the initial pitch deck, which they shared when they pivoted the company, It said, Slack is a product for teams of five to 50 people. The initial conception of Slack was, after 50 people, this thing probably won't scale. No one's gonna wanna work this way, so let's just design for the small, medium-sized teams and companies. I think the biggest change was when we realized, just looking at the data, that actually small teams at large companies were loving using Slack in all these different pockets as they were springing up, but to actually make Slack work at a scale of thousands or tens of thousands of people, the needs of that type of company looked very different. The end users wanted the exact Slack product, but the organization wanted something very different, and so I think, you know, we had to spend, it was this probably End of 20 16, 20 17, really immersing ourselves in the world of, like, enterprise controls, scale, security, compliance, uh, talking to executives at companies instead of just being the insurgent, and getting closer to them, not because everything they said we should …

AI assessment note: “You have to actually go talk to them and find out and then incorporate it”

Q How do you do product reviews now? I'm fascinated. How often do you do them? Who's invited? What do they look like?

A Yeah. It's evolved a lot over time. I would say where we are now and, you know, for context, Slack has probably around 1200 people across product design and engineering. So it's a pretty, you know, sizable team. Where we kind of are structured now is there's basic product pillars, which are kind of teams of teams that are responsible for areas of the product. So there might be an enterprise product team or the virtual HQ team that belongs for huddles and clips and so on. And what we've figured out works pretty well is that we have Those pillars, the leads for those pillars do product reviews or product workshops on a weekly basis within the team. So the leads can kind of weigh in and give feedback and unblock feature developments that's happening. And then what we wind up doing is usually on maybe a biweekly or depending on their monthly basis, an exec review with the leads of each pillar, the PD kind of executive leadership. So the head of design, the head of engineering, the head of product and try to focus those discussions less on, okay, let's run through the 15 features that might launch in the next couple of months. And instead be like, what are those one way door decisions that we need to really focus on? What are things around the product roadmap and the portfolio that we need to refine? Uh, or if it's a really major launch, let's go taste the soup. How's it feeling? Is…

AI assessment note: “leads for those pillars do product reviews or product workshops on a weekly basis”

Q You mentioned speed that I'm asking a tough. I used to be so nice on the show when I was younger. Um, I'm asking the tougher ones. If we're honest, I'm sure you hear what I hear. People say the speed of innovation at Slack is slower today. What are the biggest bottlenecks to the speed of innovation in Slack?

A Yeah. I mean, I think where internet was most true was 2018 to 2020. And I think I would, I think we would fess up to it entirely because back then, you know, this is again, I don't know if we could have done it differently. You're a small company. You can't do everything at once, but that's when we really made this kind of hard rotation on focusing on the enterprise buyer, the enterprise organization. And I think we did prioritize for a while kind of scalability and solving those really complex, you know, fortune, 500 use cases and compliance and security needs. And I think we did take the eye off a little bit, that core pace of product innovation, of pushing the boundary of what's category can be forward. I think in some strange ways, like COVID was a real wake up call for us because suddenly even our existing customers were coming to us and saying, Oh my God, I'm living all day in Slack. That's amazing. But also now have all these other needs and can Slack fill these needs or do I need to look in other places for them? And so I think starting the end of 20 20 through now, I would say, and this is not a rebuttal, but my perspective of these is that I think, and our customers are feeling this as well, that the pace of innovation has kind of increased pretty dramatically. You know, you have huddles, you have clips, you have canvas, which was just launched, you have workflow.

AI assessment note: “we really made this kind of hard rotation on focusing on the enterprise buyer”

Q Can I ask, how do you know when's the right time to move into enterprise?

A So I think there's two paths and, you know, I've talked to folks at lots of different companies, lots of different SaaS companies and I think there are some product categories where you need to start in the enterprise because there isn't an S&D buyer. So I think typically things in the like security compliance infrastructure space, you know, there are exceptions or open source projects that Get adopted bottoms up that then become commercialized. But I think often those buyers for good or for bad are going to be the CIO or the CISO at an organization. And so to start with enterprise is often the answer and don't sweat that you don't have a bottoms up motion or a PLG motion. I think if you start with SMBs, I think the thing to look out for is, and it's fine. I don't, I don't think we were deliberate about this early on, but eventually, obviously we saw in my data is, are you seeing pockets of teams or, or subsets of an organization that are starting to use your product kind of independent of each other? And if you start seeing that, so for example, I can imagine where I've heard interviews too and talked to folks at Figma, you know, they started seeing different pockets of a larger organization start adopting Figma. This is very similar to Slack story. And then once you see that, you're like, okay, maybe we don't have all the control and administration that a large company needs,…

AI assessment note: “are you seeing pockets of teams or, or subsets of an organization”

Q Love that one. Is product more art or science? What's the ratio? And if you were to put a number on it, what would it be?

A Here's my somewhat equivocating answer, which is Out of a really mature feature area, it's more science than art, because it's about optimization, and you have so much data on the scale. So there, I would say, 80, 20, science, art. I think, if you're at an early stage company, or at a really early, you know, part of the product development life cycle for a new feature or new product capability, I would say it's like, 75% art, 25% science, and you can be informed by the science and the measurement, but there's so much art In the curation, the editing, the creative approach, the vision that you have to focus on before you have enough scale to get it to optimization mode.

AI assessment note: “there, I would say, 80, 20, science, art.”

Q How do you do that? Is that with mirror boards? Is that with, what does that look like?

A Yeah Uh,, I mean I,, I'll hate to confess, but obviously, you know, we use Slack for a lot of these things, but what I would say is the most typical flow would be someone will write a doc that kind of frames what the discussion is, the key context decisions, you know, whether they use Google Docs or uh, Notion or Canvas, which Slack just released, but I think the big thing that's actually happened is Designers and engineers now will record clips with screen sharing in Slack, and it'll be a quick three or five minute clip. And if it's a designer, they'll be like walking through a prototype and stigma, or if it's an engineer, they'll be doing the same, but with a real life code. And they'll actually show you the thing instead of say, Hey, let me, you know, the classic meeting. Otherwise there's a 20 minute presentation. Everyone's sitting there being like, okay, I wish I could just go through this quickly on my own. Now it's Everyone pre-watch this thing and then come in with your perspective, your ideas, your feedback, so you can get straight into the discussion instead of having half the meeting via presentation. Um, so I think that's made a big difference, honestly.

AI assessment note: “Designers and engineers now will record clips with screen sharing in Slack”

Q How do you do that? And how much do you listen to your customers versus independently progress on your own research and thought processes?

A I think the easy answer or the straightforward answer is, I think you have to get even deeper into your customers' lives and better understand by, by customing the next set of customers who aren't using your product. Uh, so, you know, in the case of Slack, I think it was initially, if you read the initial pitch deck, which they shared when they pivoted the company, It said, Slack is a product for teams of five to 50 people. The initial conception of Slack was, after 50 people, this thing probably won't scale. No one's gonna wanna work this way, so let's just design for the small, medium-sized teams and companies. I think the biggest change was when we realized, just looking at the data, that actually small teams at large companies were loving using Slack in all these different pockets as they were springing up, but to actually make Slack work at a scale of thousands or tens of thousands of people, the needs of that type of company looked very different. The end users wanted the exact Slack product, but the organization wanted something very different, and so I think, you know, we had to spend, it was this probably End of 20 16, 20 17, really immersing ourselves in the world of, like, enterprise controls, scale, security, compliance, uh, talking to executives at companies instead of just being the insurgent, and getting closer to them, not because everything they said we should …

AI assessment note: “You have to actually go talk to them and find out and then incorporate it”

Q How do you do product reviews now? I'm fascinated. How often do you do them? Who's invited? What do they look like?

A Yeah. It's evolved a lot over time. I would say where we are now and, you know, for context, Slack has probably around 1200 people across product design and engineering. So it's a pretty, you know, sizable team. Where we kind of are structured now is there's basic product pillars, which are kind of teams of teams that are responsible for areas of the product. So there might be an enterprise product team or the virtual HQ team that belongs for huddles and clips and so on. And what we've figured out works pretty well is that we have Those pillars, the leads for those pillars do product reviews or product workshops on a weekly basis within the team. So the leads can kind of weigh in and give feedback and unblock feature developments that's happening. And then what we wind up doing is usually on maybe a biweekly or depending on their monthly basis, an exec review with the leads of each pillar, the PD kind of executive leadership. So the head of design, the head of engineering, the head of product and try to focus those discussions less on, okay, let's run through the 15 features that might launch in the next couple of months. And instead be like, what are those one way door decisions that we need to really focus on? What are things around the product roadmap and the portfolio that we need to refine? Uh, or if it's a really major launch, let's go taste the soup. How's it feeling? Is…

AI assessment note: “Those pillars, the leads for those pillars do product reviews... on a weekly basis”

Q Can I ask, how do you know when's the right time to move into enterprise?

A So I think there's two paths and, you know, I've talked to folks at lots of different companies, lots of different SaaS companies and I think there are some product categories where you need to start in the enterprise because there isn't an S&D buyer. So I think typically things in the like security compliance infrastructure space, you know, there are exceptions or open source projects that Get adopted bottoms up that then become commercialized. But I think often those buyers for good or for bad are going to be the CIO or the CISO at an organization. And so to start with enterprise is often the answer and don't sweat that you don't have a bottoms up motion or a PLG motion. I think if you start with SMBs, I think the thing to look out for is, and it's fine. I don't, I don't think we were deliberate about this early on, but eventually, obviously we saw in my data is, are you seeing pockets of teams or, or subsets of an organization that are starting to use your product kind of independent of each other? And if you start seeing that, so for example, I can imagine where I've heard interviews too and talked to folks at Figma, you know, they started seeing different pockets of a larger organization start adopting Figma. This is very similar to Slack story. And then once you see that, you're like, okay, maybe we don't have all the control and administration that a large company needs,…

AI assessment note: “are you seeing pockets of teams or, or subsets of an organization”

Q Now, before we move into that kind of scaling up into enterprise, you mentioned that the five to 50, I do just want to touch on kind of the foundation as being kind of product principles. And you said before the show to me that your organization needs product principles. Can I ask first, what are product principles and what did you mean by this?

A Yeah. You know, I think product principles are a way of enshrining the culture and beliefs of your product organization. Into a common language that everyone at the company could easily refer to as a shorthand for making quick decisions and for making kind of qualitative assessments of the level of craft of the product. And so for Slack, I went off to walk through all of them, but I would say probably I want to say maybe five years ago. So a couple of years into the company, what we realized, I think the why behind why we created these was as a company with scaling and the average person who's working in product development is kind of further away every day from working with Stewart, who is the founder or CEO and very product led. It became harder to figure out how to instill the kind of fiber in DNA of how the product was initially built into teams that were further away from that origin and further away from the founder. And so what we realized was you couldn't just have Stuart spend all day in meetings with every single product team. How do we scale the culture and how do we make it easy and memorable to reference? So we came up with a couple things like don't make me think and be a great host and Perceptive half, and take bigger, bolder bets, and we can unpack any of them, but Okay, let's unpack them.

AI assessment note: “product principles are a way of enshrining the culture and beliefs of your product organization.”

Q Well, that is very, very kind of you. Now, I wanted to kind of chronologically unpick your career before we dive in, and start as your career starting as PM at Google, What is the single biggest product lesson you took from the three to four years or two to three years at Google, and how did that impact your mindset?

A Yeah. I mean, Google is definitely where kind of, I started my career in product and was in this formula part of my kind of journey there. And I think the thing that struck me the most, because back then I worked on a feature team within search, but you kind of saw how the executives view product strategy. In background, they used to have this model, they called it the 70, 20, 10 model. And it's actually a pretty fascinating way of thinking about just a product roadmap and the distribution within it. So, 70% of the product Teams were focused on what are things that are known valuable things for our customers that are in some ways more incremental. 20% were new product areas that had already kind of taken off, but they were trying to further refine and incubate. So, you know, apps and Gmail took off. How do you scale it to a billion users? And then 10% were the far out bets, the self-driving cars, the, you know, Android before Android existed, the building a web browser. And I think the thing that stuck out to me was the combination, that deliberate approach to what the portfolio looked like, and the constant kind of Larry and Surya refrain of whatever your ideas you bring to them, what would 10 X a bigger scale look like? So I think that caused a level of ambition for product thinking at Google that it's kind of hard to afford, I mean, early stage startups, but I think it's asp…

AI assessment note: “the thing that struck me the most... they called it the 70, 20, 10 model”

Q I'm fascinated. You said there about that acquisition on posts. From a product leader mindset, you're a massive voice in acquisitions, especially so product centric acquisitions. How do you think about that buy versus build and respectfully, like, why buy when often the price is very high?

A Yeah. To be honest, and this is maybe colored more by our experience at Slack, I think We've struggled to buy a product that we can then repurpose and incorporate that was faster at the end of the day than if we decide to build it from scratch. And I think every time, you know, the reason, so the question is, well, why does that happen? Why don't you do it? I think the reason is often Very simple, which is you look at your existing organization, and then you look at your ambitions, and when your ambitions are outstripping your ability to scale your organization, you sometimes think, well, okay, this whole area that we're excited about, can we just buy a team here? Let's say you have the, you know, equity or the dollars to do it, and will that be a faster time to market to kind of realize some of the vision that otherwise we just don't have the capacity for? And I think it's just Fundamentally very, very hard, especially if you're a hyperscaling kind of company to be able to do acquisitions of products, not teams. Teams are very different. Like we've done a lot of talent acquisitions and those have worked out amazingly well, but when they were trying to actually buy a product, I think you're right. I think, I think often the thing we've learned is that it doesn't actually Decrease time to market. Um, you might bring in expertise and that's a good reason to do it, but that's at l…

AI assessment note: “it doesn't actually Decrease time to market”

Q Can I ask, do you do the 70, 20 10 at Slack?

A You know, it's funny. I feel like it almost became so well known for Google that it would feel a little bit carboculting to bring it exactly. But we do talk a lot about kind of the portfolio and diversification within different product areas. So, you know, we might ask it to you, when you think about the breakdown of your roadmap for the next two quarters, where, or is it allocated? How much of this is maintenance performance and quality? How much of this is refining and kind of customer delight and how much of this is you're incubating new ideas. You're trying out new levers. So we don't call it some new, 20, 10, but it's definitely part of how we look at the structure of product TV roadmaps and try, and every team is different too. You know, even at Google, I would say that was at the corporate level, but take a team like AdWords, their allocation didn't look like seven, 20, 10. They might look like 95, five. So I think it's a interesting framework, but I don't think it is something that is like a perfect ratio to apply in every context.

AI assessment note: “we don't call it 70, 20, 10, but it's definitely part of how”

Q What do you think are the biggest mistakes startups make with product principles?

A My A hunch is that most companies wait too long to introduce them, whether they call them principles or maxims or design guidelines, it doesn't really matter. But I think it's really hard. If you're a product founder and you're a founder led company, I mean, there's all types of things that are hard as you transition and scale the organization. But I think one of the hardest things winds up being, uh, When do you give up enough control that your organization starts building things that you aren't even aware of? And then how do you have enough trust that the people building it are going to build it up to the standard and approach that the company was founded on? And I think that's, that's kind of the leap, but I think most companies wait far too long and the organization starts going slower and slower. And then the CEO starts complaining, why are things slower when we have twice as many people? That, I think, is usually the process that, that happens. So, I was definitely waiting too long to enshrine the culture in a way that can scale it.

AI assessment note: “most companies wait too long to introduce them”

Q How do you do product reviews now? I'm fascinated. How often do you do them? Who's invited? What do they look like?

A Yeah. It's evolved a lot over time. I would say where we are now and, you know, for context, Slack has probably around 1200 people across product design and engineering. So it's a pretty, you know, sizable team. Where we kind of are structured now is there's basic product pillars, which are kind of teams of teams that are responsible for areas of the product. So there might be an enterprise product team or the virtual HQ team that belongs for huddles and clips and so on. And what we've figured out works pretty well is that we have Those pillars, the leads for those pillars do product reviews or product workshops on a weekly basis within the team. So the leads can kind of weigh in and give feedback and unblock feature developments that's happening. And then what we wind up doing is usually on maybe a biweekly or depending on their monthly basis, an exec review with the leads of each pillar, the PD kind of executive leadership. So the head of design, the head of engineering, the head of product and try to focus those discussions less on, okay, let's run through the 15 features that might launch in the next couple of months. And instead be like, what are those one way door decisions that we need to really focus on? What are things around the product roadmap and the portfolio that we need to refine? Uh, or if it's a really major launch, let's go taste the soup. How's it feeling? Is…

AI assessment note: “leads for those pillars do product reviews or product workshops on a weekly basis”

Q Can I ask, what's the biggest broken process part of product building today for you in Slack that hasn't yet been resolved?

A I'm trying to get something that's going to be more general for other folks as well. I still think, you know, we love using Slack for building Slack, obviously, but I think the thing that is still hardest to see is kind of that bird's eye view of what is actually the latest state of the world for all the major areas going on at the company. And I think Slack itself definitely doesn't solve that. Like, yes, you can be in all the channels, but for me, if I just open up a random team channel, it's gonna be really noisy. It's gonna be hard to know, like, what is the actual latest? Should I be reviewing this thing? Is this just team discussion? Um, you know, we wind up solving this like most people do at the end of the day, you use spreadsheets. So we have a Monday meeting, PD Monday meeting, as we call it, where like literally we just review in a spreadsheet, super manual process, but the top priorities for the quarter and latest updates, and it gives a kind of operational cadence to the quarter. But that's a solution that is not very elegant, and it's not very software. It's about as old as scratch sheets, but I think a lot of organizations rely on that, and software is too rigid often to be able to solve it.

AI assessment note: “the thing that is still hardest to see is kind of that bird's eye view”

Q Can I ask, how do you know when's the right time to move into enterprise?

A So I think there's two paths and, you know, I've talked to folks at lots of different companies, lots of different SaaS companies and I think there are some product categories where you need to start in the enterprise because there isn't an S&D buyer. So I think typically things in the like security compliance infrastructure space, you know, there are exceptions or open source projects that Get adopted bottoms up that then become commercialized. But I think often those buyers for good or for bad are going to be the CIO or the CISO at an organization. And so to start with enterprise is often the answer and don't sweat that you don't have a bottoms up motion or a PLG motion. I think if you start with SMBs, I think the thing to look out for is, and it's fine. I don't, I don't think we were deliberate about this early on, but eventually, obviously we saw in my data is, are you seeing pockets of teams or, or subsets of an organization that are starting to use your product kind of independent of each other? And if you start seeing that, so for example, I can imagine where I've heard interviews too and talked to folks at Figma, you know, they started seeing different pockets of a larger organization start adopting Figma. This is very similar to Slack story. And then once you see that, you're like, okay, maybe we don't have all the control and administration that a large company needs,…

AI assessment note: “are you seeing pockets of teams or, or subsets of an organization that are starting”

Q What have you learned since Big and New that you thought passed all internal checks and then didn't hit with the public and what did you learn?

A If you go back, I want to say this must have been late,,, late late late, late,, late, late late late,, late,, late late,, late, late late late,, late late late late, late,, late, late, late Kind of WYSIWYG document composer in Slack. It was called posts. And we were like, well, obviously you would need hosts in Slack. It's like a message, but it's richer, more formatted, more visually appealing. Uh, for many reasons, this seemed obvious. And yet when we launched it, it really got very low adoption. And it never really grew. And I think what we realized, actually, this goes back to one of the things I think Google really kind of instills in you is that the most important feature by far for any product is actually speed. Above all else, that is like, that is like the oxygen for a good product experience. And it turns out to build like a rich document editing experience, if it takes a couple seconds to load, if there's latency on the key presses, if moving objects around takes longer than you think, you're going to just say, well, I'm just going to go back to the thing I use every day in some other browser tab. And I think it took us a long time, and obviously we've launched Canvas recently, or we're rolling it out actually now, and it's a different take on the same space, but I think what we realized was that the bar for just speed and quality for something that is as ubiquitous…

AI assessment note: “the most important feature by far for any product is actually speed”

Q Noah, where are you weakest as a product leader? When you do a self-reflection, me and you, whiskey at the end of the year, where are you like, I really need to improve here, and what are you going to do to improve there?

A I think the thing that I think a lot about and I'm passionate about, but I don't think I figured out how to crack, to be totally honest. And we're actually planning a product or offsite for two weeks from now. So it's very top of mind. I think it's really hard to create a team environment within a product management organization where people feel really connected to each other, where they feel energized by each other's work, where they're pushing on each other, where, uh, they have a lot of shared contacts. Most product organizations, the PMs feel like their primary team is going to be the engineers and designers that they've worked with. Those are the people they work with every day that they, uh, have the closest connection to. And I think, yeah, I'm still trying to figure this out. I'm still trying to crack it. It was like, how do you make a PM organization feel less isolating? How do you create connection between people who work on very different parts of the product to learn from each other, to push on each other, to build product with each other? Uh, I've yet to work at a place that has cracked this, and I think it's part of the reason why maybe there's so much hunger from PMs to kind of learn externally, to learn from a podcast, to learn from newsletters, to learn from other communities, because it is hard to foster that connection internally.

AI assessment note: “I don't think I figured out how to crack, to be totally honest.”

Q Can I ask, you then go to Foursquare and you spend five years plus at Foursquare, I think five years and one month according to the trusty LinkedIn. Um, what's the biggest product takeaway for you from Foursquare? It's a fascinating product actually to have the experience you did on, and how did that impact your mindset?

A I mean, the thing I would start off by saying is, I think you wind up learning a lot more, it doesn't matter what your role is, when you're actually faced with a lot of headwinds. And when everything's going up and to the right, You think everything you're doing must be brilliant. You know, you throw something against the wall and the metrics keep rising. And so I think it's really hard. And I think this is a knock on, I think sometimes folks have only worked at large companies is you have so much tailwind, you have so much momentum, you're so much distribution. You don't learn how to manufacture that from scratch, or you don't know how to turn things around when things go sour. Within the context of force for, and I've done so much soul searching and reflection and introspection, including a lot of the things through there early on. You know, I think when I joined, uh, right end of 20 10, For the next two years, the level of product market fit that Foursquare had in the early days of mobile and the early days of social and location on mobile was incredible. And, you know, you go to Austin for South by Southwest and like the whole city feels alive. You feel you're seeing a version of the future where like you can have this map of everyone or everything and everyone around you. You're like, wow, it'd be amazing if everyone on earth used this thing. But I think the thing I took a…

AI assessment note: “I think the thing I took away was that product market fit.”

Q What do you think are the biggest mistakes startups make with product principles?

A My A hunch is that most companies wait too long to introduce them, whether they call them principles or maxims or design guidelines, it doesn't really matter. But I think it's really hard. If you're a product founder and you're a founder led company, I mean, there's all types of things that are hard as you transition and scale the organization. But I think one of the hardest things winds up being, uh, When do you give up enough control that your organization starts building things that you aren't even aware of? And then how do you have enough trust that the people building it are going to build it up to the standard and approach that the company was founded on? And I think that's, that's kind of the leap, but I think most companies wait far too long and the organization starts going slower and slower. And then the CEO starts complaining, why are things slower when we have twice as many people? That, I think, is usually the process that, that happens. So, I was definitely waiting too long to enshrine the culture in a way that can scale it.

AI assessment note: “most companies wait too long to introduce them”

Q Can I ask, what's the biggest broken process part of product building today for you in Slack that hasn't yet been resolved?

A I'm trying to get something that's going to be more general for other folks as well. I still think, you know, we love using Slack for building Slack, obviously, but I think the thing that is still hardest to see is kind of that bird's eye view of what is actually the latest state of the world for all the major areas going on at the company. And I think Slack itself definitely doesn't solve that. Like, yes, you can be in all the channels, but for me, if I just open up a random team channel, it's gonna be really noisy. It's gonna be hard to know, like, what is the actual latest? Should I be reviewing this thing? Is this just team discussion? Um, you know, we wind up solving this like most people do at the end of the day, you use spreadsheets. So we have a Monday meeting, PD Monday meeting, as we call it, where like literally we just review in a spreadsheet, super manual process, but the top priorities for the quarter and latest updates, and it gives a kind of operational cadence to the quarter. But that's a solution that is not very elegant, and it's not very software. It's about as old as scratch sheets, but I think a lot of organizations rely on that, and software is too rigid often to be able to solve it.

AI assessment note: “the thing that is still hardest to see is kind of that bird's eye view”

Q No, you mentioned those three letter acronyms. Uh, most people have no idea what they mean because generally most people don't have to scale into enterprise, but many startups do, and many startups actually, I think respectfully don't understand quite what it takes. What do you think are the biggest mistakes that startups who start in SMB make when they scale into enterprise?

A Yeah. It's, it's hard because honestly, a lot of the work is really kind of removing blockers. And I think they're, what I would really recommend, honestly, is like, that's where you do want to hire people who have domain expertise. You don't want a bunch of folks who worked at an early stage startup, had never worked in enterprise before to be like, let me try and figure out from, from first principles, what like electronic key management is and why the chief security officer of a fortune 100 company cares about it. This is not a place where you should reinvent the wheel. You should not take a novel approach. But the biggest mistake I think people make, and it's a little bit kind of reflecting for ourselves, is I think over-rotating on the enterprise buyer where you think that they're inherently more conservative. They don't want features to be shipping every single day to end users because they're, in fairness, trying to, you know, centrally run an organization where they have enablement and education and so forth. And I think you can introduce, to your point about speed, it can introduce a level of cultural conservatism, because the enterprise buyer will say, hey, I have these blockers, I'm blocked then, and please stop shipping things so quickly. And then the small, medium-sized business will say, I don't even know what those acronyms are, I don't care, but what else can yo…

AI assessment note: “the biggest mistake I think people make... is I think over-rotating on the enterprise buyer”

Q I'm fascinated. You said there about that acquisition on posts. From a product leader mindset, you're a massive voice in acquisitions, especially so product centric acquisitions. How do you think about that buy versus build and respectfully, like, why buy when often the price is very high?

A Yeah. To be honest, and this is maybe colored more by our experience at Slack, I think We've struggled to buy a product that we can then repurpose and incorporate that was faster at the end of the day than if we decide to build it from scratch. And I think every time, you know, the reason, so the question is, well, why does that happen? Why don't you do it? I think the reason is often Very simple, which is you look at your existing organization, and then you look at your ambitions, and when your ambitions are outstripping your ability to scale your organization, you sometimes think, well, okay, this whole area that we're excited about, can we just buy a team here? Let's say you have the, you know, equity or the dollars to do it, and will that be a faster time to market to kind of realize some of the vision that otherwise we just don't have the capacity for? And I think it's just Fundamentally very, very hard, especially if you're a hyperscaling kind of company to be able to do acquisitions of products, not teams. Teams are very different. Like we've done a lot of talent acquisitions and those have worked out amazingly well, but when they were trying to actually buy a product, I think you're right. I think, I think often the thing we've learned is that it doesn't actually Decrease time to market. Um, you might bring in expertise and that's a good reason to do it, but that's at l…

AI assessment note: “when your ambitions are outstripping your ability to scale your organization”

Q I'm, I'm gonna be deliberately contrarian. They're all quite general, and like, bigger, bolder bets I get it, but kind of nuanced. Like, if I'm gonna, if I'm gonna come with an idea that's like, bet the company, you're telling me to take bigger, bolder bets. Why should I bet humanity? Do you know what I mean? Like, help me understand those, because they seem pretty challenging.

A Yeah, I mean, I would say, none of those, if you said them, allow it to be like, wow, that's a, that's a, Totally contrarian idea. You, you know, well, what are you talking about? But I think they mean something into the context of their organization. So for example, when you unpack these, what we mean when we say, take bigger, bolder bets is as a company scales, I think there's a tendency towards incrementalism and kind of local optimization. You know, you have bigger and bigger organizations. You have feature teams. The feature teams may have a similar KPI. That is the one thing they feel directly accountable for. And the natural tendency is, you know, I view my success, my team success to move this single metric. The easiest way to do that is incrementally with very small experiments. So I can say, Hey, we moved this metric by . And that's kind of antithetical to if you're saying, hey, actually our product is much earlier in its journey. We're defining an entirely new category. No one else has created this space. We're the ones who are creating this space. Yes, we need to do things that are incremental on refinement, but we need to balance that with taking huge swings to push the concept of this category for our customers.

AI assessment note: “what we mean when we say, take bigger, bolder bets is as a company scales”