July 18, 2022

Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more

Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more

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

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


Thinking in Systems by Donella H. Meadows

Anne Helen Petersen



Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe


Lenny (00:00:04):

When I asked in my newsletter Slack community who I should have on the podcast who's a bit under the radar, but amazing, Nickey Skarstad was the first name that I heard. And I was not surprised. I actually overlapped with Nickey at Airbnb, where she had a legendary reputation as a PM who everyone loved, but got shit done. Before Airbnb, Nickey 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.

Lenny (00:00:31):

After leaving, she went on to be VP product at The Wing, and is currently a director of product management at Duolingo. In our conversation, we cover how to set vision, translate that into goals, and then how to execute on it, making your strategy actionable, and keeping your teams aligned and focused, 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 Nickey Skarstad.

Lenny (00:01:02):

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Lenny (00:02:02):

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Lenny (00:02:41):

Dovetail 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, DataDoc, GitLab, Nielsen Norman Group, Sketch, Deloitte, all use Dovetail to get a better understanding of their customers and build better products. Try Dovetail's products for free for as long as you need. You can sign up and dive straight in at dovetailapp.com/lenny. Nickey, thank you so much for joining me today. I am really excited for our chat and to get to learn from you. So welcome.

Nickey Skarstad (00:03:28):

Thank you. Thanks for having me.

Lenny (00:03:30):

My pleasure. 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 if I were to. Can you just talk about how you got into product, and then a bit about just your journey from that point to where you are today?

Nickey Skarstad (00:03:48):

Yeah, so it's been a long, meandering journey, which is fun. And 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 at Etsy in 2010 is when I joined. And I joined them, I'd say it was 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 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.

Nickey Skarstad (00:04:38):

And the VP product at the time, his name's Mark Headland. Hey Mark, if you're listening. Was like, "Hey, Nickey, 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-y about it. And he gave me a little nudge, and was like, "I think you'd be really good at it."

Nickey Skarstad (00:04:59):

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 most of my time there, I worked on the seller side. 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.

Lenny (00:05:27):

Yeah, let's get into it. Where'd you go next?

Nickey Skarstad (00:05:29):

So after seven years at Etsy, I was kind of getting the itch to try something new. 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 says 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. And I really liked that. And it was something that I was good at.

Nickey Skarstad (00:05:54):

And so I was like, all right, where else could I go that's interesting or having a moment? And I was like, Airbnb. Has to be Airbnb. I was a huge fan of their product. They were also post-product market fit. 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.

Nickey Skarstad (00:06:18):

And so I was the first boots on the ground product manager, and really helped that team figure out how do we get product market fit? And then how do we start to think about how to scale it, which was, you can imagine, experiences is interesting because it is a very nuanced product in that, and this is similar to Airbnb if you work on homes as well, but part of it is building the digital experience 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 experience when you actually join an event or an experience.

Nickey Skarstad (00:06:52):

And I think that layer of abstraction for me was really fascinating, and something I've learned a ton about is it's not just influencing the digital product, but it's actually the consumer experience when their boots around 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 times. Left as senior product lead, I believe was my title. And forever grateful for that experience because I learned a ton about product market fit and also product quality.

Lenny (00:07:23):

Is there anything else you took away from that experience? 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 PM?

Nickey Skarstad (00:07:39):

Yeah. So part of it is more of just 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 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 the experience I had before that was definitely we were shipping things more quickly, things weren't always perfect. 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 is something I try to bring to my job today because no one does it better, in my personal opinion.

Lenny (00:08:28):

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 where it's just like, okay, here's how they keep quality so high? And then do you have any advice for just how to do that as a company?

Nickey Skarstad (00:08:40):

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 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. 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.

Nickey Skarstad (00:09:08):

And so 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 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 experience's top line goal was our review rate and quality and it trickled down for sure.

Lenny (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 build that into the way the team operates and tracks their success?

Nickey Skarstad (00:09:53):

Yeah. So a big part of that was actually operational, which was just making sure that hosts who weren't meeting those specific rigorous standards. 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? Everyone understood that it was important. And so I think that really impacted both the ops team as well as the product team who are literally building the product that would bring that to life. And I think just thinking from, especially if you're 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.

Nickey Skarstad (00:10:33):

Another thing we did a lot on the experiences team is we just dogfooded all the time. And so we were lucky in that it's a really fun product to dogfood. We were 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. I mean that really helped us too because then we would go back to the teams and be like, "All right, we were just 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 dogfooding is a good one.

Lenny (00:11:02):

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?

Nickey Skarstad (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 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.

Lenny (00:11:49):

Great. Okay. Maybe one more question on this topic because 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?

Nickey Skarstad (00:12:03):

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 we actually tanked a couple 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.

Nickey Skarstad (00:12:37):

So we did a lot of unpacking of what happened there, why did we do that, and actually does that matter? And the end answer was, yes, it matters greatly. 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." 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, into 30 days, it really impacts people.

Nickey Skarstad (00:13:06):

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. I might be wrong. But something along those lines. 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.

Lenny (00:13:32):

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 was it alongside just general growth?

Nickey Skarstad (00:13:45):

Yeah, it was alongside general growth. It wasn't 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 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. So how do you 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.

Lenny (00:14:14):

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. Okay. So you were at Airbnb, and where'd you go next?

Nickey Skarstad (00:14:40):

Yeah. So I went to a startup. And for lack of a better way to describe this, they were basically kind of building a marketplace as well, but it was more of 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 and they wanted to try to scale it so it wasn't constrained inside of their four 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.

Nickey Skarstad (00:15:16):

And so that started 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. They also had some other cultural issues, and so the whole thing kind of paused/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. I learned a lot about how to lead in that experience.

Nickey Skarstad (00:15:49):

But after that, and it was COVID, I had a eight month old, and so I spent time actually just vibing with my kids, which was kind of fun. And then ended up going to Shopify after that. And so I was looking for a more bigger scaled, not startup, and was trying to find something a little bit more something where 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, 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.

Nickey Skarstad (00:16:20):

And I realized that, honestly, pretty quickly after I took the role, I 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 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 what gives me Nickey Skarstad energy and have been really prioritizing that, especially in a post-COVID world.

Nickey Skarstad (00:16:46):

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. 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. It's super fun. So I'm also having a great time here as well.

Lenny (00:17:12):

Amazing. The companies you 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 how to know if a role or a company isn't a fit for them?

Nickey Skarstad (00:17:37):

Yeah. So I think I really learned that while I was there, and also I want to make sure 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, 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 basically if it was yellow, I was like, okay. It was a fine meeting. My energy was 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 I wanted to keep working on that.

Nickey Skarstad (00:18:17):

And when I looked back at the last few weeks, it was almost all red and yellow. And I was like, okay, this is really from an energy standpoint, I don't think I love this. And so I would say think about the work that you're doing and that lens. Get really good at 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?

Nickey Skarstad (00:18:39):

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 in the product that you're building, is very different. And so really thinking through what that work looks like, 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.

Lenny (00:19:04):

Wow. I love that tactic. I've never heard of that. Just going back to the meetings that you have in measuring, just reflecting on how much energy that meeting gave you. Great tip. Thank you for sharing that. And I'll also double down on Shopify is an amazing place to work. Just to make that clear. It's probably one of the few places I recommend PMs go try to work at.

Nickey Skarstad (00:19:23):

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. Also their product, 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 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 Shopify is at a very different stage than that. They're doing that in a couple places for sure, but that's not their day to day. And so that was interesting.

Lenny (00:20:06):

Yeah. That makes a lot of sense. Going back to what you just 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 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 in cross-functional teams versus not, and reporting lines, things like that? What do you recommend there?

Nickey Skarstad (00:20:34):

Yeah. So I feel like you're asking me to pick a favorite child, which especially as 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 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 building in public. I'm literally doing air quotes right now. I know you can't see me.

Lenny (00:20:57):

I can see them.

Nickey Skarstad (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, and basically getting people to try things and give feedback on things. I 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.

Nickey Skarstad (00:21:25):

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 Airbnb, what we talked about before, and just deeply baking in product quality and the end consumer experience into everything that you're building is also something I literally apply every day. So if I had to choose, it would be those two places, but I plan on continuing to learn.

Lenny (00:21:54):

Interesting. Both very community driven businesses.

Nickey Skarstad (00:21:57):


Lenny (00:21:58):

And then in terms of how they structured their org, is there anything there about just here's what I've learned works best for how to build product teams, structure product teams, that stuck with you?

Nickey Skarstad (00:22:07):

Yeah. So I think there's kind of two overarching popular organizational modes for product org specifically. There's either the functional organization where everyone in the product team will report up through either a VP product, or a chief 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'll have your product 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'll have a lot of either APMs or product managers who are newer in their career and need a lot of support in development. And 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.

Nickey Skarstad (00:23:00):

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 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.

Nickey Skarstad (00:23:44):

And I actually think that had they launched experiences inside of the Etsy style of organizational structure, it never would've succeeded because it had such a unique business need, and it needed its own process and ways of building product, et cetera. And because they sort of, hate to say wall it off, because it wasn't fully walled 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.

Nickey Skarstad (00:24:14):

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 so we can make sure that those 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 and the stage at which you're at.

Lenny (00:24:48):

Is there a default approach you'd suggest, just like most often you should go to the GM model, or most often you should just go with this cross-functional team?

Nickey Skarstad (00:24:58):

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 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. 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 development process across different functions to make sure that we are, to use a bad metaphor, it's like the symphony metaphor. 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.

Lenny (00:25:52):

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Lenny (00:26:54):

Something I learned at Airbnb and from many other companies at this point is there's never going to be the one right way to structure, and companies bounce back and forth between them. Like Airbnb, for example, has moved from GM model to functional reporting lines back to GM. And so things change and you try some, see how it goes, adjust, optimize for the biggest opportunity. And then you'll probably change it six months later.

Lenny (00:27:18):

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. And so can you just share any thoughts, advice, stories around that and how you do that well?

Nickey Skarstad (00:27:43):

Yeah. Well one, I want to know who you talked to. That's terrifying. Hopefully they said good things. You don't have to out them.

Lenny (00:27:49):

Unnamed sources. Unnamed sources.

Nickey Skarstad (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 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. And 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?

Nickey Skarstad (00:28:40):

And so I think that's my first principle is just bring along the team. And I think there are ways to do that where you're not voting on strategy. You should not be voting. I think 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.

Nickey Skarstad (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 that were like, "Oh, this conflates with our strategy. We're doing this, and it's very similar." Or, "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 all the way up to the CEO, and making sure the founder and the CEO is very bought 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 some of the foundations for good vision and strategy work.

Nickey Skarstad (00:29:51):

And then kind of zooming down into the weeds, I really like the vision mission strategy pyramid. I think 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 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? 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.

Nickey Skarstad (00:30:32):

And then you start, as you go down the pyramid, you get clearer and basically you bring things down to your moment in time more clearly. So if you're thinking about your mission, all right, it's another level of abstraction of 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 to hit to be able to sing that beautiful symphony, is a terrible metaphor. And now I'm open to say it. But whatever.

Lenny (00:31:10):

I get it. I get it.

Nickey Skarstad (00:31:15):

Dang it. Love a bad metaphor.

Lenny (00:31:16):

That'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 starting a Google doc and writing it out, are you using Miro or FigJam, or something like that?

Nickey Skarstad (00:31:30):

Yeah, so I think visioning exercise is a great moment to pull in your larger team. Because I'm remote now, I would use Miro or FigJam. Duolingo, we use FigJam typically because we are super embedded in Figma. In the past I've used MURAL. I actually personally like MURAL's whiteboarding product better. So I would open that up and I would walk through a number of things with the team and do a brainstorm literally. All 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.

Nickey Skarstad (00:32:05):

Good brainstorm 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,?we are going to be thinking in a five to 10 year timeline. Do not worry about what's happening today. And honestly, if you do that right, those are super fun exercises.

Lenny (00:32:30):

And you're doing this remotely, I imagine.

Nickey Skarstad (00:32:32):


Lenny (00:32:33):

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?

Nickey Skarstad (00:32:44):

So I would pre-fill out the Miro beforehand. So figure out what are the things you want to discuss with your team, create them as headers in the Miro document. So when everyone lands in there, you have a very clear 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 thinking landscape in advance. So people could have a little bit of a pre-read.

Nickey Skarstad (00:33:06):

And then when you get into the actual session, you already have the time allotments scheduled and thought through. And both Miro and FigJam have really awesome timer, and it'll play music while everyone is working. It's pretty cute. FigJam's sounds are really well done. Whoever their sound architect is, bravo. And it'll ding after, 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.

Nickey Skarstad (00:33:33):

After it's done, I like to do some synthesis together in the meeting. So basically grab ideas that are similar, bucket things into concepts that are alike. 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 come away with a vision together in a meeting that'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.

Lenny (00:33:56):

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 doing at Duolingo, but just to make it a little more concrete for people, what are some examples of things that you brainstormed?

Nickey Skarstad (00:34:11):

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 what type of experience can we create. And really thinking through 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 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 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?

Lenny (00:34:57):

Okay. So we went on kind of on a tangent around brainstorming. Did you want to share more around just going from vision to goals to execution?

Nickey Skarstad (00:35:04):

Yeah. So I think just generally, as you walk down that strategy pyramid, really getting down into the OKRs. And I think it's important because sometimes strategy is too abstract and too high level. And it's hard for people to take the step on 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's 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 feature level of we're going to create a Jira ticket for this specific thing that we need to build. It needs to connect up to a strategy and back down.

Lenny (00:35:53):

Got it. Where do you put, say, these OKRs? Do you just brainstorm, come up with vision and rough strategy, that translates into goals? Where do you do this? And then also just how long do you usually spend on this overall process?

Nickey Skarstad (00:36:06):

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 the third month in the quarter. Really thinking through, all right, how are we trending on our OKRs 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.

Nickey Skarstad (00:36:36):

And then, so what we'll do is spend a few weeks as a team 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 KRs below them? And then usually there's some sort of leadership review. I actually forget, Lenny, how did goal setting go at Airbnb? I honestly don't remember. It sounds terrible, but it was a while ago. I can't even remember if Airbnb used OKRs.

Lenny (00:37:03):

There was a long period where OKRs were a very big deal. Our head of product was really gungho on OKRs. And I think for a couple years, we were very strict OKR culture. And then it kind of evolved into just rough-

Nickey Skarstad (00:37:15):


Lenny (00:37:16):

... 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.

Nickey Skarstad (00:37:23):

Gotcha. Yeah. And I will say 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 no matter the size or the scale of your business. I think a lot of times people get hung up and they want to nitpick OKRs 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 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.

Lenny (00:37:57):

I'm going to pull out 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 bring people along to a final conclusion. Is there any advice on tips and tactics used to help with that?

Nickey Skarstad (00:38:22):

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. I think it's called Split the Difference: Negotiating As if Your Life Depends on It. Don't quote me on that.

Lenny (00:38:38):

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.

Nickey Skarstad (00:38:43):

I actually haven't watched the masterclass yet, but it's on my list after reading the book. And a lot of it, I think, especially because he's an FBI person, I thought it was going to be very much, "You're going to do this." And it's all basically his whole approach is empathy, and it's repeating things back to you, making people feel heard, making sure that you're hearing why they maybe don't like your strategy, or why they think that's a bad OKR. And I think if you can spend some time just listening to your team and really understanding why is this not resonating, you can help guide people on the right path. Or you realize you're wrong. 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 cause I'm probably not very at it. Yeah.

Lenny (00:39:25):

Good tip. I really like that.

Nickey Skarstad (00:39:28):

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 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, 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.

Lenny (00:40:09):

Do you have any examples or stories that come to mind of those sorts of decisions that you kind of help people just go for it, even though I may not necessarily agree?

Nickey Skarstad (00:40:17):

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 a many month long term project. And it was so important 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 where it was really hard to change later because we literally needed it to be relatively final.

Nickey Skarstad (00:40:53):

On Etsy, there was some big decisions that were made at certain points in time around what can be sold in the marketplace, and how to think through what constitutes something that is hand made. 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 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.

Lenny (00:41:23):

How do you know if it's a one way or a 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, we should have thought about that more?

Nickey Skarstad (00:41:34):

Yeah. I would say I think I'm good at this 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 order thinking. 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.

Nickey Skarstad (00:41:56):

A great book to read if you are a product person is Thinking in Systems by Donella Meadows. It's just about really thinking through how systems work, and then you can start to extrapolate 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 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 it's muscle, you build it over time. You make a couple of mistakes sometimes, and then you have to realize the true consequences of those mistakes and you don't make it again.

Lenny (00:42:29):

Can we talk a bit more about the second order decision framework? I know you have a awesome newsletter post about this, and it was something I wanted to chat about. Is this a framework that PMs can use to make better decisions? 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.

Nickey Skarstad (00:42:50):

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. And this feels very existential and 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.

Nickey Skarstad (00:43:23):

Let's talk about Airbnb home listing as an example. Really thinking through what are the pieces of data or all the pieces of data in the system that we need to actually 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. It gets just inherently more complex the more complex your system is. So that is probably a terribly described way of describing second order thinking.

Lenny (00:44:01):

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 any change you make and the listing 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.

Nickey Skarstad (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 and it will save you money, 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. So you can actually build in that direction and you don't constantly have to rebuild every time you're trying to change something.

Lenny (00:44:50):

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? When you're planning, do you write out in the document second order impact that we should be thinking about, or do you do something else?

Nickey Skarstad (00:45:05):

Yeah. So I think there's many ways to do this. If you have a spec-ed template or a piece of documentation that your team typically use when they're writing out product strategy or product requirements, et cetera, 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's why these things are important. And we want to make sure these are baked into what we're building. Typically you'll write those through the lens of second order thinking.

Nickey Skarstad (00:45:36):

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 before you even got into the design process, or before you had to start thinking about how do we actually technically implement this.

Nickey Skarstad (00:45:56):

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. You could use Miro to think about that. 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. 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.

Lenny (00:46:35):

Yeah. Absolutely. Happens all the time. For principles, do you put those in to say the team strategy, like the quarterly strategy document? Like here's our principles for the quarter? Is that how you generally do that?

Nickey Skarstad (00:46:47):

Yeah. I think that is a great place to put it. You can write them on the feature level too. So something that you're building, just getting clearer on here are the things that matter to us. Here's what we care about. We're going to design in service of these things. And here are the things that aren't that important. And again, those are the types of places in a product requirements doc where people will argue the most, which is a good thing because you're basically discussing and debating 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.

Lenny (00:47:16):

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 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?

Nickey Skarstad (00:47:38):

Yes. Oh, 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 OKR process for Q2 planning. They had a say in 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 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.

Nickey Skarstad (00:48:10):

So I was just trying to keep the feedback loop really quick and tight with teams rather than wait till the next meeting you have with them a week later. I was like, all right, I'm 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, and now we're working on it. I'm excited to get going.

Nickey Skarstad (00:48:29):

And then it depends. Usually depending on the project, I have some sort of kickoff. I don't usually do a quarterly kickoff or anything like that because I think there's usually 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? 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.

Nickey Skarstad (00:48:59):

And actually I found that teams who are very bought to your vision and strategy are less distractable. Where I usually have more trouble is with leadership that aren't necessarily in the weeds with your team every day. And 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."

Lenny (00:49:23):

Got it. And the way you're describing it, this is as a manager of product managers-

Nickey Skarstad (00:49:27):


Lenny (00:49:28):

... versus an ICPM? Cool. So as an ICPM, I imagine you would do a quarterly kickoff, or whatever your cycle length. You kick off with the team. Here's what we're doing. Any questions?

Nickey Skarstad (00:49:38):


Lenny (00:49:40):

Okay. Another thing I wanted to make sure we have time to chat about is product review meetings and process. 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 a product review and design process.

Nickey Skarstad (00:49:56):

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.

Nickey Skarstad (00:50:12):

Where I've seen them fail is when they happen at the function level, and they're not done or shared as a team. 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. 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.

Nickey Skarstad (00:50:43):

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, I think really helps a lot of that. I'm not saying that you shouldn't have a design review. Of course you should. I mean, you should just be really thoughtful about having moments, especially if there are moments where you're 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.

Lenny (00:51:11):

Is that a meeting that you do weekly and you invite the designer and the engineer? 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.

Nickey Skarstad (00:51:23):

Yeah. And I think especially 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 your vision, but aren't going to conflate with the larger system, 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 it's nuances, but that is something that is important.

Nickey Skarstad (00:51:49):

But when there are moments where you think it is basically a feedback gate, where it's a gate you need to walk through and a specific moment in time where you've gotten feedback, 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 the leadership is plugged in, but also so you're not standing the way of people shipping their products.

Lenny (00:52:17):

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?

Nickey Skarstad (00:52:26):

Yeah. Ideally in a perfect world, there's 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? What are you solving for? Getting approval on that, weirdly, is almost 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." So that's important.

Nickey Skarstad (00:52:49):

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 sort of how we solve the problem. Making sure that there is a technical component there too so there's some sort of infrastructure review or architecture review, or whatever you want to call it. And then it's like, 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, 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.

Lenny (00:53:27):

I love that. Such a simple framework. And then one last question along those lines, do you leave it up to the team to schedule these meetings, or are you pulling it out of them and making sure they schedule it?

Nickey Skarstad (00:53:36):

Today, because the team that I'm working on is pretty small, and we're pretty pre-product market fit, we're not doing a ton of very formal check-in moments because we don't need to be. Because it's a small team and we're all cruising together. But in bigger orgs that I've 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 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 there was feedback coming of from their users as well as from leadership.

Lenny (00:54:08):

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 product manager. I left Airbnb before COVID, and so I never lived in this world of everything is remote and product 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?

Nickey Skarstad (00:54:30):

Yeah. I would say last couple years have just been a huge shift in my ways of working. I sort of grew up as a PM in IRL environments where we did the majority of our work together in the same room. So that was whiteboarding, having a quick sync after you had an in person meeting to finalize some details or keep hashing out a problem. It's so cheesy and overhyped, but the proverbial water cooler moment where you see somebody, and you're like, "Hey, how are you doing, Hey, did you hear about this thing?" All of those things literally went away overnight.

Nickey Skarstad (00:55:01):

And I think especially the job of a PM, 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 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.

Nickey Skarstad (00:55:21):

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 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 take the burden off of an IRL or a Zoom meeting. Can we talk about this asynchronously and do it in Slack? Slack 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 have a 30 second conversation. It's good for standups and things like that. Suggest you try it if you haven't yet.

Nickey Skarstad (00:55:56):

And then a lot of the old in person whiteboarding, things like that, you can do those now using awesome tools like Miro and FigJam. And I feel like, especially at Airbnb, 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 experience of 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 a synchronous, 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.

Lenny (00:56:43):

Awesome. Super helpful. All right. Nickey, are you ready for the lightning round?

Nickey Skarstad (00:56:48):

I'm ready. Let's do this.

Lenny (00:56:49):

What's a book that you recommend most to other product managers?

Nickey Skarstad (00:56:53):

I love Thinking in Systems by Donella Meadows.

Lenny (00:56:57):

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 at or explore when they're looking for a new gig?

Nickey Skarstad (00:57:07):

Yeah, I would say Etsy hands down.

Lenny (00:57:09):

And why is that?

Nickey Skarstad (00:57:10):

I think it's a great place to learn how to be a PM. Data driven, really supportive, product leadership, and a super fun product to build.

Lenny (00:57:18):

Awesome. Love that. What's the current favorite kind of app or piece of software that helps you do your work better?

Nickey Skarstad (00:57:25):

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. I also am obsessed with Loom, which is a video recording tool that makes it really easy to share really quick video updates.

Lenny (00:57:41):

Awesome, great choices. And then outside of work, what's a current favorite app or just piece of software that you love?

Nickey Skarstad (00:57:47):

Definitely TikTok. Short form video is very fun and entertaining. Can't get enough of it, and have been creating some myself. So I'm definitely hooked.

Lenny (00:57:56):

While we're on that topic, how do people find you on TikTok?

Nickey Skarstad (00:57:58):

Yeah, it's just my name. It's Nickey Skarstad, and give me a follow.

Lenny (00:58:03):

I'm a very happy follower. And then I'll link to that in description too. Who's a favorite person that you like to follow on either Twitter, or Instagram, or even TikTok?

Nickey Skarstad (00:58:12):

Yeah, so I love, she is a cultural journalist, her name is Anne Helen Petersen. And she's really plugged into sort of 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 a disservice 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.

Lenny (00:58:53):

What's her name again?

Nickey Skarstad (00:58:54):

Her name is Anne Helen Petersen.

Lenny (00:58:56):

Anne Helen Petersen. Love it. Okay. And then final question. Who's been your favorite manager?

Nickey Skarstad (00:59:01):

Yeah, so I couldn't pick one person here, so don't be mad. But it's actually a lot of women that I worked for at Etsy. The majority of my entire reporting line the time that I was there was all women, which has never happened to me again. So shout out to Kruti Patel, who is their current chief product 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 Findley, 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.

Lenny (00:59:31):

Amazing. Thank you for sharing all that. And thank you so much for joining me, Nickey, for doing this. Where can people find you online? And then just generally, how can people that are listening to this be helpful to you?

Nickey Skarstad (00:59:43):

Yeah, so I have newly become obsessed with TikTok, like I said before. I've been creating some fun, little short form videos. One of my regrets as a long time product builder is it's very time consuming to write down the stories of building products and to share them. But I found TikTok actually really easy to do that. So I'm going to try to experiment there a little bit more.

Nickey Skarstad (01:00:01):

So you can follow me, I'm @NickeySkarstad on TikTok. And then I have a newsletter. I call it Builders. It's nickey.substack.com. Nickey is spelled like Mickey Mouse, but with an N. N-I-C-K-E-Y, .substack.com. And I publish their occasionally. I need to get it going again. But again, trying to write down more of the stories 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.

Lenny (01:00:29):

Awesome. I'm a follower and a subscriber to both. So highly recommend that.

Nickey Skarstad (01:00:32):

I love it.

Lenny (01:00:33):

And thank you so much, Nickey.

Nickey Skarstad (01:00:34):

Yeah. Thank you, Lenny.

Lenny (01:00:35):

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 lennyspodcast.com. I'll see you in the next episode.