B (3:44)

Real quick message and then we can jump back into it. You know what I'm excited about the Granola mcp. It allows you to connect your AI tools directly to your Granola meeting notes. And as somebody who's been vibe coding a lot of tools recently, this release is a pretty big deal because my meeting notes are some of the most valuable context that I have. And now I can find specific topics, pull out action items, and get any question answered based on my meeting history. This is all available today and I'm already building with it like crazy. So if you want to join me, head to everybody dive club. Granola mcp. That's Granola mcp. An even smarter version of Lovable just released. It is 71% better at solving complex tasks, which means it can do more work more autonomously. There's more intelligent planning, prompt queuing so you can stack requests while Lovable works. And my favorite part, there's automated testing, which means Lovable no now tests your apps like a real user, opens its own browser, navigates flows, investigates edge cases, and catches bugs for you. And the best part is when it finds a problem, it fixes it right on the spot. I genuinely believe Lovable is the easiest way to build software today. So head to Dive Club Lovable to try the new release. Okay, now onto the episode. You mentioned something to me earlier. You talked about how we're entering this kind of new era of design leadership. So a big thing that I would like to do is kind of just unpack what that means to you. So what are some of the shifts that you're able to see as somebody who, you know, you're now entering kind of like your third really senior design leadership role at this big company? What have been the deltas from role to role that indicate what this shift might look like at more of like a market level?

A (5:34)

I think when I was becoming a manager, a lot of the managerial advice and, you know, guidance for new managers in books that you would read were about how great managers hire really smart people and get out of their way. At this point in my career and at this point in our market and what we expect of design leadership, I could not find that to be farther from the truth. Not that we hire dumb people and get in their way, but that we hire smart people and we are a big part of the process. One way to think about that is like, earlier in my career and at a different stage of this market of design leadership, you know, there was this sentiment that junior designers require a lot more handholding on our. You know, it's a lot more time intensive to work with them. And senior staff, principal designers, you know, can be extremely independent. And I haven't really found that to be the case, actually. I think that staff and principal designers need a significant amount of support. They need design leaders who are extremely present, who can help them navigate political situations and organizational complexity, and who can help when those designers are given projects that are massively more ambiguous than a junior designer and help them break it down. No designer wants to be an island. And a design leader can really help make you feel like you are part of a team and you have somebody that you can always go to to get excellent feedback and to get great guidance and to get honest, you know, direct guidance on, on what to do next and how to actually turn not, just, you know, outputs out of your work, but outcomes out of your work and actually get things live. I think there was a few years there where we were overstaffed and like under equipped to figure out how design could be most effective in our industry. And, and now the. The shift has gone from just producing beautiful things to actually shipping them to production and landing them with customers as well. And I think design leaders are rightfully so more judged on that now than we, we were in the past. So I think it's an exciting time to be a design leader. But it's, it's also harder.

B (7:55)

There's like a few trends that kind of combine here where you have maybe the compression of team size, which is something that you kind of mentioned. And there's also this increased responsibility too. And like even you as the leader are being held accountable to like what actually ships and designers are kind of being asked to do more, but maybe there's also less designers. Like how does that dynamic play out as a leader? Like what are some of the things that you're thinking about in terms of even how to make the most of this next blank slate with Vercel a.

A (8:25)

Few years ago we all got an influx of funding and the early pandemic, you know, the first few weeks obviously were extremely challenging for a tech and then over time we all expanded our teams and it was this interesting period where we all grew exponentially. We were all talking about scaling orgs and then the reckoning came where you know, we corrected. They, they introduced this like term correction in the market. And I think that that's actually a little bit of a misunderstood term. I think that people have been seeing it as a one time correction for a one time mistake. But actually I think it's a course correction that, that is more permanent and going to be more sustained over time. This expectation that a lot of companies are going to be operating more as the early startup, in the early startup phase, as they go through a growth stage to try to get more out of their teams with less. And I think that's the theme we're hearing a lot with AI is being able to become a 10x designer or a 10x engineer with new tools. It is exhausting and it is really hard to find a way to do that without burning teams out. So I think that's now, you know, on one end of the spectrum. We don't want to overstaff teams to the point where we put people at risk of being laid off. We want to make sure we're really careful about how we hire and how we grow. But we also can't run people into the ground. And so I think one of the challenges that every design leader faces and has always faced is like the right size of team. But I think now it's even more seen with a critical eye from, from the rest of the org in ways that it wasn't as much before.

B (10:07)

Can we double Click on the tooling piece for a second. Cause I know it's top of mind for a lot of people, both ICs and leaders, and maybe even to set the stage, I want to present this hypothetical spectrum where on one end, as a leader, you're completely hands off, do what you want. If you want to play with these tools, great. If not, it's totally fine. On the other, it's like performance reviews are tied to AI usage. We're tracking everything. You got to use tools, dedicated time during the week to use them. How do you think about where you want to fit on that spectrum and what does that say more broadly about, you know, your philosophy towards adopting these new tools?

A (10:39)

Even I think where we fit on that spectrum today is probably not going to be a permanent fixture. So even the orgs that say, I want everyone to use AI tools every single day in their work and you're going to be judged on it, we're going to track it. I've been in that org and it is, you know, ruthless. You know, you're trying to, like, come up with ways like, how can I use AI today? Sometimes. But I think that it is honestly a bit of a necessary evil because every single company of a certain size is going to be disrupted by AI. And the best way for you to disrupt yourself is for your own teams to be using the tools and to be thinking how those tools will change how people solve this problem that our company solves in the future. And the future is like tomorrow, like it's like happening or yesterday even. It's happening. So, so f. And so I think I, I think that it's actually, it, it can be very annoying and can be very frustrating, but I, I actually think it's an extremely useful way to very quickly force adoption of new tools that, that you can learn from. And I think you can like, you know, you can take that with a very different mindset. Depending on who you are. You can choose to be in one sense, like curmudgeon about it or bitter about it or ethically con. Conflicted about it, like, all of those are fair and options for you. You can also see it as an opportunity to learn something new. And something that we've talked about before is that, you know, the junior designers entering our industry now are learning faster than we ever did when we were juniors. And part of that is the tool adoption. And so I'm trying to see AI adoption in my day to day work as a blessing, like an opportunity to learn new things. I think, like one of the Things that I assume all of your audience shares in common, despite how diverse it is, is that everybody listening to your podcast is somebody who wants to learn something new all the time, somebody who's craving new knowledge. And that's why I think, like, we really love that we are living through this era because it is uncomfortable, and we love being uncomfortable. We love learning new things because it's like, when you look back at your career, the times and the eras where you were learning a significant amount in a condensed amount of time, those are, like, the best times of your career where it's hard and it. And it, like, sucks and it's awesome all at the same time.

B (13:15)

Yeah, you're learning all of the exact ways that you don't want to do things moving forward, but it's kind of just part of the process. And for people that, you know, maybe have listened for a while, they know that I like to quote Soleil more than I probably should, and he refers to it as a. The great jump ball of our industry. And I'm like, yeah, that makes total sense. Like, everything's up for grabs, you know, and it doesn't really matter how old you. You could be practicing for 20 years, but the reality is, like, it's, you know, Thursday afternoon, I've done, quote, unquote, design work, which I don't really even know what that category exists. Like, what is in that category as much anymore. But, like, you know, I've been working as a designer every single day this week. I've spent a lot of time, like, in Conductor, like, wielding agents and making all of these weird code mistakes that I'd never thought before. And you're right, it's a mixed bag. Sometimes it's like, what's happening right now? But there is this sense of, I don't know, maybe I'm just a raging optimist, but, like, it's really fun, right, to just try new things and to, like, experiment. And if you are, like, two years in your career, it's just as new for you as it is for, you know, the two of us who have been practicing for a long time now.

A (14:22)

I think it's also fair to talk about the fact that, like, it's not fun for everybody. For a lot of people, like, trying new things is generally hard, and for a lot of people, like, trying new things right now at this point in their life, maybe they just had a kid or they had a death in the family, and it's like, this is not the time for them, and that's okay. I Think it's, it's good to state those things and accept them and know that like this is not always going to be the era that I'm in my life and there will come an era when I am like ready to jump into the new tools and try them out. And you talked about like having dedicated time to actually jump into new tools because we get so busy, everything is like an urgent request and everything is shipping tomorrow. And I, I think that it is absolutely critical for teams to set aside dedicated times. So at webflow we had something called builder days. At Vercel and at many places there are hackathon opportunities and I think those are the opportunities where operations teams need to be ready to give their teams the right tools and the access that they need. So that on those days teams are ready to hit the ground running trying new tools. Because in our day to day work we may not always have the time to actually fit it in.

B (15:30)

Can we go a little bit deeper on just how this moment in time and again, like that new era of design leadership, how is that influencing the way that you think about process structured collaboration? Like obviously there's so much bottoms up, especially in today's age when kind of lines are getting blurred, but I would imagine there's still some principles where it's like hey, this is the type of way that we're going to work together as a team or we're going to have like this is the meeting, you know, every Wednesday, this meeting. Like what process does still exist in today's world?

A (16:01)

I guess I can give you maybe a concrete example of how this shift is changing one of our processes that is very famous in the design world, the design Sprint. It's this like five day Google Ventures process.

B (16:14)

Give me all the red sticky dots to heat map.

A (16:16)

I love that. One of the things that is changing about that, at least in my world, from what I have seen not just in my own work, but in my peers work, is that Nobody is spending 58 hour days in a room together collaborating even, even remotely, I think rightfully so, morphed the design sprint into a new evolution where it might be five days but you're actually only doing one hour of synchronous time in the morning to kick off each day with some context, some like alignment, making sure we're, we're solving the right problem or we're diverging on the right ideas, but you're spending the other seven hours doing independent work, you know, going in a million directions of prototyping. We might also be doing that Prototyping on day one of the design sprint instead of day four or whatever it was because. Just because of the tools changing. And I've seen design sprints run in a one day process where we spend the morning understanding, in the afternoon diverging. And then by the end of the day we have a prototype and we're, you know, testing in front of customers. And so I think that's one way where we're taking some of the great things from the design thinking era and applying them. Today's world, where we have a very different set of tools and we have a different set of expectations on how fast we can ship things and what sort of outcomes we're producing. At the end of our artwork, when.

B (17:35)

You have this natural pressure to kind of collapse the design process, maybe we ax a good bit of the design theater that we've been accustomed to over the years. How do you still uphold this really high bar for craft? Because both Webflow and now Vercel, you know, they're kind of known for sweating the details and making something that is really well thought out. And I'm kind of curious, like, there feels like a little bit of tension there because there is this natural movement right now, and I'm feeling it too, where everything's just got to be faster and faster and faster.

A (18:06)

I worry less about craft getting cut in that process than I do about, are we solving the right problem? Are we solving it in the right way? I care so much about craft, and the companies that I work at care about craft, but I think when you are cutting time, a lot of times I have found that the worst time to cut is the time where you're actually aligning on the right problems to solve. But I also think that I have had a great opportunity at the last few companies that I've worked at to work in a place where everybody cares about craft. It is very hard for designers who work in an environment with people who don't care about craft to actually make that through. So I do think it gets cut in other places. I don't think it gets cut.

B (18:46)

It comes more naturally, maybe.

A (18:48)

Yeah, it comes. It comes very naturally because every single person at Vercel gives a shit about every pixel. And that environment breeds great craft.

B (18:59)

Okay, let's double click on the alignment piece then. And maybe we can speak to this hypothetical junior designer that we were hyping up earlier and they're able to get the reps with the tool, right? And maybe the craft is getting there and they're learning all these prototyping skills, but there is still a bit of a black box around, like, okay, like, how do I actually make things happen in an org, especially given tighter timelines. So when you think back on some of the really, really, really good ICs that you've worked with, what are some of the things that they're doing to effectively align the team or certain behaviors or traits that people listening could maybe glean some little tactic from?

A (19:35)

Yeah, you mean junior designers specifically.

B (19:37)

I said junior designers, but I'm actually really just asking for myself.

A (19:41)

I think the number one trait of a great designer, whether they are a junior or not, is that they are willing to share their work very often and incorporate feedback and know when feedback needs to be pushed back on and when it doesn't. I think, like, really getting good at sharing your work often. You know, we were talking about this today with my team. One of our team members asked for advice on, you know, what is the right time to share feedback? And basically the answer that we ended up getting to was like, there's really not a right time. I can tell you the wrong time to share feedback is if you wait for that weekly Speaking of process, if you wait for that weekly design critique meeting to get feedback, or if you wait for that team sync with your engineers on Friday, that's the wrong time to get feedback. You should be getting it the minute you have something to show. It doesn't matter how half baked it is. I think people historically have avoided getting feedback too early in the process because they're worried that the, you know, stakeholders are going to comment on the pixels instead of the flow. But I hope we're past that. I feel like. I feel like we're past that. And as long as you're sharing the right context, you should be getting feedback as early as and as often as you can, because the more feedback you get, the more you're going to learn quickly.

B (21:01)

Even that part of the practice of the design is changing so much because now you can hop into V0 and, like, spin up a fully functional prototype that may be loosely pointed at the right problem to solve, but you're still kind of figuring that out. And, you know, it just used to be so much more linear in my mind, where it's like, I'm early in the process. I'm able to give a disclaimer that I'm early in the process. Maybe I'm even using gray box or, you know, it's just a bunch of static mocks or, you know, sketches. And now, like, fidelity is no longer as correlated to where we're at in the process, which adds this whole wrench into the way that we think about feedback and those touch points.

A (21:38)

Yeah, it makes your prototypes, the things that you're sharing, so much more real. And so in some ways you can get better feedback. You can get feedback on what it actually feels like to flow through the process instead of relying on a PM or an engineer to imagine it based on some static mock. But they do get tripped up on the visuals at times, and that's okay. I mean, that's fine. I think it's a muscle that we're all learning as we enter the prototyping era. I think what's really hard right now for our team is what does handoff look like today where you have a collection of assets of all different kinds that you might be sharing with your team in order to say here, this is the designs. It's an AI prototype that's janky in some ways. It's a figma file that's missing the interaction design. It's a loom video with your commentary over it and a million little other things that all add up. I don't think design tooling has really solved the collaboration aspect of prototyping yet. And so I'm looking forward to our industry's tooling evolving to allow for like a lot more of the type of, of feedback we get in figma. But with prototyping tools, and I know there's figma make, we could, we could go down that whole rabbit hole.

B (22:58)

We don't go a little bit deeper there. Like where do you think this is headed? Like when you think about the ideal state of this well oiled machine that is the Vercel design team, what does that collaboration look like to you?

A (23:10)

I know that our teams are prototyping really complex interactions to solve a problem that static mockups can't. But those prototyping tools don't allow us to have the level of craft and pixel perfect details that we want control over without actually doing the engineering ourself, which is becoming more and more possible with Claude and Cursor. But it's not necessarily the way that our team wants to be doing it on every single project. And so, you know, designers want to be problem solvers. And obviously on the spectrum of designers there's people who lean more product heavy and people who lean more engineering heavy. But I think that there's probably an evolution of design tools where either our prototyping can become more more visual editing or our design tools natively have better prototyping yeah. And in whatever tool this is collaboration, you are collaboration, meaning like you're sharing this with others. You're getting feedback in like very specific, you know, screens and flows in ways that you know, you could, you could click a button and incorporate feedback and Cursor or Claude, just take takes that feedback and does it for you.

B (24:26)

Hey, really quickly let me tell you about the all new Dive Talent Network. I've hand assembled over a hundred of the most talented designers and builders that I know so I can recommend them to my friends favorite companies. So if you're listening to this and you're open to new opportunities, the Talent Network is anonymous and super low pressure. It's just an easy way to see what's out there without having to post on social media. So if you're interested in joining or maybe you're looking for your next hire, head to Dive club slash talent. Maybe we could talk just to give people context around like how close is the design team currently at Vercel sitting to production? Like how much coding's actually happening? What is the tool stack? Obviously I'm sure there's a heck of a lot of V0 dog fooding. Is anybody committing to production? I know you've only been there for five weeks, but I'm really curious, like what is the state of the world for a team that at least from my perspective it seems slightly more technically inclined?

A (25:19)

Vercel designers are all using Claude and Cursor in their day to day work. They are significantly more successful in getting their work shipped by being part of the shipping process. That doesn't mean that they're shipping every single pixel, but it might be that they're doing the design polish in the final 1% or it might be that they're shipping a prototype that helps engineer get started. There are times where a designer is partnered with a design engineer on a project where they don't really need to do that work because the design engineer is there. And then there are times where a designer is on a team that doesn't have a design engineer, doesn't have somebody who's like super, super adept in front end engineering. And that designer might choose to do more of that front end work just so that they can, they can see their work come to life exactly the way that they envisioned it. And I think it's beautiful to be able to have that option when you have the skills to have that option, even if you don't want to use them all the time or you don't want to lean into that for the Next few months to have the skills is really valuable. I myself have only been at Vercel for like five or six weeks and then I shipped a pr.

B (26:24)

What'd you ship? What'd you ship?

A (26:25)

Literally a bug fix. It was like a URL was broken and I perfect fixed a tiny little change. I was honestly shocked. I, you know, I had some help from the design engineering team just getting my local dev environment set up. That's the hardest part. If you're a designer and you like are trying to get into a little bit more coding, even with cursor. The hardest part is just getting your local dev set up. But once I did and committed my PR and I was like, wow, the merge button is not disabled. Let's see what happens when I click it. And it just went live. It was so fun. It was thrilling. I think, I think like 10 to 20 years ago in the tech industry, you had to code to design. Every designer was a front end developer. We didn't even call each other designers like you. You just, you were front end developer of some kind. And I sort of think we got away from that in a bad way. And I love that we're coming back to the material and the tools and having a more direct impact on what actually makes it out into the world. It doesn't mean we need to do that on every project or that we should, but I think it's making a meaningful change in how design is seen as influential and having like really tangible outcomes.

B (27:41)

We've talked a lot about different forces and things that are changing. So maybe we could touch on like the talent recruiting hiring piece for a second. Because I'm assuming, you know, you've been in your share of hiring conversations, interviews over these last few different roles. So maybe when you kind of zoom out, where do the biggest deltas exist in terms of the traits that you're prioritizing or what you're looking for? How has that changed over the last even maybe year or two based off of some of these different factors that we're talking about today?

A (28:16)

Much more so than two to three years ago, showcasing in your portfolio in your hiring manager interview that you tried something new lately and you used a new tool or a new process. It's like table stakes at this point that you are showing that because there is a huge swath of people who have been either hesitant to do so or have done so and like haven't been as successful. And so I think the opportunity of the last 10 years, like this is the time if there's Ever been one to showcase your side project in your portfolio? There have been times where that has been seen as not really appropriate or not really relevant, and now it feels more relevant than ever. Not to showcase like, oh, outside of work, I spend all my time thinking about tech. But that outside of the project that you're working on right now, you have tried something new and you've come up with an idea and you've shown, like, from idea to solution, I can make that time really small. It doesn't have to be outside of work, can be inside work.

B (29:21)

I love that point. I'm even just going to underline it. As somebody who looks at a lot of portfolios through the talent network, and I am seeing an uptick in the little, you know, experiments tab. Or maybe it's like the playground folder, and you click it and it's just a bunch of random stuff and it's like a. It's a gold star. Like, it really is. Like, it does display a lot when you're able to very clearly point like, hey, I'm trying new things. It might not all be amazing, but like, I'm trying stuff. And also, if you're listening and you're like, well, I just don't have time. Time, I. I think you gave a really good point. It's hard. It's like, it's not as easy for everybody. That being said, man, you can get really far in one hour. Like in one hour on a Saturday, you can actually make a thing that is worthy of putting on your website and demonstrates a lot.

A (30:05)

Yeah, I think anytime somebody says they don't have time, whether it's to try out a new tool or to learn something new or to go to the gym or to, you know, whatever it is, there's always some. Some popular thing that people say they don't have time for. And it's not that you don't have time. It's that you have chosen to fill your life with other things. And that is absolutely okay. But if this was important to you, you make time for it. And it's okay if this is not important to you right now, but that might mean that you, you miss opportunities that come your way, who are looking for people who make that time, who have prioritized it right now, I think that's what. Where a lot of people are just feeling like so much pressure is that everybody is making waves. And like you said, like you said back to something you said earlier about in the portfolio, you know, just like a tab where they're trying out experiments or something. It can even just be the portfolio itself. I don't think every portfolio needs to be the most innovative thing on earth, but it is like your sandbox. It. It is the place where you can play and show how playful you are. And not everybody's good at self branding, but, you know, I feel like right now, isn't it like cringe is in, Right? So like make your portfolio a little cringe. It's fun.

B (31:16)

Climb cringe mountain. Yeah.

A (31:18)

And I say this as like the biggest hypocrite. My portfolio is white with black text or black with white text. And all I have is a list of blogs. But that's, you know, I'm not. I'm not applying for the same type of role that these folks might be.

B (31:29)

Yeah, I love that too. I think we just were so brainwashed for years as an industry where it's like, this is what the portfolio looks like and you have the grid of cards and each one of them takes you to a case study. And it's like a case study is.

A (31:41)

A hundred percent process. I am so glad we are past this era where every case study was like, and here's how I wrote a sticky note and here's how I, like, I don't really need to know that.

B (31:53)

This is what we did on day three of the design Sprint.

A (31:57)

Yeah, exactly.

B (31:59)

Yeah. Somebody said something. Matt. We had him on for an episode recently and he talked about how he wanted his personal website to be an experience. I thought that was really cool because, like, it's not just a catalog of your information and your case studies anymore. And I think for so long we just thought of it as like a catalog for case studies. And evaluation is entirely tied to the case studies and the process where now it's like, no, no, somebody's loading your website. What's the experience that you want to give them? What's the copy? What's the feel? How do things move? What are the colors? What are the typography? All of that is creating the initial signal way before I look at your problem statements for this one specific project that you worked on 18 months ago.

A (32:37)

You know, I think this is especially important for designers who feel really restricted by the case studies that they have. It could be a designer who works in healthcare or who, who's, you know, the first job and the only job that they've been able to land is something in government or somebody who's a career switcher and trying to show that they can do something outside of, you know, the previous role that they had in as like a nurse or something. These are the folks that would benefit most from taking the time to learn something new and showing that in like a really fun, playful way in their portfolio. Because that way I can, I can look at your case studies for like, here's how this person operates in an environment where there are a lot of constraints and here's how this person operates when they run the show and when they're, when those constraints aren't there. You can't see that if, if you don't have some side project or some portfolio where you're putting in that work.

B (33:27)

I'm going to lean on you to answer a question that's currently in my email inbox that I don't have a great answer for, which is related to portfolios. And the person is basically asking, hey, you know, we're in like this craft dominated world, but that's not really what I bring to the table. That being said, I'm really good at product and I've been able to make an impact in these roles. How should I think about my portfolio when a lot of the advice that's happening on the show is very craft forward, work forward. And they're concerned that by leading with visuals it would actually get them weeded out. But they do believe that they're a very strong candidate. You have any advice for that person that I can just pass off to you?

A (34:05)

Yeah, I have two options that I think are kind of spicy. Maybe one is you have to accept that design today is more than ux. It is visual design and craft and the interaction design details. And so if you want to be a designer in this industry, you need to figure out how do I get those skills? And you need to be excited about learning something new. And there are courses out there where you can learn these things. I have heard from somebody that craft was something you couldn't learn. It's. It's an art and you have to be like a very artistic person. And I don't buy that at all. Like you can definitely learn it. So put in the time to learn it. When you do that, add that side project to your portfolio or incorporate it into your portfolio. The other option is very, have like a very reflective conversation with yourself about, do you want to be a designer? Because I think that. But now with the blended roles conversation in our industry where there are a lot of PMs who can do design and engineers who can do a little design and designers who can do a little engineering and a little product, like everybody can do a little bit of Everything. And so is this a great time for you to actually pivot into product product leaders make more. So this is not a downgrade. You could be a really effective product leader if you are a great design thinker and if that is actually where you just like to spend your time, then, then consider joining a really design forward team as a product manager. I think that that could be a really fun career switch for somebody like that.

B (35:36)

Okay, let's keep pulling on the strand then and maybe we can talk to that hypothetical junior designer that is really just me again. And if you're thinking about, okay, everything's changing so quickly, I want to continue to, you know, pay the bills as a professional designer. One, two, three, four years from now. What are the different paths that you see or ways that people can invest into future proofing themselves for a world that feels like it's moving really, really quickly?

A (36:03)

Obviously right now one of the biggest skills is being able to adapt and learn something new. So showing that you can do that and knowing that as you learn these things, don't get hooked on one thing because this is going to change. It's going to change next week, next month, next year. All the tools are moving. But the other thing is there are some forever skill that are good no matter which role you decide to end up in, whether that is staying in design and becoming, you know, a fantastic designer or moving into something else as your role blends, like storytelling, like getting buy in about this is the right problem that we should be solving and here's why. I think that a lot of designers at early stage startups get these skills in like product thinking, because they are so close to the customer and so close to the work that working, working in that kind of environment can help get you those skills quickly. A designer at a larger company can get those skills in buy in. And how do I tell this story to leadership to convince them that this is the right thing that we should be working on? You know, storytelling is a skill that brings people a long way in their careers because especially as you move from junior to senior to staff and so on, you're not necessarily doing less execution work. But execution work is not where you're spending the majority of your brain cells. Your brain cells are spent on convincing and persuading people that this is the right path moving forward. They've given you a task to do and you've said this isn't even the right task to solve and like really navigating those situations.

B (37:34)

Are there examples or practices that you've seen in Some of the best ICs that you've worked with over the years that have shaped what you think of as effective storytelling as a designer.

A (37:47)

Okay, so like an example, one designer that I worked with who was really effective at storytelling was because he knew really well how to say the elephant in the room that senior leadership in product and engineering weren't talking about. And that elephant in the room could be like the existential crisis for your company. You know, it could be how AI is disrupting this company and we're just iterating and we're not innovating and having an idea and a solution for that. I mean, that's like one of the biggest tips in terms of communicating. Whether it's managing up or convincing stakeholders about a project, it is not just complaining, but coming with ideas and having workshopped them with the right team, with the right folks at the right time.

B (38:34)

I think the elephant in the room thing is actually interesting because there's almost like a baseline level of product thinking that is required to even be able to see and accurately articulate the elephant. You know, like if you are only operating at this like low level detail, you don't even have the altitude to see and address the elephant, which then kind of is pulling me towards this. I don't even know if it's a question, more just a hypothesis. And I'm curious to get your take, which is, okay, we've talked a lot about roles or blurring. Designers kind of have to dabble in different areas, you know, and it feels like there's these two poles where you're being like pulled toward one pole over here, which is, all right, you love craft, great, here's your ide. Here's your local environment. Like, you're going to start coding, you know, you're going to start owning the front end. Everybody's going to be a design engineer, that direction. And then there's the kind of what you're talking about earlier, like, yeah, like what is kind of the difference between a product leader and a product oriented designer at the end of the day, you know, like go down the product route and that's how you have like more top level impact. Is it a true dichotomy?

A (39:43)

Yeah, I think on the spectrum of designers who lean towards product and designers who lean towards engineering, especially in the junior and mid level folks, you sort of see them pick one lane and lean really heavily on it. They might like dabble in the other lane because they're told to once in a while, but they don't. They definitely aren't going both directions. The thing that makes I think staff and principal designers different is that they are leaning in both directions at the same time. They are trying to understand the ROI of diversity design much more concretely and be able to communicate to product leadership in a way that they never could before. And they are illustrating that with a sick AI prototype that they couldn't have made two years ago. I think that that takes two very different skill sets that our most senior designers have. One is like the hands on technical skills and adopting new technologies and the other is knowing when to step back and see the forest for the trees to be able to point out those those elephants in the room.

B (40:47)

You just made me think of another maybe micro path that I guess is closer to the engineering. But like there's kind of been this uptick in the excitement about design systems recently on the show. Like I've been doing this now long enough where I saw like everybody like design systems are dead and now people are like design systems are actually kind of cool and the big deal for AI as somebody who again is like this hypothetical listener where they're just trying to be like what makes me unique? What can I put on a portfolio? What can I lean into? Where can I spike that would make me compell in this upcoming job market? Is there something there with design Systems? I'm wondering if you have a take on the relevancy from a career standpoint.

A (41:24)

Oh, design systems is so tricky because you have candidates who are applying for a product design role on a particular product area and if they come in to a portfolio round with almost solely design system work, it's never going to work. They have to be able to showcase that they have product thinking skills and there is very little product thinking when it comes to design systems. I'm sure yes. In an ideal world, those designers are also thinking about the product and know the product deeply because they're designing a system for it. But in reality it doesn't happen very often. I do think that there is a big uptick in design systems chatter because when you are relying on AI tools to build UI really quickly, it is obviously significantly better output if you have trained that system on your design system. For a while, Design systems had to beat the drum of Design systems are not just a sticker sheet. They are not just a component list. It is documentation about when to use one component or another and the anti patterns you want to avoid. And that documentation is now more important than ever because you are actually training the LLMs on the documentation that you may not have written us and we're like facing the consequences of it. I think that that design systems got a lot of shit for slowing things down or making things less exploratory. And now because of these tools, the best and most robust design systems might actually make your team significantly more efficient and be able to experiment and explore with the design system in a way that they couldn't before.

B (43:06)

Okay, I want to zoom all the way out before I let you go because we've covered a lot of ground, but I want to make sure that we got everything because something that you mentioned to me off record is that you were at a dinner recently with a group of design leaders and I'm wondering if you can let us be a little fly on the wall in that dinner for a little bit and talk about any of the other trends that were surfaced in that conversation that we haven't talked about in this episode. That point at, you know, just the state of the world or where things are headed or what's top of mind for the people that are leading some of these tech companies and design orgs.

A (43:42)

I think one of them is just this major trend for design leaders to go back to IC work. I think for a while the only people we heard of doing that were managers, like first level managers who tried it out and then went back because they didn't want, they didn't want to be a manager. But there were multiple people at the center who had made it to like VP of design and had moved back into a principal IC role. Because now more than ever in our history of our industry, we have such an exciting time to be a designer. And it is very hard to be a design leader in this space if you don't have hands on experience with the tools. And honestly I don't think it's possible you shouldn't be continuing your day to day work if you're not stopping to do some IC work. And I think some of the leaders who stopped to do IC work full time did so because they were in an org where it was not possible for them to take a project here and there. In my role right now, where I don't have enough designers for every team yet, there's only like seven or eight people on the product design team at Vercel. So we're really small.

B (44:51)

It's even smaller than I thought.

A (44:53)

I know. It's so small. Everybody says that. Everybody on the team says that when they joined they were shocked at how small the team is.

B (45:00)

I thought you would say like 30.

A (45:02)

Yeah. No, but it means that I also have the time to do some of the IC work. It's not, it's not that I'm going to do that forever and that I want to be a player coach permanently, but if I am going to do it, now's the time because I get to try out new things and really feel the empathy for the folks in the trenches, you know, learning constantly, every day. So that was one of the topics that came up at our dinner is this shift from a lot of, you know, one of one of the people that used to be my manager, Roberta Carrera, she was the VP of design at Heroku and then Hashim Corp. And now she just joined Docker and right before she joined Docker she spent a few years doing IC work. And it's just like very uncommon for somebody who was a VP who led teams of a hundred or more to go back to working at a five person startup and doing IC work. So, yeah, I think that that's a really fun trend right now. I think onboarding, I know that's like not a sexy word, but like when you join a company now, it feels like the pace is so much faster than it used to be. You know, I think that there was definitely this sentiment before about like, yeah, like, you know, take three months, make yourself like a 30, 60, 90 day plan.

B (46:14)

30, 60, 90 days?

A (46:15)

Yeah, I mean there's like literally a book called the 30, 60, 90 Day Plan and it's great and it doesn't work on that timescale anymore. My first week at Vercel, I focused on meeting one on one with as many people as I could. And my second week hosting a retro so I could see the group actually talk together what they were talking to me about in one on ones and what's working and what's not working. And by week three, I was moving people, I was like, clearly this is not working for you on this team. You know, we'll move you to another team. There are two, two folks that we've like moved around in week three, opening new roles and week four, making changes to how the whole design team works, not just product design. And it's like, that's a 30 day plan. That is like rapid fire pace. Where the traditional advice has been for the first 30 days, you need to do a listening tour. Like, my God, if I did a listening tour for 30 days, people would be like, how do you still work here?

B (47:16)

Because get her out of here.

A (47:17)

Yeah, you need to actually do something. And I think that that is a Sentiment not to just at Vercel where the pace is famously faster than anywhere on earth, but I think it is an industry trend that, you know, we talked about with some of the folks at the dinner that as a design leader you need to show outcomes so, so fast. And in order to show outcomes, you have to build trust and build relationships much faster than you ever did before. It is a sprint for sure.

B (47:47)

I know a lot of of the conversation that we've had has been more forward looking as a design leader and some of the things that are changing. But maybe before I let you go, one last question that is slightly more reflective. I'm curious, if you look back on past roles, are there clear experiences that have shaped the designer leader that you are today that you're definitely taking with you into how you approach your practice at Vercel?

A (48:10)

I would describe my experience working at webflow as very formative as a leader. Even though it wasn't my first leadership role, it shaped how I am a design leader today because I learned the early career advice you got as a manager five to ten years ago was you hire the right people and you get out of their way. And at webflow, like every staff and senior staff designer that I worked with was so grateful that I was in their way all the time. They were, they were like so grateful that they had a manager who, you know, finally got into the weeds with them on a project and got into the weeds by bringing designers across the company together to work on cross pillar, cross product collaboration in a way that their day to day work couldn't bring them together for. There really wasn't somebody to string those beads. I think that's one of the biggest impacts that a design leader can make is that horizontally work where we say like what does AI chat surfaces look like at our company? Because so and so is doing it over here in this way and this team over here is doing it in a totally different way. And then we have a toolbar over here doing it in a totally different way and really thinking through like thematic topic areas where at the altitude that I'm at, where I see initiatives across the company, I can bring those designers together to really create a cohesive design strategy that none of them could do independently on their own. Like that's like the biggest impact that I can make as a design leader. And I think, you know, at my previous company, at webflow is like a great place to be able to do that because there was so much hunger for it. And I think that it is also a theme you're going to see at every single growth stage startup where the company is no longer small, the product is no longer small. You have this bloat that you have to solve for, but you're not yet a behemoth that has every, you know, has like a insanely robust design system that's like the really, really hard stage for the cross product, cross pillar collaboration.

B (50:12)

Well, Hannah, thank you for coming on and kind of just being a window into what you're seeing and what's happening in the state of the world and what it's like being a designer today and looking forward. Like there's just so much going on and there's so much to talk about. So I appreciate you being a sounding board and sharing with us today.

A (50:29)

Thank you so much for taking the time. I'm very jealous of your job. You get to talk to lots of interesting people and have great conversations and I appreciate what you do for the industry.

B (50:40)

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, 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 Slash Partners.