Lenny's Podcast: Product | Career | Growth - Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more

Episode Date: July 18, 2022

Nickey Skarstad is a Director of Product Management at Duolingo, where she is leading a stealth 0 → 1 product. Prior to Duolingo, she was VP of Product at The Wing, Product Lead at Airbnb, where she... led much of the Experiences product team, Product Lead at Shopify, and Director of Product Management at Etsy.—Thank you to our wonderful sponsors for making this episode possible:• Mixpanel: https://mixpanel.com/startups• Dovetail: https://dovetailapp.com/lenny• Unit: https://unit.co/lenny—In this episode:[3:32] An overview of Nickey’s career[7:39] What she learned from building product at Airbnb[8:42] How to maintain and operationalize product quality[9:44] Metrics that help you maintain quality[20:08] Which company has most informed her product development approach[21:57] How to structure your product org[24:47] Should you go GM vs. functional[27:18] How you set vision, translate that into goals, and then execute on it[32:30] Brainstorming advice[35:04] How to use OKRs effectively[37:57] How to get better at influence as a PM[41:23] How to know if a decision is a one-way or two-way door[42:29] Second-order decisions, and second-order thinking[46:35] Operationalizing principles[47:17] Getting your team on board with your strategy[49:39] Designing a product review meeting[54:08] Tips for working remotely as a PM[56:44] Lightning round—Find the full transcript at: https://www.lennysnewsletter.com/p/nickey-skarstad-airbnb-etsy-shopify—Where to find Nickey:• Newsletter: https://nickey.substack.com/• TikTok: https://www.tiktok.com/@nickeyskarstad• LinkedIn: https://www.linkedin.com/in/nickeyskarstad/• Twitter: https://twitter.com/NickeySkarstad—Referenced:• Thinking in Systems by Donella H. Meadows• Anne Helen Petersen• Superhuman• Loom This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Transcript
Discussion (0)
Starting point is 00:00:00 When I asked to my newsletter Slack community, who I should have on the podcast was a bit under the radar, but amazing. Nikki Scarstad was the first name that I heard, and I was not surprised. I actually overlapped with Nikki at Airbnb, where she had a legendary reputation as a PM who everyone loved, but got shit done. Before Airbnb, Nikki worked at Etsy for over seven years, where she went from being a forum moderator to director of product management. Then she went on to work at Airbnb for a couple years. After leaving, she went on to be VP of product at the Wing and is currently the director of product management at Duolingo. In our conversation, we cover how to set vision,
Starting point is 00:00:41 translate that into goals and then how to execute on it, making your strategy actionable, and keeping your teams aligned in focus, designing your product review sessions, how to maintain product quality, and what skills have most contributed to her success in her career. I hope that you enjoy this conversation with Nikki Scarstad. This episode is brought to you by,
Starting point is 00:01:04 Mix Panel, offering powerful self-serve product analytics. Something we talk a lot about on the show is how startups can build successful and amazing products. And relying on gut feeling is a really expensive way to find out if you're heading in the right direction, especially when you're raising money, because VCs don't want to pay the price for these kinds of mistakes. That's why Mix Panel will give you $50,000 in credits when you join their startup program. With Mix Panel, startups find product market fit faster, helping you take your company, for minimal viable product to the next unicorn.
Starting point is 00:01:37 Access real-time insights with the help of their pre-built templates, and know that at every stage, MixPanel is helping you build with confidence and curiosity for free. Apply for the startup program today to claim your $50,000 in credits at MixPanel.com slash startups with an S, and even if you're not a startup, MixPanel is pricing plans for teams of every size. Grow your business like you've always imagined with MixPanel.
Starting point is 00:02:03 So many product managers are basically treated like project managers. They get a higher thinking they'll be deep in product strategy, vision, and getting to another customers, only to wind up organizing other people's work and refining backlogs and organizing tiny, tiny features. If that sounds familiar, you need Dufftail. Because Dufftail gets that the true heart of product management is understanding what customers want, why they want it,
Starting point is 00:02:32 and how to give it to them. That's why Dovetail build a suite of user research products that help you get to the core of what your customers really want and why they want it. Dufftail offers powerful analysis tools to help you identify themes, patterns, and insights in your customer interviews, allowing you to make better data-informed decisions about what solutions you should build next. Organizations the world over, like Atlassian, Canva, DataDog, GitLab, Nielsen-Norman Group, Sketch, Deloitte, all use Duttleale to get a better understanding of their customers and build better products.
Starting point is 00:03:05 Try Dovetail's products for free for as long as you need. You can sign up and dive straight in at Dovetailapp.com slash Lenny. Nikki, thank you so much for joining me today. I'm really excited for a chat and to get to learn from you. So welcome. Thank you. Thanks for having me. My pleasure.
Starting point is 00:03:31 Today you are director of product at Duolingo, which is an awesome product and something that I used to use. I'm not learning a language currently, but I know where to go where. I worked to you. Can you just talk about how you got into product and then a bit about just kind of your journey from that point to where you are today? Yeah. So it's been a long meandering journey, which is fun. So I've been in technology roles now for 12 years. I've been in PM roles, actually product roles for 10. I'm starting to be the person with experience in the room, which is really fun and kind of daunting at times. But how I got my first role in product was I was
Starting point is 00:04:07 at Etsy in 2010 is when I joined. And I joined them. It was like post-product market fit, but before they truly started to really grow and scale, and I actually joined them on their community team. So I worked as a forums moderator, and then as a seller education specialist, yeah, spent a couple years doing that. And then through that process, became sort of like one of the internal voices that had a really good understanding of how their customer, one of their core customers, their sellers, were actually using their product. And the VP of the time, this name is Mark Headland.
Starting point is 00:04:40 Hey, Mark, if you're listening, was like, like, hey, Nikki, you're in all these product meetings. Have you thought about being a product manager? And at the time, I was like, oh, God, no. Never. I was like, no. Technology. What? Engineering. I'd have to work with engineers. I know nothing about engineering. And so I was very imposter syndrome-e about it. And he gave me a little nudge and was like, I think he'd be really good at it. And so I tried it. And I started as an APM. And I was at Etsy for around, I think it was seven years total. And spent the majority of time, actually in PM product roles. So I left as a director of product. And for the most of my time there, I worked on the seller side.
Starting point is 00:05:12 So it was all seller tooling, working with sellers to figure out how they could grow and scale their businesses. And it was an awesome wild ride. But that was my first role in product. And then I went on after that into several other product roles as well. Yeah, let's get into it. Where'd you go next? So after seven years at Etsy, I was kind of getting the itch to try something new.
Starting point is 00:05:33 When I took a step back and was like, all right, what do I want to do next? I really loved the marketplace component at Etsy. And I don't know if this is just said something about my personality. or actually probably your personality too, is marketplace product is really hard, right? You have this constant balancing of both buyer and seller sides or both sides of the marketplace.
Starting point is 00:05:51 And I really liked that. And it was something that I was good at. And so I was like, all right, where else could I go? That's interesting or having a moment. And I was like, Airbnb. It has to be Airbnb. I was a huge fan of their product. They were also post-product market fit.
Starting point is 00:06:04 But sniffed around, ended up basically getting an opportunity to join the experiences team. And I joined that team when the product had just launched. So they had done sort of their early thinking, the existential thinking, had a brand new product in market, and then I joined the team. And so I was the first boots on the ground product manager and really helped that team figure
Starting point is 00:06:22 out, you know, how do we get product market fit? And then how do we start to think about how to scale it, which was, you know, you can imagine experiences is interesting because it is a very nuanced product in that, and this is similar to Airbnb, you know, if you work on homes as well, but part of it is building the digital experience, right, that someone will interact with when they're booking an Airbnb experience. And the other part is actually influencing the live event experience that you will, you know, experience when you actually join an event or an experience. And I think that actual, that layer of abstraction for me was really fascinating and something I've learned a ton about is it's not
Starting point is 00:06:59 just influencing the digital product, but it's actually the consumer experience when there are boots are on the ground. And that is another layer of complexity. And so that was super fun. I was there for about, I think a little over two and a half years. Started as a PM. I think I got promoted a couple of times left as a senior product lead, I believe, was my title. Yeah, I'm forever grateful for that experience because I learned a ton about product market fit and also product quality. Is there anything else you took away from that experience?
Starting point is 00:07:25 Because I was at Airbnb at the same time. We never really got to work together, but I just heard amazing things about you on the experiences team. And experiences was a wild ride from what I understand. Is there anything that you took away from that experience that kind of has stuck with you as a Yeah, so part of it is more just like the way Airbnb works is something that I think I use every day in my job, which is just truly thinking about product quality and the end consumer experience. And, you know, Airbnb does not ship product if it is not good. And even if they're trying new things, they are obsessed with the end consumer experience. And I learned so much from that line of thinking because just if it shipped, it was really high quality. All the edge cases had been thought through. And, you know, the experience I had before that was definitely we were shipping things more quickly. Things weren't always perfect.
Starting point is 00:08:14 And it's not to say that everything Airbnb ships is perfect, but I think that obsession with the end consumer experience really influences the quality of their product suite. And it's something I try to bring to my job today because no one does it better, in my personal opinion. I'd love to unpack that a little bit. There's kind of two questions in my mind. Is there an example of that at Airbnb or it's just like, okay, here's how they keep quality so high?
Starting point is 00:08:37 and then give any advice for just how to do that as a company? Yeah. So I don't think that's easy for sure. One of the things Airbnb did for experiences is we had this balancing metric, which was basically using the review rate as sort of our end-all be-all top-line goal. So you can imagine a business like that. Obviously, we needed to have revenue kind of moving through the platform, and we cared about high-level bookings.
Starting point is 00:08:59 But really at the end of the day in the beginning, we were obsessed with making sure every person who booked actually had a good experience when they showed up to experiences. And so as you, especially if you are building early product, really thinking about how can you pick some good quality metrics that might actually balance or conflate with growth metrics and use that as sort of your North Star because it really helped the whole team
Starting point is 00:09:23 make sure to understand what they were actually trying to do at the end of the day. Growth was important. Sure, obviously, we needed to grow for a lot of reasons. But the most important thing was that the actual customer experience was great. And I know Airbnb does that in other places. too, but that really was experiences. Topline goal was our review rate and quality, and it trickled down for sure.
Starting point is 00:09:43 How did they operationalize that? Because it sounds great. Cool. Let's make sure everything, all the reviews are five star. How do you kind of build that into the way the team operates and tracks their success? Yeah. So a big part of that was actually operational, which was just making sure that, you know, hosts who weren't meeting those specific, like, rigorous standards.
Starting point is 00:10:01 Like, there was a lot of coaching and education that was happening. some of that was in the product and some of it wasn't. It was something that was discussed at all of the meetings that we had across everyone's teams, right? It was very, everyone understood that it was important. And so I think that really impacted both the ops team as well as product team who were literally building the product that would bring that to life. And I think just thinking from how you, especially if you're like a founder and you're thinking about building your sort of early metrics, there's a lot of ways to really make sure your team really understands what that means. Another thing we did a lot on the experiences team is we just dog fooded all the time.
Starting point is 00:10:37 And so we were lucky, and that it was a really fun product to dog food, right? We were like taking experiences all over the world all the time. But it really helped because you would know right away when you showed up to an event if you were going to have a five-star experience or if it was not going to be great. And that really helped us too because then we would go back to the teams and be like, all right, we were just, you know,
Starting point is 00:10:54 in San Francisco we were on an experience last night and it did not go well. What do we do about it? So there's lots of ways to do it, but dog fooding is a good one. I know Brian is infamous for texting the team anytime anything isn't working right in the product. And I know he was very intimately involved in experiences. Is that something you've learned to do just to kind of like, hey, team, I found a big problem. Let's fix it. Or do you try to avoid that and not create that stress?
Starting point is 00:11:20 I mean, I think sometimes that can be a healthy stress if you do it in the right way. The nice thing I think is just making autonomous teams that feel like it is their goal to bring that quality experience to life can help you avoid some of that. But I do think that like pushing teams to use the product, so they firsthand experience when it is not great, is a really good way to give teams sort of the motivation to act on fixing things like that. But I don't know that I text people, but I'm on Slack all the time. So if anything, I'm going to slack you. Great. Okay.
Starting point is 00:11:50 Maybe one more question on this topic is it's so interesting. So on experiences you measured, I imagine percentage of trips that were five star, are there other quality metrics that you've used at other companies that you found helpful for keeping track of product quality and maintaining product quality. Yeah. So another one that we used at Etsy, which was an interesting one, is we realized that, so one of the pieces of product that I owned was the onboarding flow. So it was onboarding new sellers specifically. And you can imagine if you're owning that flow, you're just going to be like, all right, we just need a ton of sellers and we need them to open their shops right away. So we started and we went down that path. And then we realized
Starting point is 00:12:22 we actually tanked a couple of sort of downstream metrics that we didn't really understand at first. And those metrics were basically getting sellers to a first sale. So we opened up a lot of shops, but they actually weren't successful when they were on the platform. And they weren't successful in a certain amount of time. So we did a lot of unpacking of like, what happened there? Why did we do that? And actually does that matter? And the end answer was, yes, it matters greatly.
Starting point is 00:12:45 When Etsy sellers are opening their shop, it's really important that you get them a sale right away because it's a huge motivator, right? If you make a sale in your first day, you're like, oh, wow, okay, this is a thing. I could make money doing this. This is exciting. I get to ship something to my buyer. You know, if it takes you seven days, you start to be like, oh, no, I'm not good enough. I'm terrible at this. 10 days, you know, into 30 days.
Starting point is 00:13:04 Like, it really impacts people. And so we actually put more friction in the onboarding flow to help to start to solve for that. So we actually slowed you down. We made you be more thoughtful about what you were listing. And by doing that, we actually helped you get to a first sale faster. And so that was another good example of a quality metric that we used, which was, I think it was first sale in seven days. It might be wrong, but something along those lines.
Starting point is 00:13:25 and it actually conflated with the high-level growth metrics, but it was a huge quality predictor and it was really important for long-term seller success. So interesting. That's such a good topic, and I feel like we could explore that for an hour, but maybe for a little bit longer. Was that metric, the metric that you used to measure supply growth at that point? Or is it like alongside just general growth?
Starting point is 00:13:45 Yeah, it was alongside general growth. It wasn't like our top-top OKR, but it mattered because, again, it's sort of like you think about these things a bit as a seesaw, right? We basically were balancing our growth. growth with making sure people were successful. And the more equilibrium you had there, the better it was for their overarching marketplace. And it's similar if you think about experiences too, right? Where, all right, you could just be growing, but people are having a terrible experience.
Starting point is 00:14:08 So how do you sort of balance those two things? And if you can get those two things in balance, you're going to cruise and you're going to be more successful longer term. Got it. At Airbnb, when I was working on supply growth, our main goal for the supply growth team was similar. And that was actually the goal we had, which is new listings that got their first booking. We only counted listings that had one booking as new supply, everything else didn't really count because we knew that if it got booked at least once, at least it's got some level of quality and people want that place and it's valuable to the marketplace. Interesting.
Starting point is 00:14:38 Okay, so you were at Airbnb. Where'd you go next? Yeah, so I went to a startup and, you know, for lack of a better way to describe this, like they were basically kind of building a marketplace as well, but it was more of like a marketplace of ideas and I hate when people say that because I think it's cheesy, but it's true. They had physical co-working spaces and they were trying to take some of the magic that was happening in their spaces. So people meeting each other, networking, people getting funding for their startups, et cetera, and they wanted to bring it online,
Starting point is 00:15:02 and they wanted to try to scale it so it wasn't constrained inside of their floor walls. So I helped them basically come up with a longer-term strategy, start to figure out how to unpack that and get product market fit, and then also just build a technology team around trying to solve that. And so that was in, started like late 2019, and then I was out for a bit, had a baby, and came back and then COVID happened. And they were a physical co-working business. That was where their majority revenue came from. And so COVID was pretty horrible for what they were trying to do.
Starting point is 00:15:34 They also had some other cultural issues. And so the whole thing kind of paused slash fell over. So I actually spent a year hiring a team and then had to lay them off, which was a great lesson in leadership. I'm not going to lie, learned a lot about how to lead in that experience. But after that, it was COVID. I had eight-month-old. And so I spent time actually just vibe in with my kids, which was kind of fun.
Starting point is 00:15:58 And then ended up going to Shopify after that. And so I was looking for like a more bigger scaled, not startup and was trying to find something a little bit more, somewhere I could be longer term and was more excited about and took a platform role at Shopify. And so that was really interesting in that I had to honestly, for the most part, spent the majority of my career in super consumer-facing roles. And the role that I took was more platform. And I realized honestly pretty quickly after I took the role, was like, oh, good to know. I didn't really understand what this job was, and now I know what it is, but it does not give me energy. And so I felt like I had a lot of red energy every day. And so I made
Starting point is 00:16:32 a call pretty quickly to bounce, which was actually another good learning experience. I think I've gotten a lot, as I've advanced through my career, have learned a lot about like what gives me Nikki Scarsted energy and have been really prioritizing that, especially in a post-COVID world. And so left Shopify and made my way to Duolingo. And so Duolingo has been super fun. I've been there since September of 2021. And in the process of helping them kind of think through a zero to one product challenge, something that's newer. I can't really talk about it, unfortunately, but has been another sort of product market fit thinking exercise. It reminds me a little bit of some of the work that I did on experiences. And so it's been actually pretty challenging and super fun. So I'm also having a
Starting point is 00:17:10 great time here as well. Amazing. The companies you've worked at is incredible. And there's so much I want to explore there. Going back to Shopify briefly, a lot of PMs I imagine are trying to decide should they stay where they're at? Should they go explore other places? So you said the thing that kind of pulled you out there was just the platform role didn't feel like a fit for you. Do you have any advice for folks on just like how to know if a role or a company isn't a fit for them? Yeah. So I think I really learned that while it was there. And also I want to make sure, like I actually had a great experience at Shopify. And I think it is an awesome company. I would highly recommend people work there, especially if they like platform product work. One of the things I did when I was like,
Starting point is 00:17:51 I don't know if I love this is I actually went through my calendar and I changed the colors of all of the meetings on my calendar to red, yellow, and green after I had the meeting. And I looked and said, and it basically changed it. If it was yellow, I was like, okay, it was a fine meeting. Like my energy was like baseline. If it was red, I was either bored or I was stressed or I was not having a good time. And if it was green, it gave me energy and I felt excited and wanted to keep working on that. And when I looked back at the last few weeks, it was like almost all red and yellow. And I was like, okay, this is really like from an energy standpoint. I don't think I love this. And so I would say like think about the work that you're doing and that lens get really good at
Starting point is 00:18:31 figuring out what are the things that you love most about being a product person and how can you optimize your next role for those things that you love. We should talk a little bit more about this, but each company has a very different product org and the day to day of your job as a product manager, depending on where you go and the product that you're building, is very different. And so really thinking through what that work looks like, you know, what their process is, who your end consumer is, what will the actual work you be doing every day? What will that be? And if you can get really clear on that and then get clear on what gives you energy and what you love, it makes it a lot easier to figure out where you should go next.
Starting point is 00:19:04 Wow, I love that tactic. I've never heard of that. Just like going back to the meetings that you had in measuring, just like reflecting on how much energy that meeting gave you. Great tip. Thank you for sharing that. I'll also double down on Shopify is an amazing place to work just to like make that clear. It's probably one of the few places I recommend PMs go try to work at. Yeah, I think especially if you're newer in your PM career, they just have a really great organization. And I think it's a great place to learn how to PM.
Starting point is 00:19:30 Also, their product, you know, it's a huge scaled product. And so it's complicated to build in. So I think it's a great place to really understand second order systems and systems thinking. And especially if that type of work gives you energy, I would recommend that people look for jobs there. But again, get really good at like what you love. And I think what I've realized longer term is I really like the zero to one early stage. How do we get product market fit? And how do we really think through the early experience? And you know, Shopify is at a very different stage than that. They're doing that in a couple of places for sure, but that's not their day to day. And so that was interesting.
Starting point is 00:20:05 Yeah. Yeah. That makes a lot of sense. Going back to what you just kind of touched on, the idea of product org and structure and how different companies build product. There's kind of two ways to approach this and take whichever direction you want. Which of the companies that you've worked at did you enjoy most? And that's kind of stuck with you as a way you want to build product or just like, how would you approach building a product org and cross-functional teams versus not and who reporting lines, things like that? What do you recommend there?
Starting point is 00:20:34 Yeah. So I feel like you're asking me to pick a favorite child, which, so she's a mother. That's hard to do. But no, I don't know. I feel like I've learned things from a lot of these different places and it's hard to choose. I think some of my early work at Etsy
Starting point is 00:20:47 was very formative and it was where I learned how to be a product manager and so I feel very proud of that. I also think Etsy was out there like building in public. I'm literally doing air quotes right now and you can't see me.
Starting point is 00:20:58 But they were doing that because they had such a passionate, involved, engaged early community that they could not just ship things and have them land well if they did not involve their community early. So they were doing prototyping, beta testing, basically getting people to try things and give feedback on things.
Starting point is 00:21:15 Honestly, I think before a lot of people were, and that was something at the time that was really interesting and has really stayed with me. It's how to work with community and how to build community around the product that you're building. Because at the end of the day, especially when it's early days, it really helps scale, get people to evangelize what you're building, help teach other people how to use it, things like that. And so I learned how to do that at Etsy, and I think that was super formative. And then also just, you know, Airbnb, what we talked about before and just deeply baking in product quality and the end consumer experience into everything that you're building as also something I literally apply every day. So if I had to choose, it would be those two places,
Starting point is 00:21:52 but I plan on continuing to learn. Interesting. Both very community driven businesses. True. And then in terms of how they structured their org, is there anything they're just like, here's what I've learned works best for how to build product team, structure product teams? that stuck with you? Yeah. So I think there's kind of like two overarching popular organizational modes for product org specifically. There's either like the functional organization where, you know, everyone in the product team will report up through either a VP product or a cheap product officer or something along those lines. And I think that actually really works in certain circumstances and is great. And typically how that works is, you know, you'll have like your product
Starting point is 00:22:31 partners, your trifecta, if you will, you have your design partner and your engineering partner. they will typically also report up into functional leadership. I think in bigger organizations, that really works well, especially when you have orgs that need a lot of development in the function. So you have a lot of either APMs or product managers who are newer in their career and need a lot of support and development. I think those functional ways of building makes sense. When I was at Etsy, that was the way that the reporting structure was and it made a lot of sense. And then on the flip side, actually, when I was at Airbnb, because experiences was this new pretty, nascent business opportunity, it had a GM structure. And so basically the whole product org that worked on experiences laddered up into a business leader. And that business leader managed
Starting point is 00:23:17 all of the functions. So they were the manager of the operations team, the marketing folks, product, and whatever. And I actually think that really worked for team like experiences at a company like Airbnb, because what it did is it gave the leader of that business, a ton of autonomy to really figure out what does this business need to be successful? And they didn't have to rely on, I guess they did in some ways, but not 100% rely on the larger company's resources to get the work that they needed done. And I actually think that had they launched experiences inside of sort of the Etsy style of organizational structure, it never would have succeeded because it had such a unique business need and it needed its own process and ways of building
Starting point is 00:24:00 product, et cetera. And because they sort of like, I need to say wall it off because it wasn't fully welled off, but because they gave it its own space and its own structure, it allowed it to succeed because they were able to fund it in the right way, give it the resources that it needed, et cetera. So I've seen those two types of models work. And I think if I was a founder and I was building my initial product org, how I would think about it was basically what are we trying to build? What is the product? And then what type of process do we need to put in place for us to figure out how do we build it? And then what type of people do we need? And then really taking a step back to really figure out, all right, organizationally, how do we shape this? We can make sure that those
Starting point is 00:24:37 people have autonomy and they have what they need to just be able to cruise. So I honestly don't think there's a right way. I know that's a non-answer. I think it really depends on what you're trying to build in the stage at which you're at. Is there a default approach you suggest? Just like most often you should go to the GM model or most often you should just go with this functional, cross-functional team. Yeah, I mean, I think especially if your business is new, going functional makes sense because you don't necessarily have a lot of organizational complexity. Airbnb at the time we were there, Lenny, was a huge company, right? It had tons of different teams that were trying to tackle many different problems. So that GM model made a lot of sense because it, again, was able to
Starting point is 00:25:15 take a specific business opportunity, give it the resources that it need, and give it space to run. When your company's smaller stage, I think that matters less. And, you know, typically, especially if you're working on solving similar problems as an organization, functional makes a ton of sense, because then you're also thinking more holistically about, all right, how do we build the right product's development process across different functions to make sure that we are, to use a bad metaphor. It's like the symphony metaphor, right?
Starting point is 00:25:41 You have all these different instruments that need to figure out how do we play together at the right times. And I think that functional way of working actually allows you to do that really well. This episode is brought to you by Unit. What did gusto, Uber, Shopify, and Angelist all have in common? They've all decided to build banking into their products. According to Angelist head of product, banking makes every single feature more interesting. With it, our platform functions as financial mission control for our customers.
Starting point is 00:26:10 Without it, we're just another software tool in a big, messy stack. Embedding banking into your product not only adds differentiation, but also helps you acquire, retain, and monetize your customers. Unit is the market leader in banking as a service, combining multiple bank partners with a developer-friendly API to empower companies of all sizes to launch accounts, cards, payments and lending in just a few weeks. Unit is trusted by a leading brand such as Angelist,
Starting point is 00:26:37 high bean invoice to go, and roof stock. To hear more about how Unit enables companies like yours to build banking, visit Unit.co slash Lenny to request a demo or to try their free sandbox. That's unit.com slash Lenny. Something I learned at Airbnb for many other companies at this point is there's never going to be like the one right way to structure and companies bounce back and forth between them, Airbnb, for example, has moved from GM model to functional reporting lines back to GM.
Starting point is 00:27:09 And so things change. And you try some, see how goes, adjust, optimize for the biggest opportunity. And then you'll probably change it six months later. I asked a few people that know you and that worked with you questions that they think I should ask you. And one of the questions that came up most often is around how you set vision, translate that into goals, and then execute on those goals. And I know that's something a lot of PMs want to get better at and something that a lot of PMs aren't great at.
Starting point is 00:27:37 And so can you just share any thoughts, advice, stories around that and how you do that well? Yeah. Well, one, I want to know who you talk to. That's terrifying. Hopefully they said good things. You don't have to out them. And name sources. I named sources.
Starting point is 00:27:51 Yes. Well, I'm glad to hear that because that actually is some of the work that I honestly love the most. And those are, you know, when I look at my calendar, those are moments where I am green energy. And so I have some first principles that I like to apply when I'm thinking about setting high-level vision and strategy. And the first is make sure that you pull in your people and your team. I've seen a lot of director-level people through my career who will try to work on strategy in a vacuum alone. They'll write a document and they'll be like, okay, team, here's what we're doing, here's our strategy. And it never goes well.
Starting point is 00:28:22 And I think that happens, it doesn't go well. It might be the right strategy, but because you did not bring people along on that journey to come up with it, They did not feel like they had a hand in crafting it themselves. They are often not bought in. And getting people to buy in when they haven't been involved is very challenging and time-consuming. We don't got time, right? And so I think that's my first principle is just like bring along the team. And I think there are ways to do that where you're not voting on strategy.
Starting point is 00:28:47 You should not be voting. I think, you know, good product work is often not democratic, right? You need a clear leader who understands a lot of the signals and understands the larger competitive marketplace that can make decisions. and I think especially when you're thinking about strategy, it's great to get input, but ultimately at the end of the day, you should have one person who is responsible for it.
Starting point is 00:29:06 And the other thing is a lot of times people don't really talk to leadership or the larger business leaders to get organizational context that helps them come up with the right strategy. They'll sort of build something in a vacuum, and then they'll come up with it, and they'll get a ton of feedback from people across the org. They were like, oh, this conflates with our strategy. You know, we're doing this, and it's very similar.
Starting point is 00:29:27 or, you know, our structural platform actually does not have the capability for us to do that thing, whatever. And so just make sure that you're talking to people. And also, you know, all the way up to the CEO and making sure the founder, the CEO is very bought in in because ultimately at the end of the day, they're choosing to resource what you're working on and are going to help you meet what you need. So those are sort of like some of the foundations for good vision strategy work. And then kind of zooming down into the weeds, like I really like the vision mission strategy pyramid. I think it's, you know, it might be a little tired. I like to think it's wired. But yeah, so if you just think about a pyramid shape at the top is vision. Below it is mission and strategy and then objectives. And this is a very simple framework. You just honestly just Google vision mission strategy objectives and you'll see it in Google image results. And all it is really is thinking about hitting those specific notes and thinking about them top down. So where do you need to go long term? What is the long term vision of what you're trying to do?
Starting point is 00:30:25 If you could, in 10 years, if you could zoom up and look at what an ideal path for you would be, what is that? Write it down. And then you start, as you get on the pyramid, you get clearer and more, basically like you bring things down to your moment in time more clearly. So if you're thinking about your mission, all right, it's like another level of distraction of like, how do we make our vision come to life? And then you get into strategy. All right, how do we actually pick apart what we think is going to need to happen for us to actually be able to execute on that vision? And then your objectives can be OKRs or whatever sort of goal-setting model that you use to really one level get clear on, all right, in the next three to six months, what are the actual notes that we need
Starting point is 00:31:04 to hit to be able to, like, sing that beautiful symphony? It was a terrible metaphor, and now I'm okay. I get it. I get it. Dang. Love a bad metaphor. It's evocative. While we're on that topic, actually, just to interrupt briefly, how are you very practically doing this for, say, vision and mission? Are you like starting a Google doc and writing it out or using Miro or fig jam or something like that? Yeah. So I think visioning exercise is a great moment to pull in your larger team. Because I'm remote now, I would use Mero or FIG jam. Dual we use Fingham typically because we are super embedded in Figma. In the past, I've used Mero. I actually personally like Miro's whiteboarding product better. So I would open that up and I would
Starting point is 00:31:48 walk through a number of things with the team and do a brainstorm, literally. right, where do you all see us going in 10 years? What do we think, what is the larger competitive landscape going to do in the next 10 years that could need to influence the work that we're doing? What are their ideas and get everyone thinking? Good brainstorms are often cross-functional. So go outside of your own team. Can you pull in somebody from marketing? Can somebody from the larger policy team sit in? How do you make it really cross-functional and really zoom up and give everyone the space and the freedom to think existential and to frame it that way? Like we are going to be thinking in a five to 10 year timeline, do not worry about what's happening today.
Starting point is 00:32:26 And that those are fun. Honestly, if you do that right, those are super fun exercises. And you're doing this remotely, I imagine. Yeah. And so do you just kind of schedule a meeting, kick it off, point everyone to this Miro doc, for example, with a bunch of prompts and sticky notes and things like that? How do you actually practically do that? So I would pre-fill out the mirror beforehand. So figure out what are the things you want to discuss with your team. Create them as headers in the Mero document. So when everyone lands in there, you have a very clear art. Here's what we're talking about today. You can put that into the agenda on your calendar invite. I've actually been to some really good strategic brainstorms that will attach some kind of competitive
Starting point is 00:33:02 thinking landscape in advance. So people have a little bit of a pre-read. And then when you get into the actual session, you already have the time allotments scheduled and thought through. And both Mero and FIG jam have really awesome timer. And it'll play music while everyone is working. And so it's Like, it's pretty cute. Fig jams sounds are really well done, whoever their sound architect is. Bravo. And it'll ding after, you know, give them 10 minutes and it'll give you a nice chime. And then you can review them together. And you can go through each touchpoint that you want to talk about. After it's done, I like to do some synthesis together in the meeting. So have basically grab ideas that are similar, bucket things into concepts that are like. And then I will take it later and spend more time thinking about it. I think a lot of people think you have to actually like, come away with a vision together in a meeting. It's very clear, and you don't. You can just come up with ideas, take a stab at drafting it, and get some more feedback before it's final. One last question on this thread, which also could be an entire hour of discussion. Are there any examples of prompts or things you ideated that you could share? I know you can't talk about what you're
Starting point is 00:34:05 doing in duelinga, but just like to make it a little more concrete for people, like, what are some examples of things you brainstormed? Yeah. I mean, so to take it back to experiences because we've talked about that a lot, so people have some baseline context. Some of the early experiences visioning was really interesting because it was all about like what type of experience can we create and really thinking through like when you've traveled in the past what has brought you joy or what were the moments in your travel journey that have been really interesting provocative basically you remember the most and why and you know kind of thinking through some of those things as a group and those are good group exercises because you're like wow I got to know a lot about lenny by that
Starting point is 00:34:41 crazy travel experience that he had and so really kind of thinking through about how you craft really meaningful prompts that, again, connect to your strategy. So how does that ladder up into strategy? Obviously, thinking through the experience that you're creating is going to help you come up with the right vision and fill out your pyramid in the right way, right? Okay. So we went on kind of on a tangent around brainstorming. Did you want to share more around just like going from vision to goal to execution? Yeah. So I think just generally as you walk down that strategy pyramid, really getting into, you know, down into the OKRs. And I think it's important because a lot of sometimes strategy is too abstract and too high level. And it's hard for people to
Starting point is 00:35:15 take the step on like, how do I walk up that pyramid? And that to me is where having good strategy and having good OKRs help your team do that. And so good OKRs to me are just clear articulations of your strategy, whatever it is that are important to you. And it boils it down into the next three months, here is what we're working on. And I think that is just really good for teams. Because, again, if you're always in the clouds, it starts to get hard to really bring things down to the level of like, you know, down to the feature level of like, we're going to create a GERA ticket for this specific thing that we need to build. It needs to connect up to a strategy and back down. Got it. Where do you put, say, these OKRs? Is that like, you use the brainstorm, come up with
Starting point is 00:35:57 vision and rough strategy that translates into goals. Where do you do this? And then also just like, how long do you usually spend on this overall process? Yeah. So the way that we do it at Duolingo now is we work on quarterly OKRs. And so that process will kick off. usually like the third month in the quarter, really thinking through, all right, how are we trending on our OK, ours this quarter? Did we commit to the right number of things? How are we doing? And then it is going, all right, so what do we need to do next quarter? And ideally, again, that's going to plug into a longer term plan. Otherwise, it feels a little messy and it feels not grounded in a long term plan or strategy in any way, shape, or form. And then so what we'll do
Starting point is 00:36:37 is spend a few weeks as a team kind of coming up with, all right, what could the next quarter look like what is going to add the most impact and help us execute on that long-term strategy? And then how do we make sure that we're setting the right objectives and KR's below them? And then usually there's some sort of leadership review. I actually forget how Lenny, how did goal setting go at Airbnb? I honestly don't remember. Sounds terrible, but it was a while ago. I can't even remember if Airbnb used OKRs.
Starting point is 00:37:03 There was a long period where OKRs were a very big deal. Our head of product was really gung-ho in O-KRs. And I think for a couple years, we were very. strict OKR culture. And then it kind of evolved into just like rough interpretation of OKRs. Yeah, goals and strategy and mission and vision. And so it's kind of this morphed version at this point as far as I know. Gotcha.
Starting point is 00:37:24 Yeah. And I will say like OKR frameworks might not be the best for every single team. But having some sort of goal framework that is shared across functions is useful the matter of the size or the scale of your business. I think a lot of times people get hung up and they want to nitpick OKR specifically. And I think some of those criticisms are very fair. but you should have some sort of framework that's shared from a process standpoint across your team that everyone can use and work on together. Because again, it takes your strategy and it brings it down
Starting point is 00:37:50 into the now so you can act on in the next three months, you can bring something to life and you're very clear on what that looks like. I want to pull on a thread of something you mentioned earlier of how to finally make decisions and how in your experience, the PM kind of is often sort of a final decision maker. I'd love to hear any advice you have of how to set that up on a team where it's Either clear the PMs have a little bit more say and or just kind of bring people along to a final conclusion. Is there any advice and tips and tactics used to help with that? Yeah. So I actually just read this really great book that is slightly tangential, but I thought it really applied to this type of basically getting people to align on decisions. It's by Chris Voss. He is this famous FBI negotiator.
Starting point is 00:38:33 I think it's called Split the Difference Negotiating as if your life depends on it. Don't cope me on that. I think it's never split the difference, right? And then I think he's also, got a masterclass, which I've watched, which is really good. I actually haven't watched the masterclass yet, but it's on my list after reading the book. And a lot of it, you know, I think especially because he's an FBI person, I thought it was going to be very much like, weird, you know, you're going to do this. And it's all basically his whole approach is like empathy. And it's like repeating things back to you, making people feel hurt, making sure that you're hearing why they maybe don't like your strategy or why they think
Starting point is 00:39:05 that's a bad OKR. And I think if you can spend some time just listening to your team and really understanding, like, why is this not resonating? You can help guide people on the right path, or you realize you're wrong. Like, you know, good PMs are humble people, right? You're not always right. Not always going to be right. So how do you know when you're right and wrong is another good podcast that you should do with somebody else? Because I'm probably not very good at it. Yeah, too, I would like that. Yeah, but I think that helps. And the other thing is, I love the concept of one way versus two-way door decision making, right? If your team is making a really critical long-term decision that's going to be limiting to a lot of the future things that you could,
Starting point is 00:39:39 want or need to do, that is a one-way door decision, and you should spend time really thinking about discussing it, getting feedback and buy-in from your larger community, from your leadership team, et cetera. If it is a two-way door decision, you know, it's not going to make a huge impact. You can change it later if you need to. Let your team cruise on those things because it gives people autonomy. It helps you move fast. And then it just makes sure that when it does come down to decisions that are harder to change longer term, then those are the moments you should spend time and really think about and discuss and debate, et cetera. Do you have any examples or stories that come to mind of those sorts of decisions that you can help people just like go for it, even though
Starting point is 00:40:16 I may not necessarily agree? Let's see. Yeah. So one big one that we made at Airbnb that was pretty formative in early days was, we came up with basically an articulation of what we thought a good experience was and the standards that an experience needed to meet for it to be considered a good experience for us. And that was like a many month long term project. And it was so important because because we ended up building the product around it, building our policies around it, building how we educated our hosts around it. We had one moment in time to figure it out and get it right until it scaled everywhere. And so that was a true one-way door decision, right, where it was really hard to change later because we literally needed it to be relatively final.
Starting point is 00:40:53 On Etsy, there was some big decisions that were made at certain points of time around what can be sold in the marketplace and how to think through what constitutes something that is handmade. Those were one-way door decisions, right? It's really hard to change. that later because it's going to influence all of the listings that you have in your ecosystem. And so I think really thinking through those types of things are important, right? And really setting teams up to be able to pause and spend some time to get it right because it will influence the end product in a very real way. I do you know if it's a one way or two-way door decision? Do you find that it's generally pretty obvious when you're making the decision? Or is it sometimes like, oh, shit,
Starting point is 00:41:30 we should have thought about that more? Yeah, I would say like I think I'm good at this like 80% of the time these days, just because I've seen it done wrong in a lot of ways. But I think it's a muscle that you build, honestly, and you get better over time about thinking about second level thinking, or second order thinking, rather. And so it's starting to understand, all right, if I make this decision today, it's going to impact this next level of decisions and the next level after that. And that will cascade through our larger system. A great book to read if you are a product person is Thinking in Systems by Dinella Meadows. It's just about like really thinking through how systems work. and then you can start to extrapolate.
Starting point is 00:42:06 What is the second order effect of the system? And if you think about that through your own ecosystem, it starts to help you understand, all right, this is a linchpin in our larger ecosystem that we've got to be really careful about if we're going to touch it or change it longer term. But I do think some of that, you know, it's muscle. You build it over time.
Starting point is 00:42:21 You make a couple of mistakes sometimes. And then you see, you have to like realize the true consequences of those mistakes and you don't make it again. Can we talk a bit more about the second order decision framework? I know you have an awesome newsletter post about this And it was something I wanted to chat about. Is this like a framework that PMs can use to make better decisions?
Starting point is 00:42:40 And I guess how could they do that? And then maybe just describe a little bit more about just this concept of second order decisions because it sounds really important. Yeah. Basically what second order thinking is, is you being able to think beyond the decisions that you're making today. The decisions you make today will affect tomorrow's decisions and your ability to build on your decisions that you made today.
Starting point is 00:43:02 And this feels very existential in meta, but why it's important is that, especially when you're building product, is there's a cost associated with your time of everything you build, especially when you're building marketplaces or anything with UGC content, when you make a change today and it impacts every single user in your ecosystem that then is going to act on that change, it's really hard to make those changes later. Let's talk about Airbnb or Airbnb Home listing as an example,
Starting point is 00:43:26 really thinking through what are the pieces of data or all of the pieces of data in the system that we need to actually like list a home, And then how do we use those throughout our whole system in different ways? And then anytime you have to change those things, so that could be little simple things like truncating the length of the title of an Airbnb home when it's listed on the platform, you're going to have mad hosts. You're going to have design changes that need to be made to make sure that they can actually display something in a different way.
Starting point is 00:43:54 It gets just inherently more complex, the more complexer system is. So that is probably a terribly described way of describing second order thinking. That makes total sense. And that's something we dealt with it. Sorry to interrupt, but that's like on the host team. We dealt with this question often of just like any change you make and the listening flow is going to impact so much of the experience of a host and a guest. And so that makes total sense. Sorry, keep going.
Starting point is 00:44:16 Yeah. No. And I think that forcing yourself and your team to think in that way is just a really good thinking exercise because it will save you time. It will save you money. Like a lot of money later if you don't constantly have to rebuild things when you want to make changes to your system later. And that ladders up again into having a very clear vision and a strategy. Because what you're doing is you're starting to think on the long horizon. And so the decisions that you're making today are in service of that long horizon.
Starting point is 00:44:44 So you can actually build in that direction and you don't constantly have to rebuild every time you're trying to change something. On the second order thinking, sorry, I called it second order decision. But in this framework that you spoke of, how do you actually operationalize this concept? Like when you're planning, do you write out in the document second order impact? that we should be thinking about or do you do some else? Yeah, so I think there's many ways to do this. If you have a spec template or a piece of documentation that your team typically use when they're writing out product strategy
Starting point is 00:45:14 or product requirements, etc, you can put a line in here to force people to think about it. I also think thinking about first principles and writing out first principles for the changes that you're making, often are in service of second order thinking, where it's like, here are the things that we care about. Here is why these things are important. And we want to make sure these are baked into what we're
Starting point is 00:45:32 building, typically you'll write those through the lens of second order thinking. Shopify uses first principles a lot in everything that they build, and this is something I took away from that way of working because it's extremely effective. If you can get teams to align on first principles early on, it saves you a lot of heartache later because you've got people to align way early days for even gone into the design process or before you had to build, start thinking about how do we actually technically implement this? And then the other way I would say is there's ways to structure or have thoughtful discussion around second order effects, that could be a brainstorm.
Starting point is 00:46:03 You could use Nero to think about that. You know, we're going to make these changes today. How do they cascade through our ecosystem? What are the gotchas or the things we need to worry about? And again, I think the more complex your ecosystem is, the more you are forced to do this. A lot of founders in early stage products don't think like this because they're so focused on the product market fit.
Starting point is 00:46:22 We need to just get something that people are using, that then when they get product market fit, they realize when they get into scale mode, they didn't build something scalable and they have to rebuild things, which can actually really hurt them when they're trying to grow really quickly later on. Yeah, absolutely. It happens all the time. For principles, do you put those into, say, the team strategy, like the quarterly strategy document? Like, here's our principles for the quarters. Is that how you generally do that? Yeah, I think that is a great place to put it. You can write them on the feature level too. So, you know, something that you're building, just getting clearer on, like, here are the things that matter to us. Here's what we care about. We're going to design and service. of these things, and here are the things that aren't that important. And again, those are the types of places like in a product requirements doc where people will argue the most, which is a good thing,
Starting point is 00:47:07 because you're basically discussing and debating the sort of foundations of what you're going to build before you get into the work of building it. And so those exercises are always a good idea. Awesome. I love that. Okay, so going back, because I wanted to close this thread, you've come up with your vision, your mission, your strategy, your goals as a team. People start to align around it. What do you do to kind of kick it off and get people on board and aware of the plan and then to stay on plan with that strategy and not kind of be distracted by new priorities and shiny objects. Yes. The shiny object thing is very real. Good question. So, for example, I just did this recently where I brought my team along through the okayR process
Starting point is 00:47:45 for Q2 planning. They had a say in what was being basically what we decided we were going to work on. It went up for leadership approval. We got approval. And my process was I used loom, which is another one of my favorite products. It's just a really easy screen share and video recording tool that you can share with teams. And so I just recapped, all right, here's what I presented to leadership. Here are the feedback that we got. Here's like the strategic feedback that we got. And here are the changes we're going to make. Any questions let me know. And I posted it in Slack. So I was just trying to keep like the feedback loop really quick and tight with teams rather than wait to the next meeting you have with them a week later. I was like, all right, I'm
Starting point is 00:48:18 going to just try to spend five minutes recording this and get it out ASAP. And that helps because then it gets people excited. Okay, cool. This thing that I worked on got really great feedback from leadership. Now we're working on it. I'm excited to get going. And then it depends. Usually, depending on the project, have some sort of kickoff. I don't usually do like a quarterly kickoff or anything like that because I think there's usually like disparate teams owning different parts of strategy. But usually having a good weekly team meeting where you're really thoughtful about cascading feedback down from leadership, constantly checking in on what are we trying to do here? What is our strategy? How are these goals that we set laddering up? Are we achieving it?
Starting point is 00:48:52 Are we not? Whatever? Having a meeting like that where you're kind of constantly talking about it each week also helps people feel bought in and not get distracted. And actually, I found that teams who are very bought into your vision and strategy are less distractible. Where I usually have more trouble is with leadership that aren't necessarily in the weeds with your team every day. And they, you know, I'll get an idea. Have you thought about doing this one random obscure thing? Yes. However, it's not in service of this long-term plan. So we don't want to do that right now because we don't think it's the best use of our time. Got it. And the way you're describing it, this is as a a manager of product managers, right?
Starting point is 00:49:28 Versus an ICPM. Cool. So as an ICPM, I imagine you would do a quarterly kickoff or whatever your cycle length, right? You kick off with the team because we're doing any questions. Totally. Okay. Another thing I wanted to make sure we had time to chat about is product review meetings and process.
Starting point is 00:49:44 Just kind of like, how do you, as a product leader, make sure that you're shipping great stuff that you're proud of and that your leaders aren't surprised by? How do you design just kind of like a product review and design reprocess? Yeah, so I have a lot of strong feelings on product reviews. And it's because I've been in a lot of different organizations and I've seen a lot of bad ways of doing this, honestly. And I think it also depends on the product that you're building and the team that you've created. So I don't think that there's one right or wrong way to do this. Where I've seen them fail is when they happen at the function level and they're not done or shared as a team.
Starting point is 00:50:18 You know, typically it's normal to have a design review or to have some sort of technical review. and the more you can try to bring those different review processes into one central moment to check in, the better it tends to go because what happens is you'll have feedback in a vacuum, like the design leader will give the designer feedback and then you don't hear about it. Or there'll be some technical flaw that happens in a very specific technical review that doesn't get back to the larger team. So finding ways to make sure that those parts of your process are shared across each function and you attend them and prepare for them as a team,
Starting point is 00:50:52 I think really helps a lot of that. Not saying that you shouldn't have a design review, of course you should. You should just be really thoughtful about having moments that, especially if there are moments where you're like blessing something to move forward, to making sure the whole team is there, and that there's a very strategic check-in process to get those things approved that everyone knows about and is a part of. Is that a meeting that you do weekly and you invite the designer and the engineer?
Starting point is 00:51:17 Who do you invite, I guess, And what is the goal of that meeting? The goal of that meeting, I imagine, is approved the product to go launch and build. Yeah. And I think especially if you're going back to the one way, two way door moment, giving teams autonomy to ship some things that you think are two way doors and aren't necessarily mission critical are important to what, you know, your vision, but aren't going to conflate with the larger system.
Starting point is 00:51:37 I think trying to keep things quick and not have too many barriers for people to ship is incredibly important. So you'll have to figure that out for your own org and its nuances, but that is something. but that is something that is important. But when there are moments where you think it is a gate, basically a feedback gate, right, where it's like a gate you need to walk through a specific moment in time where you've gotten feedback,
Starting point is 00:51:57 I think having a cross-functional meeting where there's a clear pre-read or something that's sent before, it's like, here's what we're talking about today, and then aligning on do we think this meets our goals and does this meet our quality bar? And doing that in a really thoughtful way, just so the team gets feedback, so leadership is plugged in, but also so you're not like standing the way
Starting point is 00:52:15 of people shipping their products. And then do you check in throughout the process of the product being built? Or do you kind of encourage teams to get to a point where it's basically ready for approval? Yeah, and ideally in a perfect world, there's like three check-in moments. There is the first principles check-in. What are you trying to build or what are you trying to do? What are the sort of foundations that you're going to build on? What is the most important thing?
Starting point is 00:52:36 What are you solving for? Getting approval on that, weirdly, is almost like the most important thing because it saves a lot of teams a lot of time when they get later in their feedback review process. And people are like, you're not solving for the right thing. thing. So that's important. Once you've aligned on that, then it's like, all right, what approach are we going to use? What are we going to build? And that's like sort of how we solve the problem. Making sure that there is a technical component there too. So there's some sort of, you know, infrastructure review or architecture review or whatever you want to call it. And then it's like,
Starting point is 00:53:02 all right, this is ready to ship. Let's check in again. Do we think it's ready? And I think that, again, it depends on your organization. If you have a very small team, you might be very plugged in and these things might not need to happen. But in bigger organizations where, you know, especially where leadership isn't always able to be in the room, making sure that you have a clear checking in a few times to make sure that everyone is moving in the right direction and everyone feels good is, I think, a worthwhile exercise. I love that, such a simple framework.
Starting point is 00:53:29 And then one last question along those lines, do you leave it up to the team to schedule these meetings, or are you kind of pulling it out of them and making sure they schedule it? Today, because of the team that I'm working on is pretty small and we're pretty pre-product-market fit, like we're not doing a ton of very formal check-in moments because we don't need to be
Starting point is 00:53:43 because it's a small team and we're all cruising together. But in bigger orgs that I worked in for Shopify, for example, there was a process around having these meetings and who would be there. And so those would kind of be scheduled through like the larger processor system that they were working in, which really worked for them actually. And I think it allowed teams to be pretty autonomous on the day to day, but just making sure that, you know, there was feedback coming sort of like from their users as well as from leadership. Got it. One last question before we get to our exciting lightning round. And it's something that I've been thinking a lot about recently, which is around remote work as a problem. I left Airbnb before COVID, and so I never lived in this world of everything is remote and product
Starting point is 00:54:22 managing remotely. Is there anything you've picked up or learned that has been really helpful to being a product leader in a remote world? Yeah, I would say the last couple of years have just been a huge shift in my ways of working. I sort of grew up as a PM in IR in IR, IRRL environments, where we did the majority of our work together in the same room. So that was like whiteboarding, you know, having a quick sink after you had an in-person meeting to like finalize some details or keep hashing out a problem. You know, it's sort of so cheesy and overhyped, but the like proverbial water cooler moment where you see somebody, you're like, hey, how are you doing? Hey, did you hear about this thing? All of those things literally went away overnight. And I think especially the job of a PM
Starting point is 00:55:03 is it's hard under normal times because you are doing so much labor to make sure people are informed and give feedback, et cetera. And then overnight you took away a lot of of the methods that they were using to do it. And so I think that has been a pretty profound shift for a lot of people working in product roles. The good news is there's a ton of new tools and new technology that's actually being built right now. That's majorly helpful for this. So like I use Slack in very new ways today than I did two years ago. Things like just making sure to post more asynchronous updates, trying to actually like take the burden off of an IRL or a Zoom meeting. Can we talk about this asynchronously and do it in Slack? Slack,
Starting point is 00:55:44 has this really great feature called huddles where you can just quickly get on. It's just audio, so there's no video, and you can just like have a 30-second conversation. It's good for stand-ups and things like that. Suggest you try it if you haven't yet. And then a lot of the old sort of in-person whiteboarding, things like that, you can do those now using awesome tools like Miro and Fig Jam. And I feel like, you know, especially at Airbnb, you know, we had such an international team that there was always somebody who was remote typically. And I think we never really got the remote experience right. And now that the majority of our teams are remote, I'm a fully remote person. I've been a lot more thoughtful about making sure we're creating a really good
Starting point is 00:56:21 experience of like how we're working for the larger team. And so I think you have to hack on this with your team. Different teams have different ways of working, but trying to be asynchronous, using Slack, making sure you're following up in very visible ways where people can see. Don't rely on Zoom meetings to fill all of your time. Otherwise, people will literally hate you. and things like that really make a huge difference. Awesome. Super helpful. All right, Nikki, are you ready for the lightning round? I am ready. Let's do this.
Starting point is 00:56:49 What's a book that you recommend most to other product managers? I love Thinking and Systems by Donella Meadows. Awesome. Okay, we're going to link to that in the description. Other than Duolingo, what's another company that you recommend, the PMs go work out or explore when they're looking for a new gig? Yeah, I would say Etsy, hands down. And why is that? I think it's a great place to learn how to be a PM, data-driven, really supportive product
Starting point is 00:57:15 leadership and a super fun product to build. Awesome. Love that. What's the current favorite kind of app or a piece of software that helps you do your work better? I'm obsessed with Superhuman, which is a email productivity app, which once you start using it, you can't not use it. You basically have to use it for the rest of your days.
Starting point is 00:57:34 I also am obsessed with Loom, which is a video recording tool that makes it really easy. to share really quick video updates. Awesome. Great choices. And then outside of work, it's like current favorite app or just a piece of software that you love. Definitely TikTok. Short form video is very fun and entertaining.
Starting point is 00:57:52 Can't get enough of it and have been creating some myself. So I'm definitely hooked. While we're on that topic, how do people find you on TikTok? Yeah, it's just my name. It's Nikki Scarstedt and give me a follow. I'm a very happy follower. And then I'll link to that in description too.
Starting point is 00:58:06 Who's a favorite person that you like to follow on either Twitter or Instagram or even TikTok. Yeah. So I love, she is a cultural journalist. Her name is Anne Helen Peterson. And she's really plugged into sort of like the larger cultural zeitgeist of the time. And I always give people when people ask me my top advice for new PMs, it's just to be a consumer, to download new products, to try them out, to use all the things and try them, because I think it actually makes you a better product builder. And follow people that are not just tech people on Twitter. You are doing yourself.
Starting point is 00:58:39 to service if your entire feed is tech people. So find people that are plugged into cultural zeitgeist because it helps you also understand the moment in which you are shipping, and it'll make sure that you're acing your product marketing and your messaging and you're building the right thing. What's her name again? Her name is Anne Helen Peterson. Anne Helen Peterson. Love it. Okay. And then final question. Who's been your favorite manager? Yeah. So I couldn't pick one person here. So don't be mad. But it's actually a lot of women that I work for at Etsy. The majority of my entire reporting line, the time that I was there was all women, which is never happened to me again. So shout out to Kruthi Patel, who is their current chief product
Starting point is 00:59:16 officer, a woman named Heather Jassy, who ran the community team at Etsy long ago, who was a true delight to work for. And then Linda Finley, who is now the CEO of Blue Apron, but she was the chief operating officer at my time at Etsy, and she was my boss for a bit, and she was wonderful. Amazing. Thank you for sharing all that. And thank you so much for joining me, Nikki, for doing this, where can people find you online and just generally how can people that are listening to us be helpful to you yeah so i have newly become obsessed with tictock like i said before i've been creating some like fun little short form videos one of my regrets is a long-time product builders it's very time consuming to write down the stories of building products and to share them but i found ticot actually
Starting point is 00:59:57 actually really easy to do that so i'm going to try to experiment there a little bit more so you can follow me i'm at niki scarstead on ticot and then i have a newsletter i call it builder It's niki.substack.com. Nikki is spelled like Mickey Mouse, but with an N, n-I-C-E-Y dot substack.com. And I publish there occasionally. I need to get it going again, but again, trying to write down more of the stories
Starting point is 01:00:19 of actually being a builder who's been doing this for a long time because a lot of us don't have a lot of time to actually talk about it, but it's really interesting work, and I want to share it more. Awesome. I'm a follower and a subscriber to both, so highly recommend that.
Starting point is 01:00:32 I love it. And thank you so much, Nikki. Yeah, thank you, Lenny. That was awesome. Thank you for listening. If you enjoy the chat, don't forget to subscribe to the podcast. You could also learn more at lenniespodcast.com. I'll see in the next episode.

There aren't comments yet for this episode. Click on any sentence in the transcript to leave a comment.