Getting to "Why?" with Leo Gong of Apartment List

Leo Gong Final

Kayla: [00:00:00] Thanks for tuning in to Product Chats. On today's episode, I talk with Leo Gong, who is the VP of Product at Apartment List. And we talk about the why, and also putting people first. So hope you enjoy this episode and don't forget to leave us a review.

Thanks so much for coming on today.

Leo: Hey Kayla. 

Kayla: So in a minute or less, can you tell us about yourself? 

Leo: Sure. My name is Leo. I'm the VP of Product at Apartment List and I'll just give a really quick breeze through of my career. So I started off in actually consulting. I worked at Bain and Company for two and a half years.

Got bitten by the startup bug, I left, taught myself how to code and built my own startup. Bounced around between Singapore and San Francisco and Australia. And before I eventually went to join Dropbox, where I joined right before they crossed the 200 employee mark. I worked there in sales operations, where I kind of realized that we had a lot of problems where there were too many inbound leads.

[00:01:00] And so I built a really simple model that, kind of, using historical data, predicted who was likely to convert versus not. And that was like the very early version of a lead scoring algorithm. That then led me to my next company where I was hired on as the very first PM at a Series A startup that was actually offering machine learning, sort of like lead scoring, algorithmic demand generation that was EverString.

I worked there for a couple years and then I eventually left to join Evernote where I basically worked on the Evernote for business products and really launched a brand new product there. And then finally that led me to Apartment List where I've been here for the last almost four years. 

Kayla: So something I wanna kind of dive into, what are, like you said, you started out in sales operations, like what is that skill set that was really valuable in sales operations that has kind of also led to your success in product management? 

Leo: Yeah. I really think a lot of my experience in management consulting, to be honest, I think my experience at Bain really taught me that you can [00:02:00] basically solve any problem because you, you are kind of expected to come out of college and then you're expected to go figure out.

I've worked on cases for semiconductor manufacturers. I've assessed like whether or not it made sense to acquire, let's say a fish vaccine manufacturer, like a lot of these things you kind of pick up and you start learning, you see patterns around. It's not the actual technical knowledge that oftentimes you need to figure out a problem.

It's really just understanding what the issues are and kind of diving into it. And so having that basis was really helpful for me when I joined Dropbox. So I was actually in business operations, but I was doing a stint in sales operations. And at that point in time, Dropbox had only, you know, one really big floor in which we had maybe people taking up a quarter of it. And so people would be scooting from one side of the office to the other. We had six salespeople actually at that point in time. And, you know, people would be hopping onto chat while they were commuting to work on the Cal chain. Some really exciting times, but really, really unstructured.

And so that [00:03:00] experience, that management consulting was really helpful cuz you are coming into a really unstructured environment where sometimes the problem wasn't necessarily defined. So you were kind of looking around for what were the issues. And then, I think that skillset really allowed me to succeed at that point of Dropbox's, you know, maturity to, to kind of just go and figure out what was the problem, and then just figure out, you know, creative solutions to them.

Kayla: So with that, right. Figuring out the problem, obviously in product, that's what you wanna get to, right? What is the, the problem or challenge that our customers are dealing with? And so when you're actually trying to figure that out, what are things you're doing that you get to like get close to your customers?

Or what are some of your favorite things to do to really understand your customer? 

Leo: Yeah, I think it's really, that's a great question. I think it's really around talking to your customers and being very good at asking the why questions. So that's something that I've been really, you know, fortunate and excited about doing here at Apartment List.

For example, we [00:04:00] have a pretty incredible user researcher and we spend a lot of time, you know, talking to customers. And I, I think where I've seen some differences in product orgs is there's some product orgs that don't talk to customers as much. Which, I think is it makes innovation a lot more difficult. And then there are product orgs where user research is maybe set aside as almost its own siloed org.

And their job is to go talk to customers and then conduct a readout and then PMs maybe consume the readouts and figure out what to do.

That doesn't work very well either. The reason for that is because the PM oftentimes has an idea of where they want to bring their product. And a lot of these insights usually happen organically, similar to this podcast.

You know, being, being able to go into a mindset of curiosity and then see what a conversation takes you, I think gets you to a lot more interesting insights than if you came with a preprepared list of questions, which is oftentimes a little bit more what the model, where a siloed model leads you to the user researcher will pre prepare list of questions and go.

And so [00:05:00] what, what I've really liked and how I've applied, you know, research and understanding to new product development is a joint session between PM and user research. We usually start with a list of questions just to understand the customer and really dig into the why.

We probably ask why two or three, four or five times, you know, we'll ask for, just to give you an example of some recent conversations we had, we were talking to some properties and trying to understand what their thoughts were on maybe the short-term rentals market. And we asked about which competitors they work with and what their thoughts were there. And when they started talking about, oh, this thing didn't work particularly well, we would ask why, you know, okay. So this is the reason why it doesn't work well, but then why do you care about that?

And oftentimes I think people don't go down to why enough and, and I think where the PM comes in, cuz the user research is really good at digging into the why, why you want the PM there is because the PM can then live oftentimes see [00:06:00] some potential solutions just to test, you know, litmus test and see if they're, if we're getting it right.

Oh. So if I understand your pain point, if we were to do this, would that, how would that sound to you? And I think that's super invaluable to be able to get that live interaction versus taking it offline from the user research or building something and then testing it maybe two, two or three weeks later with a customer.

Kayla: So I think something that you mentioned, right? The why, and I think that's something that's super important as like a, a product manager is to always have that kind of natural curiosity of like, what is the base cause because if you try to solution, then you just hop to that and you're skipping out probably on the pain.

So how do you make sure, right. You're listening to customers, you're working with UX. Are there other ways where you're like, let's make sure we fully understand this. Besides the why. Right? Are there other ways that you're kind of setting up your team for success? 

Leo: Yeah, I think this is a, it's a work in progress, I think, because what I've [00:07:00] realized is a lot of product orgs really just don't do it very well or in a very structured way.

And so the process that we've actually laid on over time was, or the first phase when I started working and leading product here was really just introducing and being very explicit about user problems and personas, and then making it front and center. So almost every single one of our product presentations, whether it be user research or product design, product analytics, or product management- related presentations.

Almost all of them start off with what the user problem is. And beyond just saying, you know, as this person, this is what I'm trying to do, and this is why I kind of do it. I spend a lot of time actually digging into what the sub user problems are. So our user problems when we write them are usually the high level and then there'll be a sub bullet, maybe multiple sub bullets.

And then there might be multiple sub-sublets because I think that's, that's sort of a really good way to prompt people to go down into, you know, the why a couple of times. And then I think, probably surprising to, [00:08:00] to most people when they initially start working here, I spend probably 50% of the time when I'm reviewing a document on actually the user problem statement. You know, all the other stuff, what the solution is, what the mocks are.

That's the other 50% of the time, but I really really pay a lot attention to, are you framing this the right way? You know, is this truly validated? What gives you the confidence that this truly is an issue? So that's really been, I think the first phase of just building discipline around digging deep and putting it across all the parts of the org and into templates to really make that natural over time.

And then the second phase is really digging into the complexity behind the user's lives and truly understanding them. And I think that is also really really hard. I think. I've worked at Evernote and Dropbox. And I think when you look at a lot of the productivity tools out there, one of the challenges of a productivity app, and you can also put in any of the other ones like [00:09:00] Notion, or Slack, or whatever is the beauty of the productivity app is fluid, right?

You can have 20,000 different use cases in Evernote and in Dropbox. And oftentimes the product teams can get a little bit lost. Cause you kind of don't know what you're trying to build for. And then you end up just building features and then you don't really know how your features are being used, but you just keep building more.

And I think that's the bit I think a lot of productivity apps struggle with. And even as a marketplace for Apartment List, we see that too, because a lot of what we're trying to do in our mission is to make renters more productive and to make leasing agents and marketers much more productive. And the second thing that we try to do is really instill this why, or, you know, user driven approach in our product org is we're really pushing the PMs and the designers and the user researchers to go really deep. 

So I basically, you know, tell them, I want you to go so deep that our clients would want [00:10:00] to invite you to a conference to talk about how they could do their jobs better. And I think most of us never really truly get there.

It's like, I want you to understand the systems that you use. I want you to understand your workflows in and out. I want you to understand your schedules and what they care about. But you should become truly truly an expert in terms of how they should be doing their jobs. If we wanna be able to create great product.

Kayla: So one thing you talked about right, is the why, so that's when you're like building it out, but I kind of wanna dive a little bit into iteration and how you decide what you're gonna iterate on and how you kind of like prioritize. 

Leo: Yeah, I think that's an interesting one. I think prioritization is always a little bit more of an art than it is a science, but I can maybe break it out a little bit, actually in a slightly more scientific way, which is, ideally what you want, is you first want a product vision, and that's really what the product leader needs to be opinionated, and really be able to drive alignment and consistency around.

And so for Apartment List, for instance, the product vision is we wanna [00:11:00] build a rental concierge. You know, renting – it's a huge pain point.

It's super meaningful for people. But today when you look on our competitors' sites, for instance, you're sort of left to your own devices, right? It's oh, here's 10,000 pins and good luck. With five pages of data and 20 photos, go look through all of them, spend 40 hours, and then come back and tell us who you wanna contact.

And so what, what our product vision is, we wanna be that concierge that really helps people rent smarter and faster, and all of those things that help them be more productive. On both sides, for renters and for leasing agents. And I think having that overarching product vision allows you to figure out essentially between your different product ideas, which ones you do, the natural normal things, which I think, you know, everybody does, which is impact and confidence and the cost.

Right? But I think you're looking really for strategic alignment and you wanna essentially create a thread or a narrative around, "this is the thing that is gonna be really, really difficult to do over time." For instance, enabling a tour booking concierge that could tell you:" Hey, Kayla, we understand that you're free for four hours on Saturday morning.

[00:12:00] Here's a suggested itinerary based on the availabilities that we see." That's a really long term kind of roadmap that might take a year, might take two years because there's a lot of like, discreet pieces in there, but if you've got the product vision, then I think it gives you staying power to stay on one thread for a really long time.

Where I've seen also product orgs go off track is without a really clear product vision and clear belief, product teams don't know where to keep iterating. They'll try something. And if it doesn't work the first time they'll give up. But, but we try to essentially, you know, you pick the idea based on the normal prioritization, but then based on the strategic alignment or how it aligns to your vision, we usually ask teams to give it a strong couple of tries before they move on to a different idea.

Kayla: I think part of that also, right, is aligning that right company goals with how you build out your product. Always making sure there is that loop. So, what you talked about, like there can be distractions, right? And productivity tools – does this actually align with what we're trying to achieve as a company?

And so I wanna get into, I know you started your own company, [00:13:00] so like tell us a little bit about how you launch a new product or how you create a product from scratch. 

Leo: Yeah, I think I made a lot of mistakes when I launched my first company. We can definitely go into that. But if the question is not to do it, that would be a really really good one.

I think how to do it is more recently. I think, both at DropBox and the Series A company for machine learning and also at Apartment List. And I can kind of go through that, but basically the, the way I think about how you launch a new product is, there's maybe, I would say two big phases. 

The first big phase is really aligning on the why.

So, this is the why, when it comes to the company.

Why are the execs excited about this? Or, you know, why, why does steering want us to do this? I think getting really crystal clear on that I think is really important. And then once you align on the why I think it's, it's really figuring out, whether, what the product market fit is.

And that is validating that you've got the right [00:14:00] hypothesized customer. You've got the right problem that you've identified for them. And you've got a solution that works, both for them, but also for the business. So, you know, like it needs to do what it needs to accomplish for the customer, but needs to be scalable for the business.

It needs to make money for the business. Those are the two high level places where I, it's sort of my playbook that I roll out, you know, everywhere I go, whenever I try to, to launch a new product and I'm happy to go deeper on any one of those pieces. 

Kayla: So what are a few things not to do when you're creating a new product?

Leo: Yeah. A few things not to do when you're creating a new product is for example, if the CEO were to say:" Hey, it'll be really cool if we launched a new product that, this thing, and then just going off and doing it. I think a lot of times where that ends up going wrong is two ways. One way, is there isn't a clear alignment on what success looks like, because saying that you're gonna build this feature is not sufficient to answer the question of [00:15:00] what does it actually need to provide to the business for it to justify deeper investment. 

So that's one place where a lot of times things go wrong and I think what might end up happening if you don't do this is you might spend a couple months, maybe even a year, and you go and build this really, really amazing product that did exactly that. It's really cool features, you know, like the technology that no one else does, but then ultimately you launch it.

And then after a couple of months in the market, when the business is looking at where it wants to deploy its resources for the next couple years, it's kind of up there and the rest of exec and everyone else who are kind of discussing priorities, look at it. It's not really clear. Like why, why is it part of our portfolio?

Like, how does it contribute? And how much resourcing does it justify? So that's one place where it tends to go wrong. 

The second place is even where, when you don't run into issues, maybe the idea was perfect and you know, you build it and you launch it and it does all the right things. [00:16:00] And in that case, I call it like just hitting the jackpot.

And there are like really, really great companies out there who basically did just that. So if the founder story is usually, I was doing this thing and I had this problem and I built the solution for myself and I launched it. And then before I knew it, you know, there were tens of thousands of people using it.

That is one of the lucky jackpot cases. And the second thing that could go wrong in those cases is you might actually have a product that grows and grows and it becomes really, really successful. But it will struggle to grow beyond that because you don't have a really crisp articulation of the why behind it.

Like why was it successful and who was it truly for and all of those types of things. 

And so one other thing that could often go wrong is really over investing in a new idea. So whenever we have a new idea, what I really like to do is I like to keep the team really, really small. Usually it's maybe three to five people.

So it's one engineer. One designer, one product person and usually a go to market or operations person, cuz most of the time, these days, at least in the [00:17:00] marketplace, the things that you launch, aren't purely just R & D. But what I've seen it gone wrong is people throw too much fuel onto the fire before you kind of figure out what is the thing that you actually wanna light up.

Kayla: So I think with that, right, it's about figuring out that market fit, actually listening to your customers rather than just being like, let's just build this thing out because, and so I think something you talk about also to kind of go back to like your first point is as a product leader, you have to be comfortable saying no.

Right? You have to say:" Well, even if the CEO thinks this is the best idea, it may not be the best idea." So like, how do you actually push back to a CEO that's saying:" Hey, we should build this out"? Or how do you make sure there's still like alignment and you're communicating that vision around what's best for the product?

Leo: Yeah, that is, that is a really really great question. And I think it actually comes back to, I like to joke with the people I work with, that everything in life is actually just product management, but it basically comes back to the why as well. So the way it, I, and I've had [00:18:00] this conversation multiple times with multiple different CEOs or directors or others.

And it actually comes down to the why for them. So why are you, you know, really excited about this idea? And I think if you actually go a couple whys deep, you can actually, if you can echo back. Oh, okay. The reason why you're really excited about this idea is because you believe that there's a huge growing market that is really untapped.

You feel like the margins of this are gonna really compliment our business really well. You know, you feel like X, Y, and Z. I think if you're able to repeat back, oftentimes that's what the CEO is really trying to communicate. And then you can then say what your idea could be for how you could actually achieve that in a different way.

You could say, okay, understanding that's what you want, taking what you just said is the seed of it. Let me build upon that. And what do you think about this? And I think usually that goes across really really well when you're able to [00:19:00] actually reflect that back. 

Kayla: So this is kind of talking about those relationships and putting people first.

Right? So let's kind of pivot into putting people first. Do you wanna talk a little bit about that?

Leo: Yeah, for sure. I think that's one of the things I really like about Apartment List that I've honestly learned about that a lot here. I think people do their best work when they feel like their interests are taken care of because what that means is they can come into work and they can show up and really just think about the customers and less around, oh, you know, how do I get this thing that I need?

And so I think as a leader and a huge part of that really is around empathy. You can't put people first, if you don't understand what drives people or what they're struggling with. And I think empathy, I think is really the number one thing. 

And there's a couple of things that I try to do in either my 1:1s or in my interactions, even in a group setting where people that I work with. In 1:1s, I [00:20:00] think, we can get really explicit, which is after you go through and you build trust and credibility with each other, which is really important as foundations. 

I usually just ask the same couple of questions every beginning of the 1:1 which is overall, how happy are you? And then the sub questions underneath that is what's your level of excitement?

How intellectually challenged are you and how busy are you? And I ask people to rate where they are on a scale of 1 to 10. And then the other thing I do is I actually ask them to also tell me where they wanna be on the 1 to 10. Cause not everybody is a 10 out of 10 excitement, kind of a person for me, the highest I probably ever get will be a 9.5 out of 10.

And that will last for two hours before, you know, comes back down. And so my happy point is probably a 7 or 8. Some people like to be really busy. Some people like to be super intellectually challenged, and I think it shifts as well. It depends on what's going on in your life. You know, I think a lot of people over the pandemic and, you know, even me [00:21:00] personally, I've gone through ups and downs and I think being able to check in as a leader and understand where people are at and what they're looking for, where they currently are relative to that I think is really really helpful.

Then in a more maybe group setting, both with direct reports, but also with the people that you work with. And again, this people first idea, I think again, applies also to customers. I mean, it basically is central to product. The other thing I try to do is really listen. And what I mean by that is similar in concept to the asking for a why, which is, communicating is really really hard and not everybody is...

I think, I would say most of us, aren't good at communicating what we're actually thinking and what we want. Especially when you get put on the spot and someone asks you a question. Kind goes, blah, blah, blah, blah, blah. And then it's kind of in there, but it's, it's not always super clear and it can be misinterpreted in five different ways.

Right? And so what I try to do is I try to go beyond [00:22:00] thinking about what the person is saying. And I try to think about why the person is saying what they're saying, and there'll oftentimes be meetings where for instance, someone will say something and then, you'll kind of wonder: "That didn't really make sense in the context.

Like why did they say that?" And then I think what I used to do was I would respond to the actual question itself and then we would move on. What I try to do now is either in the meeting, if I, and it's a skill I'm working on, if I'm able to, in the meeting, I try to like get down to the, oh, this is why the person's actually asking that.

Or after the meeting I'll think about, oh, maybe this person was asking this because they were concerned about A, B and C. Or they were asking this and it didn't make sense to me because they had a fundamentally different assumption about what the project was trying to accomplish. So why were they asking about margins?

Like this doesn't make any sense at this point, you know, off this new product development cycle. Oh, maybe it's because they kind of are assuming that [00:23:00] that's what the project needs to accomplish. Oh, like let's make sure that I adjust that and I sync with them offline. 

Kayla: So I think with that, right, you talk about how you lead.

And so I wanna know what roles are you hiring for? 

Leo: Oh, great question. So I'm actually very happy to say that we just filled all of our roles and that's been amazing. So I'm gonna enjoy this moment and hold onto this feeling for as long as I can, but that said, we are hiring. We are always looking for roles and I always wanna be building relationships.

I think that's the other thing, which is, even though we don't have roles open, I'm always trying to reach out and talk to PMs because you never know when a role's going to open. You always want to have that really good network built up. So I'm always looking for PMs who are, you know, I think there's a couple different flavors of PMs that we hire for.

I think there's the generalist PM which is, you know, user empathy, be good at maybe analytics and has some good design sense. There's also, more recently we've started [00:24:00] actually looking more for more technical PMs. So we recently hired a machine learning PM that used to be a data scientist. I think there's probably gonna be more roles that we are gonna open up there around, whether it be machine learning or maybe platforms and infrastructure.

And then lastly, I kind of view new product PMs as sort of a whole different breed in and of themselves. Because for those, you kind of want people who are truly the Jack of all trades. Can sell, can think operationally, can think in a product way and are usually a little bit technical, cuz you need them to be able to assess what's possible or not.

But if I may. I'd love to plug some roles that are open in some of my sister org, which is product analytics in particular. We're really looking to hire a really inquisitive, curious folks to join our product analytics org to help bring both basically both the quantitative research together with the really really amazing qualitative research that we do.

Kayla: So with that, I know we've talked a lot about [00:25:00] leadership. What is one piece of advice you would give to an aspiring product leader? 

Leo: I think my one piece of advice would be empathy. I think that's really core to it. I think. The core part of being a really great product leader is to look beyond what is presented to you by either your direct reports.

When they, when they say I'm really stressed out for instance, or when, you know, a customer says, this is my certain problem. I think the biggest advice is – that's a skill that really gets you from ICE all the way to being like an amazing product leader. I think the best product leaders are just super empathetic and is able to really take a small signal and really understand what the source is and be, and, and that's, what's gonna allow you to motivate and attract amazing employees. 

That's the thing that's gonna be able to get you buy in from all of your stakeholders around you and be able to disagree with them effectively. And that's also the thing that's gonna allow you to really set an incredible, you know, product roadmap that's really gonna resonate with your customers. 

Kayla: Great. [00:26:00] Well on that note, where can people find and connect with you? 

Leo: You can find me on LinkedIn, it's just slash in slash Leo. So always happy to get any additional connections, especially if it's from aspiring PMs or, you know, analysts or designers. 

Kayla: Well, thanks for coming on today.

Leo: Thanks, Kayla really appreciate it. 

Kayla: Thanks again to Leo for joining us on today's episode of product chats. For more product management resources, head to canny.io/blog, and we will see you next time.