Sometimes You Have To Stumble To Start Running

Randy Hunt, Catherine Madden at UXDX APAC. Video: https://youtu.be/Ens2sdd50m8

Readable transcript: edited from the recording's captions for readability (fillers and false starts removed, punctuation and section headings added). Wording is the speaker's own. Timestamps are positions in the video. Names marked [?] could not be verified against the audio.

Randy's background and why Singapore

[00:00:00] Catherine: For those of you who don't know, Randy has co-founded a number of startups. He's also worked as VP of Design for Etsy, and is currently Head of Design for Grab.

[00:00:10] Please do ask your questions, and I will be happy to facilitate, but I will kick off by asking you first, Randy, if you could give people a background. You're from the US, from New York, and then you moved to Singapore. Why Singapore? And give us a little bit more on your background.

[00:00:29] Randy: I won't spend too much time on my background. I think you covered it on the high-level, resume sense. Maybe one important thing, though, that isn't quite covered there, but feels more personal to me and relates to the "why Singapore" part of your question, is that I've always been really personally interested in things that cross disciplines into unknown and unexpected ways, unexpected places. I think that often the magic in any generative creative experience, and also in many life experiences, comes at the intersection of unexpected things. You can't really plan for unexpected things, at least from my perspective, but what you can do is be open to the context, and allow yourself to encounter situations in which unexpected things may happen.

[00:01:34] To me it's that intersection, plus applying the skills and traits and methods of a designer or creative professional in those situations, that makes for really exciting work, and hopefully really valuable contributions to other people's lives and experiences.

[00:01:55] Why Singapore, then, in that context? Look, Singapore is a hub for a great amount of activity and attention that's happening in an exciting part of the world. Singapore itself is a bubble in some way. It both acts as a hub and a connection point, but also as a bit of a bubble in the context of Southeast Asia, in terms of its stage of economic development and a number of other things: the development of particular industries and the absence of other industries and resources, which have made Singapore a really interesting place that has invested a lot in human capital. It also has deep history in its political relationships and how it manages those, in financial services, in trade and in scientific innovation. There's a really interesting set of conditions under which to spend most of your day-to-day life, I suppose.

[00:02:53] But what really brought me to Singapore was Grab, and the opportunity: both a professional opportunity inside Grab, but more importantly the life experience opportunity, and the scale of the potential positive impact of an organization like Grab. When I met with the founders, somewhere along my interview journey with Grab, it became very clear to me very quickly how sincere and deeply rooted the intentions are to build a lasting business that improves the quality of life for as many people as possible in Southeast Asia.

[00:03:30] To me that felt like an easy mission to wake up and care about every day. It also contained a number of unknowns to me, which goes back to that earlier point: a bunch of giant questions, a lot of things I don't know, I'm not familiar with personally, I'm not sure how to do, I don't understand the problem space. To me that's exciting, the work of shining the light around in that dark room and trying to reveal some understanding. At the same time, I knew that the needs of the organization, as they were presented to me and as I could see from the product experience and what I knew of the team, also built upon some experiences I've had in the past, things that I've either built a track record doing well or have failed at enough times to know some of the pitfalls to avoid.

Grab as a portfolio at different stages of maturity

[00:04:24] Catherine: It's really interesting. Grab fascinates a lot of people because it's a huge company, it's everywhere, and there are several products and facets. But at the same time it's so young. At what level of maturity would you say it's at, in terms of teams, product and services?

[00:04:47] Randy: Great question, and actually one that reflects both some of the strengths and the challenges we work with internally when we think about building and growing the business to serve our customers, and also developing the teams.

[00:05:00] The way I would orient you to this is to say: think about Grab the company, the business, as really a portfolio right now. It's a portfolio of product experiences and business opportunities that are targeted at particular needs and challenges that have been observed or revealed in customers' experiences. If you hold that idea of it being a portfolio, or an ecosystem of many things, even internally, different parts of the company and different parts of the product are at very different stages of development.

[00:05:45] There are parts of the business that many people who might already be familiar with Grab, or live or work in the region, would have seen from day one, where we were a point-to-point transportation and logistics company, allowing you to get a ride from A to B safely and easily. That's still an important part of our business, but it's one of many, many things we do. You might imagine that we have the longest time working on that problem, both developing the organization around it, the processes, the methods, the underlying technology.

[00:06:19] In many ways one might say that's the most mature part of the organization, which is true, until you back up and say actually the entire company is about eight and a half, nine years old, which depending on your scale is ancient or nascent. But overall it's still a relatively young company in the grand scheme of companies, especially one with the footprint of the number of things that we do and the size and scale of influence of the organization. It's pretty young.

[00:06:53] But imagine that's the most mature part of the organization and of the product. Around that we've developed a number of other things over time, some that explicitly leverage the strengths of that part of the business. Think about our logistics intelligence: what is the right way to send a person or thing from A to B, or A to B to C, while maximizing the earning potential of our driver partners or the restaurants that we serve, and simultaneously delivering good value to the customers? There's a lot of data understanding there, as well as user behavior shaping things that manifest themselves through design, and we can build on what we've learned there.

[00:07:40] There are other parts of the business where, of course, we try to extend what we learn, but they are very different beasts to tackle. For example, over the last few years we've launched a whole suite of financial services. Initially a digital wallet experience that had a direct connection to transportation and food originally, although now you can of course pay in person for a number of other things, like you'd expect with a digital wallet, peer-to-peer transfer payments and things. Around that we've launched savings, investing, lending and insurance products.

[00:08:18] The consumer psychology, the market need, the behavior shaping and education needed to serve customers, let's pick insurance as an example: insurance needs are very different from "I want to have my lunch soon, and I want it to be fast, healthy and affordable." Lunch is very different from "I'd like to insure my physical safety," or some other thing, in the context of, say, a global pandemic. Very, very different parts of the business and customer needs we're serving that are almost radically different in their depth.

[00:09:01] And internally they're very emergent. It's almost like a new innovation from inside the organization. How do you operate that, give it its space to thrive, and judge its success differently than maybe something that's been established for a long time? While at the same time navigating the fact that all of these things are one organization. They're one company, they're one brand to consumers, and they're one product experience, at least when you imagine the consumer part. Of course we have product experiences for our driver partners and our restaurant merchants and things. But all of the things I just described live in one Android app. While the teams and the technology stacks and the approaches may be at various levels of maturity, they all need to come together and ultimately ship into the same packaged-up piece of software that lives in people's smartphones.

Local markets and shared solutions

[00:09:59] Catherine: It's really interesting, and I want to move on to teams in a second. I'll just pause, because Amna [?], who's listening in, has asked a question which I think is very interesting. You've talked about all the different products that you're in, but that in turn leads to different geographies. How often do you look at each geography separately?

[00:10:23] Randy: Interesting question. Within our geography, Grab is, I would say, aggressively focused on Southeast Asia. We don't look outside of the region in terms of the customers we serve. Of course we look at what is happening globally in a number of areas to learn from best practices, to learn from other people's successes and failures and things like that. But within the region that we focus on, our organization has essentially country- and market-focused teams.

[00:11:00] I think it actually comes back to one of the strengths of the organization from its earlier days. The early experiences and services that we started offering at the beginning had to do with on-the-ground transportation. It was a very online-to-offline experience, and there's no way to create that business without having a presence on the ground, having a team on the ground meeting and onboarding driver partners in person and things like that. From the early DNA of the organization, there are country teams and city teams across the region that are the eyes and ears, in part. In addition to doing the local and regional business operations, they're very close to the customers' experiences on the ground, and they're the primary communication avenue back to us.

[00:11:53] One version of answering the question is: all the time. Maybe one of the challenges we actually have is that there's so much information across all these different markets that the challenge is how to parse and prioritize within it. We take great pride in having very local understanding, even at the city level. Take an example of a third-tier city in Indonesia: we just treat it very differently than Jakarta. You just have to. There's not really an option not to, if you want to get any traction. And yet at the same time...

[00:12:28] Catherine: Please, Randy, do you apply it to different cities? If it was Malaysia, or Singapore, would you apply that learning to different cities?

[00:12:39] Randy: For design, that's one of the really interesting things. You need to take this intensely local consideration, because otherwise, if we assume it's generally the same, we won't discover important nuances. But what you'll also find sometimes is that you'll discover a nuance, or some customer innovation, or some customer problem, and even though you're not seeing data of it in other places in the same way, either because it's not happening yet or because it's not making its way through the feedback channels, which, while they are many, are imperfect, the way you address that problem may actually be applicable, and may address challenges or opportunities more broadly.

[00:13:22] It's really ears on the ground, ground-truth understanding, but then not trying to solve every tiny problem or opportunity we discover, and instead trying to recognize patterns across those things and find shared solutions. That's part of what you get from the advantages of being at scale. Some of the advantages that software allows you to have is to look for those common answers. And it is a mix. It's straight up a mix. This comes back to navigating the ambiguity. We decide for it to be a mix; customers' lives are a mix. And things like, let's take our financial services, regulatory considerations just exist at the country level. They just do. If you want to do that business, you have to accept that. You can't apply the same approach in each market.

[00:14:13] Catherine: That's a very valid point. It's an interesting way to be able to divide it out.

Lessons from building design teams at Etsy and Grab

[00:14:20] The other thing: we talk about the company, Grab, but in general, with regards to the team, both of those companies, Etsy and Grab, are huge scaling companies in a high-growth area. What are the biggest lessons you've had over the years when building your design teams within both of those companies?

[00:14:49] Randy: Oh goodness, that itself is probably its own conversation. I think that building teams, from my perspective, is really a long game. It's a slow-burn process that also comes with, maybe peaks and valleys, but I was going to say plateaus along the way. Meaning that the sense of progress, both at an individual level, maybe inside my own heart and mind, but also for the organization and for the team, and where they start to see benefits or not from some of the work, really varies. It's pretty rare that it's "let's build this team, everything's great." It just doesn't work that way, because team building is a people problem, and people are complex and individual and nuanced.

[00:15:47] I would say one of the lessons that has been most helpful to me is looking at strengths inside the organization already, meaning functional strengths, maybe areas adjacent to design or that partner with design regularly, and how we can leverage those strengths as we help build the team. I'll give you a quick concrete example of that.

[00:16:16] At the time of my time at Etsy, despite what people might think of this very handcraft-centric e-commerce marketplace, the greatest strength organizationally inside that company was its engineering team. A very, very strong and capable engineering team, in a way that I think surprised many people. One of the things we did then was really align design very closely with engineering, in a bunch of ways. Organizationally: let's divide the team and structure it in a parallel model; let's pair leaders and partners at similar levels and scopes of responsibility to partner on things together. We used some of the same vocabulary and terminology as we developed our processes and communicated them around the organization, so that we weren't running around saying, "Hey, design does this and works this way." It was more, "Hey, this thing you already know and trust, now it's also design."

[00:17:14] Which I think is a particular approach. For me, I tend to like to surf the waves, rather than having the assumption that we can change the tides of the ocean. It's like, okay, the waves are coming now, let's prepare ourselves. Looking for what exists, and the right things to integrate with to help enable faster growth and progress, was a really important lesson I learned through that experience.

[00:17:42] Applying that in the context of Grab, I think it's actually very different. Not to say that our engineering team isn't great. It is; it's really impressive in a bunch of ways. But when I looked at where the opportunities were for design, a lot of it looked like the throughput to begin with, the speed of execution. The organization values and prides itself on that, and I think appropriately so. In many ways that's what has allowed it to be so successful on the ground in so many markets so quickly.

[00:18:14] That was something we looked at and said: which of those attributes can we take or emphasize in the design organization early in this journey, and what does the team need to be like to be able to do that? To align with the natural, maybe I'd even say biases, internally in the organization. What do we value? Okay, let's align with what we value and begin momentum there, and then from that momentum build in other things that we believe are important or necessary, whether it's investing in different parts of the process, or different functions, or other integrations with other teams. Similar lesson, different application.

Failure as the normal state

[00:18:58] Catherine: That's amazing. You talked about successes. I'll move on to the obvious, which would be failures and challenges that you've encountered. Firstly, failure is a very, very broad term. What does failure mean to you, or how do you define it?

[00:19:22] Randy: That's a great question. I think the dictionary definition, in a way, or one that I relate to and hold in my mind all the time, is that failure is a lack of success. I think that's actually quite simple, and it's helpful for me. I don't mean failure in the sense that the system collapses, like when we talk about a banking system failure and mean that the financial institutions are no longer safe. I don't mean that kind of failure. I mean the lack of having yet achieved the success we intend to achieve.

[00:20:00] At a very personal level, I think it comes right to the roots of, I was going to say my design training, but maybe even just creative work at all. It's probably from when I tried to write bad songs on my guitar when I was 14 years old: most of the time I'm wrong.

[00:20:19] Catherine: Well, there's that too.

[00:20:22] Randy: Most of the time I'm wrong, and most of the time it's not very good. I mean that not in some self-pity way, but just to try to see the world as it is. If I believe that to be true and accept it as true, those are the conditions of failure, in a way. And then, if that's true, so what? How do we, one, get comfortable with that feeling personally, and how do we make that okay in an environment or a culture? But then also, what do we do to take best advantage of the wins when they do happen? How do we ensure that, within this world of mostly being wrong, we get it right at the right times?

[00:21:05] How do we know that being right in this moment is a strike-while-the-iron's-hot moment? I think this is a sensibility that maybe you build up over time, or some intuition, and also sometimes just a comfort with risk-taking, to say: this may be another one of those, we don't know, but the only way we're going to find out is if we lean in much harder and try to make it be so. That's how I think about failure. I actually think about it as the normal state.

[00:21:39] Catherine: Just as you're talking: so many engineering and product teams and design teams are programmed to think, let's experiment, let's fail, it's a positive thing even though it's a negative thing. It's really nice the way you framed it and put it into the context of knowing when you can celebrate the wins too.

Working with people who seem to block you

[00:22:01] Going on to innovation, which leads from failures and experimentation: when you are driving high-growth initiatives, how do you deal with the individuals that sometimes might block? There are a lot of people working in companies or teams that aren't autonomous and aligned. How do you work with people who inevitably will block your drive and your goals?

[00:22:36] Randy: Great question. A few quick things. One points to my personal mindset around this, but then also maybe some methods or techniques I prefer. I just choose to come from a place of assuming good intent in every case. I reject the idea that there are people who try to stand in the way of things. Maybe that's true and I'm just naive, but I think that more often than not they don't realize they're standing in the way of things, because their perspective is different, or their priorities, what they're focused on, are different, so they may not see that. And to accept the responsibility ourselves too, as designers, UX leaders and otherwise: maybe we haven't done a good job of helping them be aware of those things.

[00:23:23] That's one. To say, "Oh, they're standing in the way": are they standing in the way because they actively built a roadblock, or are they standing in the way because they happen to be standing where they were, and we haven't said, "Excuse me, could you step over?" or "Excuse me, do you want to walk on this journey together? I think we can be helpful to each other." I tend to take an optimistic view of that.

[00:23:48] Catherine: Assume good intentions, from their perspective.

[00:23:53] Randy: Exactly. And I think there are two key things then. One, I'll go back to this surf-the-waves metaphor. I try to identify where there's the lowest friction early in what we're trying to make happen. Is that in this part of the team, is that with this partner, is that with this business? Let's say we're trying to make some transformation across multiple parts of the business, maybe an improved user experience that cuts across many teams. We can have a master plan, a map of how we'd improve that across all these things. I'm always inclined to help the team identify areas where we can start to get momentum as early as possible with the least friction.

[00:24:35] That avoids, at first, this idea that there's something blocking the way. It's: okay, what's within our direct control? What can we do to start to make progress? It's even good just for the team to feel like progress is coming, because you need to build up some of that positive energy to apply towards the more challenging problems that are just around the corner. How can we keep things small enough to get momentum? And then, where are the partners or stakeholders that we believe need the lowest effort in order to create that next change? Rather than going straight to what we believe is the most challenging block or point of friction, is there a similar one that we're also going to need to overcome, but that is easier? Can we overcome that one and use the improvement we made there as evidence for why and how we can be helpful, or overcome the next challenge? It's very much like building blocks.

[00:25:32] The other is exactly what you pointed to when you said look at it from their perspective. I try, as much as possible, to frame things for other people in a way that aligns with what they're already trying to accomplish, or how it will benefit what they're trying to achieve. There's maybe art and science to this, but I don't mean these super compelling cases with tons of data. Sometimes you need that. What I really mean is to say: "Look, I understand your motivation here, to try to grow this part of the business, or you've got this metric you've been challenged to move. Here's this initiative we're trying to make happen, and I'd like our team to be able to work with your team to see if, in this thing we're trying to make happen, we can unlock opportunities for the thing you're trying to make happen." And really focus in there. It's not about changing your entire worldview or a new mental model. It's: can you allow us to help you, through the thing that we're trying to do?

[00:26:41] Catherine: I think what you're saying, in every aspect, is to focus on the easiest and quickest way to win and to succeed. Stop making life harder for yourself in every way.

[00:26:53] Randy: It's true. I'll mention one of the challenges with this approach. I continue with it, but it goes in that failures bucket.

[00:27:02] Catherine: The very opportunities, if you're trying to make it positive.

[00:27:05] Randy: Yes, that's right. Very often, if you're trying to make progress against large initiatives, and change in a complex organization or improving a complex product experience is in and of itself a large initiative, the early things you do and those small wins can be really powerful to the people close to them, and that's great. But you may work on that for a while and it still feels like zero progress in the context of the larger thing. The willingness to continue to push through, the faith and grit, in a way, that the continued effort will start to bear fruit later, is totally necessary. Because at the end of the day, you can project and describe how it'll be better in the future, but many, many people just won't really understand it until they experience it themselves.

Building a team from scratch versus joining one

[00:28:00] Catherine: That's very true. Sticking with teams: you've built teams from scratch, and you've gone into pre-existing teams. What are the main differences, or even similarities, between those two types of team building? Which is more difficult?

[00:28:27] Randy: My experience is that stepping into existing teams is more difficult. I do have several experiences to inform this opinion, but it's still a limited number, a very limited number in the grand scheme for anyone in the world. I'm sure many people who are part of the conference have had their own versions of these, and may take away similar lessons, or the exact opposite conclusion. But for me, building was easier.

[00:28:57] I'll explain why. One, I think this is the experience I had first, and in a way it related to a lot of my earlier professional and life experiences. I used to be the front person of a rock band, where I organized the people and wrote the music, whatever. It was very much leading this initiative with people I'd put together, taking my vision. Fast forward through time, and the experience I had at Etsy was very similar. I came in as myself and one other designer, in an organization of about 60 people at that time, six-zero. Over eight years we grew; the company was about 1,200 people when I left, and the design organization was maybe 10 or 12 percent of that.

[00:29:40] Every incremental change along the way, all the lessons learned, all the things that contributed to what it was eight years later, was something I was actively a part of, observed, got to drive, was responsible for the decision on, for better or worse, but also learned from directly and used to calibrate things over time. When you step into an organization or a team that already exists, many of those same kinds of lessons have been learned. Many people have made decisions like that before you, but you don't have the experience of them firsthand, and you haven't been able to stack them up in small bits over time, which is way easier to process than stepping into this swirling, moving, organic thing that is on some trajectory of its own, where you meet it somewhere along the way and enter the stream.

[00:30:33] Catherine: Sorry for interrupting. How have you managed to achieve that same beauty of building a team within a pre-existing team?

[00:30:44] Randy: One condition that is helpful is to join a team when it already has the remit, the resources and the need to grow. In those growth moments and those changes, you start to be able to make some of those kinds of choices and learn from the choices you make, and involve other people in the choices, which also helps you learn about the team and the culture. Each time someone comes or goes from a team, or you reconfigure it, you're shaping the culture in these micro-waves. The fact that change is needed, and there's the context for change, is really helpful, I think, more so than something being static.

[00:31:23] I've had that experience too: joining a team where it's, here's the team, it's going to stay about the same size, it's going to do about the same things. I found that difficult in hindsight, because the built-in, natural change moments aren't there in that set of expectations.

[00:31:42] The other, and it goes back to a couple of these same principles, was to really try to identify people and areas where learning about the organization, and some early choices and change that could be made, were close and familiar, and where we could establish trust early. Really, partners in and around the team who could act as the anthropologist for the team, or the historian for the team, and help me understand the context I was operating in. And then some other people I could establish trust with, who understood the context and said, "Yeah, this is going to be hard, and we understand you're going to need to change some things." As I made some choices, including choices that maybe aren't obvious at first or don't go well at first, they still have your back. They understand that's the first step of a long journey, which may have some ups and downs along the way.

Talent in Asia and imported experience

[00:32:44] Catherine: It sounds like your positivity really does help you in all of the roles that you've taken on. We're running out of time, and I want to ask you a slightly controversial question. You are imported talent to Singapore, which is becoming an increasing factor in Asia. Ashwin talked about having the dream of going to the US, and people dream of that. Is it a case of "West is best"? What's the deal with talent in Asia? What is your opinion on that?

[00:33:23] Randy: Interesting. One, I would say I can speak to this only from my perspective, and I'm no expert on talent in Asia. I don't think it's a "West is best" thing, at least on the ground.

[00:33:38] Back up for a second. We talked about Singapore and its investment in people as a natural resource, in a way, in its population. For many decades there have been long-term strategic choices from the government to embrace foreign talent in a number of sectors, and they've evolved what they view as those sectors over time, in order to bring in outside perspective, bring in people with experience in areas, and to build and create teams, teach people, become part of the professional community, become part of the academic community, et cetera, in order to build the talent and capabilities as part of their national policy. As a long-term plan, there's something very intentional there about that talent and experience exchange.

[00:34:30] Talking with people in Singapore, people have experienced that in a number of ways. I think it's valued and respected in many cases, and other times they're like, "It's not as effective for me, or in my situation, as I would have expected." Just a variety of things, like you'd expect from any big policy. That's an important context, because I'm part of that story too.

[00:34:51] But the other story I'd say I'm a part of is simply one where the kinds of organizations I've been a part of, the teams I've built, the experiences I have, are from a geography where the industry has just been happening for longer. There's been more time to accumulate some of those experiences, more permutations of the cycle in a way, and you can't really recreate that without time. But that also doesn't make it somehow obviously better. It's just different. That's why I'll get to this other point: it can be really helpful to have that experience, but of course that experience comes from a particular context, and the context of working in Southeast Asia, or serving the customers in Southeast Asia, is very different.

[00:35:39] I see my role or responsibility really as one of foundation building, in partnership with the people on our teams and the professional community, both in Singapore and across the region. My hope and dream is that Grab, given its scale, its brand visibility and its influence, becomes a really positive contributor in this professional space, from a design, user experience and customer experience standpoint. What we can do to help cultivate, elevate and amplify already great things happening in the region from a talent standpoint is something I think we can and should do.

[00:36:23] I see us as a vehicle for that, and myself as a facilitator of that vehicle. I'd be really proud if we could look back and see that that has happened. Not because imported talent from the West made Grab design better or something like that, but because Grab design is exceptional in the context of Southeast Asia and has a global reputation because the team made it so, and that team did it in large part by cultivating and growing talent locally and within the region.

Leaving things better than you found them

[00:36:56] Catherine: Which I really like. I think it's the one thing that I'm looking forward to even with UXDX. We've had the beauty of being in Europe originally and now all over the world, and what we're seeing from talking with all the teams in Asia is phenomenal. I actually think there's a lot of learning that Silicon Valley can take from it. It's a whole different world, and it's a huge and exciting time to be in it, and it's only getting bigger.

[00:37:27] Which, I'm assuming, is my final note: why you took your life opportunity, as you've called it. It's a very brave move to make. You talked about career opportunities, but also weighing it up as a life opportunity and moving there. I believe Singapore is good in that context for you.

[00:37:52] Randy: Absolutely. I think about this really as collecting experiences that make for an interesting life. That's my personal, intrinsic motivation there. And to do so in a way that, in the daily choices we make and the actions we take, we believe we'll leave things better than we found them: the contribution to the business, the contribution to the people inside the teams and the individuals, to the professional community, and most importantly to the customers of the region. That's why I would choose an organization like Grab to spend my time with. What a great way to spend your time: to have the opportunity and potential to serve so many people in ways that can improve their quality of life, after you've done your work.

[00:38:44] Catherine: On a nice ending note, "leave things better than you found them" is a really nice summary for everything. I think it's something we should all strive for in life in general. Randy, I could talk to you for a day and a week. You're amazing. Thank you. I know that everyone will have got so much value from your time. Enjoy the rest of your day, and we'll see you again. Thank you very much.

[00:39:13] Randy: Great, thanks.