Episode 222: Designing for Real User Understanding with Dheerja Kaur
Dheerja Kaur, Vice President of Product Management at Robinhood, joins Melissa Perri on the Product Thinking Podcast to discuss her journey from engineering to product leadership. Her experience integrating design and user experience into product development at Robinhood has fostered a culture of ambitious thinking and learning by doing.
Dheerja shares insights into balancing experimentation with strategic objectives and emphasizes the importance of empowering product teams to think big while aligning with organizational vision. Would you like to empower your product teams to think ambitiously while staying aligned with business goals? Don't miss out on Dheerja's insights.
You’ll hear us talk about:
07:34 - Defining the Product Manager Role
Dheerja reflects on her transition from software engineering to product management at ESPN and how she navigated the shift from a technical role to a strategic one.
13:01 - Coaching without Micromanaging
Dheerja shares strategies on finding the balance between providing guidance to new PMs and allowing them the autonomy to grow, fostering a supportive learning environment.
28:09 - Balancing Experimentation with Ambitious Goals
Dheerja discusses how to encourage teams to think big and have a portfolio of bets to achieve ambitious objectives while maintaining a culture of learning and experimentation.
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Episode Transcript:
[00:00:00] Dheerja Kaur: I started out in engineering. Had zero exposure to design. And I remember when I became a pm I was scared of that gap. And I got the chance to PM a pretty big project, which was the ESPN redesign. So it wasn't just a design update, we were overhauling the entire architecture of the site. And I worked side by side with our VP of Design at the time. And I kinda went to him and I was like, Hey, I wanna understand how you look at something and think about how to uplevel it. So I learned how to do that, how to manage a design agency. And man, I look back on that and that was an incredible learning moment because I don't deem to say that, I can design something myself, but I can partner and I think that was just an amazing opportunity.
[00:00:36] there's a mentality about that you don't always see, right? Sometimes you see different functions be like, this is my job and that's their job, and we work together and it all works out, but like we expect our designers to feel accountable to the metrics and the success of the product and vice versa.
[00:00:48] We expect PMs to feel accountable to the quality of the product. Are you proud of this thing? I think that mentality is first and foremost important at all levels, especially product leaders.
Intro
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[00:00:56] PreRoll: Creating great products isn't just about product managers and their day to day interactions with developers. It's about how an organization supports products as a whole. The systems, the processes, and cultures in place that help companies deliver value to their customers. With the help of some boundary pushing guests and inspiration from your most pressing product questions, we'll dive into this system from every angle and help you find your way.
[00:01:24] Think like a great product leader. This is the product thinking podcast. Here's your host, Melissa Perri.
[00:01:34] Melissa Perri: Hello, and welcome to another episode of the Product Thinking Podcast. Our special guest today is Dheerja Kaur, the Vice President of Product Management at Robinhood. Deirdre brings a wealth of experience from her leadership roles at The Skim and ESPN, and her unique approach to integrating design and user experience into product development is super inspiring.
[00:01:52] I'm thrilled to dive into a conversation with her about her journey to becoming a product leader and how she fosters a culture of learning and user experience at Robinhood. Before we talk to Dheerja, it's time for Dear Melissa. So this is a segment of the show where you can ask me any of your burning questions about product management.
[00:02:08] Go to dearmelissa.com and let me know what's on your mind.
[00:02:12] Hey, product people. I have some very exciting news. Our new mastering product strategy course is now live on Product Institute. I've been working on this course for years to help product leaders tackle one of the biggest challenges I see every day, creating product strategies that drive real business results.
[00:02:28] If you're ready to level up your strategy skills, head over to product institute.com and use code launch for $200 off at checkout.
[00:02:35] Here's this week's question. Dear Melissa, when organizations move from treating technology as a cost center to a profit center, do you see a shift in terms of investment in relation to revenues? Or is it simply the case that technology shifts in line with revenue rather than a constant downward pressure regardless of strategy or performance?
[00:02:53] When viewed as a cost center, I've seen benchmarks of efficiency for IT spend at 2% of revenues. Are there any patterns, generalizations, or benchmarks if there is a shift?
[00:03:02] Alright, so I'm gonna tell you this it does vary widely. If you have a company that is more SaaS focused, let's say, and sees that their profit and their business is very highly tied to technology versus companies that are making the shift.
[00:03:17] For instance, in SaaS companies, especially high growth SaaS companies. 2% of spend on technology would be like amazing. I'm sure a lot of investors would be really happy to see that. That's not the case. Usually technology investment is huge in a lot of these startups and these growth stage technology companies, 'cause that's where most of the people are.
[00:03:36] That's where most of them are creating. In larger companies, you usually will have a large operations team, we'll have a large sales team and they're moving towards technology, but they don't really know what good looks like for their tech teams yet, or what benchmarks to to measure it against. So that's why you get these weird rules of 2% of spend or anything like that.
[00:03:54] When you're thinking about what good looks like in a company that is privately held, usually what the investors are looking at is this rule of 40. For instance what that means is what is the profit margin of our business. And again, heavily the profit margin is usually people salaries if you're in a tech company.
[00:04:14] So that a lot of that could be the technology salaries as well. And then you would look at your growth percentage and you wanna add both of those up to get to 40. Anything above 40 is considered really good. So for instance, you might have negative margin. But super, super high growth, like a hundred percent growth year over year, but negative margin.
[00:04:31] And that'll even out to 40. And that's why you see a lot of investors investing in companies that are not profitable yet, but still have high growth. So now that we're in this new area, a lot of people are going towards rule of 40 and favoring profitability overgrowth, but that's just how the market is shifting right now.
[00:04:48] The rule of 40 still remains. So if you think, let me think about applying this to a large company, like a big enterprise going through this. The numbers are gonna be different. Obviously you have a much different landscape when it comes to how big the companies are and the other departments and the operations and especially if you're making the shift.
[00:05:06] But I. It's really hard to just say blanketly like it spend should be 2% of our company because you're not really tying it back to how can our business strategically evolve and what can we do to be more competitive if we spend more in technology? It's not looking at as an investment, it's looking at as just like the bottom line.
[00:05:26] And that's a really bad mentality to get into because we should be looking at using technology to scale and it can help us lower our costs. That's definitely one option there. It can also help us innovate in ways that we've never done before. So by just looking at technology as we need to hit this percentage of spend, but not tying it back to why are we investing in technology in the first place?
[00:05:48] Is it gonna increase revenue? Is it tying back to customer satisfaction to churn? If we're not putting it back into those business metrics, usually we don't know what to actually judge it by in a company, and that's where you get these weird little benchmarks with 2% or just really trying to drive it down as far as possible.
[00:06:03] So yes, moral of the story is once you actually can connect your product strategy and your technology all the way back to how it drives your business outcomes, you're gonna have a very different conversation about how much you should be investing in technology. And that is the goal for every company.
[00:06:18] That's really where we should be getting to. So I hope that helps, and I wish you luck in your product management journey with this as well. Now, let's talk to Dheerja.
[00:06:27] Welcome to the podcast Dheerja.
Dheerja’s journey into product
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[00:06:29] Dheerja Kaur: Thank you. Excited to be here.
[00:06:32] Melissa Perri: Can you share for our audience a little bit about what your journey into product management has been and how you ended up as the vice President of product Management at Robinhood?
[00:06:40] Dheerja Kaur: Yeah, absolutely. So quick, TLDR of my background. So currently I'm VP of product at Robinhood, where I lead the core product teams. I've been here almost five years actually. Five years in two weeks. You can wish me a happy early anniversary. and prior to this, I've just always been in product development.
[00:06:56] So started out my career at ESPN, where I was a software engineer building some of the very first mobile apps which was kinda dates me a little bit, but you get a sense of how I started out building the first APIs there. It was just kinda a really fun time. And at ESPN, I actually moved into product management about halfway through from engineering, which was a big decision we can talk about later. And then prior to Robinhood, I was at a startup called The Skim, where I was CPO. But started out as employee number seven. Helped build the team from the ground up, built up product, design, research, et cetera. And really got to see that true zero to one of startups. So it feels like I've operated in a lot of different stages of companies.
[00:07:34] Melissa Perri: When you look back on your career, what are some pivotal moments or challenges that you feel like really defined your path in product management?
[00:07:41] Dheerja Kaur: Yeah, absolutely. So the first one that always comes to mind is that kind of burning question of should I become a pm?
[00:07:48] And I think everybody has probably experienced that at some point. Though obviously now we have a PM programs, so not necessarily but yeah, so when I was at ESPN, like I mentioned, I was a full stack software engineer building apps, working on the website. And it really felt like a startup in those early days because mobile was brand new. You were figuring things out and it was just a fun time. But interestingly enough product management actually didn't really exist at that time.
[00:08:10] So it was very much engineering design. And then you've got, the writers on at ESPN, et cetera. And I was actually an engineering manager at some point, and, now that I look back, it felt like I was doing a lot of the role of product, right? I was helping to find the requirements helping drive all the different teams together to execute.
[00:08:27] And at some point, ESPN decided, Hey, we are going to formalize a function called product management. We're gonna create it. And I got tapped to, be one of the first people to do that. And I remember it was a really interesting decision because I had no idea what this job was like, so sorry, what is this thing called PM and how is it different from what I'm doing today?
[00:08:46] And I as I started to unpack it, I was like, okay, it's actually a lot of the qualities of the job that I'm doing that I really love. Like driving the roadmap, bringing all the teams together working on an overall strategy. And though it was a really hard decision because at the end of the day, there's nothing that's better than the satisfaction of actually building something, right?
[00:09:03] Actually shipping code to production, I was like, Hey, I really think this is the type of stuff that I'm gonna love doing more and more as my career grows. So I got to actually be in a dual role for about a year where I was both still in em, but also a pm and I got to work on a really big project as part of that and test the waters.
[00:09:20] And I was like, okay, I think I like this. I think this is the type of stuff that I wanna be doing. And so I made the switch over to the dark side and became a PM and never looked back since. And again, I can go more into that, but I just think that, that decision of, moving away from that, the original thing that you were doing and going into this kind of ambiguous role called PM was a really pivotal moment for me, but something that yeah, I look back on and is a great decision 'cause I really love my job today. The second one that I would think about is someone, something that I think everybody faces at some point, which is that shift from iCPM into more of a product leadership role because the job really fundamentally changes. You got all these challenges that start to come up that become a core part of your job that just didn't exist before. So one is it's really hard to learn how to manage pm It's very different from managing engineers or designers where you can be pretty hands on in the day to day, like when I was in em you're doing code review. And you're really in the details and in the weeds with the team on helping them execute. When you're managing PMs, the whole point is that each PM has their autonomous space, right? To make decisions to operate just at the roadmap. And so learning how to manage PMs, I think is a very unique skill in management.
[00:10:27] And like really developing that as I moved into product leadership was definitely a new challenge. And then of course, the fundamental nature of your job changes, right? A lot of your job becomes about how does your product strategy connect to moving the business overall?
[00:10:39] How does a company strategy driven by the product roadmap versus really being just within the product world? And yeah, those are kinda like the two big moments I remember, but, again many learning moments along the way.
[00:10:50] Melissa Perri: I think that's a challenge for a lot of people who move from product manager to a manager of product managers is that. How do I actually manage this team? What are some of your philosophies and what did you learn that works and doesn't work in that case?
[00:11:04] Dheerja Kaur: For sure. So I think one is you really have to, get to a point where you feel very comfortable with an authentic direct communication style. And I paused when I said that because that sounds so trite. Every manager has to have a great communication style. But to be really specific when you're managing PMs, like you have to establish an open line of communication because you're just not in the weeds on their day to day.
[00:11:27] Like your visibility is quite low, and really establishing, Hey, here's how I can help you. Here's how. We're gonna work together. Here's my feedback. Even if it's more of a spidey sense feedback, not necessarily something that I'm seeing on the ground. 'cause, again, I'm not necessarily I'm way more removed from the day-to-day than, an EM or a design manager is. And so one of the big thing for me was really figuring out how do I establish kind of lines of communication with PMs so that I could get visibility. And again, also share early feedback based on instincts or spidey senses, which can be scary, right? Because you don't have all the details and all the information.
[00:12:00] I could be like, Hey, something tells me that this isn't going, this project isn't going super well. Here's some of the signals I'm picking up on. Can you just tell me what's going on? And again, getting to that comfort level as a manager is hard because you're told that when you have those types of conversations, you're supposed to have a ton of depth than a ton of details.
[00:12:15] And again, when you're managing PMs, I think you have to feel a little bit more comfortable communicating in the gray area. And then another thing is I think really figuring out the artifacts that help you coach PMs are important and few and far between, right? So what I mean by that is that, pities roadmap docs those aren't getting pumped out every single day, and so taking. Each of those opportunities to be a coaching moment and and a moment to really work one-on-one with PMs, I think is is something that you gotta take advantage of. And you gotta communicate in a way where you're not like, Hey, I'm not trying to just micromanage you and get up all up into your business.
[00:12:48] I'm just trying to use this as an opportunity for us to work together and learn. And again you just recognize that you have fewer of those moments with PMs because you're not, again, doing code reviews every single day. And so just really taking advantage of those, I think is really important.
Coaching PMs without micromanaging
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[00:13:01] Melissa Perri: I feel like that line too, that you mentioned a little bit between micromanagement and coaching is always the hard part, I think first time leaders have how do you navigate that line? And especially with, let's say like newer product managers, right? You might not know what they're doing versus experienced product managers too.
[00:13:17] Dheerja Kaur: Yeah. It's gonna sound very basic, but I think first and foremost, people need to know where they stand with you so they can understand the context of why you're asking questions or getting into their docs or giving them feedback. Because again, sometimes what just happens is that without that mutual understanding people just get on the defensive and then it snowballs from there, right? Because it, then it feels like they're on the defensive. So then everything really just feels like micromanagement. And again, you're just all up in their business. And so like first and foremost, I just like to make sure that people know where they stand, right?
[00:13:45] Which is that as an example, high performer, high growth person, but maybe new to PM or early in their career. So you wanna just be hands-on because you wanna help them grow as quickly as possible. They should know that. So you should tell them, Hey, I think you're awesome. You have so much potential.
[00:13:59] I wanna give you all the opportunity to grow. There are these two or three things, maybe one thing that you need to learn. Because you're not quite there yet. And I think that is a critical gap that will be really important for you for your next phase of your PM career. And that could be understanding business metrics, better understanding how to do a model with finance better.
[00:14:17] It could be really building better design intuition. You pinpoint that and you say, Hey, I think you're awesome. I wanna invest in you. So on this specific thing, we're gonna spend a lot more time together and that's why, because I just want you to learn as quickly as possible. And I think when you just lay that context, they are then much more open to proactively being like, Hey, can you take a look at this? Or, Hey, can I ask you a question? Versus it feeling like they're on the defensive. And again, it sounds very basic, but you'd just be surprised, how little of that sort of context setting is there.
[00:14:44] Melissa Perri: Yeah, so it's meet them where they are and be like,
[00:14:46] Dheerja Kaur: Yeah.
[00:14:47] Melissa Perri: eh, this is for your, this is for your benefit. I'm not doing this just because I don't think you can do this. It's just that you need to learn this for your career.
[00:14:52] Dheerja Kaur: Exactly, and especially with PM I think because it's such a breadth of skill, so you typically have people who by default spike in something based on their past experience or just their core capabilities. And so there's always something, and it's, I think it's also in some ways easier to pinpoint because it tends to be a category of things, right?
[00:15:10] Somebody maybe comes from a design background and is really strong at intuition and kind of, uh, ux, and is really light on data. It's quite simple to pinpoint that and say, I'm gonna you a crash course in this. And I think with PM you have a unique aspect of that, because again, it's such a breadth of skills, so it's a little bit easier to pinpoint that.
[00:15:28] Melissa Perri: When you look back on your career too, and your experience also at ESPN and the Skim, where, how do you think that played into your role of a product leader and learning these skills to, to get there?
[00:15:40] Dheerja Kaur: Huge. As I mentioned, I started out in engineering, very much an engineer. I was a applied math major. Had zero exposure to design, for example. It was the big one. And I remember when I became a pm I was scared of that gap. I was like, I don't really know if I think I can look at something and know if it's good or not, but it's hard for me to go past that to let me brainstorm solutions, right?
[00:16:02] Or let me really figure out how do you take something that's like good, but you uplevel it from a design perspective and, I think a lot of how I've approached my career is just be very humble and open about what I still need to learn, and I think you end up learning faster that way. And so I got the chance to PM a pretty big project, which was the ESPN redesign.
[00:16:22] So it wasn't just a design update, we were overhauling the entire architecture of the site. We were applying a new brand. It was kinda like the full gamut of what a redesign could be. And I got to. Worked side by side with our VP of Design at the time, who was like, a had an amazing career, amazing background in both brand and product design.
[00:16:39] And I kinda went to him and I was like, Hey, I'm a little nervous about working together on this because I, this is a new space for me. But can we just spend the first few months where you just give me, like I said, a crash course on the nitty gritty of it. I wanna nerd out about type, I wanna understand how you look at something and think about how to uplevel it. And really exciting into brand design as well. Like I really wanted to build more of that knowledge and understanding. And I think I got lucky 'cause in that project that was like, it really did feel like that crash course. I think I spent the first three to six months, just like really learning the ins and outs of how to look at something, what works, what doesn't.
[00:17:12] And we actually worked with an agency as well, so I learned how to do that, how to manage a design agency. And man, I look back on that and that was an incredible learning moment because I think it really helped me then build a design team from the ground up at the skim, and learn how to work with designers, and build the right rapport because at the end of the day, I'm still a product leader.
[00:17:28] I don't deem to say that, I can. I can design something myself, but I can partner and I think that was an, that was just an amazing opportunity, I think.
[00:17:35] Melissa Perri: What's your philosophy on this? 'cause I, I feel like this comes up a lot with product leaders about how product leaders should be versed in design. You've got the engineering background, right? You can do that part like cold. Where do you feel like product leaders need to level up in design and like, how should they think about design as part of their core competencies?
Learning Design
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[00:17:53] Dheerja Kaur: I will say it's different depending on what space you're in. I've always worked in consumer product where I think it's extremely critical. I, it's not something that you can be like, Hey, I can see what, see if something looks good or not.
[00:18:04] But generally I defer that your success as a product leader like hinges on the success of the product itself and in consumer product. The design is one of the most critical, if not the most critical aspect of that. And again, I think it depends. I think it, if you're in, there are many different industries or spaces where maybe, it's less important.
[00:18:21] But I think in consumer products is, hands down, one of the most important things. But then again, kinda like I was saying earlier, I think you have to learn how to how to partner and how to uplevel design or how to brainstorm with design without overstepping.
[00:18:35] And I think that that is an art, and for me some of it comes from a couple kind of key skills that I also try to ingrain in PM here. One is a mentality I think, which is an ownership mentality where both our PMs and designers feel equally accountable to the outcome and success and the quality of the product.
[00:18:53] And there's a mentality about that you don't always see, right? Sometimes you see different functions be like, this is my job and that's their job, and we work together and it all works out, but like we expect our designers to feel accountable to the metrics and the success of the product and vice versa.
[00:19:06] We expect PMs to feel accountable to the quality of the product. Are you proud of this thing? I think that mentality is first and foremost important for at all levels, especially product leaders. The second is, you gotta just get the reps and build intuition, and some of that just comes from experience of launching things that aren't great or great and seeing things that work and what don't work and feel a little bit of that confidence in being able to share feedback on something again without saying: Hey, I have the exact solution for it.
[00:19:33] And I think that tends to be a little bit of the line for me, which is I can look at something and say: Hey I have this feedback or here's my intuition on what works and what doesn't. Y'all are the experts. Let's come back and let's see, let's do a rev on it.
[00:19:44] And I think you have to build a little of that confidence and knowledge around what's good, what's not good, what works, what doesn't work, so that you can give feedback in a very concrete way and push the team. But again, not expected to actually do the solution space.
[00:19:58] Melissa Perri: I love your philosophy on that because I agree with it so much. I find that so many product leaders, especially ones who, let's say come from engineering, right? They're not approaching things from the user experience perspective and even in like B2B companies that I work with. You can tell like nobody actually thought about the UX here.
[00:20:14] So it leads them to not hire good design talent, not invest in good design, not actually make it there. And to me, so many of the issues that I've found with companies coming in is their user experience is broken, right? Like it's just not good. And I feel like that's such a critical part for your product success, but there is such a war sometimes between design being like, Hey, product, you shouldn't have any say in the design, right?
[00:20:35] Versus product being like, no, I need to, because it's part of the success of this product. And finding that careful balance. I feel like it's hard.
[00:20:43] Dheerja Kaur: It's tough. And some of it is just also like pm v to have good eq, and know that, we're how do you with a designer without overstepping? Because at the end of the day, like especially at Robinhood, this is what I love. Like we have an incredibly talented design team.
[00:20:59] Like they're the best in class, and I really mean that, I'm not just saying that 'cause I'm a company girl. and, our PMs also as part of that learn how to build that intuition, how to jam with them, how to, really like work together to uplevel things, but then also be like: you're the expert. I can look at things from a customer's POV can have ideas and opinions by end of the day, like we have an amazing design team for a reason. And again, there's, that's an art, right? It's really under having the EQ to know how to partner and push without overstepping and that's what makes a great PM.
[00:21:30] Melissa Perri: When I look at Robinhood's journey too, I think design has been so core to your story, like over time. So I remember signing up for Robinhood, like back in the day when it first came out. And I know like the mission was always to make it easy for, everyday people to just invest. But when I logged in, I noticed it was the same kind of functionality that I would get on Schwab or TD Ameritrade like I had to be an expert, kind of, to use it. And I didn't see a lot of differentiation from it, but recently, like I go back on and now it's, it's teaching me about options if I wanna go place an option. It's teaching me about all these different financial concepts. Can you talk a little bit about the design journey at Robinhood and how do you think about your approach design when you are, you're building a tool, let's say, that's existed for other types of customers out there, but now it's for a totally different audience.
UX In Finance
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[00:22:16] Dheerja Kaur: Absolutely. Yeah. And it's definitely an evolution as you probably have seen yourself. Because as you can imagine, the early adopters of Robinhood, this was before my time, so I'm speaking on behalf of an amazing team. But the early adopters of Robinhood were people who were already investing, but, there was terrible products and also the economic structure was terrible, right? There was a fee for every single trade you placed. And so the early product really appealed to people who were already investing who were like, let me let me have an amazing experience and let me stop paying fees, but then that very quickly evolved beyond that, right? Because as you can imagine during the pandemic, during kind of the rise of retail trading, Robinhood became kind of the forefront of how people gain access to the markets for the first time. And so that really evolved our thinking as well of, hey, we now have all these people coming in who maybe you've never done this before, which is an amazing opportunity for us, but we kinda have to think about it a little bit differently. Fundamentally, I think we have this ethos of we help you learn by doing. We believe that the best way to learn is you actually place your first trade. And you have that magical moment where you're now a shareholder in a company. That's incredible, and we wanna guide you on that journey.
[00:23:24] And what we've really approached how we've really approached that from a product and design perspective is every single first time moment or, later on as you increase your assets on Robinhood, et cetera, you've all these sort of milestones in your journey. How do we help you in the product flows themselves?
[00:23:39] Learn as you're doing these things, right? And it devils in the details, but at a very basic way, it means we don't have like a separate place where you take a class on how to invest, right? We help, navigate your very first investment on Robinhood, and help you learn about that and help you have that feeling of being a shareholder for the first time. And the same is true of every single product that we have, whether it's options or retirement. Retirement, let's help you understand, what the difference is between, Roth IRA and a traditional IRA and how you can make that decision and really approaching it with that kind of customer first mentality.
[00:24:11] And I've loved that because I think that is the, a winning strategy, right? To help people learn, especially in finance, where there's a lot of theory out there, but there's a huge barrier to then actually take action, right?
[00:24:22] Melissa Perri: Yeah. And I think that's so important. What you're getting at to too is like I see people try to cover up bad design by putting little walkthroughs or like, walk me, right, let me tell you how to actually use this instead of you should know how to use it and I'll guide you through.
[00:24:36] Dheerja Kaur: yes.
[00:24:37] Melissa Perri: I love about the design now with Robinhood is it's. You click on something and it's gonna tell you exactly what you're gonna see on the next page. It's Hey, just so you know, you are about to place an option. Options are risky, options. Have, X, Y, and Z in here. And when you get to the next page, this is what you're gonna experience.
[00:24:50] But don't worry don't place it. We'll tell you what's going on here. How do you make sure the design team and the product team are locked step in this. Think about embedding the knowledge in your product, rather than what you said, go into a separate training or going somewhere else and having to teach people how to do it.
[00:25:05] Dheerja Kaur: So part of this I think, is core company culture and structure. So we have a amazing content design team that is embedded with every single product team, and so content, the words like how we frame things, how we preview things to you, how we explain where you are in this journey or in this flow is just as important to us as the visuals and the UX. The like it's all one product experience. And I think, again, it sounds basic, but you'd be surprised, right? I think that part of product design is, or design is actually often underestimated, and especially when you're working in finance the words matter, jargon, lingo or not explaining it to people where they are is the difference between whether somebody converts into a product or not, it just is. Because it's a big, it's a big hurdle to cross, to sign up for a new account or deposit money into it or invest. And so I think a lot of it really actually boils down to just the way we approach designing products and how embedded content is into that.
[00:26:00] And kinda that earlier ethos that I was mentioning, which is really meet people where they are and figure out how you're gonna help them overcome each mini hurdle every step of the way in this flow.
[00:26:08] Melissa Perri: How do you like kick off, let's say designing a whole journey with that, with the teams? What do you encourage them to do? Is it, designers, product and content all kicking off at the same time? Is there a process or a flow for it to ideate? What? Walk me through how this all works so that you can think about the end-to-end journey.
[00:26:23] Dheerja Kaur: Yeah, for sure. What I will say is, I'm gonna give you a very, somewhat generic framework, but obviously it looks very different if you're going like full zero to one net new product versus kind of an improvement to let's say, like an onboarding flow, for example. But, it there's similar, structure.
[00:26:37] The way we think about it is, obviously it starts with what problem are we trying to solve? What is the landscape look like. So as an example of, hey, we wanna improve the onboarding flow for this product or for Robinhood overall that includes looking at the metrics, looking at any research insights that we have already, and understanding what are like the biggest gaps or opportunity areas for us to think about improving this product experience overall.
[00:26:58] And we'll, what I like about it is that all the functions are involved in even that process. It's not just pm going and talking to data, talking to research and putting it in a doc and then presenting it to everybody, so product and design, which includes product design and content design includes research, and we have Eng Leads it's come along for the, for that as well. Are just really ingrained in what is the problem we're trying to solve. Again, it's not just like an output doc that everybody reads, like they're we expect everybody to like really feel the problem, and feel that ownership. And then yeah, typically, we'll the team will kick off. Do a go wide brainstorming exploration. And the brainstorm, again, they teach, they like to involve everybody that, not just the kind of core UX functions that includes engineering, et cetera on, hey, what are the different ways we can solve this problem?
[00:27:42] Whether that's a really wacky, crazy idea to like, here are the, here are like four screens that really need some improvement, and then they'll, usually run some research either, we'll do some kind of like quick and dirty, throw up some flows, get some reactions, or we'll do some more in depth research. We'll do some employee, dog fooding too. And we'll, basically have the team narrow in and figure out, hey, here are the, either an experiment, roadmap, or here's the way that we want to design this. Let's go forth. But it's a very collaborative process from day one.
Balancing experimentation with ambitious goals
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[00:28:09] Melissa Perri: That's nice. I feel like sometimes when we see issues with something like let's say the onboarding or flow or whatever, people tend to narrow in really close to whatever is the one little tiny piece or the screen on the problem. Instead of thinking the whole end-to-end flow. How do you also, like planning wise, let's say give teams space to go bigger, right? Or to think about things end to end.
[00:28:29] Dheerja Kaur: Again, I think some of this comes down to the product culture of the company. We're very ambitious. We believe that there's often a very short term solve for something in the example of an onboarding flow, hey, you can go really narrow and say, Hey, let's improve, the content on this screen 'cause this is where the drop off is happening. But we also want people to have the space to think really big and say: Hey, what's like a step change function improvement to this, where, we might be hitting a local maxima, for example. Like how do we think really ambitiously and big and give people the room to experiment?
[00:28:57] And so generally I think, our culture is very much think ambitiously, set ambitious goals for the team and empower them to have a portfolio of bets to hit those goals. Whether that's small, short-term experimentation, bigger swings, like I, I generally expect teams to have, like I said, like a portfolio of, in their roadmap of how they're gonna approach this bigger higher order problem. I think when you're prescribing like a smaller problem space for people, that then leads to shorter term thinking and like local maxima. So again, if I could think of like a concrete example, let's take the onboarding flow example, hey, here's our kind of overall like install to, invest conversion. Obviously, I could say, Hey, we're seeing drop off on this specific part of the flow. Can you hone in on that? But you just give them a big ambitious, what would it look like to double that. And give them the space to think, oh shit, like a big swing could be warranted here.
[00:29:45] And then you push them to again have a mix of bets, right? Because you want like a combination of short-term experimentation and also like bigger swings and then it can, and then that ties into having a culture of learning and experimentation and potentially failure, right?
[00:29:58] Set the expectation for them that like, it's okay if you take a big swing and it fails. Like I wanna see more of that. I wanna see you learn and try stuff. And I think it's just a lot of that culture and context setting so that people are given the space to think big.
[00:30:11] Melissa Perri: When you're trying to balance like these bigger bets and swing for the fences type moments with stakeholder needs or things that are coming out. How are you balancing that and how are you communicating and, making space for your team with the other stakeholders?
[00:30:23] Dheerja Kaur: One is I think a lot of times, people don't do a great job of bringing along stakeholders for the full ride and thinking, and it's not that hard. So I think as an example, if I just told a stakeholder what I just told you, which is, Hey, there's a bigger problem we wanna solve here.
[00:30:37] We think it'll take a couple big swings to learn what could work, and then we'll also have some short term experimentation on kind of some of the more obvious stuff. And you should expect that some of these things won't work and that is an okay thing. We want the team to be trying and learning and failing. I think both people are on board with that. I think where it fails is when they're brought along in the pure execution phase, right? Where it's like, Hey, here are the next four experiments we're running. You good? Okay, cool. And then they're like, okay, but then why aren't we doing this?
[00:31:06] Or, have you thought about this? And then you kinda get into that like litigation a little bit, right? Where they're just like questioning the prioritization of a team and they're like I think you should do this. And it just becomes, again, every stakeholder's a little bit different, every function a little different. But generally I feel like that's like a general thing that happens and I think the sort of strategic alignment around: Hey, we want this team to think big. We have this big ambitious goal. We expect some of these things to fail. If you have ideas like we wanna hear them because you might have insights that we don't. But generally we wanna have a mix of things on the roadmap. That's a lot of my role. It's just making sure that context is set, so the team is set up to, to try and fail a little.
[00:31:41] Melissa Perri: What are your like methodologies or your practices for communicating with those stakeholders and then getting them aligned around where you wanna go or where you're uncovering for the product strategy?
[00:31:51] Dheerja Kaur: Tends to be in two formats. One is with the key stakeholders, either have recurring one-on-ones, or we actually have the teams meet with them to share their kinda strategy for the year, for the quarter, for a half, you know, depending on what the roadmap looks like. And ask for input. Again, like you, you'd be surprised, like sometimes people just wanna be heard, and you wanna debate them a little bit too. I think sometimes when stakeholders share what's happen on strategy, it's like a, people treat it as like a box to check, and I think.
[00:32:15] They can tell, they know that if your entire point of this meeting is to just one way, communicate my plan and, I'll pretend like I care about your opinions and insights, but really I'm not really taking them into account. We actually do expect our teams to really like, engage with stakeholders because they have very unique insights.
[00:32:32] I think a really good example of this is our CX team, right? Our agents, this is common at every company, but definitely here our agents have the best, most high fidelity feedback from our customers out of anybody at the company. And they're, and they bubble stuff up. And, sometimes if you don't, really take that seriously you're ignoring things that are like real problems on the ground in, in lieu of like a, some big strategy that you wanna accomplish. And so I think really engaging with stakeholders on their insights and explaining the prioritization, the why, and letting them debate a little, actually debating them is really important. And so I think that happens on a recurring basis, whether it's like monthly or quarterly or even weekly sometimes.
[00:33:07] And then on the ground we have a core cross-functional team beyond core product development, that is really like with the team every step of the way. Whether that's compliance partners, legal partners, CX partners, and similar to what I mentioned about the kind of the ownership mentality, we have that with those functions as well, right? They should feel ownership of the outcomes and the product and kind of the success of it. And I think that culture has really helped a lot.
Proving the business value of great design
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[00:33:32] Melissa Perri: The customer service thing that you said I think is so important. I find that in a lot of teams we are like locked off from the feedback coming through repeatedly from customer service or if you have a sales team, from your sales team. What do you do to keep those lines of communication open? And do you use any like tools or data streams to help people actually see on the product team what customers are saying in real time?
[00:33:52] Dheerja Kaur: For sure. A couple things. One is for a very long time we've had very strong reporting around what are the top kind of issues that customers see. And kinda the volumes and kinda week over week, what are the trends that we're seeing and that, we have reporting on that. That's the I'm pretty full fledged. What I also love and this is kudos to that team we have the concept of like leads that are paired with each product area, who are that bridge, and so they're on the ground with the agents, but they're also understanding the roadmap and the strategy, and they're like helping connect the dots, and that I think is really helpful, especially because it really bubbles up the big stuff.
[00:34:25] It helps push the team a little bit on the roadmap and then it gives them visibility to share out with the agents on what's coming up. And I think that role has been very helpful and critical.
[00:34:34] Melissa Perri: Cool. That's really neat. Yeah, that it's I feel like getting that data or that real time feedback either from customers or internal metrics, things like that sometimes is a struggle for product managers. So we covered like the customer research side. Are there any other things that you would recommend for product teams or like product leaders to set up for their product teams so they can keep on track of the data? What works for you?
[00:34:55] Dheerja Kaur: Another one that again, I think is pretty common is we leverage in-app surveys pretty frequently so that we have ongoing, research and insights on customers. And again, that doesn't work for everything. It's really good for flows, for example, right? Like understanding drop off or understanding why somebody did something. And really having like an ongoing pulse I think is really important. 'cause otherwise you're like really reliant on these kind of one time, or two time research moments to, carry you through and I think having a pulse on what are the trends, why are people doing things in the app? And all of that is a really good compliment to our classic research work.
[00:35:31] Melissa Perri: Nice. One thing I was gonna ask you about too, with the the design part of this that we were going back to. As like a product leader, I've heard some frustrations from like the design counterparts, right? Of how can I get my product leader to advocate for design or to go up and say, Hey, we need to actually do this. Especially when the team is maybe not as design focused as Robinhood is.
[00:35:53] You sound like you have an ethos at this company that's like design is critical to what we do. What's your advice for people who are trying to level up the importance of design in their organization and to sell it to maybe executives or a product leader who doesn't quite grasp design?
[00:36:07] Dheerja Kaur: Yeah, so I think where people tend to hit this issue the most, and don't worry, don't get me wrong, we hit that sometimes too, right? I wouldn't say we're, it's all perfect and all of that is very specifically, there's often this like delta between design that functionally solves the problem and a design that is elevated and and feels like an awesome experience, and sometimes those things are the same, which is great, and so you're just like a win-win. But sometimes there's just okay, did I check the box and solve the problem I'm supposed to solve and then we can like move on? Or am I committed to: what is the best version of this product experience? And I think that's often where you hear some of this frustration or tension because designers are like, Hey, I can, this can feel better, this can look better, this could be a better experience. But when a PM or the business looks at it, it's like hard to see, what the incremental value is of putting additional engineering work into upleveling, that experience.
[00:37:02] And I think, that is, that can be cultural, right? Because I think culturally you fundamentally have to believe as a company, not just your design team, but your whole company, that great, beautiful products do better for the business, have better outcomes and there is an incremental impact you have to believe it. And so I will acknowledge that, I think at a company like Robinhood, that has a very strong design ethos, there is a fundamental belief, and I think as a very specific example even when we do like growth work, which tends to be the most area that has a lot of this, right?
[00:37:29] Because growthy work tends to be smaller experimentation and it's very easy to just, move some stuff around and like true symmetric or something, but I think the way we approach it is, even growth work and any type of work should feel beautiful. It should feel elegant, should feel elevated, should be have like a high product quality bar.
[00:37:44] We talk a lot about our product quality bar, and that applies to anything, not just a zero to one product, but like an incremental improvement to a specific screen. And I think if you don't have that culture, then you're fighting that in each of these little examples. So to answer your question, the advice I would have is, pick one opportunity to prove it. Because I think we've seen it time and time again that a better product performs better. And if you can carve out an opportunity where, let's say you have a specific problem that you're trying to solve, maybe it's a smaller experiment where you have a little bit of room to play with the scope a little bit. You pick something small and again, there's often like the obvious solution and then you give the team a little bit of time to explore and ship it and see, because I think sometimes companies don't realize that these things also impact the business, creating beautiful products.
[00:38:30] And I think there's only so much you can get by with just arguing or explaining this I think sometimes like picking an opportunity to prove it, I'm pretty sure. The majority of the time that it'll perform better and do better. I think we've seen that too.
Embracing risk
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[00:38:43] Melissa Perri: I like it. Come with data, show them that I actually worked.
[00:38:45] Dheerja Kaur: Especially if your culture is very metrics oriented.
[00:38:47] Melissa Perri: Yeah. So Dheerja , it's been so good talking to you. I have one last question for you. When you reflect on your career and your past so far, what advice would you give to your younger self?
[00:38:58] Dheerja Kaur: Yeah. So I try to tell myself this and sometimes I listen, sometimes I don't. But it's like a way that I push myself and I definitely wish I told myself this earlier but I have this mantra that I have tried to keep telling myself, and sometimes it's still hard. And I definitely wish I had told myself that earlier on in my career, which is, everything you do, should have a 30 to 50% chance of failure. And I think the, it's super scary, right? Even just saying it makes you wanna throw up a little bit, because I'm like, wait, that's terrifying.
[00:39:24] I don't fail. I'm like the A student, who always, does well and gets good performance reviews and stuff. But I think for me especially there've been a lot of moments where, whether it's like early imposter syndrome or just like fear of failure just makes me super, super nervous to take a little bit of a leap, right?
[00:39:39] Whether that's a brand new project or challenge, like the redesign where I do nothing about design, or a new role like joining the Skim as an early stage startup from like an established company where I need something like that to really push myself to take that leap. And every time I've done it, I've been, it's been great because I've learned something's new.
[00:39:57] It's been like a huge step change for my career and my growth and my learning. But I think a lot of people who operate in this, kind of feeling of I don't wanna fail, I wanna keep being successful in my career tend to not push themselves as hard as they should.
[00:40:08] And I think having something that helps you keep challenging yourself is really important.
[00:40:12] Melissa Perri: I think that's great advice for people out there. Thank you so much, Dheerja, for being here. And if you if people wanna learn more about you or Robinhood or anything you're doing, where can they go?
[00:40:22] Dheerja Kaur: Yeah, so for me I am on LinkedIn, I'm on Twitter. I don't post as much on Twitter these days. Things are crazy. You can always find me in either those places. And then more importantly, we are hiring a ton at Robinhood. We actually have some awesome PM roles open, including on my team.
[00:40:36] Check out the Robinhood career site. We'd love to hear from you, and it's an awesome team and hopefully you got a little bit of insight into that from this podcast.
[00:40:43] Melissa Perri: I love that and I know a lot of people are looking out there, so make sure that you head to that careers page, and we'll put all of those links on our show notes at productthinkingpodcast.com. Thank you so much for listening to Product Thinking Podcast. We'll be back next week with another amazing guest.
[00:40:56] In the meantime, if you have any questions for me, go to dear melissa.com and I'll answer them on every single episode. Also, make sure that you like and subscribe so that you never miss another podcast episode, and we'll see you next time.