YouSaid · the spoken record

Nickey Skarstad

lines on the record: 68
first: 2022-07-18
most recent: 2022-07-18
sittings or episodes: 1
sources: podcast

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“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 longtime 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. So you can follow me. I'm at Nikki Scarstead on TikTok. And then I have a newsletter. I call it Bill Gers. It's nikki.substack.com. Nikki is spelled like Mickey Mouse, but with an N, and I C-K-E-Y.substack.com. And I publish there 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 has never happened to me again. So shout out to Kruthy 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 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 PNs. 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Obsessed with superhuman, which is an email productivity app, which once you start using it, you can't 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I would say Etsy. Hands down. 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Sure, we're creating a really good 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 like 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 like have a 30 second conversation. It's good for standups 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 FigJam. And I feel like, you know, 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I would say the 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. You know, so that was like whiteboarding, 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 and 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 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 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”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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? What are you solving for? Getting approval on that weirdly is almost like being 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 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”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 its nuances, 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. 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 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 like standing the way of people shipping their products”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Have a design review, of course you should. You should just be really thoughtful about having moments that are 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so I have a lot of strong feelings on product reviews. 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. 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 like 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 I think really helps a lot of that. Not saying that you should”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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? 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 distractable where I usually have more trouble is with like 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 just trying to keep like 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. 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”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 in 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 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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. 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 is why these things are important.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, basically what second order thinking 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 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, really thinking through what are the pieces of data or all 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”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 start to, you get better over time about thinking about second level thinking or second order thinking rather. And so 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 Danella Meadows. It's just about like really thinking through how systems work. And then you can start to extrapolate what is a 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, you know, it's muscle. You build it over time. You make a couple of mistakes sometimes and then you see you have to like realize the true consequences of those mistakes.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 to our decision, right? Where it was really hard to change later because we literally needed it to be relatively final. 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 to 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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, 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 a ton of money. 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Actually, I 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 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. You're 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so I should 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Gotcha. Yeah. And I will say, like, okay, our 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 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 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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. And then so what we'll do 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 KRs below them? And then usually there's some sort of leadership review. I actually forget 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah. So I think just generally as you walk down that strategy pyramid, really getting into 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 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 and 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 teens 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 JIRA ticket for this specific thing that we need to build. It needs to connect up to a strategy and back down.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I mean, I'm 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 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 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?”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 touch point 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“So, I would prefill out the mirror 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 who have a little bit of a preread. 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. And so it's like.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 Miro. I actually personally like Miro'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 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 ten year timeline. Do not worry about what's happening.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“An ideal 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 abstraction 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 to hit to be able to like sing that beautiful symphony is a terrible metaphor. And now I'm open to it. I get it.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 and 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? If you could in 10 years, if you could zoom up and look at what”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“And so I think that's my first principle just like 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, 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. 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. Or, you know, our structural platform actually does not have the”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Hopefully they said good things. You don't have to out them. 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. 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?”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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. And 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, right? 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 don't 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 product, et cetera. And because they sort of like hate to say wallet 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, etc. 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 take”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, so I think there's kind of like 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 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 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 in development. And I think those functional ways of building make sense. When I was at Etsy, that was the way that the reporting structure was and it made a lot of sense.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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, you know, 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 like building in public and literally doing air quotes right now. I know you can't see me. But they were doing that because they had such a passionate, 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. 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. 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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, 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 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. Yeah.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 in 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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 said, and I basically changed 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 figuring out what”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source
“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 like what gives me Nikki Scarstead energy and have been really prioritizing that, especially in a post-COVID world.”
2022-07-18 · Lenny's Podcast · Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more · IDENTIFIED FROM THE TRANSCRIPT · source