Lenny's Podcast: Product | Career | Growth - The 10 traits of great PMs, how AI will impact your product, and Slack’s product development process | Noah Weiss (Slack, Foursquare, Google)

Starting point is 00:00:00 We have this mental metaphor that we talk a lot about, getting to the next hill. The actual wording is take bigger boulder beds. I think teams can often get lost crawling up that hill, not realizing that there's a huge, incredibly beautiful range behind it. We've over time, freighted kind of new teams from scratch that YouTubeated in a new area before the area is mature. So we did that with a lot of these kind of native audiovisual products like huddles and clips early in the pandemic because our customers were demanding it from us.

Starting point is 00:00:26 And I think in the AI space, we're trying to hear from customers. What do you wish Slack could do if it had these new superpowers? And let's incubate a couple teams, a prototype, give them space to run and pilot and then get something to launch that's amazing blows people away. That's kind of the formula that we've seen. Welcome to Lenny's podcast, where I interview world-class product leaders and growth experts

Starting point is 00:00:49 to learn from their hard-win experiences building and growing today's most successful products. Today, my guest is Noah Weiss. Noah is Chief Product Officer at Slack, where he spent the last seven years. Prior to that, he was head of product at Foursquare, which is near and dear to my heart, as you'll hear at the top of this episode. Prior to that, he was a PM at Google and at Fawcrete Software. And in our conversation, we cover the 10 traits of great product managers,

Starting point is 00:01:13 how to work effectively with strongly opinionated and product-minded founders. What Noah has learned about working effectively with AI in your product over his last 15 years at Google and Foursquare and now Slack. We talk about a process called Complaint Storms that helps Slack build better product, Plus, what he's learned from Slack's self-service business plateauing back in 2019 and how they turned it around and what they took away from that experience. Also, how he thinks about competition with Microsoft Teams and with Discord. Also a bunch of new data advice, which I found very helpful.

Starting point is 00:01:46 This was such a great in-depth conversation about all things product and leadership, and I'm really excited for you to hear this episode. With that, I bring you Noah Weiss after a short word from our sponsors. This episode is brought to you by Sidebar. Are you looking to land your next big career move or start your own thing? One of the most effective ways to create a big leap in your career, and something that worked really well for me a few years ago, is to create a personal board of directors,

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Starting point is 00:03:51 To reduce context switching, and make sure you never miss an important email. You can set reminders if you don't hear back so that you can follow up and never drop the ball on an email thread. You can also work faster than ever before with powerful AI features like writing, editing, summarizing, and even translating. Join the ranks of the most productive teams and unleash the power of superhuman. Try one month free at superhuman.com slash Lenny. That's superhuman.com slash Lenny. Noah, welcome to the podcast. Thank you for having me. I'm excited to find you.

Starting point is 00:04:27 get to join and be a long-time listener. I feel the same way in reverse. I've been really excited that you're finally on the podcast. And I don't know if you know this, but this is actually going to be the last podcast I'm recording before I go on Pat Leave. This is going to play while I'm on break. And coincidentally, you're actually just returning from Pat Leave is what I just learned. And so let me ask you a question. What advice do you have for someone about to enter the beginning of baby life from someone that is exiting that and going back to work? So first off, I mean, obviously, congratulations. You're about to go on a roller coaster of emotion, sleep, and everything else. You know, I literally went back to work two days ago. So I think my maybe advice about being

Starting point is 00:05:07 your parents is better than my advice about being at PM right now. Here are the three, my wife and I want to come up with like three maxims that we want to be using throughout the first two months to keep ourselves grounded. So first one, I would say a little bit better every day. No matter how many books you read, you know, and how much, how much, you'll posture you consume. There's nothing like actually doing it. And it's a physical thing being a new parent. And so getting a little bit better every day, giving yourself permission to be like, that didn't go great and that's okay. That's number one. Number two, don't over extrapolate from the early days. Like, they are going to have the fourth trimester is a real thing. These babies

Starting point is 00:05:48 come out. They are not fully baked. They can't even support their own heads. So if you try to extrapolate and think the next 18 years are going to be like the first. 18 days, it's going to be sobering. So like keep that perspective. It gets, they develop so much every week with Father of the Sun. And then the third thing, which I got advice from this from a good friend is like, you got to fully get into it as a parent. Like there's nothing that replaces actually you got to change the diapers. You got to do the feeds when they're up, even though they can't talk. You got to talk to them. You got to like listen to what they're saying and just be fully kind of presence near the moment. I kind of realized for myself and then like basically a full

Starting point is 00:06:26 digital detox. You saw how long it took from your reply to your emails. I was like, put all the devices away, just kind of be fully with our daughter, Willow and our family. And I feel like it was so much more rewarding. I felt really connected with her now after just a couple months. So it's a crazy time. You're going to love it. It's going to drive you mad at times as well. And that's all okay. All right. We're going to be pivoting this podcast into a parenting podcast. This is awesome advice. I wrote everything you just said on this little post-it as you're talking, so I'm going to put that up in my inner nursery and see, see how it all goes. One thing that's tough about my career path in this weird life is I don't get a nice pat leave, you know, paid pat leave from a big company.

Starting point is 00:07:06 So I've actually been working on stacking guest posts and podcast ahead of my leave so that I can actually, as exactly as you said, just get fully into it. So you have six awesome. Yeah. So I have awesome guest posts come in. All these podcasts are backlogged. So I'm hoping it all works out. That's a smart way to do it. Yeah. On a totally different topic, you're a head of product at Foursquare, and I don't know if you know this. I actually built a startup on Foursquare's API.

Starting point is 00:07:32 It's a company called Local Mind. And for folks that don't know about it, the way it worked is basically let you talk to someone, checked in on Foursquare anywhere in the world, if you're thinking about going there, so you could be like, it is this bar fun right now, what's happening there before you actually show up.

Starting point is 00:07:45 And we ended up selling the company to Airbnb. Ended up not being a big problem for enough people. And that's how I ended up at Airbnb, but it was, it was like quite magical, and API was amazing. And so I guess just say, I just want to say thank you for building an awesome product and awesome API. Thank you for being a developer on top of the ecosystem. I mean, it's interesting with Foursquare. I will talk about this until later.

Starting point is 00:08:04 I feel like I have more lessons learned and more scar tissue from the, you know, crazy up and down of, I don't know, what it was 2010 to 2015, roughly. and I think there's something actually where you learn more from the things that don't fully work out or don't quite achieve what you want it to achieve. And you actually have a feedback loop where you get a lot of negative signal about like, if that didn't work, that didn't work, what can I actually learn to take away from that? So it's still great. I still love using Foursquare. I think, you know, we got caught in the Death Star of Instagram's ascent, you know, back in 2012-13.

Starting point is 00:08:43 But, you know, I hope a product like that exists forever in the future. and I'm glad you got to build a company landed Airbnb through it. That's a great story. Looking back at Foursquare, do you think there was a path to building a massive consumer app type business or is that just never going to work out? And I know they went in direction of B2B data sort of business. So I guess was there a path or was it just like, no, that was never going to work out?

Starting point is 00:09:08 It's true. I mean, I'm not going to do like 30-minute post-mortem because I'd probably bore everyone. But I've thought about this. We've all thought about this a lot, kind of on the early team there. I think, you know, the biggest probably lesson learned, frankly, is that, you know, we were really close with Instagram folks early on. They were, like, big developers on our platform, they used a for Spore API before they were bought by Facebook. And I think, in hindsight, we were a little bit mistaken to believe that the idea that the atomic unit would be a person talking about a place that they're at. And you have to have a physical place to type to versus a person sharing a moment or an experience that they're having in the world. and sometimes I might have a place connected to it.

Starting point is 00:09:47 I think that one change in frame or what you would say, like the customer actually wanted to do, that probably was the thing that took this away on the social side. I think on the more kind of local discovery side, it's actually what people want to be using the product much more for over time, getting kind of personalized recommendations and getting tips when you go to a place and all the push notifications. But I think there, again, it was kind of hard to stay ahead,

Starting point is 00:10:13 I think specifically of Google because they had, you know, billion plus Google Maps users distributed on Android and iOS. And even though they might only, you know, take a couple of years, eventually they would wind up replicating a lot of the functionality. And then I think that was hard to regain that momentum. So, you know, so much of this stuff is luck in timing and just coincidences of history. I think there was a path. I think in the end we kind of lost our social sales. and then Google was able to catch up on the utility side. And now the company has built a really valuable kind of B2B API company,

Starting point is 00:10:49 which offers the story. I mean, Slack is in some ways of pivot, obviously, from a consumer company to a B2B company. But yeah, that's my mini post-mortem. What could have been with Fourswear. It's interesting how many consumer companies pivot to B2B, because it turns out that's where the money ends up being. Yeah, and I think the feedback you get from are people willing to pay for the product that you're building is so.

Starting point is 00:11:12 much faster than can I build a large-scale consumer business and one day hope to have enough reach to then slap ads onto it. That's a much more of a kind of try to hit a home run and hope it works out, but you don't really know if you're doing it a long way. So yeah, I think B2B is easier to have a more incremental successfully business than pure consumer. Okay, so speaking of four square, Dennis Crowley was the CEO and founder, a very strong product-minded founder. I know you've worked with a number of very strong product-minded founders, including Stuart Butterfield, Dennis, obviously we just talked about, maybe others. I'm curious what you've learned as a product leader working with very opinionated founders. And I think this is interesting, not just as like a product

Starting point is 00:11:58 leader working with very product-minded CEOs, but also as a first PM at a startup. You're often put in this tough spot of just like the founders just telling you what to do and you have to go build it versus having a lot of say in agency. So I'm curious what you've learned about working and being successful in that position, which is often really hard. I kind of say to folks in general, if you're joining a company and the CEO does the rule that is your functional area of expertise, it's probably the area where you'll learn the most because they're hopefully world-class at it, but also what will you, you'll be the most fresh in at times because you're going to feel like you have less agency.

Starting point is 00:12:32 And so you just know that going to it. If you go to come in to run by a former marketer and you're in marketing, they'll probably want to have a lot of say and influence over that. And I think just going into knowing that is good. You know, looking back, I would say probably two main things stand out of what's really worked with both Dennis and Stewart, not just for me, but I think for the teams that kind of work with them as well. The first is, I think as much as possible, I think maybe we'll talk about this a little bit later as well, is kind of getting to the point where you have alignment on the principles for what it means to build a great product of that company.

Starting point is 00:13:03 Not just about the intuition and tasting gut, but how do you distill that to principles that become the language of the company? so that everybody else can start thinking through a similar frame or similar lens when you're a design product. Because otherwise, it can feel a little bit kind of Goldilocks every time a team builds at something. They take it to the CEO. The CEO is like, no, not quite right. Again, no, not exactly that. And then you don't have the language to actually have a more constructive review. And then doing that at the little strategy as well.

Starting point is 00:13:31 I think the product founder's CEO is always going to be the holder of the vision for the company. I'm sure at Airbnb, I imagine, and Brian was very much. like that as well. Absolutely. And I think it's actually great to say, okay, the overall vision for the company is it the responsibility of any one team to everyone buy into that vision, but then to have space for teams to be able to actually do creative work, do explorations, because you know that it's aligned with that high-level vision.

Starting point is 00:13:57 So if you can get that alignment and you can get those principles as the common language of what great software looks like, I think you can have a really good working relationship. And then the other bit I would just say is I think when to involve the founder's CEO in a project is really important. And the short version, I think that works the best is almost like a U-curve where the X-axis is time and the Y-axis level of involvement. I think you want to get the founder's CEO really evolved early on, especially this is a big new project to make sure that there's strategic buy-in. You agree on the principles and strategy and approach. You agree on the goals and the anti-goals. getting that to them that team can run and explore.

Starting point is 00:14:36 And then I think at the very end, you want them to really be bought in that, did you build something up to the quality product of the company? Is this something that's going to like customers, like literally taste the soup? What's missing in it? And I think at most companies that have a maniacally kind of customer-focused founder,

Starting point is 00:14:53 if you don't do that last step, it's going to be much more painful after you launch because they weren't part of that co-creation of the team. And so I think that kind of formula winds up. of working pretty well if you throw in that kind of alignment on principles and vision. That usually sounds nice in theory, but I often imagine you get to that final step

Starting point is 00:15:13 and the founders like, what the hell is this? This is not at all what I was hoping it'd be. There's an example of that that comes to mind where you maybe went through that and then it's just like, no, that did not work out the way we expected. And if not, no problem. Yeah. I mean, I think that does happen. The USIP is maybe the end of the year

Starting point is 00:15:31 is kind of like the level of engagement. And often that last whole of engagement, that's where there's actually the most rapid refinement that you're doing. And I think what's important there is that hopefully you're refining in code and you're not still at like static design mocks because using the software is so different than looking at what the software will visually appear. And so I think what we would want to do with Stewart at Slack, for example, is like we would get the entire development team, engineers, design, product, user research, and Stewart together in a room. And we kind of almost do. like a bug bash together. And the idea was like, we're doing all together. We're trying to make

Starting point is 00:16:07 the best product possible. Making great software is really messy. And we're all trying to kind of clean up the mess together. You know, sometimes you might find things like, okay, this entry point really isn't working. Maybe we have to move this entry point. That's maybe a bigger change. But I think often what you'd find is just all those bits of polish and refinement and doing the little delightful things that might otherwise be missing to kind of raise that craft bar and doing a real collective way, so it doesn't just feel like the team says, we want to ship. And the founder says, no, it's not ready. Ideally, as a group, you're saying, we want to get it to a bar that to delight our users. And here's the gap from where we are today to what we want to ship.

Starting point is 00:16:48 I think that mentality winds up being a lot more constructive, but that's not always easy to do. You talked about creating these principles, which is an awesome approach of just like creating guardrails for the team. So they kind of think the way the founder and the head of product think. What are some examples of principles you have and had early on maybe at Foursquare or Slack? I mean, Slack, I think, is where we kind of enshrined them much more because we scaled at org, so much more that we needed principles. And I think for us, they were really about unpacking just the mission, which for Slack is making people's working life simple or more pleasant, more productive. That's the mission of the company. The question is, how does

Starting point is 00:17:27 software help do that? That's what the principles are there to answer. So, for us, we've got five, four principles. They've largely saved the same. Some of the language has changed over the last couple of years, but at least for the last four or five years, we've had these. So the first is be a great host, which is all about kind of that level of craft, the relentless of so they're saving people's steps. If you're, let's say, a host at an Airbnb, it's like putting clean towels on the bed. So no one has to wonder, are these for me? Like that type of foresight. That's actually a value at Airbnb, exactly. It's actually be a host at Airbnb is one of the, of four core values.

Starting point is 00:18:03 Right. So maybe we borrowed that or someone was inspired by it. But be a great kind of sad and aspirational. I love that. Yeah, yeah. It's a little bigger. There's a famous user design book called Don't Make Me Think, which we sold the title of for our next principle.

Starting point is 00:18:18 And that's really just about as people building the software, you know how it works so well. You care about all the nuances and intricacies. And you really want your, you know, users to love it as much as you do. But often actually that kind of owner's delusion that someone else will care as much about the software that you built as you do prevents you from actually making something that's simple, comprehensible, understandable. And so one of the core tenants, because Slack is pretty complex under the surface is how do we actually make people not have to think? How do we not reinvent the wheel if there's existing design patterns to use? How do we actually, you know, wind up designing for people who come from many different backgrounds and we kind of cater to their needs in ways that don't make them. have to customize it too much. There's a saying we also have, which is more clicks can often

Starting point is 00:19:06 be okay. You know, you often have in, you know, optimization, you know, experimentation circles, like, oh, every click, remove it. But I actually think in a lot of software, when it's not transactional, helping people understand what they're doing, giving them confidence, helping them have trust in the steps. We've seen that that can actually be a better experience. So like, that's another example of don't make it trustful, help people chill out when they're using the software. That's the idea behind that one. Shifting a little bit. I know you guys have been working on a bunch of AI stuff at Slack, and I believe you've been working on AI-related stuff for many years. I think at Google,

Starting point is 00:19:42 you worked on a lot of AI-related products. I feel like a lot of people are just getting into this and trying to figure out how do we integrate AI and ML and LLMs into our product, and how do we not just waste our time chasing things. So I want to ask you just in your time working with AI over the many years you've been doing and share a little bit about what you've been doing there. What are some things you've learned about how to be actually effective and build valuable products and not just kind of fall for the shiny object issue and trap? I mean, it's almost 15 years ago now that I was working at Google in search on what later became called the knowledge graph. So this idea of building kind of a canonical repository

Starting point is 00:20:22 of kind of information that people places things in the world and relationships between them. And back then, it was a lot of the same ideas, but obviously the techniques I've got a lot more mature. So we used natural language processing to extract all this information from the web and try to build this kind of database of facts. An idea then was, could you take queries people have, like, what are the tallest mountains in Europe or one of the most popular beaches in Southern California and be able to actually give answers, not just 10 blue links? I think the thing that's really changed and super exciting in the last six, 12 months with LLMs and chat GPT and everything else is the idea that now you can take

Starting point is 00:21:04 not just knowledge about the world, but actually you have natural language generation where suddenly the computer can kind of talk back to you in a way that feels extremely human. And then the creative applications of that are pretty massive and exciting. So that's kind of, I guess, the lineage there. I think from over the years back at Google, at Forkshire, we did a lot of personalization

Starting point is 00:21:25 and recommendations at Slack. We have search and email that's kind of infused out the product. I think a couple things come out as kind of, I guess, maybe principles that we've kind of used over the years. Back then at Google, one of the big ones was that the promise of the UI has to match the quality of that underlying data, which is to say, and I think there's actually one of the failings of the various LMs right now is they all appear supremely confident. even when they're completely hallucinating.

Starting point is 00:21:53 And I think that's going to be something that people are going to have to work on a lot, which is to figure out how to be not so faultless to acknowledge when you're not sure, because otherwise it undermines the trust people have in the system, using a lot of transparency about where the data comes from, so people can actually build credibility in the tools really important. And then I think making sure that as you're designing the products that you have, virtuous cycles that are naturally part of the product experience, where you can get training data

Starting point is 00:22:19 as a byproduct of people naturally using the software and then can make the model that you're building behind the scenes smarter, more accurate, more predictive. So, yeah, a classic example of that would be Netflix back in the day of their rating system.

Starting point is 00:22:33 They actually have a feedback loop from their customers and then make the system better at predicting. And I think people are still trying to figure out what does that look like in this world in LLMs. Something I hope that you're all building at Slack is a way to ask a bot questions based on all the conversations,

Starting point is 00:22:48 in the Slack. I've been looking for that product for a while now. I can safely say we have a lot of prototypes internally where we are playing with this. And I think it's actually funny as a side. And one of the original Slack product vision decks back in 2014, there was our kind of whole strategy of four parts. And then part number four, which was a joke at the time, was then do magic AI stuff on top. And the idea is we didn't even know what the state of AI would be by the time, hopefully companies had their collective knowledge in Slack.

Starting point is 00:23:18 And now we're finally at the period where the magic AI stuff seems finally pretty amazing, pretty magical. So, yeah, we're doing a lot of prototyping internally and also trying to work with the ecosystem around as well, because there's so many companies doing amazing work in the space. So that if you work at a company where you have so much knowledge in your kind of Slack channel repository, that you can suddenly get amazing leaps in productivity to help you better do your job, because that knowledge is in Slack, but it's sometimes hard to reach. and I think these technologies can make that possible. This reminds me of something Gustav,

Starting point is 00:23:51 the CPO and CTO and co-president of Spotify, share that they always have a deck and a vision of just like a play button within Spotify. You just play and all magic happens and it's the best music and exactly what you want to hear and just how that isn't actually possible and it's still not possible. And so exactly to your point, you have to like really think about how does it act, like how close is it to the reality and if it's not actually there? like he's like he was saying how like we'll pick two songs that are correct at a 10 just because

Starting point is 00:24:19 we don't really know exactly what you want to hear right now and it's just there's no point trying to design that right now because it's not actually going to be delivering on the promise right yeah I think I love that our version of that has always been that you open up slack and suddenly instead of having to read through dozens of channels or find all these mentions that magically slack could just tell you in the order that you would care about kind of a summary of all the interesting things that have happened and then like you dig in if you want to, like your very own kind of like personal chief of staff who knew everything that you cared about and read everything that you could read. I don't think that's going to quite be possible

Starting point is 00:24:54 anytime soon, but I think like Spotify heading towards that North Star, you end up developing, I hope a lot of really compelling project experiences along the way. Yeah, man, the more to think about it, the more the more amazing opportunities exist in Slack. It's like all text. It's amazing. Okay, there's a lot of cool stuff coming, I imagine. Yes. I can't wait. Yes. On that topic, how do you think about creating teams within Slack and AI specifically, are you like recommending each team think about how AI can make their stuff better or are you dedicating here's the AI team and they're going to work on stuff and you guys just keep shipping what you're shipping and keep moving your metrics. Mead the unfair answer is a hybrid of the two, which is to say we have a kind of

Starting point is 00:25:34 central machine learning and church team. There's a lot of people have expertise in this field to build an infrastructure that everybody can use. And what we've done is, because the space is evolving so quickly, like literally every month, like the capabilities are evolving, the risks and trainups are evolving a ton. What we want to do is actually kind of spin up a couple different teams that are focused on prototyping using that common infrastructure,

Starting point is 00:26:01 but in specific directions that are all a little bit different. So we've got a common ML, let's say, search team, and now we have a bunch of teams that are kind of working in parallel in different kind of customer problems that we're trying to solve using that shared infrastructure. So I think this isn't the steady state. I think over time what it'll probably look like is that all the existing product areas as soon as we kind of know more of the shape of what the technology is capable of,

Starting point is 00:26:27 we'll just have, you know, AI capabilities as part of their roadmaps, just like every product team is responsible for their own mobile roadmap. They don't have, they don't outsource it to someone else. But I think today when things are moving so quickly, you actually want a little bit of a more kind of ad hoc, flexible approach to move quickly. And that's what we're doing. That's kind of what I've been hearing from everyone I've been asking this question. The search ranking team, as always seems to be the center of all this. And then it's a few experiments here and there.

Starting point is 00:26:56 So that's an interesting pattern I've been noticing. Good to know. I heard that you have a process internally called complaint storms. And I'd love to understand what that is. It's something that started, I want to say, back in 20, in the 2019, maybe early 2020. And the idea a little bit was, how do we help as a team look at the software that we build with fresh eyes? Because we've been started at Slack for a long time. And Slack, maybe more than almost any other company, maybe like Figma is probably similar.

Starting point is 00:27:25 I was listening to the podcast just earlier today, where if you work on Figma, you work on Slack, you also live in Slack and you live in Figma all day. So you can become more of a power user than anyone else on Earth. And what we were realizing, especially for people trying to build Slack for the next million customers, the people who have never used Slack before, it was becoming increasingly hard to kind of have empathy for what their usage of Slack would look like. How would they look at it in a more critical way? How would they care less than we care? And so what we started doing was these complaint storms. An idea was really simple, which is we'd get a team together.

Starting point is 00:28:00 often Stewart or myself would also join and we'd actually start off with other products first like in adjacent spaces and we'd say okay as a group we're going to go through like the customer journey from the moment you land on the website through let's say it's a workplace product getting your first account going getting the first couple of users on board getting to the point of value

Starting point is 00:28:21 we're going to do it on one screen someone's going to project and then people are going to fill in every issue everything that's confusing every pain point out bugs, but ways in which if you didn't care about this software, you don't work on it, what would actually confuse you? What would stop you in your tracks? And from that, you went generating a bunch of amazing inspiration by looking at someone else's product in a really critical way for things you might want to try your own product.

Starting point is 00:28:48 Once you get to that, then it becomes easier to actually do with your own software, but it is a little painful, obviously. Same with watching usability tests to look at your own, you know, baby in a way that is, okay, I'm trying to find all the words. I'm trying to find all the problems. But that's wind up being a pretty great source whenever a team, I think, either gets stuck or it feels like they reach like a dead end

Starting point is 00:29:08 in a direction, is doing complaints towards about the product area that they're in or using adjacent products just to get inspiration. And then I think it kind of unlocks a lot more kind of creative views than the problem space. It's similar to a process that I learned Stripe has called friction logging.

Starting point is 00:29:26 But I love the nuance here of starting with someone else's product, because I could totally see how that makes you feel better looking your product than real life. Like, it's not like we suck. It's, okay, everyone's has so much opportunity. Exactly. Yeah, I've heard that from Stripe, too. I think it gets a similar place. And I think it's the doing, I think the byproducts is that you also get like calibration on product taste, product quality. And as a team, you kind of develop that together. Again, similar to the principles. It's like, how do you get these things that are kind of hard to actually feel collectively out on the same page about and how do you calibre? And how do you

Starting point is 00:29:58 calibrate, it's another good way to do it. I'm imagining some PMs might be hearing this and wonder, okay, great, now the founders and the execs have all these things that they want us to fix. I have like goals to hit. I got a roadmap. How do you think about prioritizing things that come up in these sorts of sessions for the team and how do they mix and match versus all the other stuff they want to do? Or is it just like they don't actually have a huge roadmap and this is a way to form the roadmap? No, I mean, I think more broadly, I think the way that we think about or I like us to think about our roadmap for any feature team at Slack is that it's a portfolio and it's meant to be a portfolio that's diversified a couple of different ways right i think one is you want to diversify things that are meant to be new capabilities versus making the thing you've already built a little bit better every day similar to parenting uh are there things that are meant to be risky that you aren't sure are going to work but might have a lot of outside for things that are kind of known bets and then i think often you're kind of balancing are you doing things that are meant to have impact that you're already very confident in versus things that are

Starting point is 00:31:02 meant to learn about a new possibility space. And so I think for most teams, this stuff usually wind up tactically filling up that bucket of let's make the existing product a little bit better every day for users. And at Slack, we have this thing called customer-love sprints, which is an interesting way teams that throughout, how to get this on the roadmap is it's hard to allocate that work throughout the quarter. So what we wind up doing often is have a team do a truly customer love sprint, almost like a hackathon, but with that kind of burned down a list of what we think is the lowest, effort, highest impact changes we can make to generate more love from our customers

Starting point is 00:31:40 and whatever that feature area is. And then people just sprint for two weeks, design, product engineering, and then you have a bunch of things that you celebrate at the end, and the goal is to ship all of them. So this isn't like hacks that you throw away. So that's kind of how we wind up prioritizing it off and that kind of work is actually kind of making it this really fun total change of pace throughout the quarter to not do big feature work that may take months but to do all these small delightful things that you know customers are going to love at the end so that's the other way that we kind of figure out how to balance it in I love that and how often do these sorts of customer love sprints I think teams that work on very user-facing products do it

Starting point is 00:32:17 at least once a quarter so I think other teams that work on maybe less user-facing might do it maybe twice a year, but quarterly is a pretty healthy cadence. Wow, I didn't know about that. And that kind of connects to Slack has always been a very delightful product. I remember early on the animations were so awesome, the little twirly, I don't know, pound hashtag thing. And it feels like Slack has always invested in delight. How do you operationalize that?

Starting point is 00:32:43 Is it these customer left sprints? Is there something else that's just like we need to allocate some percentage just like make things really fun, even though it's not going to move any metric? I would say it's a little bit of the company, honestly, which is that four co-founders were trying to build a massive online role-playing game for many years that was called Glitch. And their kind of background was all in like building the playful, playful experiences. Glitch didn't work out, but, you know, there's a whole long back story. But the short version is a tool they had built internally that they then wound up spitting out a company from, which became a slot.

Starting point is 00:33:18 I think that DNA we're trying to build a consumer-grade experience that just happens to be for work is really great in the company. It's also a big part of how we hire. I would say certainly the majority of PMs, designers, and engineers who join Slack had never worked at enterprise software company before. It's not like most people have worked at Oracle or SAP. It's most people have worked at consumer companies or game companies. And so they bring that focus in the spirit.

Starting point is 00:33:45 And then I'm saying the last bit beyond kind of the principles or the complaint storms and the customer love is that we have this amazing team that we call the CE team, the customer experience team. And they're kind of in some ways the team that is doing our scale support, but is most often in touch with our customers. And from the very early days, you know, people used to do CEE shifts if you worked in products so that you can actually figure out what's frustrating, what's confusing. And we have a really great kind of pipeline for getting the insights from the CET team. team, what are the obstacles, the pinpoints, the most frequent complaints into the hands of the product teams to be able to prioritize to figure out, yeah, not all these are going to move a given metric. They might not achieve something for the business, but collectively, I think the way that Slack thinks about competition is we obsess it up customers. We build something

Starting point is 00:34:35 they'll love enough to tell their field workers, and the rest kind of takes care of itself. Speaking of competition, something I wanted to ask you a bit about. So early on, Slack was competing against this product called HipChat. And that's actually what I used at our startup. And we love HipChat. It's so hilarious. Just these memes everywhere and their billboards are amazing. But then Slack ate their lunch.

Starting point is 00:34:56 Later on, I'm just kind of thinking out loud. Discord feels like that was the big threat. And now Microsoft Teams, obviously. I'm curious just how you think about competition and even just what you've learned about working in a space where there's a lot of competition and thinking about that long term and even short term. Yeah. I mean, each of those is kind of like an interesting mini kind of less and learned about those. And I think the through line for all of them, I would say, is still the

Starting point is 00:35:20 maxim that we have in Toronto, which is we're customer-obsessed, but competitor-aware. So I think it's a little bit different. I think some companies are like, I don't know, Uber, for example, I think it was notorious, like, competitor-obsessed. And, yeah, they tried to tell you like customers when they could. I think hip chat, I don't think Slack saw it out to, like, kill hip-chat and force where we used, I think it was all campfire back in the day from the 37 single people. So there's a whole generation of those products. And I think Slack came along. I think they had a couple of innovations.

Starting point is 00:35:49 One was they had a great mobile experience that synced across every client. Search actually worked. And then they brought a lot of the best parts of consumer messaging into the workplace, like emoji and reactions and all those bits. And I think it turns out that, you know, if you're 10x fed on a couple of those axes, then you can see a huge changing behavior. And so I think that's what happened with that, moved from like the hip chat, campfire to Slack world.

Starting point is 00:36:15 Discord is interesting. I mean, we keep aware of Discord, but it is so much more focused on the kind of consumer. It really was damning out for community space. And I think at Slack, the lesson I would have, I think we learn in a good way is we've always really been a focus on groups of people who are trying to do work together. And that ends up being a completely different audience to build for than communities. And so I think that focus has been really helpful. And I think Discord is amazing. And many people love it. And the people who use Discord, to really use it in a very different way than people use Slack at work. I think Microsoft obviously has become over time the biggest competitor there. I think the origin of teams really was a defensive move for them to protect Office, because Office is an incredible, very profitable kind of monopoly in the productivity space. And so I think when they built teams, it was more of a kind of covering their flank versus Slack kind of on the ascent.

Starting point is 00:37:10 I think as Teams has evolved over time, it's become much more of a video conferencing product that compete with like Zoom Google Meet, the people who use teams, use it completely different than Slack where you live and breathe in channels and work and kind of workflows all day long. And I think what we've seen there too is that a lot of our customers, they have to use both. Most Fortune 500 companies have either an office subscription

Starting point is 00:37:34 or a Google Workplace subscription, and all of those customers who use those, also use Slack. And we like to say that Slack is this connected tissue that makes all the rest of your tools that much better. So I think there we've kind of taken very much an open ecosystem and platform approach. And we've just been focused on how do we keep building the best version of what Slack can be as a new category of software for our customers. And, you know, staying aware of our competitors, but really obsessed on what are the new ways that we can delight our users as the years go by.

Starting point is 00:38:04 So Slack is kind of a big-ish company within now, let's say, a big company. But it feels like you still are launching really interesting stuff. You launch huddles, clips. There's this AI stuff coming, sounds like. I'm curious what you have done at Slack to enable these sorts of zero to one bets and what you've seen is important to allow for sort of, for innovation along those lines. I think maybe we're all self-delusional because I think everyone who works at Slack likes to think that we're still at a small startup.

Starting point is 00:38:32 And I think keeping that spirit alive, honestly, culturally has been a big part of it. You know, I think good back to the principles early on, one of the ones that we to talk about literally one of the actual wording is take bigger boulder bets and the idea there is that it's really easy to fall into the trap of just constant incrementalism you know the concept it's a feature team and you have like a kPI and you feel like your whole life is measured by that similar kPI going up 1% a quarter and then you kind of lose sight of what's beyond the horizon and so we have this kind of mental metaphor that we talk a lot about getting to the next hill and the idea is that if you're in a mountain range or maybe in a little valley, you can kind of see what's right in

Starting point is 00:39:12 front of you, but you have no idea how tall the mountains are behind. I think teams can often get lost kind of crawling up that hill, not really good. There's a huge, incredibly beautiful range behind it. So take bigger, bolder bets, get to the next hill to see what the horizon wants like around you. That's kind of how we think about it strategically. And then I think structurally the way we've approached it is that we've over-time freighted kind of new teams, from scratch that incubated in a new area before the area is mature. So we did that with a lot of these kind of native audiovisual products like huddles and clips early in the pandemic because our customers were demanding it from us.

Starting point is 00:39:49 They were like, we love living in Slack a day, but we feel disconnected from our teammates where we can't be the same physical place, like, what can you do to help us and match where that came from? And I think in the AI space now, it's a similar thing, which is what we're trying to hear from customers like, what do you wish Slack could do if it had these new superpowers? and let's incubate a couple teams, a prototype there, and then figure out what can get to real product market fit.

Starting point is 00:40:13 And I think when we have those teams, I think it's important just give them space to run to give them kind of a gel-free card for maybe the normal process of, you know, okay, our planning, quarterly reviews, and make it feel something that is, like, the pace of learning is what matters. Like how fast you prototyping,

Starting point is 00:40:32 how fast are you learning from users, and then getting to do that publicly and pilot, and then get something. to launch that's amazing blows people away. That's kind of the formula that we've seen. This episode is brought to you by Vanta, helping you streamline your security compliance to accelerate your growth. Thousands of fast-growing companies like Gusto, Com, Cora, and modern treasury trust VANTA to help build, scale, manage, and demonstrate their security and compliance programs and get ready for audits in weeks, not months. By offering the most in-demand

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Starting point is 00:41:33 That's V-A-N-T-A-com slash Lenny to learn more. to claim your discounts. Get started today. One of the things I love learning about from product teams is their unique rituals and traditions. And I'm curious what's maybe the most interesting or unique or funny ritual or tradition on the product team of things you all maybe do regularly? One of the things that we do, which is kind of always a little bit funny. I mean, it's more of a emotional thing rather than a practical thing, is that at all hands will often wind up taking like specific tweets that people had about their product and you know Twitter people say

Starting point is 00:42:10 the craziest thing sometimes uh and sometimes they're like really heartwarming like customer love but often it's just the the meanest most frustrated complaints that people have and it's honestly for us to just have a pulse on like where people actually saying and feeling in the wild and not thinking too seriously but keeping that sense of you know i think that the distance you have from your user as your user base gets more and more diverse and larger i think kind of make it harder to actually develop the product because you're not designing for yourself anymore. And so I think all the ways that we help keep people grounded in like what are actual users actually saying, that's one big way. And the other that reminding me of, which is actually

Starting point is 00:42:51 probably better maybe delete that last one because it's kind of worrying. No, that's great. We're not deleting nothing. Fine. You know, user, so I'm a big believer in you want to be data, you know, informed, but you don't want to be so data-driven that you actually don't have a pulse on what real people feel when they're using your product. So we're really big into user research, not as it gives you the answer, but it helps at least pose a lot of questions for you when you watch how someone actually uses the software. And historically, it's really hard to get PMs, let alone engineers, actually like 10 user research sessions. And so what we wanted to do, especially been in the pandemic when we first want to promote is, you know, now you can dial into usability

Starting point is 00:43:34 sessions. And to make it really attractive for the team, what we would do is have people live kind of like in a thread, write their real-time thoughts of like, so people how they use that, or I can't believe they missed that or, oh, that gave me this idea from seeing how they were doing that to do this other thing. And so then you wind up having the PMs, engineers, designers, and the user researcher all in one Slack thread, like live responding, you're acting for usability session. And then suddenly that thread becomes actually the best kind of source of truth for the research report that then gets rid of up. But I think most importantly, it gets the team, almost like the complaint storms, but actually watching someone else do it, like in the shoes of

Starting point is 00:44:12 an actual human being trying to use the thing that you thought was so brilliant and yet has all these flaws. And it's humbling. It's filled with humor. And also it's, I think, really constructed for the teams to do it that way. I was going to ask where they actually share these thoughts and in Slack makes a lot of sense. Yeah, I mean, it turns into a report at some point, but literally you just link back to the original thread, and then you have like a hundred people's reactions as the report is kind of ongoing.

Starting point is 00:44:41 If only there was a AI tool to summarize all of your thoughts. We've got a prototype for that. Hopefully it'll work well enough. That actually would be useful for customers too. You tweeted once about how, I think maybe around the time you joined Slack around 2019, that the self-service business of Slack basically plateaued, and it wasn't clear why.

Starting point is 00:45:03 I'm curious just what that period was like, and how did you kind of get to the bottom of what was going on and turn things around? Yeah, it was actually a clear that after I joined, but it was a point where I was kind of focused on the self-service business because we had this period with Slack where, I would say maybe 2014 to 2017, where it was almost all self-service,

Starting point is 00:45:23 and it was just growing like gamebusters, and then we started spinning up the sales team, and an enterprise team, we started focusing mostly on that. And I think we kind of, you know, we saw the team that was working on self-serve, but it was primarily the company's focus was all driving enterprise deals, kind of getting to that next level of maturity. And then in 2019, I think we started to see that when we look beneath the surface, the, you know, fundamentals of the self-service business weren't looking as healthy as they used to be.

Starting point is 00:45:50 I think kind of the biggest thing as we kind of dug into it was a little bit to what we're talking about earlier with the motivation you had complained storms is it was getting harder to understand what the next generation of Slack customers really want from the product. And whether your finger medicines crossing the Kazim or moving from like kind of early adopters, the needs of kind of the more majority or later adopters, I think we're at that point where not every technologically sophisticated company at Earth was using Slack, but most were. And we were getting into a market that customers have different needs, they had different levels of sophistication. And so we get a lot of user research, we look at all these cohort curves, which you can imagine,

Starting point is 00:46:28 suddenly they're like, how they're not as healthy as they used to be, like, what's going on? And I think, you know, we got a bunch of insights from it, but I think really what we want of changing about how we were operating was instead of to continue to try to optimize the things that had worked over the last couple of years, we said, okay, let's kind of throw the whole road map away. And instead, let's come up with a bunch of hypotheses about what could be new levers that can actually help based on the insights that we now have about the next set of customers. And we're going to try to quickly learn which of these levers are real and which of these are just totally off the mark.

Starting point is 00:47:04 And we kind of had to say for the next six months, we're probably not going to drive any impact at all. It's only going to be about learning. But at the end of that, hopefully we wind up finding a couple different levers that had years of room to run. And that's what wound up happening. We wound up kind of doubling the rate of our new paid customer growth in a year, in a couple of years after that and kind of re-accelerating the self-service business. And I think it really came from stepping back, being humble, not feeling like we deserve to have every company at Earth sign up and then figuring out how to optimize for learning so in the long term you can get the impact.

Starting point is 00:47:39 But knowing that for the next couple quarters, we're going to sacrifice impact for the sake of learning. And I think there's a good muscle to build, but it was definitely not easy to do at the time. Well, this story begs the question. What are the levers that worked, whatever you can share? One of the big things that we wanted to focusing on is what we talk about is comprehension, desirability. So the fundamental challenge, I think, for new users or new teams using your product, once you get past the kind of tech early adopters is, do they comprehend what this thing is for?

Starting point is 00:48:08 Do they understand how it works? And then desirability is, why should they care? You know, most people at work are not like, hey, you know what I want to do today is starting an entirely new tool and convince all my coworkers to get on board. That is not part of your job. Your job has goals and measurements and everything else. So really deeply understanding that and how do you push on that in that new user experience? It sounds maybe a little ludicrous, but Slack has a premium product.

Starting point is 00:48:36 Obviously, there's a free tier that you can use, but we had never actually figured out a trial strategy where we actually gave you a taste of the paid product. Either we're on the free tier or you had to pay for the paid tier. And that one of being one of, I think, the ripest veins is figuring out how to give people a taste of the full premium Slack experience so that they would never want to go back in doing that in a variety of different points in the customer journey. And I think the other biggest thing I would call the one out is we really need to figure out a new North Star metric for motivating the teams across Slack. At that point in time, we basically had paid customers and then we had created teams, which is like the very, very beginning, very, very end of the journey. And we did a lot of quantitative research and data science and one of coming up, there's a new metric we called successful teams, which is a little bit, you know,

Starting point is 00:49:24 I feel a lot of them has like Facebook's, I don't know, looking number seven or whatever it was, where what we found was that if you could get five people using Slack, the majority of the work week, to just communicate at all, that would be a successful team. They're going to be 400% more likely to upgrade over the next six months. And that seems like a very low bar, like five people to use, Slack throughout the work week, not even every day. But it turns out that if you could get that level of critical mass, kind of the rest would take care of itself.

Starting point is 00:49:54 And we wind up motivating not just the team that's focus on self-service, but all these other feature teams across the company to drive more new successful teams, knowing that if we can move that, which is much early in the funnel, but not a top of funnel metric, then it would actually drive upfraids and paid customers and thus revenue long term. and that was a huge kind of turning point for how we rally product teams around to me and actually drive that self-service business. Man, this feels like its own podcast just to analyze the things you learned down this journey.

Starting point is 00:50:26 And there's so many takeaways here. One is just the importance of an activation metric that is predictive of retention. So it sounds like you landed on five people in a company like DAU basically for a week, something like that. That's awesome. And then the other interesting takeaway here is I'm actually doing a bunch of interviews. with founders of the most successful B2B companies. And interestingly, they all, not all, maybe half are like,

Starting point is 00:50:50 I still don't think we have product market fit. Like they're at like a billion dollars valuation growing like crazy. And they're like, I feel like I have product market fit with the current users, but I don't with the people I want. And that's what you're describing, right? It's like the new, you stopped having product market fit with people that you wanted next. I think it's exactly right. I think of like product market fit is almost like you keep stacking these esterves

Starting point is 00:51:12 where you get product market fit in a small group, and then you suddenly reach exponential growth because you can crack that whole group, that type of audience. But then you start declining because you start hitting the ceiling of, like we've gotten, I don't know what it might be, every development team in the U.S. to be using this product. And then you jump up to the nexus curve, which is like, how do we get technology-savvy teams that aren't developers?

Starting point is 00:51:35 Or how do we get people who are, you know, even large enterprises who are outside the U.S.? And these each become the new curves that you have to build product market fit for. And I think this is all a huge exercise in like being self-critical, being humble, not presuming that you've cracked this thing forever and keeping kind of a very beginner's mindset of what does the next audience need that their previous audience didn't need at all. If you think about the pie chart of what you had to change to make it work, how much of it was like messaging, positioning, onboarding optimization versus like product

Starting point is 00:52:09 features? I would say maybe 60-40 in the sense of the early journey, I mean, not just obviously positioning, messaging, but like the entire threads of like unboxing Slack, if you will, with your team. You know, we called it the day one journey, but extended to really kind of like day 30 in reality. And it's a single player and multiplayer experience. So it is really complex. But then I think what we realized was you can make that incredible. but if fundamental parts of the product were missing that would make it comprehensible to the next audience, then you're going to have problems.

Starting point is 00:52:45 So like it sounds maybe impossible to remember, but Slack used to not have whissywig message composition. You used to have to use Markdown. And so making Matt Whissywig was a huge boost, making mobile work offline. So it worked no matter where you were in the world was another big one. All the things about configuring your sidebar notification. so that as you scale your usage of Slack,

Starting point is 00:53:09 it didn't become overwhelming. Those are some of the kind of foundational product investments that we wound up making so that that next generation of Slack customers could get value and not be overwhelmed or daunted by it. Maybe one last question along these lines. People look at Slack as kind of the, maybe the first major product-led growth success story

Starting point is 00:53:29 and they always look at Slack of like, oh, we just want to grow like Slack. Let's see what they did. For people that are studying Slack's journey and success, What do you think Slack did write early on that maybe people don't recognize or don't appreciate enough that founders today should be thinking about more so versus just like, let's just make a freemium product. Right. I mean, I think maybe the most telling thing is when Slack started, it's really when I joined. So I don't think a word or acronym product like growth existed.

Starting point is 00:53:58 So it wasn't like we were really good at taking this playbook and applying it. I think it was more that whole term of art became a thing as maybe many other. kind of freemium SaaS products kind of took off. You know, I really think, not to be repetitive, but I think the core of it really was building a product that customers loved enough that they would put their own social capital on the line to get their coworkers on board. And that was easy enough to use and get the value from that without ever talking to a salesperson, you could put a credit card down or expensive if you wanted to for just your

Starting point is 00:54:35 team. I think when people think about this product, like growth notion, I think there are really two very different audiences. And I think Slack was able to crack both. One is when your team is small and your company is small, it is the entire company if you're an S&B. And I think that's the most like Slack's sweet spot. When the original pitch deck came to the investors, they said Slack is the companies of five to 50 people. At the time, the biggest company imagine using Slack was 50 people because I don't know how this is going to work beyond that. It'll become pandemonium. Obviously, that was the initial, I think, real, real strong product market fit.

Starting point is 00:55:11 But the other bit, which then was what powered the enterprise business, was teams of five to 50 people who worked at larger companies. And I think what wound up happening was that you would have teams independently at a company like IBM or Disney or Capital One or whatever it might be or Comcast discovering Slack, using it for themselves because they thought it would just make their working lives simpler, more pleasant, more productive. and maybe not even know that any of us at the company was using Slack. And then by the time we didn't scale their enterprise sales team, I mean, truly the exercise initially was just take customer domain, sort by number of active users, and call them in the order of that, which is, you know, hey, by the way, you have a couple thousand people actually using Slack at your company. Like, do you want to think about a broader deployment or controls or analytics?

Starting point is 00:56:00 And so I think that that was it. That's consumer-grade experience that customers love enough to get their co-workers on and pay for themselves. And then at enterprise companies, like having a bunch of different flowers, sprouting so that eventually you could roll up at enterprise-wide kind of deal. And then there's all the tactics. But I think that that was where it started.

Starting point is 00:56:20 The way you described at the beginning, make a product that people want to share with their colleagues. Reminds me about I was just listening to an interview with Seth Godin, who's this, you know, marketing legend. I think he has a new book, so he's on every podcast. And he had this really great quote that the products that win are ones that you want to tell your friends about. And it's a really simple concept.

Starting point is 00:56:39 And basically it's like it's word of mouth is how you have to win. But I think that's so true. Like every successful company I talk to ends up being like, we just want to build something. People want to share with their friends. Even if it's growing in some other way, SEO, paid, feels like that's always at the root of it. You just like want to tell your friends about it because you love it. And Slack, I think is a great example of that. I think that's true.

Starting point is 00:56:59 And I mean, obviously there are categories of enterprise software that isn't true for like in security or data. Like, I think if it's an awesome security product, you're like, hey, you got to check out this like Century or whatever or sneak. Yeah. Like, I'm good friends with Vance to see you, Christine. I mean, I think they'd remind those stories where whoever would have thought on like a compliance company would be something that people raved about to their other startup friends like,

Starting point is 00:57:24 oh my God, you don't want to deal with like socks compliance. You got you in advance. It's amazing. So yeah, maybe that is true. I think especially in the same age where all the marketing, position channels have been so saturated, people optimize them so much. I think it's really hard to scale a big enough business if you don't have some amount of word of mouth and customer love-driven growth.

Starting point is 00:57:46 I think it's hard to scale it on like we're going to just play a cat game and hopes that the numbers work out. I remember Slack rolling out at Airbnb and all the designers getting so excited about it, creating their channels and everyone's just like, what the hell are they doing? What is this thing? And then it did exactly what you're describing. Just spread. And everyone's just like, whoa, this is cool.

Starting point is 00:58:03 And they're all telling each other that how useful it is to them and spread like crazy. I love that. Is there anything else on Slack that you think would be interesting to share in terms of what makes it a successful product team, product business, before I move on to another topic? The other thing I think is maybe a little bit interesting in terms of how we develop product. And it's really a different change over time, which is that obviously the easiest person to build for is yourself. and the next thing is people who look almost exactly like you or have similar preferences and sophistication. And I think in the early days of Slack,

Starting point is 00:58:40 that's basically what we did. I mean, it was like really just trying to build for small, technologically savvy teams in terms of, you can build a pretty big business making a great product for them. Over the years, obviously, that's changed. And so one of the things I think that we've done, which has worked really well.

Starting point is 00:58:55 One, obviously, is we figured out how to do experimentation in a SaaS product, which is not always obvious because the metrics are much, longer term than, you know, you land out a checkout page and then you hit checkout. But I think the other thing is we figure out how to scale up getting real customers using Slack in the wilds for new functionality. And so we have this really robust program that we call kind of pilot program where we have probably thousands of different customers that have all signed different agreements now where we can actually roll out to progressively larger user bases. Because Slack is a multiplayer product, you often have to roll out.

Starting point is 00:59:31 real net new functionality to a whole company or whole team, because otherwise, you know, you can't use huddles by yourself, for example. And then we have a really great program for actually getting feedback from those customers, but through Slack Connect itself, through surveys, and this winds up being kind of a lifeblood of feature teams where you can, by the time to actually launch a big net new feature for Slack, have gotten so much customer feedback from people actually using in the wild to get work done, and so much more confidence in what you're building from the metrics, surveys that we do that you can't guarantee it's going to be a hit, but you can be really confident, not because it just worked well eternally, which is no longer that predictive, but because

Starting point is 01:00:11 it worked well for a thousand different companies, 50 different countries, and 20 different industries. And so I think, you know, early on, SaaS companies don't need to figure that out, but I think as you grow and as you have them more diverse, customer base, as you know, you said all these SaaS founders who said, hey, you got to like keep reestablishing your product market fit. I think that is like a programmatic way of being able to do that with your product development process. That's pretty interesting. Any tips for how to choose who to include in this group if someone wants to build something

Starting point is 01:00:42 like this for themselves? I think the two most important things are you want a lot of diversity in terms of industry, company size, location, and so on. And I think you want to pick people who are actually motivated to want to be part of the development process and have a slightly higher risk tolerance. not every company wants to actually be beta testing new functionality that might get removed. So making sure we have kind of a, there's like champion network that we built to people who love Slack enough that they're willing to put up with a little bit of pain in that

Starting point is 01:01:12 rougher period or are willing to have something that they tried to use. And then we decide actually we're going to fill that feature before we ever shift it to everybody. So diversity and, you know, pain tolerance. This reminds me of something else. The CTO of Stripe shared it of how they build new product, which is they pick a couple customers that need a problem solved, and they just build it for them essentially and with them. And in B2B, generally, it's a lot easier to build something people really want

Starting point is 01:01:39 because they are very motivated for you to solve their problem and they're going to put in the time. And there's like, you don't need thousands of people involved. You just need a couple. Yeah, I definitely think it's one of those things where if you could do it away and they say, like, I can't live without it, like the classic, like, not like, you know, do you like it? Sure.

Starting point is 01:01:56 But can you work without this thing? if the answer is definitely not, you've built something that probably a lot of other companies will want to. All right. I'm going to shift to a totally different topic, which could also be its own whole podcast,

Starting point is 01:02:08 but let's just see how it goes. So you wrote this, I'd say, famous block post on product management called the 10 traits of great product managers. And I want to just try to go through this list briefly and just see how it goes. I don't want to, you know, this could be an hour of conversation,

Starting point is 01:02:23 but they just kind of run through it because I think it'd be useful for people to hear. And I think these are all 100% true even though you wrote this number of years ago at this point. And just let's just see what comes up. And then I have a few follow questions on this list. These traits are kind of, came after,

Starting point is 01:02:36 I wrote this other thing, which are like the five minutes about product management, which are all the things that people think product management is and why they switch to the job and they're disappointed by. And then I was like, let me actually write a positive version of this, which is the things that the job actually is about.

Starting point is 01:02:49 It's not a career ladder. It's not like the, you know, here's the structured interview things that you should interview for. But I think it's the actual job product around here. What is it about what does success look like? And I don't think they're really in a particular order in hindsight, but I'll read it in order. So living the future and work backwards, I think it's very much kind of the idea of as a PM is the one thing you're responsible for. It's kind of having a longer term vision and time horizon. So how do you carve out time to not just

Starting point is 01:03:19 be what are we doing on the next two weeks, but six months, a year, two years from now, how you immerse yourself in that and then bring ideas back, bring inspiration back to the team? I'm just going to throw comments out as you're going through them just add to them. So I love that this is like exactly Amazon's like approach of like work backwards, working backwards process. At Airbnb, this is actually like the main thing Brian wants pushed everyone to do is just think about the idealized product of like a magical world where this is totally solved and then work backwards from that. And then Paul Graham talks about this too, right? Just like live in the future and build it. I definitely rift off at least the Paul Graham thing because I remember reading that essay.

Starting point is 01:03:56 So he thinks, you know, everyone thinks that you can give sort of ideas by like, I don't know, sitting with their co-founder, laying in Dolores Park, looking up at the sky and like conjuring up the next unicorn or something. Definitely not how that works. You have to actually like immerse yourself in the problem space and try to imagine what the future will look like. And then what's missing for people to get to that future state. So yeah, I agree.

Starting point is 01:04:19 I also saw a great tweet by Shreyas the other day about how if you're working at a company with good leaders, they're never going to be. sad that your vision is too big and too ambitious if there's some reality to it that often they want that just like let's go let's think bigger let's how do we how do we change the way we think about the future of all this stuff yeah i mean that was when i was at google the thing i took away most from any review and larry and sergey was they would ask like how could we get like a hundred x the scale or how could this work for this what seemed like an outlandish use case but would like push the team to think much further into the future yeah i think the other the founders always want

Starting point is 01:04:56 That's what Brian Jusky always said too, just like, how do we 10X this? What would it take to 10X this idea? Yeah. So awesome. Okay. The second one, which is maybe obvious, but thinking about how do you actually amplify your team, so how do you facilitate ideas, how do you create energy, how do you create momentum?

Starting point is 01:05:13 A PM role, I think, can be a little bit unsatisfying you for usual where you create things yourself, opposed to you are the one who's amplifying what the work that's being created by everyone else is. So you have to kind of get into that, more of a facilitator, mindset. What I think about here is a lot of teams like don't want PMs on their team or don't like PMs or don't think PMs are valuable. What I find is that just means your PM is not good because if you have a good PM, they're just going to help you do the best work of your life. They're going to help you clarify things, prioritize well, unblock you, all that stuff. Totally.

Starting point is 01:05:46 And we should find out who wrote that expression early on of like PM should be mini CEOs. I think that's the most dangerous piece of advice ever in the history of product management, because I think that is how you end up having PMs who try to act like dictators instead of kind of leaders and facilitators. Because if you're acting like that, yeah, your team can completely reject you because I never want another PM again. Yeah. Like so many new PMs are just like, I'm finally going to have the power.

Starting point is 01:06:12 Finally, like if they move from engineering or some other role and then they get there and like, oh, what the hell? Yeah. To convince everyone of all these things I want to do. That actually, I'm going to skip in a slightly different direction of the order of this post. but the fifth one that I wrote in there was, your job is to facilitate the pace and quality of decision-making. And that is very different than you are the person who makes all the decisions.

Starting point is 01:06:36 And in fact, one of the things that PM struggle with early on is how do you actually get the team to be able to make high-quality decisions quickly without you kind of arbitrarily playing tie-break all the time? And it's a soft art to be able to do that. But I think that is actually how you have a really healthy team dynamic. Instead of PM2, I want to say, okay, now it's my turn to get to make the decision. It's definitely not what the job is in that. What that makes me think about is I taught a course on product management at one point that I paused for now. I've just like the core job of a PM is to figure out what's next for every single person on the team.

Starting point is 01:07:10 And there's this meme or gif of a dog on a train. And he's just laying the tracks as the team is moving forward ahead of them, just one step at a time. And to do that, this is such an important part of that. just help people make decisions and unblock them. Totally. I'll kind of combine two of these together. So one is you do have to have impeccable execution. This is kind of more of a baseline thing.

Starting point is 01:07:32 But I've never seen a PM who was like disorganized or didn't do follow up or wasn't clear about expectations or timelines. It's not high in Masel's hierarchy of kind of PM enjoyment. But I do think it's like a baseline expectation. The thing I think is more enjoyable. And probably the move. important thing in the long term is focusing on impact primarily to the customer experience but also to the business and I think you know there's that saying like

Starting point is 01:08:00 Worth solves all problems I think impact solves all like PM issues which is if the team is consistently building things people love and changing the direction of the business everything else is an input and so I think that focus and understanding as it's your point about laying the tracks is like what direction do you need to go as a team to actually drive that impact? That's probably the single thing that PM can most control. I love that. I always recommend exactly that. If like if your career is not going as well as you'd hoped or you're not getting promoted, it's usually you're not delivering impact, whatever that means to the company. Like it may be moving a metric may mean

Starting point is 01:08:40 building great product that the founders really love. Yeah. It may impact can mean a lot of different things. But it's so true. On the execution, executing impactably bucket, the way I think about that is as a great PM, you need to kind of have this aura of, I've got this. Anytime someone put something on your plate, it's not going to fall off. You're not going to forget about it. You're not going to let a ball drop. The more you can create this aura of like, I got this, the more responsibility if you were going to give you,

Starting point is 01:09:07 the more impact you'll end up having, the more people want to work with you and all that. Yeah, Ben Horowitz was a board member back at Foursquare. And I just remember you used to have this saying very good to like of, you know, good leaders need to, say what they're going to do and then do what they said. And if they can't, then they need to follow up and explain why. I mean, that's like the amendment.

Starting point is 01:09:30 And I think that is kind of a good execution looks like. That last point is so important. Like, you may not be able to do all the things on your plate, but just telling people, hey, I'm not going to get to this thing. Let's reprioritize as such a small thing you could do and really creates that or have you got this. They're not going to forget about this thing asked you to do. Yeah, you're kind of the shock absorber for the team.

Starting point is 01:09:50 You're the thing that builds people's confidence that things are going to be running smoothly, and you'll get over the inevitable speed bumps and whatever else. So I'll combine two or three of these that are kind of related or just more skills. I said, write well. Like, I actually think, especially as you get to more senior positions, writing is the only scalable way of having confluence on a larger and larger product org. There's a book called On Writing by Stephen King, which I recommend that literally everybody. you know, Stephen King, you're like, he's not maybe the most like literary, like critical acclaimed author,

Starting point is 01:10:26 but he's a prolific author who publishes things that people love and tell their friends about. And he has a great short book on like the practice of writing high quality, high volume production. Before you move on, I'll throw out a couple more books that I found useful in my writing. One is actually called On Writing Well, so that's kind of funny that they're so similarly titled, which basically every chapter is just another way to. it cut more from your writing. Like more and more parts you should cut. And interestingly, I do have a lot of guest posts at my newsletter and I find 90% of the

Starting point is 01:10:58 time, if I just cut the first paragraph of what they first took a crack at and jumped straight into the thing, immediately gets better. And this book talks a lot about that. Another book that is amazing for writing better is nobody wants to read your shit by the guy that wrote the War of Art. Forget his name. But that book is awesome. and it's just like nobody wants to read what you're writing.

Starting point is 01:11:20 Here's how to maybe make it something people want to read. And then recently I read one called several short sentences or something like that. And it's all about just writing short sentences and that helps a lot. So there you go. Three more recommendations. Okay. I got to read the last year. I haven't read those, but they sound perfect.

Starting point is 01:11:36 Okay. Maybe I'll throw a little more, let's say, we talked about it's earlier, but actually wrote this from a post many years ago is like optimizing for the pace of learning and knowing that long-term, that's a thing that's kind of drive impact. I think it can be hard if you're a PM for a feature team. You're part of a big company. I don't know, making this up. You're on the AdWords team at Google and you're responsible for the, you know, bid input selector or something. It probably is a whole team, honestly, now at this point. You've got such a set of blinders on that I think it can be hard to think about, like,

Starting point is 01:12:10 what else could this team become? What else could you drive beyond a thing that's right in front of view. So opt for learning, being willing to take those bolder bets, knowing you can be wrong in the short term, but that you'll learn new levers that will be really fruitful in the long term. It's a portfolio approach to product, but I think a really important one. I was just interviewing a product leader at Asana, Paige Costello, and we were talking about how she's often the youngest person in the room and often manages people that are much older than her and more experienced than her and asked her just, how do you do you do that? How do you succeed in that sort of environment. And what she's found is just being the person that has the answers and the

Starting point is 01:12:50 insights in meetings, people obviously run to her. Like, hey, what do you think of this? Because she just knows what people are going to need. And so I think that's exactly what you're talking about here is just be the person that knows the most about the problem, the customers, the space. Yeah. And then I'll remind the last two, just because I know time, but the combination of data fluency, which is not to say that every PM needs to be a statistician, I mean, it's great. I mean, you've had a lot of great posts about, like, how to understand some of the basics of experimentation, correlation, causation, and statistical significance. That's all great.

Starting point is 01:13:23 But by data fluency, I think it's more actually what you were just saying, which is, like, you know enough about the insights about your customers that can then inform making higher likelihood product bets. And that data can be quantitative. That data can be survey-based. It can be from doing 100 meetings with customers yourself. those are all types of data inputs to me. So being really fluent. And then I think combining that with great product taste. I know it's like a controversial statement now.

Starting point is 01:13:51 It's to say that there is taste for product. But I do think in all the love of the frameworks and the analytics and everything else in the field of product, I think people sometimes lose sight of it's a creative field. It's not art on its own, but you get all the inspiration from art. And I actually think, you know, there's a look, I think it's called like creative selection. I forget the exact name of it about some of the early like iPhone development teams at Apple and working with Sue Jobs there. And I never worked at Apple.

Starting point is 01:14:22 But I actually think it's the best book I read about the just iterative creative work of building new products. And what it means to have taste, which is to say you've developed some amount of intuition for what people will likely love before you're able to. to test it. So anyway, I think taste plus fluency and data, that too is a combination. Is it a pretty powerful combo? Let me ask you just a couple questions about this list before we get to a very exciting lightning round and I can let you go. Okay.

Starting point is 01:14:54 Of these 10 attributes, say your new product manager, if you have to pick two or three that you think are most important to get right and focus on in your early career, which would you say they would be? I think for early on in your career, what I would say is getting great in execution, it's a thing that you can most control. Then I think building that news for impact, even if the impact is more local, because that's how you actually will demonstrate momentum and build credibility. And then actually do you think early on getting really fluent on the data and the research

Starting point is 01:15:25 sides that you can have insights, that you can bring back to your team. Those are, to me, like, the most slammed-up ways of becoming someone who starts to build credibility as a product manager in any organization. Awesome. That's what I always tell in UPMs, too, is just getting really good at execution because that creates that war of, oh, this person's just killing it.

Starting point is 01:15:44 They're just shipping on time. People know what's happening. They're hitting dates, things like that. Yeah. The last question is just say you're a senior, more of a senior product leader, say, I don't know, director. Are there three other attributes,

Starting point is 01:15:56 you think, are ones they should focus on most? Or maybe the same? I mean, I think this is where that case in quality decision making starts to matter a lot more because you're selling responsible sometimes for like teams of teams and you're helping to facilitate high-quality decisions, often ones that have a lot of uncertainty or risk or ambiguity. So how do you keep the organization unblocked, not just a team moving well? I think the living in the future and working backwards, I think the more senior you get,

Starting point is 01:16:26 you know, it's always going to be the product founder who is responsible for the ultimate mission, but you become more responsible for the meeting a longer-term strategy. to realize that vision. And so becoming just someone who can dedicate more of their time to be out of the fray of the day to day and think more about the longer-term strategy that you want to pursue.

Starting point is 01:16:47 And the last one, and we talked about just earlier, but I think being a really good writer, it is just the highest leverage usage of your time if you want to influence an organization, at least for one that doesn't, to spend all day in meetings. But I think it's really hard to dedicate the time to it because you're probably spending most of your day in meetings.

Starting point is 01:17:06 So it's the antidote to that to kind of scale your ability to influence the product direction and maybe even the principles and how you develop product at a company. Well, with that, we've reached our very exciting lightning round. I've got six questions for you. Are you ready? Let's do it. What are two or three books that you've recommended most to other people? These may not be the most unique, but I will say that, which is inter-reseloma by claiming Christians in.

Starting point is 01:17:33 whether you're working a large company and you're suffering it or you're working a startup and you're trying to outflank an incumbent, I still do think that and interviewer solution, the fall on are the best books on product strategy to read. If you're moving to more of a leadership or management position, I think radical candor by Kim Scott is just incredible and worth everyone reading. Frankly, if you're a PM and you're doing kind of soft kind of influence, I think it's really important. And then the third one, which is made a little off the beaten path, there's a book called Leadership in Turbulent Times by Dors Goodwin, who's a kind of presidential historian.

Starting point is 01:18:12 And it's this amazing book that looks at four of the most notable presidents and how their leadership style evolved when they were in really critical hard times in their presidency. And I just think it's actually the best book about like leadership style and how do you evolve and how do you deal with crises with. which again is maybe later on in your career, but I love getting inspiration from not just reading books about tech and product, and I think that's one of the best ones. What is the favorite recent movie or TV show you really enjoyed? The obvious answer, which I'm sure many people would say, would be succession.

Starting point is 01:18:48 I'm not going to ruin anything for the finale, because people haven't seen it all, but they're writing that Shakespearean-level drama at all. It's just incredible and just part-wrenching that you wind up kind of losing most of the characters, but you can't take yourself out of it. The one that's maybe less common, and I watched right when we started paternity leave,

Starting point is 01:19:08 is the bear, I don't know if you heard about it. The restaurant. Yeah. Yeah. I was sucker for, like, incredible cinematography, and just like what they do and basically the single room of this restaurant and kitchen and just the pace of it, I think it's just like an incredible piece of art.

Starting point is 01:19:25 I don't know if it's the best show ever, but it is a really moving like emotionally like jarring piece of TV. Also quite stressful to watch. Very sure. I would not relax to it to go to see. But awesome.

Starting point is 01:19:40 Okay. Favorite interview question that you'd like to ask candidates? You know, that would depend a lot, I think, on obviously the seniority level and things like that. But I think the more general, and I always left to ask people, is what unfair secrets have you learned to improve the velocity and energy level of a product team? Am I say unfair? Are you in secret?

Starting point is 01:20:03 I usually mean like not something that you probably read on like a medium put. What did you learn? How did you learn it? And how does it work and how do you apply it? You also just get amazing, interesting, like bits of inspiration from asking that. What is a favorite product you've recently discovered that you love? This will also serve for recommendations for you based or you not read about parenting points because none of the products I've learned or loved recently have been like software.

Starting point is 01:20:29 But they're all maybe software enable. So the nanit, which is like a kind of weird name, but it's just like AI enable camera for basically, you know, watching your baby as they sleep. It's like incredible. It's like to like sleep analytics and like really helps you be a less neurotic parent. I would highly recommend it. The snoo, which is basically like this amazing device that can help soothe your kid when all they need is like a little bit of like that, you know, soothing while they sleep so that you can sleep a little bit more. you can tell the scene here is sleep. And the last one is this criminal

Starting point is 01:21:03 up and maybe that has this whole like elaborate stroller system with interchangeable parts. And honestly, it's just like an incredibly well-designed piece of like hardware that works did now of the car. So yeah, I think I've re-appreciated really well-designed, like hard products that are not necessarily hardware from Apple.

Starting point is 01:21:24 And that has been what being in your parents is about. I have all three. Also a huge shout out to the Nanatine. who sent me a nanit and all the stuff around the nanit. So thank you. I'm not going to name the specific PM who sent it to me because I don't remember his name off the top of my head. But thank you, Nanit.

Starting point is 01:21:40 Yeah, it turned out as a whole world of baby tech, which I had no idea. I mean, it makes sense of existence, but you never know about until you're a parent. And now I'm obsessed. One tip that we, for Nanit, so my wife and I have been playing with different names for our kid, and we have been changing his name in the Nanit,

Starting point is 01:21:59 so that anytime we go into the room, it sends us a push, hey, there's activity in the room with the name so that we could kind of feel the different names. I really love that. Yeah, my wife and I did something similar where we had like three or four final name contenders and we didn't use the nanop for it. But we just picked a week and said on Monday we're going to like refer to the future baby buy that name for the entire week and like give some, you know, personification to it. And that helped us, yeah, get down from four to one.

Starting point is 01:22:26 So, yeah. What a ride ranging set up. of pieces of advice we got on this podcast. Two more questions. What is something relatively minor you've changed in how you develop product at Slack that has had a lot of impact on your ability to execute? By far, the biggest thing was more of cultural shift is that we stopped spending so many cycles on design explorations of like static mocks or walkthroughs and said, how quickly can

Starting point is 01:22:50 we get into prototyping the path in real software, even if it's messy and you throw it away, at least for something like Slack, like you've got to kind of live and we're touch and smell the software, you can't just look at it. And that's been a huge unlock for avoiding spending months on design debates and just getting to, well, how does the software feel? That's what matters. Speaking of Slack, final question, what is your favorite Slack pro tip that people may not be aware of? I'm going to give two, because if someone asked me this, I'm like, these are the two things that if you're not in love of Slack, you'll fall in love of Slack. So the first is, obviously, you have the sidebar, it can be unruly, but you can customize the sidebar into sections.

Starting point is 01:23:34 In each of those sections, you can have settings like show unred only or short by recency or short by alphabet, a whole, whatever might be, and you can collapse the section so you don't see it all at once. So I think having a well-managed sidebar, which doesn't actually take that long, it's like this amazing thing because then all this inbound is structured in an order and a grouping that fits how you. want to view your working life. So customizing sidebar. And the second thing is just use the quick switcher for everything. Just hit Apple K and just start typing. And it feels like they're playing a video game, just hopping around, channels, people, files, search,

Starting point is 01:24:12 pretty much all the actions you can take around as well. I think most SaaS products now have borrowed that pattern. So, you know, you can use another software, but it works particularly well in Slack. No, I know the last thing you needed was to record a podcast, your first week back to work. I so appreciate you making time. It feels like we're two ships passing in the night

Starting point is 01:24:31 from Pat Leave into New Pat Leave. And so two final questions, where can folks find you online if they want to reach out and learn more? And how can listeners be useful to you? I will confess that I haven't used Twitter or months because I was doing digital detox, but still I think at No underscore Weiss

Starting point is 01:24:46 is a pretty good place to find me online and whether there or anywhere else. Still love to have people's like Slack feature requests, especially about things that you wish for possible where that would get the rest of your company to join on Slack because you love it, but you can't convince them. Those are always golden nuggets. Awesome. Noah, thank you so much for being here. Thank you so much for having me.

Starting point is 01:25:07 Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about that. the show at lenniespodcast.com. See you in the next episode.

Lenny's Podcast: Product | Career | Growth - The 10 traits of great PMs, how AI will impact your product, and Slack’s product development process | Noah Weiss (Slack, Foursquare, Google)

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