42. Celeste Ridlen of Robinhood

For this episode of Dollars to Donuts I had a wonderful conversation with Celeste Ridlen, the Head of Research at Robinhood

This is a fundamental leadership-y thing where no two people are going to do that same leadership role the same way. You’re never going to do them the same way as somebody else. And that’s actually a really good thing because the situation may call for exactly what you can offer. But because of that, if you’re looking to other people to decide whether or not you’re going to be suited to doing that role, it’s kind of like thinking about whether or not you should be a writer based on whether or not you can write exactly like Mary Shelley. – Celeste Ridlen

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Steve Portigal: Welcome to Dollars to Donuts, the podcast where I talk with the people who lead user research in their organization. I’m Steve Portigal.

Did you know there’s a new, significantly updated second edition of Interviewing Users? Of course you did. I hope you’ve checked it out and are recommending it to everyone you know. Shortly after the book came out, I had a conversation with Adrian Brady-Cesana for his CX Chronicles podcast. The link to the whole episode is in the show notes, but here’s a quick excerpt where we talk about domain expertise in user research.

Adrian Brady-Cesana: I’d love for you to share a couple examples or a couple stories of some of the things that you’ve seen working with your clients and working in your business around sort of how you’ve seen some of the companies that had really incredible teams or some of the commonalities or some of the things that you saw again and again and again with your clients that really had a solid handle on how they sort of built up their team, built out the different roles and really kind of stratified how their team was going to be taking care of their customers.

Steve: I think there’s a lot of pressure on people doing research right now to carry it yourself all the way through. And I think this is such collaborative work. And I just, I think I’ve seen more success when there is some collaboration and that’s a big, collaboration is a big, big term.

But one thing that, you know, your question makes me think of is complexity. Like I think as user research as a practice has grown, it’s finding its way into many more complex domains like installing and maintaining and configuring servers and network devices, not even just servers, but the whole, the whole infrastructure. I worked years ago on a credit default swap trading, and you might or might not have heard that phrase, but boy, just dig and dig and dig. And it’s like, it doesn’t make any sense until you’ve really been involved.

And, you know, so for me as a consultant, but even my clients who are on teams, like they’re, they’re not necessarily domain experts. And so I think this really interesting challenge comes up for whether you’re a researcher, whether you’re someone else in the organization that’s out talking to customers is, is trying to navigate that balance between like, how much do I need to understand about this?

And so for me, I think one thing I’ve seen that to be really successful, it goes back to the collaboration thing is when you pair up someone who’s great at research, which is, okay, I don’t know about this. I want you to explain it to me. And someone who is great at the domain, whose job isn’t to ask questions. Their job is to hear what doesn’t make sense about the technology or about the deployment or about the process. And that collaboration is really, really sharp, I think, and has a great effect on, you know, when you’re talking to customers and users, I think sometimes we’re nervous because while we want to be seen as credible, especially if it’s an actual customer, right? We ask for their time. We want to go talk to them. You’re going to send some idiot that doesn’t know what they’re talking about. That isn’t necessarily the reaction you’ll get, but I think it’s sometimes the reaction that we fear.

And so it can be really a really great triangle between a user or a customer who has, who’s a practitioner of something very complex, you know, and a person from the producer or, you know, maker side of it, the company side, who’s knows the domain and someone who knows how to listen and ask questions and follow up and sort of facilitate this.

When I see researchers kind of getting immersed into a domain, they do build up some competency, but some of these things are decades of specificity and really kind of elusive stuff. So I think just to go back to your question, I think teams where there’s bandwidth for collaboration and you can bring in people with different perspectives, different domain and process expertise to create a great interview for the customer that you’re talking to.

Like it’s a good experience to talk to a researcher and a domain expert because you just, you can watch who they make eye contact with as they kind of see like, oh, you’re the, I’ve had people even tell me, oh, okay, you’re the question asker and you’re the person that knows that you’re the engineer. Like people can figure that out. And it’s a really, nobody’s pretending to be anything that they aren’t.

And it really, I think can be very harmonious, but you have to create the bandwidth that kind of support that collaboration on the team. So everybody can work together to get the insights that we want to get from the people we’re building for.

Again, that was from the CX Chronicles podcast. Now let’s get to my conversation with Celeste Ridlen. She’s the head of research at Robinhood.

Celeste, thank you so much for being on Dollars to Donuts. It’s really great to have you here.

Celeste Ridlen: It’s awesome to be here. Thanks for inviting me.

Steve: Can we start with an introduction from you, build the rest of the conversation off from that?

Celeste: Yeah. What would you like to know in my introduction? I exist.

Steve: You exist.

Celeste: My name is Celeste. I’m the head of research at Robinhood. I’ve been doing research for 15 years now. My background is in human factors and ergonomics. I live in San Francisco, long walks on the beach, that kind of stuff.

Steve: How did you discover the field of human factors?

Celeste: I was in a cognitive psych lab, like working in a cognitive psych lab at Florida State University, and I was trying to think about my next step. I liked to joke that with a psychology degree and an English degree, you basically are qualified to be a mall security guard. I was looking at grad school and I decided that I was going to talk to Dr. Kashak who was running the lab at the time about my interests, because I had tried on neuroscience and I didn’t want to hurt animals and place electrodes on rats’ brains, so I cast aside neuroscience and then social psychology. I worked with Baumeister and Tice and that was interesting, but also so vague and not applicable, and much love to social psychology, but just so vague. I was in Dr. Kashak’s lab and I was asking him about what his advice would be for what I should study if I was most interested in cognitive psych. He asked me if I liked technology, if I liked industrial engineering, like making things. We had this great conversation about human factors, which is essentially cognitive ergonomics. As a field that started blooming right around the time we started industrializing weapons, which is a weird historical fact that I got excited about. That’s how I got into that.

Steve: How did you find a program for yourself? This was grad school. You did choose grad school.

Celeste: I did. Well, no, there wasn’t any, I mean, now there’s HCI and stuff like that, but at the time there weren’t programs dedicated to that yet. I looked around, there were a few programs. One of them was at Georgia Tech. One of them, I don’t even remember where they all were, but they were approximations of what I was looking for. Some of them were called human factors, some of them weren’t. The one I ended up going with was at San Jose State, and yes, right up there in terms of name and stature with Georgia Tech. But I chose San Jose State specifically because they had an applied, terminal master’s degree program, there was an applied emphasis. Where they had relationships with tech companies in the Bay Area and NASA, and they were working directly with these companies to get students into exactly the jobs that I was excited about. That’s why I chose it. I knew I didn’t want to be an academic. I had an end goal. I didn’t want things to be vague. I wanted to see the fruits of my labor immediately. Then I, sight unseen, came out to California, have never looked back.

Steve: Was there a first applied job or project or something that came to you through that program?

Celeste: Yeah, a lot of people had stuff come directly from school. I happened to sit next to somebody in one of my classes. I mean, I don’t know if it was like a stats class or I don’t remember which one it was. But there was somebody who was already working at Oracle, and she let me know about a job opening. And I wasn’t even done with grad school, and they took a chance on me. I was a contract physician. In retrospect, it was probably like a low lift, but it was my first sort of foray into things. And so, no, it wasn’t like a direct, it wasn’t directly because of like this, the program itself, but it was the people inside of it. Like you literally never know who you’re sitting next to. So it was lucky for me.

Steve: What kind of things were you doing in that first Oracle job?

Celeste: Oh, God. One time I transcribed an offsite, like a field visit that I did not attend. So I had headphones on, and I had to hand transcribe 20 plus hours of people spewing acronyms that I didn’t know or understand. So that was fun. I did a lot of like participant recruiting. This was a joy, but definitely a labor of love there. I did a lot of like synthesis and conducting studies, but I did a lot of the stuff that people either have automated now or would not consider in like an entry level research job now, which is character building, let’s call it. Without sort of going through your resume step by step, but what’s,

Steve: I don’t know, you can assess what the next marker is like, what’s another role that came after that, that was significant for you?

Celeste: Yeah. So I hopped from that to a full time position at Symantec about a year later. I don’t even think Symantec is a company anymore, which is at the time it was like 25, 30 years old. And so there’s sort of like two camps in tech, or at least there were at the time. These old, like slow moving companies with long, long product cycles, like Oracle, Symantec, it’s like there’s a lot to an implementation. And so you’ve got like a five year release cycle, like it’s really, really long. And then you had new companies that were very young, right, like on the edge of being what I would call startupy, like where it’s, everybody’s doing everything. And so I jumped from Symantec, which was like, it was a great job. They also took a chance on me. And I shifted into working in sort of like the newer building phase of tech where like there were almost no researchers. And we had to sort of build a process and perspective and relationships as the company’s like trying to grow like crazy. So Twitter was a really, really pivotal point in my career where I got really, really excited. It was like a dream job. I always wanted to work on Twitter. Like it was, you know, this 2013 Twitter, that means something different now, for sure. But I was so excited. And it was amazing to be surrounded by people that had that much passion and energy. And I, you know, I was part of that bricklaying process, right? Like I had a boss. And I loved it so much that I got invited to do another bricklaying at Airbnb a few years later. I was at Airbnb for a very long time. We went from 20 researchers to like, I don’t know, over 100 at our peak. So that was a lot of bricks.

Steve: Can you explain the bricklaying metaphor?

Celeste: Yeah, what? That doesn’t make sense to you?

Okay, so what I mean by that is you have this sort of like nascent or non-existent research team, like research function, let’s call it like a discipline. Maybe there’s one person, maybe there’s five people, but everyone’s just kind of like still being very reactive because the company doesn’t know how to work with research yet and doesn’t really know what part of the culture it fits in, where it fits, so on and so forth, like how to engage, that kind of stuff. So what I mean by bricklaying is like there’s process, right? So how do you recruit participants? What are sort of like the safety issues with your research participant agreement or your NDA? What are the safety issues with the way that you reach out to your participants? So I was like building a lot of programmatic structure on top of then hiring people, trying to identify and prioritize research questions, all the things, like all the how-to’s, all the — so I was interviewing like a million people every week. I was participating in like a crap ton of interviews for the company and then also of the users. So it was just nonstop assessing things, basically, but figuring out like do we have a crit, as an example, as a research team? Do we do like a weekly critique? What does that culture look like? Is it required? Are we forcing you to do that? Those kinds of things are the bricklaying. Like they’re all part of the bricklaying. It’s not just like hiring and setting up process, but it’s also like what kind of culture do we want to have and what’s mandatory, what’s optional, and like what needs to be grassroots versus top-down, that sort of thing. It’s fun. It’s really, really fun.

Steve: I don’t know if this is part of the bricklaying metaphor, but what about things like how much we know or don’t know about people that we’re building for?

Celeste: Yeah, that’s a big one. I mean, when you first start — let’s keep going with the bricklaying metaphor — when you first start, like you could put a brick anywhere, so to speak, and you would have impact, right? Because you didn’t know anything and now you know something. But that gets like more complicated and more nuances is necessary when you start, when you’re sort of saturating on a particular topic. There is a moment to either move on or rethink it. And so, yeah, that’s definitely a part of it.

Steve: Right. Now you got me thinking of the Tetris metaphor where the more bricks you put down, the more difficulty placing those future bricks. There’s more scrutiny and impact on that choice.

Celeste: Yeah. Yeah. I’m very good at Tetris. I don’t know if I’m good at bricklaying, but this is the third company I’ve moved to where I felt like that was a part of what my role entailed. Because it’s not just in research, too. It’s the company at large. You’re defining process and practice as a group of people who’s maybe under a thousand to then like three thousand, five thousand people in a very fast — like the only way to address any of that is to just figure out how to scale yourself and figure out what’s important and what isn’t, because you have to make some decisions very quickly there.

Steve: I do want to move on to Robinhod in a moment, but I have a question that I want to go back. So what’s your title at Robinhood?

Celeste: I am the head of research at Robinhood.

Steve: And hearing you talk, I’m inferring that bricklaying is not just the purview of people who have leadership titles. You’re describing Twitter and Airbnb as roles where you didn’t have a leadership title, I think, but your job bricklaying was part of what you were doing. It was the context for your work.

Celeste: Yeah, you and I could go on forever on a much belabored subject about the difference between management and leadership. I was a manager at Airbnb, but you’re right that the bricklaying metaphor is not specific to somebody with a leadership title or somebody who is a people manager. It’s something everybody has to build together. And it depends a lot on the chemistry of both the research team and the broader company you’re at. So it never looks the same way twice.

Steve: Well, I’d love to hear if it’s possible, you know, different companies, different roles, but being an individual contributor, being a people manager, being a leader, again, the companies are different. So maybe at the question, the comparison isn’t right. But would you be able to characterize either ways that one could or ways that you have been involved in bricklaying? I love the metaphor. Just these three different contexts for bricklaying, you’re coming into it with what seem like different responsibilities or titles.

Celeste: Totally.

Steve: What is it like? How do you compare and contrast across the three?

Celeste: I think in all three cases, the similarities were around, no one’s going to tell you that you absolutely need to be doing that unless you’re like, you know, the pet of something that is kind of objectively, everything is your job, right, to some degree. So I think that one, it’s a little bit easier to believe that everything is within your purview. But for other roles, I came in and there are opportunities, there are problems everywhere, and you can either decide that they’re not your problem, which is an approach, or you decide that you’d like to solve it. Nobody’s going to probably yell at you for solving it. So you take it on.

So things like rewriting interview questions, like that’s something small that I did. Creating processes and how-to docs was something I did like every five minutes at Twitter. And there was like a running joke that no one was going to know how to do anything after I quit, because there was no one to write how-to docs anymore. I’m sure they wrote them plenty.

But I think it’s just about deciding if you have a perspective or a skill that can be lent to that particular problem or like opportunity, and then just doing it. I mean, there’s nuance there, right? You have to ask questions and make sure you’re not hurting anybody’s feelings, someone else isn’t working on it, that kind of thing.

But a lot of times in those environments, the best thing you can do is just say, “Hey, no one has a problem. I’m going to do this. Good? Good? Yes? Anyone want to weigh in? No? Awesome. I’m going to take this on.” And then everyone is pretty thankful if they remember that you did it at all, which is, you shouldn’t be doing it for credit anyway.

Steve: Over the course of your history, have you worked in environments that weren’t in the bricklaying mode? It seems like the first two you described were that.

Celeste: Yes. Yeah. So both Symantec and Oracle had very well-funded and staffed research disciplines. They weren’t massive. I think Symantec, there were still only like six of us, but it’s not enormous for a 20,000-person company at the time. But there was already a way of doing things within the broader UX team, within the company. We had a process, we had practices, we had tooling. No one was starving for those sorts of things. And so everything was kind of plug and play. There were great jobs, but the environments themselves are different. You learn different. You get reps for doing the work there a lot more than doing the work and the stuff around the work, if that makes sense.

Steve: If I’m applying for a job in user research, let’s just imagine that’s the thing I’m doing. It’s like, ask your doctor if Flonase is right for you. Ask what kind of environment is right for whom? Having seen both and participated in both these, if there are only two, and I’m sure there’s nuances here.

Celeste: There’s a lot.

Steve: Yeah. If places where it’s more plug and play versus places where there’s a lot of problems to be solved and opportunity to solve them, what’s your advice for people into, I guess to me, I hear two parts. How do I assess what the situation is? And then how do I self-assess about what works for me?

Celeste: I think it seems to me like there are a lot of ways to do all of those things, but I’m going to tell you a couple of things. One is how to assess or how to self-assess. But then the second or third, depending on how you just numbered those in your head, would be people that I’ve seen succeed in either of those situations, of which there are probably shades, it’s a spectrum or something like that, because they might be different too. So when I think about assessing, when you’re interviewing for a job, I think the thing that I would look for is who’s funding the research team and why do they think that a research team should exist? Those are things that you would think you get the same answer every time, but you extremely do not. Sometimes people want a research team or have a research team because it’s a box to check. This is what we do to make products. This seems like a thing past a certain point of company maturity that we would definitely want to have. So I’m not entirely sure, but I’m going to, here you go. I’m going to just check that box and it’s going to be great. And you’re going to be my researcher. So there’s stuff like that that can kind of give you a glimpse into the research maturity of the organization or whatever you want to call it.

Another question I like to ask, so around funding, do you have the research? Do you have the tooling you feel like you need to do your job? If you needed a new tool, what would it take to get it? Is it a procurement question? Do you have a budget? Do you have to go talk to somebody else about budget? Those are other things.

And then asking questions even about headcount. So like, how did this role open? Why does someone think it’s important? Why did someone decide to do this over hiring another engineer? Sometimes those yield interesting answers too. And you can kind of tell where in a research maturity a company is based on that. What I see in terms of success for one sort of a person over another, I hate putting it like that because I think you can be a different sort of person at different places in your career too. But if you’re interested in sort of the bricklaying, let’s call it, I’ve seen people say they want to do that. And then they jump in, they realize like, oh shit, nobody writes anything down here. There is leadership lacking and cross-functional ways. And I can either take the reins or just get really upset. And you never know how you’re going to react in that situation until you find yourself in it.

So I’ve seen people who were like, yes, I want that. I want that. I’m excited about that. And then they get there and they’re just very uncomfortable, very frustrated. And what they actually wanted was the excitement of moving quickly, but they didn’t understand all of the things that surround that, that you need to take along with the moving quickly and the excitement.

Steve: What led you to Robinhood and the role that you have?

Celeste: Yeah. So this is a complicated question. So Twitter, Airbnb, and Robinhood, while they are pretty disparate in terms of topic, like your customers, things like that, they’re not in the same vertical. The similarities they have besides the company phase and stage is that they’re all very, very mission driven, like very strongly mission driven. And once you’ve worked at a company like that, I should just speak for myself here because maybe this is not exciting to everyone else, but once I worked at Twitter, I was like, I can never have anything but this ever again. Because when people really believe in it, when people really believe in the work you’re doing and believe it’s for a purpose that isn’t just like contributing to the capitalist abyss, it’s more motivating and more exciting to me to get up every day and like, and focus on a mission. It’s what I return to when I’m trying to prioritize things, when I’m feeling like I don’t know what to do. It’s a nice way to hold the center.

So on top of that, when I was leaving my last job, I interviewed, you know, there are many mission driven companies. And so like I interviewed for some heads of research roles actually, and I was even surprised to be offered some. I was leading the largest team at Airbnb when I left. It was like, it’s called hosting, which was Homes, which is the biggest part of the business, Homes, Community. We had an Olympics team and then experiences was also a part of it. I just felt like I was collecting Pokemon at that point. Like they just kept giving me stuff.

But so I basically decided that I didn’t want to be a head of research. This is why this is a funny story. I opted for Robinhood for the mission. And also because I was excited to lead research and like a lateral move across a few teams reporting to the head of research at the time. It was okay with me because I had all these like ideas about what being a head of research would mean, which is why I didn’t want to be one. So like I won’t be as close to the work anymore, or I’m going to spend all my days like writing and rewriting career frameworks, or I have to be super front and center. That’s another one that like comes up for me all the time. I’m not, I’m chatty, but I’m like fairly introverted. And I don’t personally love being like the star of the show.

So I was also kind of looking at people that I had reported to over the years and or known that like then went on to be heads of research. And I just couldn’t see myself doing what they were doing, or at least what I thought they were doing. And anyway, this is all about me joining Robinhood. But basically, through a series of twists and turns in my first few months, I found myself in the role I was avoiding, which is fun.

But looking back, I think my biggest gap in thinking at the time was that I forgot or I didn’t know that leadership roles are what you make them. So this isn’t very researchy, or even like UX-y. I think this is just like a fundamental leadership-y thing where no two people are going to do that same leadership role, whether it’s the head of research, the CEO, the COO, whatever, because those are all equivalent roles, right? The same way. Like you’re never going to do them the same way as somebody else. And that’s actually a really good thing because the situation may call for exactly what you can offer. But because of that, if you’re looking to other people to decide like whether or not you’re going to be suited to doing that role, it’s kind of like thinking about whether or not you should be a writer based on whether or not you can write exactly like, I don’t know, Mary Shelley. I love that that’s the first one I thought of. But she did it her way and she wrote Frankenstein, right? And then you’re going to do it your way and maybe not write Frankenstein. And just because you can’t write Frankenstein doesn’t immediately invalidate whatever it is you are going to write.

So that was a really long answer for why are you doing this job? But it was like a personal growth moment where the very thing I was avoiding, I had to confront. And I learned a lot about it.

Steve: Maybe there’s some blurring between what we think we can’t do and what we think or we know that we don’t want to do.

Celeste: That’s beautiful. Thank you. Oh, yeah. I agree.

Steve: Because I think you’re talking about like you’re looking at other, right, we all compare ourselves to people, whether we compare ourselves to Mary Shelley or someone who’s been ahead of research, but you’re calling out just to reflect back and kind of make sure I understand. You’re kind of calling out, well, you didn’t want to do the job because you didn’t want to sort of spend your energy and time and focus doing the things you saw other people doing. But the aha is that there’s a way for you to be being a leadership role that isn’t those things.

Celeste: That’s exactly it. The things that you’re good at are the things you should be doing as a head of research or as literally any other leadership role. And you should be surrounding yourself with people that are good at the things that you’re bad at, because together you’re going to make beautiful music or write Frankenstein, you know, whatever. Right. Whatever you want to extend there. I really like that that’s the first person I thought.

Steve: That’s a good improv moment. Don’t think about it. Just say it. I want to ask about “mission driven.” I think you’re saying, you know, once you sort of had a taste of that at Twitter, that became important to you. It was. And you wanted to. I guess I want to ask, is there a distinction between mission driven as just kind of a cultural quality and like the specific mission? Which of the bits of it are the ones that are calling to you so strongly?

Celeste: No shade to the broader corporate lifestyle or maybe much shade. I don’t know. But I think when you’re every company has like a mission and a vision and like values and they there’s lots of pomp and circumstance around those things. And I think the distinction is in the discussions that they’re integrating into every day. So at Oracle and Symantec, as much as I loved the people there and I respect and admire the work that they were doing, we weren’t talking about the broader like, what are all of us collectively across all these products trying to do together? What is our ultimate goal beyond making money? Like what’s important to us? What is the legacy we want to leave as a company? And yeah, it exists somewhere written down in some wiki, corporate wiki. But like it just it wasn’t a part of the day to day conversation.

Whereas like at Twitter, we were obsessed with being the global town square. We were obsessed with making it with enabling people to discuss and connect and like communicate. And it was really exciting and invigorating to be working side by side with people that were like, I don’t know how we’re going to do this, but we’re going to do it and it’s going to be amazing.

And then at Airbnb, belong anywhere isn’t just like an advertising tagline. Like everybody is talking about the ways that we’re going to make people feel more or less like they belong based on design choices, strategic directions. Like it’s infused in everything.

And it’s the same with Robinhood, ours is democratized finance for all. We talk about it literally every week. It is a constant in every meeting. It emerges, the language emerges, we’re weighing trade-offs and thinking about it.

And it sounds a little culty at its worst, but I like to think that at its best it’s a force for good. I think you are what you measure. And so when you’re running a lot of experimentation and you’re looking at all these metrics that maybe build up to something that you didn’t actually want to aim towards, but just made sense in the individual examples, you can return to the mission as like, okay, but are these metrics democratizing finance or are they doing this other thing over here? Have we lost sight of it? Whereas at Oracle, at Symantec, I felt like that was not necessarily the lighthouse.

Steve: Let me throw a different metaphor in here because we’re doing so well with them.

Celeste: We’re killing it with the metaphors.

Steve: I wouldn’t go to a, well, I guess we’d have to turn on a time machine, but I wouldn’t go to a Grateful Dead concert for absolutely anything. But if I was going to go to one, going with a friend of mine that loves music and loves the dead would be the way to do it, to be in that experience with someone who is into it. I’m using that as an analogy for the mission-driven thing. I don’t care about if the dead and whatever the dead is about is the mission. I don’t actually care about it. It’s not my mission. Belong anywhere might or might not be my mission.

But if you’re going to go to a concert or if you’re going to work in an environment, one where that kind of passion and commitment and attention to detail and thoroughly building out every aspect of decisions being made based on that, you’re kind of highlighting how powerful that is and how rewarding that is. I guess I’m asking, is that still true if the mission is one that you are ambivalent about, say, versus 100% bought into? That’s what I’m probing on here.

Celeste: Yeah. First of all, I love the metaphor because you’re right. You could go to a show, and if you went to the show with your best friend and they were crazy about the dead, you would have a completely different experience because energy is a very human thing. Energy is infectious that way. The passion, the enthusiasm, you can’t help but kind of like, “Oh man, I was going to say ‘Catch a whiff.’ That’s a little too on the nose with the Grateful Dead reference.” But we’re going to do this all day.

Yes, I actually do think that if you are fairly ambivalent about the mission. I don’t think I woke up in 2021 and was like, “You know, what really needs to happen in the world is finance needs to be democratized for everyone, for all.” I don’t think that I woke up feeling that way. I definitely don’t think that I looked at Twitter’s mission and was like, “Man, I have never been more like — it is my life’s calling to be a part of the global town square.” I think the difference is that the mission has to resonate at least a little bit. You have to be like, “Yeah, of course. I mean, yes. Do I agree with the idea of democratizing finance for all? Absolutely. I love that.” I didn’t know I wanted to do that until I started looking into it. But it doesn’t make it any less important to me, especially if I’m surrounded by people that are all agreeing and believing in the same thing. So it helps, but I don’t think — it’s not like you have to be born with that passion in mind in order for it to be infectious. I was looking for a less disgusting word, but that’s what we’re going with.

Steve: When we’re talking today, start of spring 2024, how long have you been at Robinhood?

Celeste: Oh boy. How long have I been at Robinhood? I’ve been at Robinhood for two years, and I’m sighing deeply because every year is getting shorter in my life. Just like Pink Floyd promised. I’ve been here for two years. I just celebrated my two-year anniversary in the beginning of December, so a lot has happened during that time. I started in December of 2021. A few months after that, the head of research left.

My job changed every two to three months for probably over a year, which isn’t inherently weird, except that 2022 happened, which meant that the crypto markets and the stock markets, everything was going down in 2022. There was a huge wave of layoffs across tech. We also had to lay people off. All of that is super difficult as an employee, but also as a leader of a team. It’s really, really tough, especially when you spend some time thinking that this is not what you wanted to do. So when I look back at the two years, it feels like more than two years, but it also feels like I just blinked and two years passed. So there’s a lot of cognitive dissonance in that length of time.

Steve: What’s the cognitive dissonance?

Celeste: It feels like a lot and like a little at the same time.

Steve: Yeah. So over those two years, what are some bricks that you’ve laid?

Celeste: So the team predates me by a lot. It’s not like I built the team and built all these processes. The team predates me by a lot. It was originally put together by my predecessors. I deeply appreciate everybody who did that for what and who they left behind. Those have been gifts. But the bricklaying in this case was that Robinhood had just IPO’d over the summer and was sort of nestling into everything changes when you IPO.

Airbnb IPO’d while I was there, Twitter IPO’d while I was there. Everything changes. There’s a lot more you need to do. Because your funding looks different, there’s a lot more that you need to be held accountable to. And so a lot of process changes when that happens. The research team had also been through a lot. There were some big, dramatic leadership and team changes during the entire year of 2021, and I showed up in December. So a lot of my bricklaying, I wouldn’t say it was like building a team from the ground up, but it was sort of like there was a lot of healing that had to happen as a group of people.

When I started, I was hearing a lot about people not trusting each other or feeling like if so-and-so got promoted, why didn’t I? I don’t even think their work is good. There wasn’t really very much teaminess. So a lot of the bricklaying was rebuilding cohesion and trust, thinking about things differently, re-evaluating tooling because everybody, when you’re laying people off, are also reassessing the budget and the tools that you need or don’t need. So a lot of really tricky stuff like that happening at the same time. And then kind of re-evaluating research’s relationship with the company, which was a pretty tall order, but it’s been fun.

Steve: What are things that you can do to build teaminess?

Celeste: Not sure I have a good answer to this because I’m going to give you that delicious research answer, it depends.

Steve: Yes!

Celeste: You’re welcome.

Steve: You’re going to ring a bell right now.

Celeste: Yeah. Someone somewhere is furious at me for this, but it depends on the situation. We had layoffs at Airbnb when I was still there and it was devastating and we had to sort of rebuild our emotional baseline also. And it was tough to find all the loose ends and figure out what work still needed to be done, what work had fallen off and that was okay, who we were without the people that we had lost and things like that. It’s really, it’s hard to be laid off and it’s very hard to lay off. It’s just like a no one wins situation.

So in that, in like the Airbnb case, the teaminess came from just, actually it might be the same as Robinhood, being consistent. Everybody showing up and being exposed to each other and just talking about what was hard, what wasn’t working, do people have ideas, here’s what I’m doing, what are you doing, but being really active and pushing for contact and like pretty regular consistent contact and trying to foster moments of recognition when something was going well. There was a lot of stuff like that.

I don’t know if I have like a silver bullet answer though, because it depends so much on like the way that things are bad or that need healing. We definitely went from people not being willing to help each other because they were worried about not getting credit to people helping each other without thinking twice about getting credit and those were signals to me that we were like nature was healing. We’re on the right track.

Steve: I know you’re apologizing a little bit for the answer not being like a full list of three things like you didn’t say, oh, we had an offsite or we had a cake, so it’s like, but I really am struck by the fact that you’re talking about like intentional ways of being that are maybe smallish, but that are sustained over time. But that sounds much harder and much sort of less obvious to come up with or to execute. And that seems like, well, if you want to make change, it does depend, but there’s a set of tools that you’re drawing from and a set of principles is, I don’t know, subtler than a fix it kind of approach.

Celeste: Fixing it, especially with something as fragile as like people’s chemistry and sentiments feels like a fool’s errand. Like coming in and being like, let me show you how to do things. I’m going to fix these feelings. That’s not really, I don’t think you’re going to get anywhere if you approach it that way. Someone has probably done that, but I don’t think that’s possible in the toolkit that I have. Maybe Mary Shelley’s done it.

Steve: She was a great management and leadership consultant in her coaching business.

Celeste: Yeah, good call. What comes to mind is that there were two things that were similar about both circumstances. One was sort of the community that I’m talking about, which like you can’t inauthentically build community. You have to push it through connection. You have to get people to connect with each other. And sometimes it’s awkward and it’s not mandatory fun. That doesn’t work. But if you can give people real reasons to show up and be there for each other and be honest with each other, you’re going to, it would be hard for that not to move in a positive direction. I think human beings just crave connection and community. Even the introverted ones, it turns out.

But the second thing is like, this is a businessy answer, but just hear me out. Transparency. So here’s what I know. Here’s what I don’t know. Here’s what I’m doing. Things like that are during, especially things like layoffs or moments where the team has really lost a lot of trust in either each other, the situation around them, the circumstances. They know that you’re doing everything you can to contribute to a shared understanding. It’s again, it’s hard not to move in a positive direction if people are like, you’re being as honest as you can with me. And that opens the opportunities for, I’m having a hard time with this and I didn’t want to say anything until I felt like you were also showing up and spilling your guts about what’s happening. So yeah.

Steve: You also mentioned re-evaluating researchers’ relationship with the company. What is that about?

Celeste: The company loves research. I don’t think the company will ever stop loving research. Some of that, again, love dearly my predecessors and their approach to it. I got really lucky, but, and it was always going to have a place because our co-founders started doing research themselves. When they started the business, they focused a lot on listening to people, on observing people do things, like on very researchy things. So the research team was always going to be a core function at Robinhood. I didn’t invent that. I’m not going to create that. But when I started, there was this, they had grown a ton very quickly, like the entire company did. And every kind of PM, GM, executive marketer up and down the chain was and still is asking about research. We need to do it on every last thing.

We have an unholy amount of opportunities to be user-centered in what we’re doing. And the tone for that is consistently being set at the top, which is delightful. And I don’t feel like I’ll ever see that quite in the same way in my career. So it just feels like I’ve struck gold. They’re always asking about our customers and their perspective. They know that our co-founders are doing the same. Everybody’s asking about this.

But when no one ever questions if research should be involved, and if everyone is insisting that research study everything all the time, you’re faced with a different set of problems. Your relationship to the organization is different because researchers, as I’m sure you’ve seen this too, we’re so happy to be included and consulted because we’re so unused to that that our relationship ends up being, yes, I’m going to say yes to everything because I’m so excited to be in this position and be consulted and be listened to.

And so that’s going to take anybody who starts at Robinhood by complete surprise. Everyone’s always like, “You said we had a seat at the table, but holy smokes, we really have a seat at the table.” Not prioritizing, not saying no. You end up spreading yourself really thin. You end up studying things you really don’t need to study because the leverage isn’t there. It’s not some sort of force multiplier all the time. Not everything needs research.

Actually there’s a general manager that I work with that loves to use this metaphor. Speaking of our metaphors, he likes to say, “If I’m opening up an ice cream shop, do I really need to do research that I should offer vanilla? I just know that vanilla should be on the menu. So do we really need to do research on that and why?” My response to that, of course, is like, in the vanilla answer, sure, but do we know that where you’re opening the ice cream shop is actually a place where people are interested in vanilla? Because you’re assuming a really narrow, maybe it’s Americans only, but whatever. There’s a group of people that like vanilla generally universally, but very generally. Is that target market where you’re opening up your shop? On top of that, is it a fancy vanilla? Are we using elaborate beans from some rare island or whatever? Or is it this just straight up vanilla, no frills? What is resonating? What’s needed based on the context of the situation?

But also I kind of agree with him that maybe we don’t need to do a study about vanilla at all. Maybe we need to understand everything around the vanilla. And that to me is I think the relationship with research that is ongoing and needs to change. If you can’t, as a product manager or some other leader, have a perspective on something without research, I feel a little uncomfortable with that. You should have a point of view. I want information to inform it. But if I don’t, because it’s a fairly inconsequential thing, I think you should still be able to make that choice anyway so that I can work on the stuff, my team can work on the stuff that’s the most important based on the things we’re good at. Not every question is going to be able to be answered by research. So that’s what I mean by the relationship. And it’s nobody’s fault that this is the state of affairs. It’s just what happens when the pendulum swings really hard in the other direction.

Steve: Right. You talked a little bit about saying no, but in the vanilla example, it’s almost like, hey, here’s seven more questions that are harder to parse out, riskier if your assumptions are wrong, and that create more context to the vanilla question begs a bunch of larger questions. And so that’s not saying no, though. That’s like, no, we’re not going to do the vanilla thing. But hey, how’s about…

Celeste: There you go. That’s what I mean. It’s not that I think we should be disengaging from every part of the conversation. It’s just that we need to be asking the right questions. And sometimes the questions that we’re being asked that we say yes to are still vanilla ice cream questions, like just the baseline yes or no vanilla without the nuance, the subtext, all the stuff around the things. And again, it’s just because research is such a part of the product building and marketing culture at Robinhood that people come to you with very strong requests about doing vanilla ice cream research. And we just have to keep making sure that we’re working on the things that are the most important from a business UX timing perspective to make sure that we’re not just answering lower leverage questions. What’s the approach to changing that relationship in the way that you’re articulating?

I spent a lot of time with product leaders and GMs and things like that talking about what the most important decisions they need to make, questions they have are, and then kind of going over… I’ve been made fun of before because I’m like, that’s an experimental question. Like straight up, just run an experiment. It’s faster and more reliable. You’ll have more confidence if you run an experiment. People laugh at me because they’re like, well, wait, don’t you collect data a different way? Yeah. I mean, just because I’m a hammer doesn’t mean everything looks like a nail to me. So I spend a lot of time doing that because it does need to come from the top. But then making sure that people have the tools to be able to feel like they can say no because a lot of researchers feel like it’s going to damage the relationship between them and their product teams if they’re not able to do everything that’s being asked of them, which is disheartening. So we work a lot on that.

We talk a lot about what a higher leverage question looks like or how to meet the short-term moment of what the team needs while making it into a longer-term study also. So I don’t mean in length of time, but I mean, I’m sure you’ve heard this a bunch, Steve. You know how there’s this debate within research about whether strategic or tactical is a better use of our time? I find that interesting because I don’t think they are separate. I think that you can make sort of like what people would refer to as very highly tactical research like, “Do people understand this? Whoa!” You can make it strategic by asking questions inside of it and putting together a broader narrative. If you’re telling me that like, “I’m too senior to do usability testing,” or whatever it is, I’ve heard that multiple times, which is unholy. But it tells me more about how you’re thinking about structuring your research in a way that you’re thinking about insights and what value you bring to the team. It tells me a lot more about that than it does about your seniority or anything else. And so it’s not about like doing less usability research, but it’s about doing the research that really needs to be done. And so we talk about how to prioritize, we talk a lot about like this over that, and we’re just pretty open about what’s important and why. Back to your point about transparency, I think. I’ve been wrong before.

Steve: Yeah? Not in this conversation.

Celeste: Probably several times in this conversation, but never about Mary Shelley. You’re welcome for that.

Steve: I’m thinking about this relationship between researchers on your team and any particular product team and so on, where, yeah, what you said, there might be a near-term question, but there’s a way to do that research that also… \Either you refactor that question into a higher value question, or you do, and you didn’t say this, but I am going to say yes and, you do kind of a yes and of the short-term implication and the longer-term implication. But just this whole exploration of like, what are research being asked for? What does research provide? Just makes me think about questions that come up, like, do we give recommendations? Like what are the kind of outputs of research? And I know it depends. Of course it depends. But does this, I don’t know, does this area provoke anything for you, a point of view, or something you’re thinking about?

Celeste: On the topic of recommendations, I’ve seen at some companies the idea that if people aren’t taking your recommendations, that you have not had impact, which I find charming. Like I personally do not want to work somewhere. I’d be really concerned if someone was taking 100% of my team’s advice all the time. We’re looking through a really specific lens. There’s all these other inputs to consider. It’s really great when the research is informing a decision, but sometimes the decision is not going to go with what the research is recommending. And I don’t think that’s a failure on the researcher, as long as everybody’s aware of the trade-offs and everyone understands the insights.

And by insights, what I mean is like what the data itself translates to for us as a product, as a business, whatever the case may be. It’s okay to have wrong recommendations, but it would be weird if you were taking my advice all the time because it would mean that you’re really only considering one input or weighing it heavier than others. So that feels weird, but I do think, to your point about it being a bit of a controversial topic, I do think we should have recommendations, like be giving recommendations, not because we’re all geniuses, although maybe that’s true. But because we are the most informed about what the data means, what we can say and what we can’t say based on what we did, thinking about things like intellectual honesty and rigor and all of that, I don’t know why we would ever think that we were not suited to making some sort of recommendation.

Because other people are going to take the information that you give and then just make their own recommendation, but that’s filtered through an entirely different lens with way less of the broader context that you’ve collected. It’s okay if your recommendation is bad, and you should probably shape it in a way that makes it shelf-stable, right? If you say, “Move the button to the right,” that’s not shelf-stable, because at some point someone will probably look at your research years down the line and go, “What in the hell were they talking about when they made that recommendation?” But people preferring design A over design B is just sharing data. People preferring design A over design B because the information they were looking for was a lot easier to find, that’s more shelf-stable, right? You understand why, you understand the context of the insight itself, and even if I don’t do exactly what you say, maybe I end up going with design B anyway, maybe I can make design B better based on the way that you frame that. So there’s a lot in there.

Steve: I want to pick out what a recommendation is, because people prefer design A over design B, that’s data. People prefer design A over design B because they can find the information. Okay, that’s an insight. So then the recommendation would be, go with design A.

Celeste: Right. Yeah, but you have to have that other piece in there for it to make any sense at all.

Steve: We should go with design A because it helps people to find the information they’re looking for.

Celeste: Words are hard, Steve.

Steve: I don’t know, just as a counter-argument a little bit, and I think you’re on board with this, the risk of being wrong there is you only know what you know about that. So design B makes us more money, design B we can implement faster, design B is compliant with something, design B is consistent with what we’re doing in three other platforms.

Celeste: Absolutely.

Steve: So I think that’s an example of them not going with design B and that being okay because you’ve given them the information that you have to make that recommendation.

Celeste: Yes. So I would argue that if you’re not incorporating things like which design would make us more money or if you’re not incorporating those pieces of information into your process, you’re leaving value on the table. You should be helping the person who needs to make the decision make it with all that context in there. Anything you can help them with. You have an amazing sense of synthesis and distillation and not everybody’s fantastic at that. So if you can pull that in, you probably should do that. But yes, you’re right that even if your recommendation is wrong, it’s not always that you’re completely incorrect. It’s like not right now because we would prefer to make more money with design B or whatever it is. But you’ve planted this seed and I understand that what people need is not what this is providing and so we can get successive approximations closer to it.

Steve: Right. I think the recommendation discussion sometimes leaves me cold because it loses all the context that you’re providing. It’s the recommendation and the insight in the larger context of the set of things that might be factors for this team. And I think you’re saying you should try to know all of them.

Celeste: Why not?

Steve: I’ll just add there’s always going to be something that you won’t know.

Celeste: Of course.

Steve: I don’t know, it reminds me of like trying to write like Mary Shelley. I think if you do, if you do like creative writing and you do workshops like you get feedback that says, here’s what the problem is and here’s what the solution is. And I think it can be really helpful when you’re the writer to choose not to do that, but to do it, ignore the advice in an informed way. Well, that’s not what my objective is. That’s not my strategy. We need short term wins here, whatever. And I think we’re agreeing strongly here. And it’s just some of the language gets oversimplified when it gets, you know, boiled down to like a social media posts.

Celeste: Yeah, I think this particular topic is one that is not great for like a LinkedIn rant. And yet, it’s all we see.

Steve: But great for a podcast episode, right? Because we can dig in.

Celeste: Sure.

Steve: You brought up my other another one that I take umbrage at which is the, you know, not we’re not having impact if it doesn’t get taken up. And I liked what you said. I’ve also heard people say my research doesn’t have value. If no one takes action, it’s even more binary, right? If that my research impact is sort of higher level than value. My work is worthless. If someone doesn’t do the thing that I told them to do. And I feel so sad because that’s researchers saying that, like as if we don’t have enough people telling us we’re without value. We’ve sort of taken on as a profession taken on some of that, you know, willingly devaluing proactively. I’m going to devalue it for you. It’s depressing. And that makes me sad.

Celeste: Yeah, I agree. It also not to I’m sure that the folks saying this are perfectly smart people. But to me, when I hear that kind of stuff, it feels like it lacks curiosity. So you’re saying that unless there’s like something I can see in front of me, or unless there’s like a direct action being taken, that I have failed when I think if you had a little more curiosity about it, you could notice little hints like, well, but these people are changing their language. And they’re using the language of the people that we’re studying instead of whatever business bullshit we’ve come up with. And that’s impact.

I think there’s we’ve changed the roadmap where we’ve just decided not to go this route. We’ve saved three months of engineering. So it’s almost that inaction is action. There is there’s lots of stuff like that. And I think if you are open to seeing it, it makes itself known to you. But if you are not curious how your research is sort of creeping through an organization, you’re going to end up with it flying right over your head. And then you assume you have no value or whatever it is you said, it’s depressing.

Steve: You know, you’re bringing your the same way that you talked about bringing teaminess is it seems very analogous to the way you’re talking about both creating and sort of realizing the value that it’s smaller signals over a longer period of time with some I’m not sure if the constancy thing applies here or not.

Celeste: Maybe.

Steve: But it’s a binary outcome kind of thing that yeah, taking a slower and more looking for looking for those subtle more subtle signals.

Celeste: Yeah, you’re reminding me of I’ve had this conversation a few times after becoming a manager where people are like just shouldn’t do research on this area because they’re not valuing it the way they should, which often the subtext is they’re not taking my advice or they’re doing things the way that I fundamentally disagree with. You probably know this better than anybody, but this is not a field for the faint of heart. This is like a full on eternal marathon. It took me three years at Airbnb and many different approaches to convince people that non drip pricing was the right call. It cost us a lot of money and we had to find ways to offset that. And every time I got knocked down about it, I could have chosen to never bring it up again.

But it’s chipping away. It’s finding advocates. It’s finding other people that agree or believe it. If I can convince one person each time of something that I thought that I believe in, I’m doing great. That’s impact. And so you’re right that there’s like little subtleties, but it’s also just a long game. Like all of this is a long game. You’re lucky if you have a short term win. You’re super lucky.

Steve: Anything else to add today?

Celeste: No, I mean, thanks for inviting me to do this. It’s very flattering to talk about my thoughts and feelings on things we mutually like for however long this just was. It was very nice. Thank you.

Steve: Yeah, thank you. You shared a lot of interesting perspectives and good history. So yeah, thanks a lot for taking the time.

Celeste: This was awesome.

Steve: Over and out, good buddies. That’s all for this episode. Thanks for listening. Recommend Dollars to Donuts to your peers. You can find this podcast in all of the usual places. A review on Apple Podcasts helps others find it. Go to portugal.com/podcast to find all the episodes, including show notes and transcripts. Our theme music is by Bruce Todd.

Celeste: Did you say a favorite puppet?

Steve: Favorite puppet.

Celeste: What came up for you just now?

Steve: You know so many things about so many things and I was just trying to open up the possibility space.

Celeste: Favorite puppet. I’m going to be thinking about that. What is my favorite puppet? Now I know exactly. It’s the, I can’t remember the other guy’s name, but it’s the two angry balcony dudes in the Muppets. One of them is named Astoria or something like that, or Waldorf, and the other is named after another hotel and it’s just not coming to me. But those are.

Steve: His name is, his name is Statler. Statler. I just Muppet, Muppetsplained you here.

Celeste: You win. You win the Muppets.

Steve: Yeah.

Celeste: I also just like that there’s no, nothing is sacred to them. They just go after whatever, whatever is in front of them. And they do a lot of like lame dad joke moments too.

Steve: So. That’s excellent. I’m not going to get any actual puppet content.

Celeste: Puppet content

Steve: So thank you for, thank you for taking that literally. I didn’t know what you were going to share, but…

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