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- [00:00]
A
We're entering a world where roles and responsibilities are kind of up for grabs. So how can we as designers think strategically about our career?
- [00:10]
B
Some of the tactical skills of design that have been a moat for us for a long time no longer are. They're not differentiators.
- [00:16]
A
How can we create the type of impact that makes us irreplaceable?
- [00:21]
B
There are skills that designers are getting hired for right now, which are like visual design skills, high craft. But what they're getting promoted for is providing more value to the business, being really high roi.
- [00:33]
A
What skills will be the most sought after in the coming years?
- [00:36]
B
If you want to be more strategic, if you want to get promoted, if you want to drive value for organization and be seen as someone who is extremely valuable, that's what I teach.
- [00:47]
A
Welcome to Dive Club. My name is Rid. And this is where designers never stop learning. This week's episode with Ryan Scott is a deep dive into how designers can think more strategically about their career. He shares a ton of practical lessons learned from his time at Doordash and Airbnb. And we go deep into how you can make data a part of your practice as a designer, different ways to think about getting buy in for your ideas, and a lot more. But before we get into all of that, I wanted to get Ryan's MBA perspective on what the heck is happening in today's job market.
- [01:24]
B
So important for designers to have a good understanding of what, not just what is changing, we all feel that, but why it's changing. Because if we don't understand why, we can't really come up with a strategy on how to get ahead. And that's when we get exhausted, we burn out, or we just kind of start chasing trends. What happened during the pandemic is that everything shut down. We have to think about this as an economic function. So businesses respond and they change their strategy, which is why you're seeing adoption of AI, a lot of layoffs and people hiring very differently. And the job requirements, like the job market is so bizarre right now in terms of companies wanting, like a very specific person with a very specific background for every hire to the point where they're probably like filtering out really qualified people because they have this really specific need for something they have in mind. So we're seeing all these things. And I saw this quote on LinkedIn from a design leader who said, honestly, no one knows what's going on in the current market. And I think that perfectly encapsulates how designers are feeling right now, which is like, what the heck is going on we're seeing all these signals, but we're having a difficult time contextualizing them. And when we have a difficult time contextualizing them, then it makes it very difficult to have a strategy on how to get ahead in that environment. And then we burn out because we're just trying so many different things and everything is changing so rapidly that we're just ping ponging back and forth between, well, I think I need to learn AI and this job wanted this specific thing, so maybe I should go do that. And I hope I don't get laid off. And. And it's exhausting, to be honest.
- [02:53]
A
Real quick message and then we can jump back into it. AI is making it a lot easier to contribute to the in flight code base. So I'm knocking out polish tickets all the time. And now AI agents inside of Raycast make that easier than ever. Like, let's say that I see something that I want to fix in a single hotkey. I can launch a cursor background agent, add a screenshot or any context that's needed, and then manage the entire process directly inside of Raycast. You can ship code as quickly as it would take you to type up a new issue in linear. It's a big deal for designers and you can start using it today. Just head to Dive Club Raycast. All right, here's the thing. You don't need another dashboard. What you need to do is to talk to customers. So I want to introduce you to genway AI. You can think of it kind of like Vibe researching. To validate your ideas quickly. Just draft your questions, select an icp and then their AI agent runs interviews on your behalf by pulling from a panel of global participants. You could literally set it up in the morning and get actionable insights by lunchtime. It's validation at your fingertips and you can try it out free for 14 days. Just head to dive.club/genway to get started. That's G, E, N W A Y. Okay, now on to the episode. There's so much demand. Like the job market is actually exploding, but for a like singular slice. And then you go on. And then there's people who are talking about how they haven't been able to get an interview for like eight months. And it's so weird to see the combination of that. Like, what's happening there? You think, you know, like, I'm like, let's try to make sense of it for a second.
- [04:39]
B
Yeah, I just was having this conversation with a designer this morning who's applying to Jobs and the Way I kind of articulated is it's not. She was saying, I think there's too much competition. I don't think there's too much competition. I don't think that you're getting beat out by a bunch of other people who are more qualified than you are. I think what's happening to a lot of designers is that the, the bar change, the standard, what companies are doing is they've defined something so narrow that they want. They're only willing to hire that one person with that one specific profile that that standard has shifted. It's not a competition problem. It's a do you meet this specific puzzle piece problem that most people actually don't. And the way I describe it is a lot of companies are just over right now where they might say, we want you to be in this industry for exactly this many years. I saw a design leader on LinkedIn say that they got rejected for a job because they had managed five direct reports and this job required they had experience with six. Like really finite level of detail here, which they're over filtering. Right. They're going to lose out a ton of candidates because they're so narrowly focused. And so I think that's why you see this specific Persona of designer is in high demand and everyone else is kind of left trying to figure out what to do. I think that comes down to the company having a specific strategy in mind and maybe not knowing how to execute that strategy very effectively. And a lot of it has to do with kind of macroeconomic environment, how businesses respond and then how hiring managers have to respond to that.
- [06:07]
A
Let's talk to the person who is feeling the pain of this a little bit. Maybe they aren't having as much success getting interviews. They feel the fact that they're being screened out prematurely. How do you even think as a designer right now about repositioning yourself and the right knobs to turn, what changes to make, what to experiment with? Like, do you have any thoughts on how the individual designer can react to the changes that some of these macroeconomic pressures are bringing on?
- [06:34]
B
The problem that I see for a lot of designers are two things. One, they're not selling the right thing anymore, and then they're also not selling to the right people anymore. Hang Shu just posted on LinkedIn a couple days ago survey a poll and said who's most responsible for driving these changing hiring trends in design. And about 50% of people responded that the design leaders themselves, the hiring managers themselves are responsible for these changes. I think that's not the case. The Design managers often don't have budget control. They're not the final approver. They're the person that has to take that candidate and then pitch that candidate to someone else. And it's typically a product leader. And product leaders care about completely different things. I also saw someone mentioned that they had been approved by the design hiring manager, and then the PM said, nah, and they lost the opportunity. So I think that designers are still thinking of, I need to get this design manager to hire me, when really that manager doesn't have the final say. And so what we need to be thinking about is instead of trying to pitch that designer on why to hire us, we should be thinking about how do we pitch ourselves to the business? How do we talk about the impact that we're going to have? Hiring is one of the most expensive investments that a company can make, and we need to think about it that way. We need to think about it as, this is an investment, and they want to know, if I'm going to put 150, $200,000 or more behind this person, what am I going to get for that? And so that's the story we really need to tell. Instead of, I make these pretty things or whatever argument we're trying to make, look at the craft, look at the delight I'm creating. We need to talk about hard numbers. And, you know, this is how I'm shaping behavior. This is how the money is going to come out, how the metrics are going to move as a result, because the design manager cares about those things, but the pm, the product leader, who probably has the final say, really cares about those things. So we need to be selling the right thing, that impact, and we need to be thinking about who the ultimate approver is. And it might not be the designer we think it is.
- [08:30]
A
Can we go a little bit deeper there and talk about some of the ways that the messaging might change depending on who you're speaking to? Like, if I understand that I'm trying to sell myself to the business, what are some of the words or phrases or positioning mechanics that I would be using that maybe it would be easy to miss if I was speaking just to the design manager? Yeah.
- [08:50]
B
So when designers are speaking to other designers, we kind of have like a shorthand, and it's okay for us to do this. We think about, oh, I did XYZ feature, I reduced cognitive load, I changed the friction in this flow. And other designers understand that, typically product leaders or business leaders, there's a bit of a gap, there's a miscommunication. There's something that gets lost in translation there. We're not saying the impact that this creates. And you see this in portfolios all the time. People will typically label their portfolio projects as, you know, XYZ project for Y company, redesign of booking for Airbnb. It doesn't mention what actually came out of that project, why it was worth doing, how much money it created, whether it moved, metrics, you know, what design work happened, but not what business impact was created. And so one of the things I really talk to designers about and train them on is to not just say, I did XYZ work and hope and pray that someone on the other end of that conversation understands that that is impactful. You have to really try to bring it back into their world, use their language and say, this work drove this metric in this direction. Be much more specific, because that's ultimately what that person who's making that final decision really cares about.
- [10:03]
A
Okay, then I'm going to be the voice of the person who's listening, who has worked at a mid tier agency for the last three years, and the nature of the work means that they'll take on this complex project in a various industry, but then they're kind of handing it off and they don't always get the nice dashboards and cohort retention over the next six months. And they feel at a loss when it comes to being able to wield data as a part of their own personal story. Any thoughts for that person?
- [10:33]
B
Data and metrics are only one type of business value and designers kind of get put in this box. We kind of get trained to think this way because we work so closely with PMs and we often report up to product teams. So we care about the metrics and we should be thinking about those things. They are really tangible. People are gold on them. So their careers and their career trajectory is really dependent upon hitting those metrics. So that's a really important place to start. But not every project has all the metrics. You need to tell that story. Not every project can be measured with certain metrics. You. So it's important to zoom out and think about what other types of business value are created. There were projects that I worked on where we just repositioned ourselves against the competition. Maybe we made our team internally more efficient or increased the velocity or the quality. We reduced the bugs that were being created as a result of work that we were doing, maybe just change the culture and we started to work better as a team and have a greater sense of ownership. Those are all things that a CEO really cares about. And when you go to business school, they train you to think about everything as holistically as possible. Business school is not here's what metrics matter. It's here's how to think about the holistic health of the business. And so the metrics have to be in the right place. The culture has to be good. You have to be hiring the right way. You need to be positioned against the competition, you need to be gaining market share. You need to have good, like, brand awareness with consumers, and you need to have a good kind of brand reputation with consumers. All of those things matter. And every project might have bits and pieces, might be moving the needle across the board for any of those things. So maybe you don't have the perfect metric, and that's really common if it's not being measured, or the data science team or the PMs won't give it to you, or you left the company years ago and you just don't have access to it anymore. Super common for that to be the case. In that case, look at did the company launch it? Then it's probably producing value for them. Even if I don't have the numbers, I can say, look, we know this is producing value because they launched it and it's been a couple years and it's still driving value for them. So we know it's directionally doing the right thing. Then you think about, you know, what was the purpose of the project? Was it just to hit a metric or was it for something else? So many projects are about just neutralizing some competitor's advantage. If that was the purpose of the project or that was something the project did, even if you don't have the metric, you can say, like, one of the projects I worked on was launching food photography at Doordash. That absolutely moved product metrics. But Doordash was the only company that didn't have food photography. Everyone else did. And so when Uber Eats launched, from day one, they had beautiful food photography. We were kind of like, I guess we should probably do this too. So, yeah. Did it move metrics? Absolutely. And it moved metrics in a really significant way. But that's not the only way to tell that story. The other way to say is like, look, Uber Eats launched. We had to respond. They have this thing we're trying to sign national deals with McDonald's and McDonald's on, you know, we're on these corporate calls with McDonald's, McDonald's saying, why don't you guys have photos? We spend millions of dollars on photography. Why can't you help us? We have an answer for that. And so did it move metrics? Sure. Did it also accomplish other things for the business? Absolutely. And so you tell the best story you can with the evidence you have at hand, and that should really help mitigate if you don't have all the perfect numbers.
- [13:43]
A
I love that reframing because it definitely feels in a lot of the dialogue that I see that it's metrics. Check yes, check no. And you're basically saying no. We're just telling a story that is going to be compelling to somebody that is using a business lens to evaluate me as an investment from which statistical evidence is one way that you can say something that is compelling and moves the needle. So definitely makes a lot of sense. And even for myself, I'm like kind of reflecting back on some of my old projects. Like, huh, how would I spin that in a way where it doesn't feel like just a label, but I'm telling it in as if I'm almost writing it to the executive or the PM that would be evaluating my case and.
- [14:23]
B
What I see in interviews, and I've done this before, I kind of. My approach for telling about the results of my work is I call it shock and awe. I want to talk about so many different things that the project produce, so many different types of value or impact that it really kind of takes the pressure off, all the numbers being exactly right or all the numbers being impressive in some way. So I'm going to mention metrics for sure, but I'm also going to talk. Talk about the way the team learned to operate differently and more efficiently, how that unlocked future strategic value, how it moved us competitively. I'm going to mention every one of those things almost on their own slide in an interview. And the impression after doing that, it's like, yeah, this project did this and this and this and this. In addition to hitting some metrics too, the impression is that's amazing. Like, we want that value here too. We want retention and we want conversion and we also want to work better and we want to have more ownership and we want all those things as a product leader or a business leader, we want all of those things producing like. Or they're talking about the results of our work in that way has a huge impact in people understanding our value. As long as we're zooming out and thinking holistically like a business leader would.
- [15:32]
A
Okay, so we've been talking about this idea of positioning, and I want to transition into a Little bit more like personal skill investment, because I think a lot of people are feeling the need, especially given the macro uncertainty that we were kind of touching on earlier. And I want to just read a line that you brought up when we were talking before we hit record where you said the only designers in trouble are the ones that are standing still. So where do we move from here? Like a designer who feels the reality of the moment. How should we even think about future proofing ourselves so that we can continue to earn a living as a professional UX designer in the years to come?
- [16:13]
B
Yeah, I really see there being two paths. If you go to business school, you might study strategy and game theory, and I think those create a good roadmap for us to move forward and think about our design career as really strategic. What is happening with AI is that it's really rapidly collapsing all these roles onto each other. So designers can do more PME type work, we can vibe code and do engineering work. All those people can also do our work. They can go into magic patterns and they can create some mock ups really quickly. So we all have more overlap with each other. We need to think about ourselves as really valuable partners. And I want to think about my relationship with PMs and engineers as a true partnership. But we're also competing for resources, which function is going to be invested in, who's going to get promoted, who gets more headcount. There's always a little bit of tension there and that's really worth acknowledging. So I don't want to say that, hey, we're competing with these people because we're partners, but we are in some ways. If we study game theory, we're thinking about different companies. How does one company position itself in the marketplace and then how do we respond? And it's about playing out all the steps that are going to happen. So if we have PMs and engineers moving towards design, they're starting to use these AI tools. Some of the tactical skills of design that have been a moat for us for a long time, no longer are. They're not differentiators. I don't need to have a deep understanding of Photoshop necessarily to get in there and make the thing I want. So we can't claim that anymore. So if they're moving towards us, the answer is we need to move towards them. You see this in businesses all the time, where Airbnb has home sharing and booking.com has hotels and then eventually, eventually booking.com's like, we should have some home sharing. And Airbnb is Like, we should have some hotels, as they start to compete, they start to become more similar to each other, to kind of neutralize each other and get a little bit of bites of each other's market share. We're seeing the same thing happen with designers and PMs and engineers right now. So if PMs and engineers are coming for a little bit of our market share, we should do the same thing and we should respond in the same way. How designers are predominantly thinking about that right now is things like vibe coding, all these AI tools to do more technical engineering work. And I think that is really valuable. That is one path that is us becoming more like an engineer and knowing how to ship things on our own, knowing how to get into the code base and change the button color, change the quarter radius, the things that we had to, like, beg resources for before. Now we're just empowered to go in there and make it work. And I think that's great for everyone. Right? The engineer did not become an engineer so they could work with the designer to make sure every tiny little pixel is perfect. It's not necessarily what excites them about their job, but it is what excites us about our job. Now we can go in there and we can make things the way we want. That's really powerful. The side that I see missing is designers being equally or more excited about being able to do the more strategic work. So if PMs are moving towards designers, we need to move towards engineers. We also need to move towards PMs and neutralize that a little bit. So we need to start thinking about ourselves as driving this business impact, and being equally responsible for that makes total sense to me.
- [19:22]
A
I think that part of the reason a lot of the discussion has been, at least from my vantage point, quite technical, is there's almost a clarity when this other path is buoyed by specific tools and tactics and workflows that you can learn. If I can use this tool, then I can create value down this path. Whereas when you kind of stand at the fork of the road and look down the product path, it's a little bit murkier and a little bit more uncertain what it looks like to actually grow in that direction. So maybe we could talk a little bit about how designers should even think about charting that path down the product lane.
- [20:01]
B
Yeah. I think the first place to start is that designers have a lot of these skills already, and I don't think we give ourselves credit for that. There are things like kind of our customer first thinking. Right. How business Value is created is by solving a problem for the customer, and then you see the metrics be impacted. Sometimes companies will want to start with business metrics first, and they'll say, well, if we start selling customer data, we'll make a lot of money. That typically doesn't end up being very sustainable or create some kind of conflict later on. One thing I loved about working at Airbnb was that we always knew that if we create customer value first, then the business metrics are going to take care of themselves. That's how designers think, and that's a great way to think. So we've already got this foot in the right direction. We're also really strong about systems thinking. So we understand that sometimes some of the tools that we have at our disposal, like ab testing, are great in some instances and not great in other instances. We know that. How would you AB test a design system? Design systems. It's a system. You can't pick it apart. It all works together to create value. So designers have a really good understanding of that system's impact. And we also think really holistically and a little bit further ahead, perhaps, than our roadmaps. And I think that's great. That's what C suite executives do. If you're a C suite executive, you have to have that holistic perspective on the entire business, and you have to be thinking ahead about what comes next, what comes beyond. I saw Andy Budd give a talk a few months ago in Berlin, and he mentioned how designers are like chess players, always thinking a few steps ahead. And PMs and product teams are often like poker players. They're wanting to just maximize the number of hands they play because statistically, it works out in their benefit. If you fold a bad hand and you move on to the next hand, that's how you're going to ultimately win. I think that's a great metaphor for the difference between designers and product managers. But I also think that C suite executives are chess players, not just poker players. And so there's this really nice relationship and similarity between how designers think and actually how C suite executives think. So I think we have a lot of things going for us already that if we acknowledge that, the whole idea of moving in that direction becomes a little less intimidating.
- [22:17]
A
Before we get into, like, the specific skills that exist in these buckets that you've kind of laid out, I'm sure somebody's listening. That's like, well, I have a PM already, you know, and is this complicating things? If I start moving in that Direction. What does effective collaboration even look like in a world where people are kind of infringing on each other's territory? And maybe the PM is spinning up lovable and making a quick prototype?
- [22:43]
B
Yeah, I think that is an ongoing negotiation, and it's going to depend a lot on who the person is and what the company culture is like. I was just speaking to a VP of design who's been working in Builder IO and working with the engineers, and the engineers have helped set up Builder IO for the designers. But there was also this conversation that needed to happen about, well, who does what now? If we're going to empower you to take things on your own, what does that mean? I think that's a really valuable conversation. I think everyone can win out of that. What do engineers want, not want to do, that we do want to do? Can we take over some of those things? Maybe there's things that the PM doesn't like doing that the designer really cares about. And so you can start there. You can also start with, what do you need to be successful? What metrics are you trying to hit? What's going to get you promoted? What's going to get you recognized? What I do is try to say the things that I can bring to the table are going to help you as a product person in these ways. I'm not trying to take your scope, I'm not trying to reduce your footprint or reduce your influence. I'm trying to get us to all win together. And if I can take something off your plate that you don't want to do or I'm really excited about or can handle, then that's great. If you need support in some way, I have some skills to support you in those ways as well. So I think those conversations are delicate, but we're all having them. The same conversation goes for designers. Like, they can go in and vibe, code something or use magic patterns to spin up some mocks. Okay, maybe we actually want that. Maybe it's great for some of the lower tactical types of things for other teams to take them over. And we are advisors on those projects and say, like, the engineers move forward with this, that's totally fine. We checked the box and said, looks great. Go ahead and ship it. And we can focus on larger, more strategic projects because other people are empowered to do the little things themselves. So I think that that could be true in all directions. And if we approach the conversation that way, it's important to acknowledge that people across the spectrum are probably feeling a little insecure right now. Everything's changing and we're all having to renegotiate everything. But there is a future where we've all now had the chance to reorient our roles in a way that fits better for all of us. So I think that's a good place to start.
- [24:55]
A
I've been designing products every day for the last 15 years, but. But in the last six months, everything has changed. With AI in the mix, I'm cranking out ideas faster than ever. But none of that matters if I can't get the feedback that I need to get the team aligned. And right now getting async feedback still kinda sucks. So I'm building the product I've always wanted and it's called Inflight. I use it every day to share ideas and get feedback from the team and it's totally changing the way that I work. So I'm excited to show you. Right now I'm only giving access to Dive Club listeners, so head to Dive Club slash Inflight to claim your spot. And we're kind of figuring out where the new lines are getting drawn. Even leaning into a new era of my relationship with my technical co founder right now, like, I got pretty comfortable jumping in and doing a lot of the front end polish. And you know, I get this text message, wow, you know, that was so helpful. Thank you. And then one day I'm like, okay, I'll do a little bit more. And I, you know, shipped the PR and then got the next test message and it was like, hey man, never again. Like, never again do this. Like, this is way over that line. Yeah, we found the line. Everybody's kind of got to find the line again.
- [26:07]
B
Yeah. And I think that it's good to set expectations that it's going to be a little bit of trial and error. And again, it comes down to that person's personal preference. It comes down to the culture of the organization as a whole and what the tolerance is for this. But I see a lot of companies kind of mandating the use of AI and the problem with those mandates is they're not very specific, doesn't say what tool or how. And it also doesn't acknowledge the fact that we're going to have to change the way we all work with each other and draw those lines. And there's going to be some pain in that process. I do think there are better things beyond that process for all of us. It's going to be worth that, but that doesn't mean it's going to be easy getting there right away. And so I would Say, be experimental about this, right? Push and try some things, see what feels right, see where you get some pushback. Then say, okay, that's where the line is. That's fine. Let's agree that this is how we'll operate, you know, in this new world. And you'll take care of this and I'll take care of that. And maybe project by project it changes. But it's worth having that conversation maybe a little more literally, really stopping and taking a moment to say, okay, how do we want to approach this right now? Because all of our pathways of working are kind of being remixed at the moment and it's all back on the table. So it's worth being really conscious of it, asking the question out loud, having the conversation in a really literal way. And then we'll find kind of a new normal, all of us together. But it is going to take some time.
- [27:27]
A
Okay, so I want to get specific about some of these more PME skills and ways that designers can invest and can pursue that path that we kind of laid out earlier. And maybe we could start to use your metaphor again of playing chess. I really like that. And I'd like to know what the traits of great chess playing designers even look like. Not only to be able to see a little bit further into the future, but given an array of opportunities, how do you know which ones are actually worth pursuing and putting your name behind?
- [28:03]
B
One of the best things designers can do, and this typically falls to product teams, but I don't think there's any reason designers can't do this as well, is to find new opportunities for your business. That is something that I have kind of specialized in and I've always considered myself a hybrid designer, PM type person. I identify as a designer, but I realize it's not really accurate. One of the things that I have always enjoyed doing is going and finding new opportunities for the business. And I didn't understand in the past why it's like, no, that's not your lane. Don't find new value for us. There are skills that designers are getting hired for right now, which are like visual design skills, high craft. But what they're getting promoted for is providing more value to the business, being really high roi. If you want to be part of the strategic conversation, I think we need to be comfortable being willing to start and then drive that conversation. So a good example, finding new opportunities. There's a lot of ways to do that. One thing that designers do is we kind of over index on user research. That's our primary tool. And engineers and PMs, they want to ab test everything and we're both kind of stuck in these camps. But there are so many other ways to uncover new opportunities that are going to also provide a lot of evidence that something is worth doing. So you can do some competitive analysis. You can look at the market, you can see what competitors are doing and not just the product, not just what the competitor is building, not just the pixels or the features or the scope, but also how are they positioning themselves, how are they pricing their product? Think really holistically about what it is you're seeing in the market and how they're. They're operating. I started working at DoorDash when it was like 50 people. And I reported to a co founder there were four designers, eight engineers, and no PMs at all. And so it just fell on us to kind of figure out what to do. One of the things I noticed was that from a design perspective, from an empathy perspective, when I was the design lead on the Dasher product, I really wanted Dashers to get paid faster. Oftentimes drivers have a little less financial security. That's why they're on a platform like DoorDash. But we were only paying them once a week. And so we would say, hey, there's a rush right now. You need to get off your couch and go do the lunch rush. We'll pay you in six days. And it's not a very compelling argument. You're not going to drive a lot of behavior like that. And so I realized, like, from an empathy design perspective, what I wanted to do is say, hey, these people need this money. Let's do that for them. Let's help them. That wasn't a very compelling argument just by itself. So I analyzed what competitors were doing and realized that this once a week pay structure was the least flexible system on the market. If you were driving for Uber or Lyft, you could get paid instantly. If you were driving for Amazon, it was like rolling every three days. You'd get paid. We were making people wait the longest, so we were the least effective from a competitive standpoint. And then I just posted a survey onto a Facebook group and said, would you use this if we launched it? And a bunch of people raised their hand and said they would. So I started with user research as there's maybe something here, but I was also able to move beyond that and say, and there's competitive value here. We're going to neutralize a lot of the competitors, we're going to get ahead, we're going to Stay really relevant and there's customer demand. All of those things really matter.
- [31:20]
A
Okay, I'm going to paint a hypothetical scenario here, because what you're describing is you kind of have the voice of leadership in that world, but maybe there's somebody listening who perhaps they work at a larger company where there's at least one level of separation between the true decision makers. And maybe they actually haven't cemented themselves as this opportunity spotter and they're inspired by this episode. They kind of want to try to do it for the first time. They have something. Maybe they've even went out and done the research and they've put together what the story, what the angle is. It's going to be a very specific question, but how do you then think about strategically introducing that? At what levels, in what format? That's a black box of its own. So could we speak to a person in that situation for a second?
- [32:08]
B
There are right ways and wrong ways to do this, and I've done them both. The ways that I found is the wrong way is to skip a bunch of levels. I've literally just gone to the CEO of a company and said, here's my idea, I think we should do this. And I got buy in. And that person said, yeah, go take us to the teams. And then I took it to teams and said, CEO said, we should do this, we should do this. And ended up pissing off a lot of people because I didn't include them in that process. So that would be the wrong way to approach it. Even if you have great evidence. You know, great evidence is about user research, but it's also about all these other things. And if you can bundle them all together, you've got a really compelling argument. But if you just take it to the CEO and use that to strong arm everyone, they're not going to be very happy and you're going to lose credibility as a designer. I have done that. Do not make that mistake. A better way to approach it is to more casually introduce ideas. I think designers think about our work in terms of either low fidelity or high fidelity. And you're seeing this strong push for jumping to high fidelity right now as quickly as possible. Because we can just prototype everything so fast and it's so cheap and easy to do that. Where PM's Excel is in no fidelity. It's just the idea. What do you think about this? What do you think about that? You have to be sensitive to how you approach this conversation depending on the culture of your environment. If you're in a really accepting, open, warm culture where people want to collaborate. It's easy to put yourself out there if you're in a really competitive environment where people are, like, competing for resources and butting heads a lot and holding grudges. You have to be really careful about how you propose your ideas. What works really well in both environments is to say, hey, guys, what do you think about XYZ things? And you might not have everyone in the room think that's the best idea. But what you need are just a few people, these kind of early adopters for our idea that we're bringing to the market, bringing to our company. And if we've got a couple people who are like, yes, and type people who are. How might we type people? Those are the people we want to start with because they'll help us bring this to fruition. They'll help us bring it to life. They'll kick the tires a little bit with us in a collaborative sort of way. Not everyone's going to be on board right away. They're going to want to see some traction and see some evidence, and that's okay. We can build that progressively over time. So what's worked really well for me is to say, hey, I'm seeing this opportunity. Here's a bunch of evidence. I've got user research, I've got some product data. We've done past experiments that say something along these lines as well. I'm looking at the competitive landscape and other companies are doing it. We should probably pay attention to this. Put that out in a meeting, see who responds. Go develop relationships with the people who are potentially interested in that. Start with that smaller and safer group and then bring it to people and say, look, we've kicked the tires on this. There's really something here. Let us show you the evidence and kind of bring that to larger and larger and larger groups. That's worked really well for me as a way to carefully bring my ideas to market in a way that is inoffensive but also really effective.
- [34:56]
A
Returning to our kind of metaphorical PME path that we're talking about, what are some of the other skills that exist that you think are kind of top of the list, that designers who are interested in growing in this area could start to not only adopt, but actually grow the muscle and think about ways that they can bring more of this to the table in their org?
- [35:15]
B
Two other areas I think are really important are prioritization and metrics. And those are two things that can be challenging for users. We're not trained in either of those things. If you went to art school like I did, or you went to a boot camp, you're learning about the tactical aspects of design, but you're not trained on those types of business thinking. The first thing I'll say about prioritization is that I've been so guilty of this. I will do some user research, and a user will say, I want this. And I'll go to the team and say, user says they want this. We should do this right away. The answer is almost always no. And I, for a long time, felt like PMs just existed to tell designers no. And what I realized when I went to business school was that there are so many variables that go into making these decisions. The joke in business school, especially the first year, was that the correct answer to every question is, it depends. And that's what they train you to do. They train you to look at every possible variable and think about, well, yeah, that might be the right idea, but is now the right time for that right idea? Maybe not. It depends on a bunch of different variables. One thing that can feel unintuitive when it comes to prioritization for designers are some of these existing product frameworks. So things like rice reach impact, confidence, and effort. And you kind of use that to calculate what's the value of a project. Now, I don't know about you, but outside of work, I have never used rice as a prioritization framework to make any other decision in my life. It's something that's really specific to the work, but then as soon as you leave the office, you never think about it again. A more intuitive way for me to think about prioritization as a designer is a relationship between value, cost, and risk. And what's great about this is humans evaluate value, cost, and risk in every decision that we make, from what car to buy, who to marry, where to live, what to eat for lunch. We're always thinking about, is this going to be worth it? And is there any risk that I'm taking on by making this decision of where to live or what car to buy? You can actually evaluate projects that same way. And it's useful because when we talk about rice and we think about impact, often that gets boiled down to a single metric. Impact equals conversion. Okay? That's what we're gold on. That's what the business needs from us right now. But let's not joke ourselves that that's the only form of business value that's being created by this project. There are so many other things that we need to acknowledge that competitive positioning, the strategic opportunities that are unlocked by this project, does it impact our overall brand awareness or overall brand reputation? Those are all forms of value that we should consider across every project if we're going to compare apples to apples. The problem with value is that it is so intangible. Feeling a lot of this is just estimation. And so what's useful is if you can come up with a bunch of different ideas on the value this project creates, we can have a more holistic conversation about it. The thing about cost, if we're thinking about value, cost and risk being the three things that drive all decision making, cost is super tangible. Engineers will just say, I think that will take 20 hours, and you know exactly how much money it's going to cost you. I think engineering effort is one form of cost. You also need to think about other forms of costs in terms of, like, organizational costs. Do we need to get legal involved? Does marketing need to be involved? How complex is this? All of those things factor into cost. Now, cost is tangible and so it can dominate the conversation. But there are really tactical things we can do to mitigate cost in any project. We can ship an mvp. We can ship just a pilot. We can do a little bit less in scope. There are levers we can absolutely pull to make it acceptable. If cost is dominating the conversation, we should talk about reducing costs where we can and upplaying how much value is created. The last thing designers can think about is risk. And I love this for designers because risk is a really human psychological factor that drives all of our decision making. It's kind of the fight or flight that occurs when I do the mental math on anything that's proposed. So what do I think this is going to do? How much do I think it's going to cost? And am I exposing myself in this project, or is the business exposing itself? Do we have the right team in place? Is the morale good enough to handle this project? Is the project too complex? Do we have enough time? Maybe there's some external risks, like, are we going to trigger any type of legal repercussions from this project? And so risk is something that's worth thinking about. And if you acknowledge that those three things exist, you can pull on those levers to push people towards the direction you want. So you can say we should do this project because the value is really high and there is some risk, but we can mitigate it this way and there are some costs and we can mitigate it in that way. You can also use it in the opposite direction, you can say, if we don't do this, we're leaving a lot of value off the table. We're potentially increasing a lot of risks by letting this debt just compile forever, then risks are increasing. At Airbnb, I use this really effectively once. The last large redesign that I let was of the entire host calendar. And this is how all hosts on Airbnb open all their nights and settle their prices, which, if you think about it, is the foundation for all of Airbnb supply and all of its revenue. So huge, huge pressure.
- [40:27]
A
The fundamental unit economics are at stake.
- [40:29]
B
Don't mess it up. Another, like, high risk project that I led at Airbnb, and literally I was talking to the CTO of homes and presented a few different options. And one of the options was, if we go down this route, like Brian's brand, probably want to get really involved and have a lot of opinions on this direction because it's really different and really kind of shocking. And so we decided that maybe we didn't want to open that can of worms. That wasn't the thing we wanted to do because it would increase cost of the project, it would increase risk of the project. We were going to do something a little more in this direction. So you can use value and cost and risk as a way to move people towards an idea or emphasize what's being left if we don't pursue an idea. But it is far more intuitive for designers because that's how all humans make all decisions anyway. It's not a really PME type framework. You have to memorize. You can think about it at a human level. And designers really excel when we think about things on human levels.
- [41:21]
A
I like the Brian example a lot because I actually do think some of these calculations are becoming a little bit murky because in past years, for me, the dominant anchor of these discussions is engineering effort, which is something that you were alluding to. It's so easy to understand the cost of something as a function of time. But now we're entering this world where it's like, goodness, you can make really significant changes to the software element of a product in days, not weeks or months. That changes the discussion a little bit. You know, you can. You almost sit from this vantage point of we can do anything. You know, in three months, we can do anything. So now how do we think about sequencing and the right levers to pull and risk kind of changes? You know, I spend my time thinking more about the potential for bloat and complexity than, gosh, we only have this many man Hours to allocate. What is the best way to use them? You know, it's really kind of changing. Even in the last six months, I've started to feel it.
- [42:16]
B
Absolutely. I created this framework as a way to understand the complexity of the interactions between all of these different levers. Right. If you reduce cost and you say we can ship so much more, so much faster, you may or may not be producing value. You might just be shipping a lot of stuff.
- [42:33]
A
And so you might be going backwards.
- [42:35]
B
You might be going backwards. You might need to think about value more holistically, realistically, and say, cool, we can do anything. Should we do everything? Probably not. So we should think about how does the value lever change in our perspective on value? If cost is dramatically reduced, like everything at the grocery store is super cheap, does that mean you should buy and eat it all? Probably not. Some of those things aren't as healthy for you. I think there's also that kind of risk lever. If cost goes down and you can do everything, does that increase the risk of. Now everyone's just doing everything all the time, and there's not. We've lost some organization, we've lost some stringency in how we decide what to do. And so it can be beneficial. But you have to balance all of these things against each other. And so I think that framework creates a really nice visualization of, yeah, cost might have gone down, but maybe that correspondingly increases risk. One thing you'll see is sometimes a really great other way of looking at this is you have to invest a sufficient amount to get value. And this is where designers really struggle with MVPs, is if you don't actually meet a need or solve a problem for someone because you're under investing in the solution, then you didn't check the box for them and no value is created. So you can't just reduce cost to nothing and think you'll still get value. There's a, there's a line where cost has been reduced too much, it's too sub mvp and then value just plummets as a result. And so I think sometimes teams think about like, oh, we get all this value and if we just reduce cost, then that all that value is preserved. Not always the case. And so it's worth thinking about those three levers. And they do influence each other. If cost goes down, maybe that impacts value, maybe that impacts risk.
- [44:15]
A
So the other thing that you mentioned outside of the sequencing piece was more of the data analytics getting into the numbers. And I know that comes more naturally for you a Lot of designers, frankly, don't spend any time in postdoc or metabase or wherever this is living. Maybe they have access, but it's not part of their practice. So I kind of want to take this in two pieces, if that's cool. Maybe first we could talk about easier on ramps. For someone who is not considering this a regular part of their practice, they're completely reliant on the PM for access to data, even. How do you get started? And then maybe we can jump into some slightly more advanced use cases from there.
- [44:58]
B
The right place for designers to start if they want to get involved in metrics is actually not just opening a tool and trying to find a dashboard and jumping right, right in. A couple things have to happen first if you're going to get there eventually. That's like step number three. The first step is if the product team or executives or data science has these numbers, are they willing to share them with you or not? Sometimes you just need to ask and they will provide access. And if you're in that type of environment and people are collaborative, they might help, you know, coach you on it, walk you through, explain it to you. They might not want to share those things with you, in which case this isn't a tooling problem, it's a relationship problem. And so we need to get to that point of why does that person not feel like they want to share this with me? Is it because they don't think designers should have an opinion on that? Maybe. Oftentimes it's because they don't want designers kind of taking control or having more power, having more influence and being empowered in that way. So that's where starting with that relationship and if someone's pushing back, start to understand what might their incentives be? Maybe they feel a little insecure about their position at the company. Maybe if designers start talking about metric, they feel like they're losing some control. If we start to understand where they're really coming from, then we can work on our relationship where we are seen as someone who's going to help them with their goals, not take away from their goals. We're not going to go rogue and start advocating for all these things. And they're going to lose control of the narrative or they're going to lose control of the roadmap in some way. We're here to compliment them and support them and find opportunities and bring those opportunities to them. If someone's feeling really insecure, I'm just going to try to make them feel as safe as possible so they don't get defensive and kind of block me out. So that's the first thing that is the most important, is the foundation of that relationship. The next thing that has to happen, if you're going to like go into a dashboard and figure out what's going on, you have to have some good foundation in those key metrics. I, over the last year have run data science workshops like four hours with designers. And one of the first things we do is just brainstorm what metrics do you know? And you'd be surprised. Like sometimes groups of people know quite a few, sometimes they struggle. So knowing having some familiarity with kind of the metrics and especially the metrics that matter to your business and matter to your team. So you should be aware of conversion and retention and customer acquisition costs and annually recurring revenue and all of these basics. But your team might not be gold on all of those things or that might not be the OKR for the quarter. So start with what is the highest priority right now? What is the success metric on this project? Or a few? We should probably be measuring multiple metrics for every project and want to understand what's being created, what's being moved. Rarely does one project move just a single metric. So let's be part of that conversation. And if you're not the first place, you can start just by asking, hey, I want to do a good job as a designer. Pm, can you tell me what we're trying to hit here so I can shape the design in a way that's going to help the team be successful? So having that familiarity and developing that relationship are really important. And, and honestly, the best thing you can do to check the box on both of those things is just start talking to those stakeholders and showing curiosity, not coming out strong with an opinion, not saying, I'm a designer, I deserve access to this, or I need access to be able to convince you otherwise. Like say, hey, I care about us all winning. I care about being successful. I care about this product being impactful. I care about us all getting credit and promoted for those things. I'm sure you do too. Help me understand what we're trying to do here so that I can help us do that. That's a good way to develop that relationship. It's a good way to then leverage their expertise and have you learn some of those things and then you can get access to the tool. But those two things have to come first.
- [48:38]
A
If level three is getting into the tool, what do some of those more advanced levels even look like for people who understand the importance of writing out the list of the key metrics that matter most and keeping tabs on them, but maybe want to go a little bit further. You know, even spotting patterns that are slightly not obvious, or being able to make connections that would spark new ideas that otherwise wouldn't surface in a roadmap discussion. What does that look like in practice for you?
- [49:08]
B
Yeah, I've got a few good examples of that. One of the first things you can do is just look for weird outliers. And when it comes to data, the thing that really matters about all data is about human behavior. Changes everything. We're measuring someone's doing something differently. So when you see an outlier that's really bizarre, it might signal this human behavior or human attitude. That's where metrics and data becomes really accessible for designers. If we don't think about it as a math function, but we think about it as a reflection of what humans are doing differently. I'm comfortable with human behavior. That's what I'm here to shape is human behavior in our product. So looking at outliers is a really good way to get started. Anything just, like, seem really unusual or out of place. Designers might look at the data, the same data as a PM or a data scientist, but have a different perspective because they're looking at it from that human angle. A really good example is when I was at doordash very early on, eight engineers, no PMs. I just asked for access to amplitude just to look at what was going on on the website. And the first thing I noticed was you have this, like, perfect funnel. You got a lot of views on the homepage, and then fewer views on the restaurant, and then even fewer in the cart. But after the cart, once someone checked out, the page that showed people the status of their order had three times more page views than the homepage. So people were there just clicking, clicking, refresh, refresh, refresh. And what was happening was they're getting hangry, they're getting upset. They're getting nervous about, where, where's my order? Where's my order? Where's my order? So I noticed this really strange behavior. This does not look like a funnel. This looks like a funnel. And then kaboom. Huge number of page views. So I thought maybe people are angry, hangry, getting frustrated, getting nervous. Refresh, refresh, refresh. We might want to just surface this information to them in a more dynamic sort of way before they start contacting us. Every support call is like $8. If we can mitigate traffic away from that, it would Be huge for the small business we are. And so I was the person who at DoorDash proposed live order Tracking. I said, you should be able to go to the website and it should just update its status for you in real time and you shouldn't have to refresh. You should always feel confident you've got the most up to date information. And we launched a super minimal text only MVP of that. But that was the foundation of Live Order Tracking. And now you go to DoorDash and you can see exactly where your driver is on a map. All of that is about preventing that hanger, preventing that anxiety. And that just came from looking at a dashboard and seeing something that seemed out of place and coming up with a hypothesis about it.
- [51:38]
A
I love it because it's the perfect example of wrapping the data in that human story that's coming from the user empathy. That design is unique. You could qualify to bring to the table.
- [51:47]
B
Absolutely. Another thing designers can do are kind of look for patterns. Even in past experiments, as a designer, it was difficult for me to sometimes advocate for resources for new experiments. The roadmap is already set and they'd say, well, we need evidence to go expend these resources. I'd say, great, can I have some resources to go get the evidence? And they say, no. And you get stuck in this Catch 22. One thing you can do is go look at maybe past experiments and reinterpret the data with your designer lens. So at Airbnb, we had a system called erf and it was all the experiment data from the past. And I just kind of had access to it. I'd look around at all of the different experiments we had done. And there was one experiment in particular is really interesting, which was we were not showing guests the final price until they went through the entire booking flow. This was years ago. And so you had to like go all the way through. I want to book this home. I want to introduce myself to the host. I want to make a bunch of decisions, step, step, step. And then you get to this final page and that's where we took the time to calculate. This is the taxes, these are the fees. Here's the total price. And so the team realized, like, that's not a great experience. You don't want to make people jump through a bunch of hoops to get to the end and realize that, oh, I can't afford this place. All the fees make it too expensive. You want to surface that information as early as possible. So the team launched an experiment and they put a little modal that calculated everything. And what was great is that you could go right from the listing to that modal and it would show you how much it costs and you could decide whether to move forward from that point or not. Page views through the whole flow went way down because people didn't have to go through it anymore. And conversion went way up. And the team was like, great, successful. This is a win. I looked at that and I thought, this is great. But it signals something so much larger. It's that people really value when this information is at their fingertips. And it occurred to me, why are we making people go through this flow at all then? Why can't all of this information just be a single page? And so that was kind of the insight of looking at past experiments and kind of recontextualizing it. I'm like, this shows us what works. Why don't we really commit to this direction? And so I was a person at Airbnb who proposed, why do we have a five step checkout flow? Let's have a single page with a single button that people can just tap. All the information is there and the action is now there as well. And that really dramatically improved conversion for Airbnb right before the ipo.
- [54:09]
A
One of my favorite parts of interviewing you is you have this unique combination of past experience and very clear stories that you can learn from by listening. But then also you're just an educator at heart. You know, like, it's just clear listening to you talk that you thoroughly enjoy teaching. And I want to give people an opportunity if they're interested in going deeper. You have, you know, best selling courses on all of Maven for, you know, it's an important time basically for designers who want to grow in these areas. So can you just take a minute to give people an idea of what do you teach, who's it for, and what can people expect to get out of it?
- [54:46]
B
What I teach are business skills for designers, and it is that piece of the pie. It's like, yes, if engineers and product managers are moving towards us, we have to move towards both of them. There are a million vibe coding courses and learning how to do the technical side of engineering. And that is awesome. I teach the other half of the coin. The if you want to be more strategic, if you want to get promoted, if you want to drive value for organization and be seen as someone who is extremely valuable, that's what I teach. So I bring everything from all of my experience working at all these companies and being a designer for 20 years and everything I'VE learned succeeding and failing a lot at some of these companies on these big projects. I like to bring designers behind the scenes on a lot of these projects, but I also complement that with everything I've learned in my MBA about how businesses work, how people think about, you know, making decisions in a business, and how designers can get involved in that process. And so I've got a few courses. The most popular one this year has been my PM Masterclass for Designers and is teaching designers how to find opportunities, assess them and pitch them using data and some really strong stakeholder analysis and negotiation skills to bring ideas to the table and actually see them through to launch. And that is not only really good for users, it's good for the business when designers participate and drive that process. And it's really good for our careers and really good for our portfolios.
- [56:07]
A
Hey, real quick, if you're listening to this and you want to learn directly from Ryan, I asked him if he'd be up for giving a discount code for the Dive Club community and he said yes. So if you go to Dive Deeper Doc Club Ryan, you can get a special offer on his PM Masterclass course. Okay, back to the episode. Yeah, one of my favorite lines from this talk is the visual skills get you hired, but it's this more product strategy business skills that get you promoted resonates completely. I never thought about it quite that way, but you're right. This is the way that you if you really want to advance your career, ultimately you're employed to drive value for an employer and thinking very strategically about how to make that work is the way.
- [56:51]
B
Yeah, you are an investment that they're making and they want to understand what they're getting for that investment. And that is not wrong. That makes a lot of sense especially when the macroeconomic environment is so bizarre. It has been so disrupted over the last few years. We all are spending money differently, care more about what we're getting for our money. Businesses are the same so they just want to have a clear picture of what's going on and the more value we can produce and the more clear we can be about that value, you the more we're going to be rewarded and the less likely we are to be laid off. It works really better for everyone.
- [57:22]
A
Well, I feel very confident in the ROI of people listening to this discussion. It's always dense, action packed when we talk to you. So Ryan, thank you so much for coming on today and dropping the knowledge bombs. It's always fun.
- [57:34]
B
Thank you for having me again. I really appreciate it it's been a great time.
- [57:38]
A
Before I let you go, I want to take just one minute to run you through my favorite products because I'm constantly asked what's in my stack. Framer is how I build websites. Genway is how I do research, Granola is how I take notes during crit. Jitter is how I animate my designs. Lovable is how I build my ideas in code. Marvin is how I find design inspiration. Paper is how I design like a creative. And Raycast is my shortcut every step of the way. Now, I've hand selected these companies so that I can do these episodes full time. So by far the number one way to support the show is to check them out. You can find the full list at Dive Club Partners.