The 10 traits of great PMs, AI, and Slack’s approach to product | Noah Weiss (Slack, Google)

We have this mental metaphor that we talk a lot about getting to the next hill. The actual wording is take bigger, bolder bets. 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 created kind of new teams from scratch that incubate in a new area before the areas 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. And I think in the AI space, we're trying to hear from customers. What did you wish Slack could do if it had these new superpowers? And let's incubate a couple teams, 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 to learn from their hard-won 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 7 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 Fawk Creek Software. And in our conversation, we cover the 10 traits of great product managers, 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 dad advice, which I found very helpful. 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, a trusted peer group where you can discuss challenges you're having, get career advice, and just kind of gut-check how you're thinking about your work, your career, and your life. This has been a big trajectory changer for me, but it's hard to build this trusted group. With Sidebar, senior leaders are matched with highly vetted, private, supportive peer groups to lean on for unbiased opinions, diverse perspectives, and raw feedback. Everyone has their own zone of genius, so together we're better prepared to navigate professional pitfalls. Leading to more responsibility, faster promotions, and bigger impact. Guided by world-class programming and facilitation, Sidebar enables you to get focused, tactical feedback at every step of your journey. If you're a listener of this podcast, you're likely already driven and committed to growth. A Sidebar personal board of directors is the missing piece to catalyze that journey. Why spend a decade finding your people when you could meet them at Sidebar today? Jump the growing waitlist of thousands of leaders from top tech companies By visiting sidebar.com/lenny to learn more. That's sidebar.com/lenny. This episode is brought to you by Superhuman. How much time do you spend in email each day? How about your team? You may not realize this, but your email tools are wasting your time. Superhuman is blazingly fast email for high-performing teams. Built to work with Gmail and Outlook, teams who use Superhuman spend half the time in their inboxes versus respond to twice the number of emails, and save over 4 hours a week. That's over a month of saved time per year. With Superhuman, you can split your inbox into streams for VIPs, team members, and emails from your favorite products 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 1 month free at superhuman.com/lenny. That's superhuman.com/lenny. Noah, welcome to the podcast.

Thank you for having me. I'm excited to finally get to join and been a longtime listener.

I feel the same way in reverse. I'm 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. Uh, this is, 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. I literally went back to work 2 days ago. So I think my advice about being a new parent is better than my advice about being a PM right now. Here are the 3— my wife and I wound up coming up with 3 maxims that we want to be using throughout the first 2 months to keep ourselves grounded. First one, I would say, a little bit better every day. No matter how many books you read, no matter how much Emily Oster 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 overextrapolate from the early days. Like they are, you know, the fourth trimester is a real thing. These babies 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 gonna be like the first 18 days. It's gonna be sobering. So like, keep that perspective. It gets, they develop so much every week. It's part of the fun. And then the third thing, which I got advice from this from a good friend, is like, you gotta fully get into it as a parent. Like, there's nothing that replaces actually, you gotta change the diapers, you gotta do the feeds when they're up, even though they can't talk, you gotta talk to them. You gotta like listen to what they're saying and just be fully kind of present in the moment. I kind of realized for myself, I've been like basically at full digital detox. You saw how long it took for me to reply to your emails. Uh, 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 feel really connected with her now after just a couple months. So it's a crazy time. You're gonna love it. It's gonna drive you mad at times as well, and that's all okay.

All right, we're gonna 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 were talking, so I'm gonna put that up in my, in our nursery and see, see, uh, see how it all goes. One thing that's tough about my career path in this weird life is I don't get, uh, a nice, uh, pat leave, you know, paid pat leave from a big company. So I've actually been working on stacking guest posts and podcasts ahead of my leave so that I can actually, as exactly as you said, just get fully into it. So I have 6 awesome— yeah, so I have awesome guest posts coming. 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 were head of product at Foursquare. And I don't know if you know this, I actually built a startup on Foursquare's API. It was a company called LocalMind. 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, hey, is this bar fun right now? What's happening there before you actually show up? 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 the 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, I'm sure, later. 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, okay, that didn't work. That didn't work. What can I actually learn and 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, 2013. But, uh, Yeah. You know, I hope a product like that exists forever in the future, and I'm glad you got to build the company and land at Airbnb through it. Uh, it'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 the direction of B2B data sort of business. So I guess, was there, was there a path or was it just like, no, that was never going to work out?

It's tricky. I mean, I'm not going to do like a 30-minute postmortem 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 the biggest probably lesson learned, frankly, is that we were really close to the Instagram folks early on. They were big developers on our platform. They used the Foursquare 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 tie it to, versus a person sharing a moment or an experience that they're having in the world. Yeah. And sometimes that might have a place connected to it. I think that one change in framing or what you would say, like the customer actually wanted to do, that probably was the thing that took us away on the social side. I think on the more kind of local discovery side, it's actually what people wind up 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, I think specifically of Google. Because they had a billion-plus Google Maps users distributed on Android and iOS. And even though they might only take a couple years, eventually they would wind up replicating a lot of the functionality. And then I think it was hard to regain that momentum. So much of this stuff is luck and timing and just coincidences of history. I think there was a path. I think in the end we lost our social sales and then Google was able to catch up on the utility side. And now the company's built a really valuable kind of B2B API company, which offers a story. I mean, Slack is in some ways a pivot, obviously from a consumer company to a B2B company. But yeah, that's my mini postmortem on what could have been with Foursquare.

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 signal you get from, are people willing to pay for the product that you're building? Is so 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 along the way. So yeah, I think B2B is easier to have a more incremental, successful business than pure consumer.

Okay. So speaking of Foursquare, 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 Stewart 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 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 founder's just telling you what to do and you have to go build it. Versus having a lot of say and agency. So I'm curious what you've learned about working and being successful in that position, which is often really hard.

I would kind of say to folks in general, if you're joining a company and the CEO does the role 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 one where you'll be the most frustrated at times because you're going to feel like you have less agency. And so you should just know that going into it. If you go to a company that's 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 it knowing that is good. Looking back, I would say probably 2 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 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 getting To the point where you have alignment on the principles for what it means to build a great product at that company. Not just about intuition and taste and gut, but how do you distill that into principles that become the language of the company so that everybody else can start thinking through a similar frame or a similar lens when you're designing product? Because otherwise it can feel a little bit kind of Goldilocks. Every time a team builds something, they take it to the CEO. CEO's 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 level of strategy as well. I think the product founder CEO is always going to be the holder of the vision for the company. I'm sure at Airbnb, I imagine 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 isn't the responsibility of any one team. Have 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. 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 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 is level of involvement. I think you want to get the founder CEO really involved early on, especially if it's a big new project, to make sure that there's strategic buy-in, that you agree on the principles for how you're going to approach it, you agree on the goals and the anti-goals. Getting that so then the team can run and explore. And then I think at the very end, you want them to really be bought in that, did you build something that's up to the quality bar of the company? Yeah. Is this something that's going to delight customers? Literally taste the soup. What's missing in it? And I think at most companies that have a maniacally customer-focused founder, 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 formula winds up working pretty well if you throw in that alignment on principles and vision.

That U-shape sounds nice in theory, but I often imagine you get to that final step and the founder is like, what the hell is this? This is not at all what I was hoping it'd be. Is there 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 U-shape is maybe the end of the U is kind of like the level of engagement, and often that last level 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 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 wind up doing with Stuart at Slack, for example, is we would get the entire development team, engineers, design, product, user research, and Stuart together in a room. And we kind of almost do like a bug bash together. And the idea was like, we're doing it all together. We're trying to make the best product possible. Making great software is really messy and we're all trying to kind of clean up the mess together. 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 it in 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's going to delight our users, and here's the gap from where we are today to what we want to ship. 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 the 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 lives simpler, more pleasant, more productive. That's the mission of the company. The question is, how does software help do that? That's what the principles are there to answer. So for us, we've got 5 core principles. They've largely stayed the same. Some of the language has changed over the last couple years, but at least for the last 4 or 5 years, we've had these. So the first is be a great host, which is all about kind of that level of craft that relates to saving people steps. If you're, let's say, a host at 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 4 core values.

Right. So maybe we borrowed that or someone was inspired by it, but be a great host sounded 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 stole the title of for our next principle. 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 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 tenets, 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 wind up designing for people who come from many different backgrounds and we 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 be okay. You'll often have in optimization 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 stressful, 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, for many years. I think at Google 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 it 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? 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 of information about 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 have gotten a lot more mature. So we used natural language processing to extract all this information from the web and try to build this database of facts. And the idea then was, could you take queries people have like, what are the tallest mountains in Europe? Or what are 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 6 to 12 months with LLMs and ChatGPT and everything else is The idea that now you can take not just knowledge about the world, but actually have natural language generation where suddenly the computer can 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 Foursquare, we did a lot of personalization and recommendations. At Slack, we have search and ML that's infused throughout the product. I think a couple things come out as principles that we've 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 the underlying data. Which is to say, and I think this is actually one of the failings of the various LLMs right now, is they all appear supremely confident even when they're completely hallucinating. 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 tool is 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 as a byproduct of people naturally using the software. that then can make the model that you're building behind the scenes smarter, more accurate, more predictive. So a classic example of that would be Netflix back in the day, their rating system. They actually got a feedback loop from their customers to 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 of LLMs.

Something I hope that you're all building at Slack is a way to ask a bot questions based on all the conversations 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 an aside, in one of the original Slack product vision decks back in 2014, there was our whole strategy. There's 4 parts. And then part number 4, which was a joke at the time, was then do magic AI stuff on top. And the idea was we didn't even know what the state of AI would be by the time hopefully companies had their collective knowledge in Slack. Yeah. And now we're finally at the period where the magic AI stuff seems finally pretty amazing and 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 this space so that if you work at a company where you have so much knowledge in your 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, the CPO and CTO and co-president of Spotify, shared 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 think 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 2 songs that are correct out of 10, just because we don't really know exactly what you want to hear right now. And it's just, there's no point in trying to design that right now because it's not actually going to be delivering on the promise.

Right. Yeah. I think our, 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 let 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 anytime soon, but I think like Spotify heading towards that North Star, you wind up developing, I hope, a lot of really compelling projects for answers along the way.

Yeah, man, the more I 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, 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?

I mean, the unfair answer is a hybrid of the two, which is to say we have a kind of central machine learning and search team. Where there's a lot of people who have expertise in this field to build infrastructure that everybody can use. And what we've done is, because the space is evolving so quickly, literally every month, the capabilities are evolving, the risks and trade-offs are evolving a ton. What we want to do is actually spin up a couple different teams that are focused on prototyping using that common infrastructure, 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, will 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 where 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 always seems to be the center of all this. And then it's a few experiments here and there. 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 end of 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 staring at Slack for a long time and Slack, maybe more than almost any other company, maybe like Figma is probably similar. I was listening to the podcast just earlier today where if you work on Figma or 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 cared? And so what we started doing was these complaint storms. And the idea was really simple, which is we'd get a team together, often Stuart 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 gonna 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. And we're gonna do it on one screen. Someone's gonna project and then people are gonna fill in every issue, everything that's confusing, every pain point, not bugs, but ways in which if you didn't care about this software, you didn't work on it, what would actually confuse you? What would stop you in your tracks? And from that, you wind up generating a bunch of amazing inspiration by looking at someone else's product in a really critical way. For things you might wanna try in your own product. Once you get to that, then it becomes easier to actually deal with your own software. But it is a little painful, obviously. Same with watching usability tests to look at your own baby in a way that is, okay, I'm trying to find all the warts. I'm trying to find all the problems. But that's wound up being a pretty great source whenever a team, I think, either gets stuck or feels like they reach a dead end in a direction. Yeah. Doing complaint storms about the product area that they're in or using adjacent products just to get inspiration. Uh, and then I think it kind of unlocks a lot more kind of creative views of the problem space.

It's similar to a process that I learned Stripe has called friction logging, but I love, I love the nuance here of starting with someone else's product because I could totally see how that makes you feel better looking at your product and realize like, it's not like we suck. It's okay. Everyone has so much opportunity.

Exactly. Yeah. I've heard that from Stripe too. And I think it gets to a similar place. And I think the byproduct is that you also get calibration on product pace, 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 on the same page about and how do you 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 it, 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 different ways. 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. Are there things that are meant to be risky that you aren't sure are going to work but might have a lot of upside versus things that are known bets? And then I think often you're balancing, are you doing things that are meant to have impact that you're already very confident in versus things that are meant to learn about a new possibility space. And so I think for most teams, this stuff usually winds 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 we call Customer Love Sprints, which is an interesting way teams have figured out how to get this on the roadmap. It's hard to allocate that work throughout the quarter. So what we wind up doing often is have a team do a 2-week customer love sprint, almost like a hackathon, but with that kind of burndown list of what we think is the lowest effort, highest impact changes that we can make to generate more love from our customers in whatever that feature area is. And then people just sprint for 2 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 often 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 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 you do these sorts of customer love sprints?

I would think teams that work on very user-facing products do it 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? How do you, is it, is it these customer love 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 DNA of the company, honestly, which is that the 4 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 delightful, playful experiences. Glitch didn't work out, but you know, there's a whole long backstory, but the short version is a tool they had built internally that they then wound up spinning out a company from. Which became Slack. I think that DNA of, we're trying to build a consumer-grade experience that just happens to be for work, is really ingrained 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 joined Slack had never worked at an enterprise software company before. It's not like most people had worked at Oracle or SAP. It's most people had worked at consumer companies or game companies. And so they bring that focus and spirit. And then I would say the last bit beyond kind of the principles and 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 scaled support, but is most often in touch with our customers. And from the very early days, people used to do CE shifts if you worked in product so that you can actually figure out what's frustrating, what's confusing. And we have a really great pipeline for getting the insights from the CE team. What are the obstacles, the pain points, 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 about customers. We build something they'll love enough to tell their coworkers, 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 loved HipChat. It was so hilarious, just these memes everywhere, and their billboards were amazing. But then Slack ate their lunch. 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 lesson learned about those. And I think the through line for all of them, I would say, is still the maxim that we have internally, 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 was notorious, like competitor obsessed. And yeah, they tried to delight customers when they could. I think HipChat, I don't think Slack sought out to like kill HipChat. At Foursquare, we used, I think it was called Campfire back in the day from the 37signals people. So there's a whole generation of those products. And I think Slack came along and I think they had a couple of innovations. 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 if you're 10x better on a couple of those axes, then you can see a huge change in behavior. And so I think that's what happened with that move from the HipChat campfire to Slack world. Discord's interesting. I mean, we keep aware of Discord, but it is so much more focused on the kind of consumer Originally it was gaming, now it's more community space. And I think at Slack, the lesson I would have, I think we learned in a good way, is we've always really been focused on groups of people who are trying to do work together. And that winds 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's amazing and many people love it. And the people who use Discord truly use it in a very different way than people who 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. I think as Teams has evolved over time, it's become much more of a video conferencing product. competes with like Zoom and Google Meet. The people who use Teams use it completely different than Slack, where you live and breathe in channels and work in kind of workflows all day long. And I think what we've seen there too is that like a lot of our customers, they happily use both. Most Fortune 500 companies have either an Office subscription 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 connective 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 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.

So Slack is kind of a biggish company. Within now, let's say a big company, but it feels like you still are launching really interesting stuff. You launched 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 a little self-delusional because I think everyone who works at Slack likes to think that we're still at a small startup and I think keeping that spirit alive, honestly, culturally has been a big part of it. I think going back to the principles early on, one of the ones that we didn't talk about, literally one of the actual wording is take bigger, bolder bets. And the idea there is that it's really easy to fall into the trap of just constant incrementalism. You know, the classic, it's like a feature team and you have like a KPI and you feel like your whole life is measured by that single 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 and you're maybe in a little valley, you can kind of see what's right in 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 realizing that there's a huge, incredibly beautiful range behind it. Yeah. So take bigger, bolder bets, get to the next hill to see what the horizon looks like around you. That's kind of how we think about it strategically. And then I think structurally, the way that we've approached it is that we've over time created kind of new teams from scratch that incubate in a new area before the area's 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. They were like, we love living in Slack all day. but we feel disconnected from our teammates when we can't be in the same physical place. Like, what can you do to help us? And that's 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 to prototype there and then figure out what can get to real product market fit. And I think when we have those teams, I think it's important to just give them space to run, to give them kind of a get-out-of-jail-free card from maybe the normal process of, you know, OKR planning and quarterly reviews and make it feel something that is like the pace of learning is what matters. Like how fast are you prototyping? 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, Calm, Quora, 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 security and privacy frameworks such as SOC 2, ISO 27001, GDPR, HIPAA, and many more, Vanta helps companies obtain the reports they need to accelerate growth, build efficient compliance processes, mitigate risks to their businesses, and build trust with external stakeholders. Over 5,000 fast-growing companies use Vanta to automate up to 90% of the work involved with SOC 2 and these other frameworks. For a limited time, Lenny's podcast listeners get $1,000 off Vanta. Go to vanta.com/lenny. That's V-A-N-T-A.com/lenny to learn more and 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 fun 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 an emotional thing rather than a practical thing, is that at all hands, we'll often wind up taking specific tweets that people had about the product. And Twitter, people say the craziest things sometimes. And sometimes they're really heartwarming, like customer love, but often it's just the meanest, most frustrating complaints that people have. And it's honestly meant for us to just have a pulse on what people are actually saying and feeling in the wild and not taking it too seriously, but keeping that sense of— I think that the distance you have from your users as your user base gets more and more diverse and larger, I think can 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, that's one big way. And the other that reminded me of, which is actually probably better, maybe delete that last one because it's kind of boring.

No, that's great. We're not deleting nothing.

Fine. You know, usability. So I'm a big believer in You want to be data-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, to actually attend user research sessions. And so what we wound up doing, especially in the pandemic when we first went remote, is now you can dial into usability sessions. And to make it really interactive for the team, what we would do is have people live, kind of like in a thread, write their real-time thoughts of like, oh, so painful 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 and reacting to usability session. And then suddenly that thread becomes actually the best kind of source of truth for the research report that then gets written 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 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 constructive 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 just link back to the original thread and then you have 100 people's reactions as the report is ongoing.

If only there was an AI tool to summarize all of your thoughts.

We've got a prototype for that. Hopefully it'll work well enough that actually it'll be useful for customers.

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. 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 couple years after I joined, but it was a point when 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 and it was just growing like gangbusters. And then we started spinning up a sales team and an enterprise team. We started focusing mostly on that. And I think we kind of, you know, we still had a 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 you look beneath the surface, the fundamentals of the self-service business weren't looking as healthy as they used to be. I think kind of the biggest thing as we kind of dug into it was a little bit to what we were talking about earlier with the motivation and the brainstorms is it was getting harder to understand what the next generation of Slack customers really wanted from the product. And whether you're thinking about this as crossing the chasm or moving from kind of early adopters to the needs of kind of the more majority or later adopters, I think we're at that point where not every technologically sophisticated company on earth was using Slack, but most were. And we were getting into a market that customers just had different needs, they had different levels of sophistication. And so we did a lot of user research. We looked at all these cohort curves, which you can imagine, suddenly they're like, oh, they're not as healthy as they used to be. Like, what's going on? And I think we got a bunch of insights from it, but I think really what we wanted to change about how we were operating Was instead of to continue to try to optimize the things that had worked over the last couple years, we said, okay, let's kind of throw the whole roadmap away. And instead, let's come up with a bunch of hypotheses about what could be new levers that could actually help based on the insights that we now have about the next set of customers. And we're gonna try to quickly learn which of these levers are real and which of these are just totally off the mark. And We kind of had to say for the next 6 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 the year and a couple years after that and kind of reaccelerating the self-service business. And I think it really came from stepping back, being humble, Not feeling like we deserve to have every company on earth sign up and then figuring out how to optimize for learning so in the long term you could get the impact. But knowing that for the next couple quarters, we're going to sacrifice impact for the sake of learning. And I think that was 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 wound up focusing on is what we talk about as 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? 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 start using an entirely new tool and convince all my coworkers to get on board. That is not like part of your job. Your job— Yeah. 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 always had a freemium product. 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 have to pay for the paid tier. And that wound up 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, and doing that at a variety of different points in the customer journey. And then I'd say the other biggest thing I would call 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 or very, very end of the journey. And we did a lot of quantitative research and data science and wound up coming up with this new metric we called successful teams, which is a little bit, you know, I feel a lot of companies have this, like Facebook's, I don't know, lucky number 7 or whatever it was, where what we found was that if you could get 5 people using Slack the majority of the work week to just communicate at all, that would be a successful team. They were gonna be 400% more likely to upgrade over the next 6 months. And that seems like a very low bar, like 5 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. And we wound up motivating not just the team that was focused 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 earlier in the funnel, but not a top-of-funnel metric, then it would actually drive upgrades and paid customers and thus revenue long-term. Yeah. And that was a huge kind of turning point for how we rallied product teams around something that would actually drive that self-service business.

Man, this feels like its own podcast just to analyze the things you learned down this journey. 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 5 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, 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. Yeah.

I think that's exactly right. I think of product-market fit as almost like you keep stacking these S-curves 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 US to be using this product. And then you jump up to the next S-curve, which is like, how do we get technology savvy teams that aren't developers? Or how do we get people who are in large enterprises who are outside the US? And these each become new curves that you have to build product market fit for. And I think it's just all a huge exercise in being self-critical, being humble, not presuming that you've cracked this thing forever and keeping a very beginner's mindset of what does the next audience need that your previous audience If you

think about the pie chart of what you had to change to make it work, how much of it was messaging, positioning, onboarding optimization versus product features?

I would say maybe 60/40 in the sense of the early journey. I mean, not just obviously positioning messaging, but the entire experience of unboxing Slack, if you will, with your team. We called it the day 1 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. So it sounds maybe impossible to remember, but Slack used to not have WYSIWYG message composition. You used to have to use Markdown. And so making that WYSIWYG 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 notifications so that as you scale the usage of Slack, 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, 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 right 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 and Right.

I mean, I think maybe the most telling thing is when Slack started, certainly when I joined still, I don't think the word or acronym product-led growth existed. 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. 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 expense it if you wanted to for just your team. And I think when people think about this product-led growth notion, I think there are really 2 very different audiences. And I think Slack was able to crack both. One is when your team is small and your company's small, it is the entire company if you're an SMB. And I think that's almost Slack's sweet spot. When the original pitch deck came to the investors, they said Slack is for companies of 5 to 50 people. At the time, the biggest company they imagined using Slack was 50 people because they're like, I don't know how this is going to work beyond that. Maybe it'll become pandemonium. Obviously, that was the initial, I think, real, real strong product-market fit. market fit. But the other bit, which then was what powered the enterprise business, was teams of 5 to 50 people who worked at larger companies. And I think what wound up happening was that you would have teams almost independently at a company like IBM or Disney or Capital One or whoever 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 anyone else at the company was using Slack. And then by the time we then scaled our 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, hey, by the way, you have a couple thousand people actually using Slack at your company. Do you want to think about a broader deployment or controls or analytics? And so I think that that was it. Consumer-grade experience that customers love enough to get their coworkers 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 an enterprise-wide kind of deal. And then there's all the tactics, but I think that was where it started.

The way you described it at the beginning of make a product that people want to share with their colleagues reminds me of a, I was just listening to an interview with Seth Godin. who's this 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. And basically it's like, it's word of mouth is how you have to win. But I think that's so true. And 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 is 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. And I mean, obviously there are categories of enterprise software that isn't true for, like in security or—

But even then,

I think, yeah,

like I think they, if it's an awesome security product, you're like, hey, you got to check out this, like Sentry or whatever, or Snyk.

Yeah. Like, uh, I'm good friends with Vanta CEO Christina. And I feel like they've got a lot of those stories where whoever would have thought that like a compliance company would be something that people raved about to their other startup friends, like, Oh my God, you don't wanna deal with like SOX compliance? You got to know Vanta. It's amazing. So yeah, maybe that is true. I, I think especially in this day and age where all the marketing acquisition channels have been so saturated, people have optimized them so much. I think it's really hard to like scale a big enough business if you don't have some amount of word of mouth and customer love driven growth. I think it's hard to scale it on like, we're gonna just play the CAC game and, and hope 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. Everyone's just like, whoa, this is cool. And they're all telling each other about 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 only thing I think is maybe a little bit interesting in terms of how we develop product, and it's really different and it's changed over time, which is that obviously the easiest person to build for is yourself. And the next easiest is people who look almost exactly like you or have similar preferences and sophistication. And I think in the early days of Slack, 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 could 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, one obviously is we've 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 at a checkout page and then you hit checkout. But I think the other thing is we figured out how to scale up getting real customers using Slack in the wild for new functionality. And so we have this really robust program that we call our 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. And because Slack is a multiplayer product, you often have to roll out 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, both through Slack Connect itself, through surveys. And this winds up being kind of a lifeblood of feature teams where you can, by the time you actually launch a big net new feature for Slack, have gotten so much customer feedback from people actually using it in the wild to get work done, and so much more confidence in what you're building from the metrics and the surveys that we do. that you can't guarantee it's gonna be a hit, but you can be really confident, not because it just worked well internally, which is no longer that predictive, but because it worked well for 1,000 different companies, 50 different countries, in 20 different industries. And so I think early on, SaaS companies don't need to figure that out. But I think as you grow and as you have a more diverse customer base, as you said, all these SaaS founders who said, hey, you gotta keep reestablishing product market fit. I think that is 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 like this for themselves?

I think the 2 most important things are you want a lot of diversity in terms of industry, company size, location, and so on. And then 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 of people who love Slack enough that they're willing to put up with a little bit of pain in that rougher period or are willing to have something that they try to use. And then we decide actually we're going to kill that feature before we ever ship it to everybody. So diversity and, you know, pain tolerance.

This reminds me of something else the CTO of Stripe shared of how they build new product, which is they pick a couple of 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 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 can do it in a way and they say like, I can't live without it, like the classic, like, not like, you know, do you like it? Sure. But can you, 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 too.

All right. I'm going to shift to a totally different topic, which could also be its own whole podcast, but let's just see how it goes. So you wrote this, I'd say famous blog 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, this could be an hour of conversation, but let's 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 a number of years ago at this point. And just, let's just see what comes up. And then I have a few follow-up questions on this list.

These traits are kind of, it came after I wrote this other thing, which is like the 5 myths 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 the positive version of this, which is the things that the job actually is about. It's not a career ladder. It's not like the here's the structured interview things that you should interview for, but I think it's the actual job of product management. 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 them in order. So live in the future and work backwards. I think it's very much kind of the idea of as a PM, if there's 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 be, what are we doing over the next 2 weeks, but 6 months, a year, 2 years from now, how do 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 and 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 pushed everyone to do is just think about the idealized product of like a put of magical world where this is totally solved and then work backwards from that. And then Paul Graham talks about this too, right? Just live in the future and build it.

I definitely riffed off at least the Paul Graham thing because I remember reading that essay of he thinks everyone thinks that you get startup ideas by sitting with your co-founder or laying in Dolores Park, looking up at the sky and conjuring up the next unicorn or something. Definitely not how that works. You have to actually immerse yourself in problem space and try to imagine what the future world looks like and then what's missing for people to get to that future state. So yeah, I agree.

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, you know, 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 with Larry and Sergey was they would ask, how could we get 100x the scale? Or how could this work for this? What seemed like an outlandish use case that would push the team to think much further into the future. I think that's what the founders always want.

That's what Brian Chesky always said too. Just like, how do we 10x this? What would it take to 10x this idea? 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? A PM role, I think, can be a little bit unsatisfying if you're used to a role 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 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 gonna help you do the best work of your life. They're gonna help you clarify things, prioritize well, unblock you, all that stuff.

Totally. Who— I wish I could find out who wrote that expression early on of like, PMs 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 wind 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 and say, I never want another PM again.

Yeah. Like so many new PMs are just like, I'm finally going to have the power. Finally, like if they move from engineering or some other role and then they get there and like, oh, what the hell? Yeah. I have 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 yeah. The 5th one that I wrote on 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. And in fact, I think one of the things that PMs struggle with early on is how do you actually get the team to be able to make high-quality decisions quickly without you arbitrarily playing tiebreaker 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. Yeah. Instead of PMs who want to say, okay, now it's my turn to get to make the decision. It's definitely not what the job is about.

What that makes me think about is I taught a course on product management at one point that I paused for now of just like, like the core job of a PM is to figure out what's next for every single person on the team. And you're this, 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 is just help people

Totally. I'll combine 2 of these together. One is you do have to have impeccable execution. This is more of a baseline thing, but I've never seen a PM who was disorganized or didn't do follow-up or wasn't clear about expectations or timelines. It's not high on Asil's hierarchy of PM enjoyment, but I do think it's a baseline expectation. The thing I think is more enjoyable And probably the most 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 growth 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 trajectory of the business, everything else is just an input. Yeah. And so I think that focus and understanding, as to 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 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. It may be moving a metric, it may mean building great product that the founders really love.

Yeah.

Impact can mean a lot of different things, but it's so true. On the execution, executing impeccably 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 puts 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 that if you, the more you can create this aura of like, I got this, the more responsibility people are going to give you, 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, I assume you remember, he used to have this saying, it's very Yoda-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. And I think that is kind of what good execution looks like.

That last point is so important. 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, is such a small thing you could do and really creates that aura of you got this. They're not going to forget about this thing I asked you to do.

Yeah, you're kind of the shock absorber for the team. 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. I'll combine 2 or 3 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 influence on a larger and larger product org. There's a book called On Writing by Stephen King, which I recommend to literally everybody. Yeah. Stephen King, you're like, is he, he's not maybe the most literary, critical, acclaimed author, 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, uh, 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 cut more from your writing. Like more and more parts you should cut. And interestingly, I do have a lot of guest posts on my newsletter and I find 90% of the time if I just cut the first paragraph of what they first took a crack at and jump 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.

Yeah.

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. Here's how to maybe make it something people wanna read. And then recently I read one called Several Short Sentences or something like that. It's, and it's all about just writing short sentences and that helps a lot. So there you go. 3, 3 more recommendations.

Nice. Okay. I got, I gotta read the last 2. I haven't read those, but they sound perfect. So, okay, maybe I'll throw one more. Let's say we talked about this earlier, but I actually read this in a post many years ago, is like optimizing for the pace of learning. And knowing that long-term, that's the thing that's gonna 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, I'm making this up. You're on the AdWords team at Google and you're responsible for the bid input selector or something. And 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 what else could this team become? What else could you drive beyond the thing that's right in front of you? So optimizing 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 I asked her just, how do you, how 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 insights in meetings. People obviously run, 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 combine the last 2 just because I know I'm out of 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. 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 it 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 or 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 to say that there is taste for product, but I do think in all of the love of the frameworks and the analytics and everything else that I think build a product, I think people sometimes lose sight of it's a creative field. It's not art on its own, but you could get all the inspiration from art. And I actually think, you know, there's a lot, there's a book, 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 Steve Jobs there. And I've never worked at Apple, but I actually think it's the best book I've 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 test it. So anyway, I think taste plus fluency in data, that too as a combination is a pretty powerful combo.

Let me ask you just a couple questions about this list before we get to our very exciting lightning round and I can let you go.

Okay.

Of these 10 attributes, say you're a new product manager. If you had to pick 2 or 3 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 at execution. It's the thing that you can most control. Then I think building that nose for impact, even if the impact is more local, because that's how you actually will demonstrate create momentum and build credibility. And then I actually do think early on getting really fluent on the data and the research side so that you can have insights that you can bring back to your team. Those are to me like the most slam dunk ways of becoming someone who starts to build credibility as a product manager in any organization.

Awesome. That's what I always tell new PMs too, is just get really good at execution because that creates that aura of, oh, this person's just killing it. 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 3 other attributes you think are ones they should focus on most, or maybe the same?

I mean, I think this is where the pace and quality of decision-making starts to matter a lot more because you're suddenly responsible sometimes for teams of teams and you're helping facilitate high-quality decisions, often ones that 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, it's always going to be the product founder who is responsible for the ultimate vision, but you become more responsible for the medium and longer-term strategy to realize that vision. And so becoming just someone who can dedicate more of your time to be out of the fray of the day-to-day and Think more about the longer-term strategy that you wanna pursue. 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 wanna influence an organization, at least for one that doesn't just 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. 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 6 questions for you. Are you ready?

Let's do it.

What are 2 or 3 books that you've recommended most to other people?

These may not be the most unique, but I will say them, which is Innovator's Dilemma by Clayton Christensen. Whether you're working at a large company and you're suffering it or you're working at a startup and you're trying to outflank an incumbent, I still do think that and Innovative Solution, the follow-on, are the best books on product strategy to read. If you're moving into 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 Maybe a little off the beaten path. There's a book called Leadership in Turbulent Times by Doris Goodwin, who's a kind of presidential historian. And it's this amazing book that looks at 4 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 leadership style and how do you evolve and how do you deal with crises, which Again, this may be 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 a favorite recent movie or TV show you've really enjoyed?

The obvious answer, which I'm sure many people would say, would be Succession. I'm not going to ruin anything for the finale in case people haven't seen it all, but the writing, the Shakespearean-level drama of it all, it's just incredible. And just heart-wrenching that you wind up kind of loathing most of the characters, but you can't take yourself out of it. The one that's maybe less common, uh, and I watched right when we started paternity leave, is The Bear. I don't know if you heard about it.

The, uh, restaurant?

Yeah.

Yeah. Seen it.

I'm a sucker for like incredible cinematography and just like what they do in basically the single room of this restaurant and kitchen and just the pace of it. I think it's just an incredible piece of art. I don't know if it's the best show ever, but it is a really moving, emotionally jarring piece of TV.

Also quite stressful to watch.

Very stressful. I would not relax to it to go to sleep at night.

But awesome. Favorite interview question that you like to ask candidates?

That would depend a lot on obviously the seniority level and things like that. But I think The more general one I always love to ask people is, what unfair secrets have you learned to improve the velocity and energy level of a product team? And when I say unfair and secret, I usually mean not something that you probably read on a Medium post, but 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 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 on our email thread about parenting products, because none of the products I've learned or loved recently have been like software, but they're all maybe software enabled. So the Nanit, which is like a kind of weird name, but it's this like AI-enabled camera for basically, you know, watching your baby as they sleep. It's like Incredible. It gives you like sleep analytics and like really helps you be a less neurotic parent. I would highly recommend it. Uh, 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 theme here is sleep. And the last one is, there's this company called UPPAbaby 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, that works in and out of the car. So yeah, I, I think I've really appreciated really well-designed, like hard products that are not necessarily hardware from Apple. And that has been what Being Your Parents is about.

I have all 3. Also a huge shout out to the Nanit team 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.

Yeah, it turned out there's a whole world of baby tech, which I had no idea. I mean, it makes sense that it existed, but you never know about it 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. 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, we had like 3 or 4 final name contenders and we didn't use the Nanit for it, but we literally just picked a week and said on Monday, we're going to like refer to the future baby by that name for the entire week and like give some, you know, personification to it. And that helped us get down from 4 What a

wide-ranging set of pieces of advice we got on this podcast. 2 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, which is more of a cultural shift, is that we stopped spending so many cycles on design explorations of static mocks or walkthroughs and said, how quickly can 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 gotta kind of live and 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 gonna give 2 because if someone asks me this, I'm like, these are the 2 things that if you're not in love with Slack, you'll be, you'll fall in love with Slack. So the first is obviously you have the sidebar, it can be unruly, but you can customize the sidebar into sections. And each of those sections, you can have settings like show unread only or sort by recency or sort by alphabetical, whatever it might be. And you can collapse the section so you don't see it all at once. So I think having a well-manicured 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 the 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 you're playing a video game, just hopping around channels, people, files, search. Pretty much all the actions you can take are done as well. I think most SaaS products now have borrowed that pattern. So, you know, you can use it in other software, but it works particularly well in Slack.

Noah, I know the last thing you needed was to record a podcast your first week back to work. I so appreciate you making the time. It feels like we're 2 ships passing in the night from pat leave into new pat leave. And so 2 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 in months because I was like doing digital detox, but still, I think @noah_weiss is a pretty good place to find me online. And whether there or anywhere else, still love to hear people's like Slack feature requests, especially about things that you wish were possible or 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.

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 the show at lennyspodcast.com. See you in the next episode.