Hiroki Asai: Designing the Journey

0:00The training you get as a creative or a designer doesn't necessarily have to be pigeonholed just to design and just to making. That way of thinking, that way of communicating, that understanding how to talk, the empathy of having to communicate something can really just transcend that craft of design into something much bigger.

0:24Welcome to Design Tangents, a podcast from Cool Hunting exploring the creative processes and inspirations that drive changemakers. I'm Evan Ornston. And I'm Josh Rubin. We're in San Francisco, a city that we love and have been to dozens and dozens of times. Today, we're at the Airbnb headquarters. But the last time we were here, we went on an Airbnb experience with Ted Barrow, who hosts Thrasher Magazine's YouTube series, This Old Ledge. What was interesting about it was that we know the city so well, we've been here so many times. but seeing it through his lens about modern architecture and the history of where architecture and skating meet was really really interesting for us yeah and he he knows his shit like he's a he is a phd in art and architecture and he's a skater and his ability to bring those two worlds together was super fascinating yeah we're not just here to talk about ted though we're here to talk with Hiroki Asai, Airbnb's Chief Experience Officer.

1:26And coincidentally, we've recently learned about Hiroki's love of skateboarding. But more on that later. Welcome to Design Tangents, Hiroki. Thank you. Thanks for having me. Happy to be here. How do you think about your work? What I'm responsible for at Airbnb is the, it's basically, I like to think about it as the customer's experience or the customer's journey before they get to us and when they travel with So it's the marketing, the advertising, the design of the app, the product features and the product itself, and then the on-trip experience. And so I tend to be the one that connects all the dots.

2:04It's not a small portfolio. No, it's smaller than it sounds. It sounds much more impressive than it actually is. It's fascinating because the customer's experience is so largely influenced by the place that they're staying or the experience that they've signed up for or the service that they're using, yet it all navigates through or is managed through the app or through the website. Yeah. Yeah. And I think that's where we have a really interesting place to play is because, you know, when you, we're a great booking app, but what we would like to be is a great app that you travel on. And so we know when you're going to check in, we know where you're going, we know what's happening around you, we have experiences and other things and points of interest that we could offer you.

2:54So we're really excited about taking the app to a place from just researching and booking to actually traveling. Your background's in graphic design, is that right? Yeah, yeah. So let's start there and kind of do the quick overview from studying graphic design to today. Yeah, yeah, yeah. Okay, so I grew up in Cupertino, California of all places. And I went to school down in San Luis Obispo and studied graphic design. And I thought for sure, you know, my life goal was to move to San Francisco, work in some kind of a lofty place where, you know, cool black leather shoes, carry a cool bag. And that was my life's ambition.

3:35I think that's our job. Yeah. Kind of like that. Working a small design studio. Yeah. I mean, you're doing, you know, you're doing pretty well. It's a pretty cool space you got. So I moved to San Francisco, was a graphic designer, and then very quickly realized that, you know, I'm a pretty good graphic designer, but I should probably start thinking about doing more than just graphic design because there's a lot of graphic designers that were coming out of art schools and they're working on different studios. And so I started to work for a bunch of different consultancies and then was lucky enough to be connected with Apple, a really kind of pivotal time in its history.

4:13After that, took a little bit of a break to collect myself and then kind of ended up here. You were at Apple for a pretty long stretch, right? It wasn't just a couple of years. You were there for a big period of time during a really transformational era for that company and for culture, I think, too. Yeah. Our adaption of a device's software. Yeah. Yeah. I feel so lucky that I kind of had a front seat to all of that change that was happening. I think for a lot of people that were there at that time, it was really a pivotal time in culture and technology. But I think for a lot of us, it was some of the best experiences that we've ever had.

4:50And I think for all of us, too, we kind of, you know, made some of the best professional relationships that we've ever had also. So over that arc that you just described, how has your practice grown or shifted or evolved? It evolved from me being a designer and actually doing the work to then managing the work to then managing teams to then managing departments. And so I think my trajectory took the course of a lot of designers where, you know, you find yourself for a good part of the career, you know, fingers on the keyboards or with the mouse actually designing things, moving type around, whatever, to then kind of, you know, art directing to then, you know, just directing whole teams through through conversations.

5:37So, yeah, you know, I think my trajectory probably maps to a lot of creatives where we went from doer to talker. And not everyone's geared for that, though, right? Sometimes you realize I'm a really good designer, a really good director of design, and I'm not really geared towards managing all these other larger groups and dealing with non-design entities within the organization. But obviously you have both skills. Yeah, it was really, really difficult because it's easy when you want to make something because you just put your hands to it. You have this idea in your head and you just make it. It was so difficult making the transition to helping people to make things, then helping teams to make things.

6:24Because really all you have is the words that come out of your mouth. And it's a very thin, linear flow that comes out of your mouth. But your mind is working at 10 million miles an hour and all these different spaces. And being able to communicate what you want, but then in a way that other people understand it and action it was really difficult for me to learn. But I think, you know, the more I went on that journey and the more I practiced that, I really started to love it. Actually, kind of oddly more than actually doing the work myself. I've labeled what you're describing as synthesis, right?

7:02You're a synthesizer, you're listening and kind of distilling, as you said, down to a focus or an articulation of a mess of information and notes and feedback. I'm fascinated that you said that that was learned. I feel like that would be hard to learn. It seems like something that is sort of intrinsic or it's in someone's nature to be able to process a lot of information down and distill it to a clear message. Is it just practice? Like, how did you learn? How did you learn? It was just, it was a lot of practice, some coaching too, you know, but a lot of practice. And it really, you know, basically what I learned is if we're sitting in a room together, talking about an idea, everyone brings their own history, perception, the way they see the world, the way they hear things, the way they process things, the way they see things to the table.

7:53And no matter how aligned you think you are, there's three totally separate points of view, right? And so, you know, there's always a starting point, which is usually just a common language for things. You know, that this means this, this means that. And then just a simple framework of how you use that language to define what you're doing. And then once you feel like you're actually talking and speaking the same language, you still actually have to look at something and be able to match what you're talking about, the framework, the language to the thing that you're looking at. And that's when people and ideas tend to be aligned.

8:26It took me a while to learn that, that, you know, even when people's heads are nodding And even when you think you're communicating and, you know, what you see in your head, you imagine they're seeing in their head and everything seems great. You're usually still miles off. And so you have to go through that process of like language, framework, the thing, you know, then conversation before you actually get aligned. And, you know, once you're aligned and you're working on the same idea, you're working on the same project, it still drifts, you know, day to day, week to week as the project changes and more constraints, you know, fall in front of you.

9:00things. It's a constant process of language and framework and alignment. And it took me a while to learn it. In some ways, you're living, I think, a creative or a designer's dream, right? You work at Airbnb, you were at Apple, two companies where design not only is important and regarded and respected, but where design has a seat at the table and design is part of the decision-making. And I think most designers dream of having that opportunity of having that respect instead of just being the people who are pushing the pixels around to, you know, at the end of that process, making it look good to go to market.

9:38Yeah, you know, we're really lucky here because I think we're one of the few companies around at this scale that was founded by designers and where the CEO and co-founder is a designer. And I think it's incredibly rare to have the chief decision maker understand the creative process and appreciate the creative process and understand the value of it, even though it's incredibly hard to measure the value of it and the value of a brand and the emotional impact of a brand. And that's really credit to Brian, the CEO and co-founder, who really drives a lot of the work day to day, that he can create this environment where creatives really have a seat at the table and can succeed.

10:20And it really changes you. Like my first intern in college, I worked at Esprit, not too far from here, in its heyday. And that forever changed my view of the importance of design and brand and how important those things were alongside of traditional things like product and marketing and, you know, sales strategy and all of that. To be able to work in that environment, I think, is truly inspiring and doesn't happen as frequently as those of us who have experienced it would like to see elsewhere. Yeah, it's really special. And I think we're really blessed to work in this company that understands customers are humans and hosts and guests are all humans.

11:00And humans make decisions for rational and emotional reasons. And sometimes one overpowers the other. Sometimes they're equal. But you have to really kind of speak to both. No. And I think to have a culture and a leader that understands both and can balance the two is very, very unique. Before we started this conversation, we had an opportunity to tour the office. And there are one of the things that really stood out for me are the portraits of people, the humans and their stories that have been really moving in the in the ecosystem of Airbnb. You know, hosts who help a guest that might be sick, for example.

11:38And I really appreciate that approach to bringing the humans into the office because it would be very easy to just focus on the product, just focus on the interface, just focus on the flow of booking or whatever the mechanics are and lose sight of who it's for. It's really easy in the world of user experience to talk about cohorts and personas. They're generalized, though. So, some of these really specific stories that are kind of scattered around the office, I think, I would imagine are super impactful and super helpful. Yeah, they are. And a lot of that stuff you see really predates me because I think at the founding of the company, long before I came on board, they were very, very conscious and still are to really understand that these are people.

12:25I think that's one thing that's kind of interesting when you think about Airbnb is that there's a lot of companies that you work for that create things, websites, products, software, hardware, whatever. And their mission is that someone uses that thing to do something and something great, hopefully. But the reality is there's kind of an abstraction with what you create and the change that happens or what that person does with it, that tool. What's interesting about here is we're putting human beings in other human beings' houses, you know, and you have to embrace the messiness of that experience and kind of the beauty of, you know, people's homes that aren't perfect, that are homey and neighborhoods that are interesting or have an edge and, you know, humans that are there and interacting and joy that could come out of it.

13:19And, you know, sometimes the friction that can come out of it, but you kind of have to embrace all of humanity, you know, when you're, when you're working here and working on the products here. And I think that's probably what you notice is that, you know, it's not super sterile or super pristine or super clean because we, I think, you know, we're, we're really about putting people together and kind of embracing the imperfection, but then the serendipity that happens when you do that. Speaking of humans and people outside of your work, what are the things that you enjoy in your free time doing?

13:56Is skating still important to you? Yeah, skating is important to me, although my body doesn't think it's that important anymore. So I have to be careful in damaging it. No, but what's important to me, my wife and I have three kids, three boys. They're all teenagers, which is really interesting. and my wife is an avid, avid world traveler and travel planner. And she's the kind of person that a year in advance will start booking trips, sometimes over a year in advance. And are you involved in that or she tells you like, we're going here and I've - Oh, no, no, no. Yeah, no, we're all involved, but she's definitely the executive producer of our adventures and they are extreme and exotic, you know, and they tend to be in the far reaches of the planet.

14:40And so, you know, between us traveling as a pod and the food that we encounter and photos that we take, we all love photography. That's kind of our hobby. So we either think about traveling, we talk about traveling, we cook the things that we did while we were traveling, or we're, you know, helping my wife to plan the next trip. Such a great gift, not only for you and your wife to experience, but for the kids to experience to see the world through a different lens is truly is life-changing. I think it helps form you as a human when you see how other people live. Yeah. It's really, yeah, it's really a gift that, I mean, credit to my wife, it was really her pushing to do this, but it's really a gift that we wanted to give to the kids is, you know, just seeing these parts of the world and seeing people and eating food that's different.

15:36And I think it just makes you probably a lot more confident and a lot less intimidated by the world, you know? Yeah. It's, we, we often describe our, our experience cause we travel a lot as well. And, you know, sometimes it's easy, familiar places, and sometimes they're very exotic and extreme and that is calibrating, right? Kind of resets your perspective on the world. And I, and, and I really appreciate that about travel and about new experiences that just kind of, you know, having, having a new, an adjusted point of view or adjusting context, um, kind of resets the, the center point. Like I'm, I'm just intrigued, like what's one of the recent trips or one of the past trips that, that was really memorable or destinations rather.

16:22Yeah, we did a true, there was a couple that we did that were really memorable. We did a trip to Ethiopia, um, kind of central and Western side of Ethiopia and was, we're basically kind of camping with some of the tribes that were out there. That was unbelievable. It was just like unbelievable. And then after that, we did a backpacking trip through Northern Sweden and it was just us and a guide. And so I think, you know, those two adventures and us experiencing it together. And I think kind of suffering through some of those experiences together was pretty wonderful. Have you been to Mongolia?

16:59No, that's on our list. That's on our list though. Selfishly asking because we're planning a trip. Yeah, places like that are like, you know, the last few places on the planet where you can have an adventure. I think that's what it probably taught our kids too is that there's like endlessly interesting things in the world. This is a great chance for us to cut to a break. So we'll be back in a minute.

17:47to explore how we can partner up during Neocon. That's surroundpodcasts.com and click Let's Collaborate.

18:00And we're back. Hiroki, Airbnb's been on a journey, right? And we've seen some really exciting things happening at Airbnb in the last couple of years in terms of experiences and in terms of services, which recently launched. And one of the newer things that you've also added to that is social. Can you just take us through a little bit of the thinking of why these things are important in booking a travel experience? Sure. Experiences and services really came from this idea that when people travel, they don't just want to stay in a place. They want to experience a city or a destination. They want to do it authentically, you know, with locals and do interesting things that, you know, may be on their checklist to get done, but then also can take them deeper into a culture or a city or just some hidden gems.

18:52And so that was what was behind experiences. And then, of course, the services that they would want when they're traveling. One of the interesting things that we found with experiences is that there's a lot of people that after they take an experience, want to connect with the people that were on it together. And in fact, I think it's like, I'll rattle off a stat, but I think a third of people that book an experience are actually doing so to meet other people. you know, which is really kind of fascinating. It's a really interesting insight. It is. It is. Yeah. And I think, you know, and it makes sense.

19:29You're traveling, you want to be out, want to see the world. And it's probably likely a big trip if you're going overseas. And for most people, you've been saving up for a long time to do it. You want to make the most of it. You want to meet people and have an incredible experience. And, you know, even from like firsthand experience, what we discovered is like, you're taking an experience with people that you're talking about, oh, where are you from? Where else have you traveled? Oh, that's interesting. Where did you stay? You know, where are you going to eat tonight? What are the restaurants?

19:57And a lot of people will ask the host, you know, can you recommend some great places to eat? But you're so, I mean, you know, my experience of it is you're so busy doing the thing. Suddenly it's like time to go and you don't really have the time to exchange or, you know, it's a little awkward to exchange phone numbers or your email or whatever. And so, we added this feature where you could just connect through the app with people that you've either traveled with or just taken the experience with. It's really cool. Super, super cool. How did that idea kind of evolve within the organization? I think it was, you know, a lot of it comes from this basic place of creating a magical trip or a magical experience for someone.

20:42And I think a lot of us have discovered firsthand that when you travel someplace and take some of these experiences that they're incredibly by nature, social, you know, and people want to connect. And there was a bit of an insight that, you know, there's a need for people and a desire to connect with each other in real life, real life first, then digital, not digital first, real life. And, you know, that's where that insight and inspiration has come from. But I think there's a, you know, there's a lot of opportunity for us that I'm really excited about and thinking about people traveling and connecting with each other and connecting with other people, especially, you know, fellow Airbnb travelers.

21:26It's funny. It's like we used to go on the surf trip to Costa Rica every year. And it was kind of this like, you know, not very well known place at the time. And you'd show up and, you know, it was always like, wow, you know, we met another family, we made friends, you know, it was really interesting. And oh, they're staying in an Airbnb. And it's because those kinds of places attract like-minded people. And so, of course, you're likely if you're in a, you know, little surf town in Costa Rica, you're going to meet other travelers that are interested in surfing that are probably similar to you.

21:59And so, you know, as people travel and collect around destinations, I think giving them the opportunity to then create an ongoing connection is interesting. From a UI UX point of view, moving from a platform to find a place, book a place and manage or stay at a place to what it is today, which is so much more. Can you tell us a little bit about the design philosophy or design evolution to help existing guests, hosts, experience leaders, everyone in the Airbnb ecosystem make this transition from what they were used to Airbnb offering to what it is becoming? Yeah, I think where we started is with the journey of a traveler, you know, and it's this kind of well-worn journey that everyone takes where you go, you start thinking about a trip and you're at like maximum love because it's dreaming, you know, where should you go?

23:04Where could you go? What could you do? And then as the plans get real, the satisfaction actually goes down and down and down because you're having to commit to a place, commit to a location, and suddenly things get more absolute. And booking either your plane ticket or your accommodation is actually the most dissatisfying, stressful, and not fun part of the process. It's true. You know, it's like you're at bottom of the enjoyment scale there. And so much so that it usually takes people a bit of time to kind of, you know, come back from the trauma and get excited about the trip again. And then they're on the trip.

23:42Day one, you're in love all over again. You know, the place is new. Everything is fantastic. The colors are brighter. And, you know, it's max travel love. And then, you know, it goes on from there. And it lasts. And then it, you know, gets you excited enough. to plan the next trip. And so we really just designed the app, both the guest and host side to map that experience, you know, to make the booking experience as simple, as frictionless, as quick as possible to make sure that, you know, we, it's a painful process and we want to make it simple for people. So you book and then as you get excited and as you get closer to your trip, you know, the app then transforms and starts to offer you things and show you things and help you along your journey and, uh, you know, show you things that are available, things that are happening near you, things that are happening that night, um, seats that we have available for you that evening, the next morning.

24:38Uh, and then, you know, the, the social capabilities are on top of that experience of doing the experience itself or, uh, you know, a trip that you take or a journey then now can become social, you know, when you're actually traveling. Obviously, the big part of it is the people engaging with the platform to participate and go on these experiences and these travel journeys. But how are you also thinking about the people who are creating them and offering them? Right. So how are the hosts or the service providers part of your thinking in terms of the, I guess, the back end or the way in which they engage with Airbnb?

25:18be? Yeah, I think, you know, hosts are definitely the core of Airbnb and without hosts, there would be no Airbnb. And I think when it comes to experienced hosts or especially experienced hosts, the opportunity for them to be able to connect with their guest through the app before the trip even starts and the ability for them to see who's going to be on their experience has been a big deal for them. It's made that journey to inviting guests and speaking to them a lot, a lot simpler. And we're, you know, as we call it the host app, there is the guest app, which we're all familiar with. And there's the host app, which are the tools and the booking software that we have that help people actually host and list their experience or list their home.

26:03And that's an area where there's tremendous amount of energy and teams that are focusing on making that really, really simple. One of the things we did when we were here before, we were talking about that skating experience. We also hired a chef and invited some friends over for dinner at the Airbnb we were staying at. And it was a super fun experience. Meal was amazing. And what was so fun about it was that chef, her full-time job is working in tech and her passion is working in her garden and creating meals for friends and for people. And so she was talking about how the platform was giving her a really fun opportunity to share that with people.

26:46And some of our friends were local and they were like, oh, wow, we would hire you. But what was really fun about it was that she participated in the dinner. You know, she wasn't just cooking. She wasn't just staff, you know. We had so much fun talking to her and learning about the things that she was passionate about in terms of food and why she was serving the things she was that week. And that was super fun. Her name is Chef Claire. And it just was really great because she was very much part of the conversation throughout the evening and we learned a lot from her and it was great just you know nice to see how she could turn her passion for growing food and preparing food and presenting food to people into actual practice the way she interacted with us was in her nature and you know it i think was her inclination to look to a platform like airbnb to be able to offer this service and find people to cook for.

27:41I wonder if there are people who are offering services or who are hosting that need a little more encouragement. They know they have something to give, but they don't necessarily have the social skills or the hospitality perspective to ensure that they're providing the best possible experience for their guest or the person they're cooking for or the person they're taking pictures for or whatever the services that they're offering. On that host side, are there tools or tips or is there work that you all do to help hosts learn about hosting? We do. We do. We have an experienced design team that sits within our design team that helps hosts map out the journey from the greeting to the conversation to farewell and what good hosting looks like.