What Founders Can Do To Improve Their Design Game

In this special episode of Design Review, Aaron sits down with Raphael Schaad, the Head of Calendar at Notion to discuss his leap from designer to founder, why illustration is an important first step when building a new product, and what ultimately makes designers uniquely qualified to start a company today.

• 0:00Speaker 00

  Rafael Shad is a unique figure in the startup world. He's both a designer and the successful founder of Kron, a next-gen calendar for professionals, which was acquired by Notion and has gone on to become Notion Calendar, which is used by millions of people all around the world.

• 0:16Speaker 01

  Design is not just how it looks, but design is famously, you know, how it works. You see another dimension to the world when you start kind of understanding design.

• 0:25Speaker 00

  So today, we'll be chatting with Rafael to learn more about his design process and find out how founders can level up their design game.

• 0:41Speaker 00

  So one of the things that I care a lot about is encouraging more designers to become founders and encouraging more founders to care about design in the earliest days of starting their company. So who better to have on than Rafael? Thank you for joining us.

• 0:56Speaker 01

  Awesome. Excited to be here.

• 0:57Speaker 00

  You've made the jump from designer to founder. Why do you think that there aren't more designers out there making that same leap?

• 1:06Speaker 01

  Well, first of all, I kind of think, you know, there should just be more talented people building companies in general, not just designers. But designers actually have something really valuable to bring to the table when it comes to starting companies. To build a product that people, you know, really, really want, I think you need kind of like three things to build a successful product in the company. You need to have something that, you know, desirable, that people want. You need it to be viable, so kind of like you can build a business out of it. And you need it to be feasible. You need to be uniquely positioned to actually build it, you and your team, right? And if you think about these three things, desirability, feasibility, and viability, kind of three overlapping circles, and you can map them to more traditional disciplines,

• 1:47Speaker 01

  it's actually design and business and technology. And design is really kind of like, you know, back to the YC ethos, make something people want. Design is essentially figuring that out.

• 2:00Speaker 00

  It's that mentality that I think a lot of designers think about. What do you think is holding designers back from starting more companies if they're so well-suited? Because it's how they spend a lot of their days and hone their craft.

• 2:12Speaker 01

  Yeah, it maybe kind of goes back almost historically, kind of the context. Maybe back in the day, design was much closer kind of to an artistic pursuit, right? Where art is more about kind of like asking questions. Whereas design these days is more actually about kind of problem solving and answering questions. They're learning solutions, basically. And so that probably happened sometimes during the industrialization is my guess. Where design kind of moved closer to be part of sort of like the problem solving, you know, engineering kind of apparatus. But back then, in the industrialization, designers didn't necessarily control the means of production, right? And so that is really changing now, where designers can essentially, through software, through code, can actually be really close to building the object, right?

• 2:58Speaker 01

  Versus kind of like, you know, back in the day, maybe it's furniture or like other objects. And so I think that's what makes this moment in time so interesting for designers to build companies and build products.

• 3:09Speaker 00

  Yeah, and tell us a little bit about your journey going from designer to founder of your company to ultimately selling it to Notion.

• 3:16Speaker 01

  So I actually have a technical background where I have, have in love with kind of like CS degree from back in the day. That really allowed me to build things. I never kind of studied CS because I wanted to, you know, go extra deep on that aspect. But really, I wanted it to be a tool for me to build my own designs. And so very much sort of like maker at heart, always had kind of like, you know, dreamed up things, designed things, and then wanted to be able to build in the medium. So I spent my graduate studies at the MIT Media Lab where I built a lot of physical things. So again, kind of designing things and then building it in the medium that the ultimate sort of like object is in. That's really important to me.

• 4:00Speaker 01

  And of course, you know, these days where so much is software and so many of the products that I've built throughout my career are basically software, being, you know, capable to prototype, feel, but also sometimes even like build the real thing is sort of like what got me to this technical, you know, education.

• 4:19Speaker 00

  That's such a great point, actually, because that's kind of my journey too. Is, you know, I started learning design and learning how to code because I wanted to create the thing that I envisioned in my head. And to have the ability to execute and build it yourself is like

• 4:34Speaker 01

  So powerful.

• 4:35Speaker 00

  Yeah, exactly. It's like the ultimate, you know, form of that. And so do you think designers should learn to code?

• 4:42Speaker 01

  You should be comfortable in the medium that you're building in. And if software is what you're building, made out of code, but also, you know, pixels, being relatively close to like how the actual thing gets built gives you such a huge advantage, especially now kind of like in the AI age where, you know, the thing that we design is less, um, kind of like the nouns, kind of the buttons and the text fields and the sidebars, but really think more about kind of like the verbs. You know, autocomplete, auto suggest, summarize, send an agent to do something. Those are things that are kind of hard expressed just by drawing a rectangle within the rectangle, within the rectangle. But you really need to start to think about time as an aspect in your designs, et cetera.

• 5:25Speaker 01

  And static prototypes oftentimes kind of break down, don't quite give you the feedback that you get with real data. And so I think whatever gives you sort of like ability to play with the real thing, I think is what gives designers the edge.

• 5:39Speaker 00

  Yeah, that's actually a great point. I've never thought about it like that. It'd be like if you were a sculptor and you just created the plans for the sculpture and then handed it off to somebody else to do the thing, that would sound crazy, right?

• 5:50Speaker 01

  Yeah. So why would we think that kind of software design and software engineering are these entirely separate disciplines, right?

• 5:56Speaker 00

  Yes. What about for maybe technical people, engineers, that don't have a good eye for design, you know, don't know how to create something that is user friendly and think through all those considerations? What would you recommend to them?

• 6:11Speaker 01

  You know, top three things, um, what to do for people to become more design minded. First of all, I would say, uh, just kind of do, um, uh, learning by doing, right? Um, when you start to, when you look at designs, you oftentimes kind of can tell this is a good design or this is not as good of a design. This design works, this design doesn't work as much, but you don't really know why. When you start doing, you will probably produce bad designs, uh, at the beginning, but at least you can understand the material. And you start to understand why a design works and doesn't work. What are the constraints that a designer that created a design that maybe doesn't work as well? What are the constraints that that designer had, right?

• 6:54Speaker 01

  You really start to kind of almost see the world through sort of like, you know, reading the world kind of through like like matrix. And you see another dimension to the world when you start kind of understanding design. The second thing that I would say is to surround yourself with beauty. Surround yourself with like really nicely designed objects. Can be physical, but also can be the ergonomics of software, right? If you don't tolerate and let in sort of like just that noise of like bad designed objects or not designed objects and all that cheap stuff. By the way, like well, good design can also be cheap. Like, that's an aspect of kind of like good design production. But surround yourself with well-designed objects to sort of like absorb and and sort of like develop a taste.

• 7:38Speaker 01

  And the third thing I would say is is read some design books. There's so much deep knowledge in some of these classics. I would say top three would be grid systems, which is what taught me all about text and layout. Actually, a fun fun fact about grid systems is that the crone orange, FF4700, and then a fiery orange was inspired by the cover of that iconic orange book. Yeah, very cool. A second great book is the elements of typographic design. It kind of taught me everything about type, not just kind of choosing a font, but how to use type as a graphic and as an interface element.

• 8:19Speaker 01

  And once you sort of like, you know, you kind of know about kerning and ligatures and micro typography, line spacing, etc., you see the world in a completely different way. It's kind of like a little bit of blessing and a curse, but extremely powerful. A third great book is the design of everyday things. It's a classic. It's the the the book with the cover that has a teapot where the spout comes on at the wrong, wrong, wrong end, kind of showing you about usability. Yeah. Main takeaway from that one, actually, is to convey the importance of conveying the mental model of the apparatus or software that you build to the user through through UI, through design. But this is a tried and true classic in the design. And I have a whole thread on Twitter about some of the top design books

• 9:03Speaker 01

  that goes into more, you know, graphic design and traction design, etc., that we I'm sure can link down in the description below.

• 9:10Speaker 00

  And you said an interesting word there, taste. How do people do that? Is that something that can be learned? And if so, like, how should somebody go about getting better design taste?

• 9:20Speaker 01

  You can't maybe learn taste, but you can certainly kind of like acquire it. And again, kind of to the earlier point, by surrounding yourself and not tolerating kind of bad design. It's not about kind of being snobby. It's more about separating, like even even thinking about the design dimension and separating something from being well-designed and not well-designed, something that works and something that doesn't. And so going through life with this lens and every interaction, every doorknob that you, you know, touch, kind of thinking of it. Is this a pleasant experience? Is this a reliable design? Is this a lasting design? Is it a design that gets better with age? And I don't just mean kind of like, you know, physical patina, but also in software.

• 10:03Speaker 01

  Something that gets better over time by, you know, the the interface getting adaptive, for example. Making it more obvious how I use it, muscle memory, keyboard shortcuts, kind of peeling the onion of of sort of like, you know, interfaces. I think that's that that is where if you study that, that is where you can become a great designer. Or if you're an engineer, kind of a design-minded engineer.

• 10:24Speaker 00

  Like 20, 25 years ago, when you were kind of coming up, how did you develop that taste? Like, did you kind of have it early on? Or was it something that you just acquired over many years of surrounding yourself with great design?

• 10:37Speaker 01

  I think it was probably more the latter.

• 10:40Speaker 01

  Especially early on for me, it was not software. It was kind of more physical objects. But the importance of surrounding yourself with good things, that was sort of more a family thing. You know, don't buy like a lot of things, buy a few things that really like last and have high quality. And then evaluating kind of the object like, hmm, you know, like, why is this so pleasant to hold? Why is this, you know, work so well? How can you repair things? So repairability is also kind of like a hallmark of good design. That's where I developed kind of the sensibility and interest in, hey, like, I want to shape this myself. And once I realized, like, everything is designed, whether it's proactively designed or not, like, everything is designed, even like kind of accidental design, right? Every pen, every Every table, everything is designed. And even things that we don't think of like a designer sofa.

• 11:24Speaker 01

  Like, everything has like someone that made it. Now you can kind of consciously made it better. And especially once you understand this simple fact that everything around us is designed. There's like, well, there's not, I think this is a famous Steve Jobs quote. Like, there's people around me are not that much smarter than me, you know? So you mean like, I can actually influence all of this? And that's when I was like, aha, like naturally I need to become a designer.

• 11:47Speaker 00

  Yeah, that's actually a really interesting point, which is everything is designed. The question is whether it was intentional or not.

• 11:53Speaker 01

  Totally.

• 11:53Speaker 00

  And whether thought went into it or not.

• 11:55Speaker 01

  Totally.

• 11:55Speaker 00

  And so, you know, if you're a founder, maybe that doesn't have experience with, you know, focusing or really caring about design, because you just like to crank out the code and, you know, build the thing. What would you tell them as ways to try to acquire more of that? And things that they should focus on for why they should care about this? And why it matters to have really great design and be thoughtful and intentional about it?

• 12:19Speaker 01

  Hmm, there was a recent tweet by Gary, President here at Y Combinator. And he says kind of like, good design, especially in the early stage startups, is a lost art. And I was like, interesting, why is that? Especially now that it feels like with AI, basically, everything is getting reimagined. Design first, right? And so I was like, now is the moment where design can have the, have like a huge outside, outside impact, I feel. I think companies that recognize the value of design, especially right now, when everything is shifting, have a huge edge.

• 12:59Speaker 00

  Mm hmm. Yeah, it seems like the focus has become so much on speed, rightly so. Shipping product, building it. We don't have time to be thoughtful about the design. So whatever, you know, comes out is what comes out. And those that do put in the time to be thoughtful and focus on the things that really matter. It's felt, I think, by the end users and appreciated in a different way.

• 13:21Speaker 01

  Totally, and I think kind of design, you know, is not just kind of how it looks, but design is famously, you know, how it works. I would even take this a step further. I would say design is just how it looks, how it works, but design is how it's built. You can feel it end to end, kind of like how, you know, was there a design involved when it was built? And what technology was used? Were there, you know, loading states, latencies, all of that is in my mind kind of design. So the material that is used to create an object, a piece of software, the framework, whatever, like to me, that is part of the design.

• 13:55Speaker 00

  Yeah, absolutely. What are some tactical things that founders can do to level up their design game?

• 13:59Speaker 01

  Thinking about hiring for design early on is a really important one. So first, kind of like designers, design founders, you know, that's one aspect. But then also to, for more technical people or even designer founders, to really kind of like amplify their design, hiring talented designers relatively early on. I think that's a huge leverage. Tapping into, you know, networks such as, you know, Y Combinator or the Designer Fund here in San Francisco, that have built out these networks and bringing designers more into tech companies early on. I think this is one way to, for founders to really level up the design of their companies.

• 14:39Speaker 00

  Cool, I'd love to hear more about your design process.

• 14:42Speaker 01

  Yeah, so typically kind of for me starts sketching. I mean, you know, you oftentimes kind of first talk to users, right? You may have some intuition, but you really want to in the end solve user problems. So that's where it really starts, right? Intuition or kind of like user problems. But then when you kind of want to quickly visualize something, like very quickly move from insight to capture that insight. I still found it most efficiently to just quickly jot it down on a piece of paper. And so that's what I still kind of like use my sketchbooks for. Still just sketching a ton of interface ideas and kind of whatever is easiest for you to quickly capture the idea. I think that's most important for me is sketching. And then moving pretty quickly from capturing that sort of like visual insight

• 15:24Speaker 01

  and give it some form to starting to play with it as high fidelity as possible. For some people, this may kind of be You know, maybe taking a photo of the sketch and putting it in Figma and starting to kind of like, you know, wireframing it out or directly kind of more pixel perfect designs. What I sometimes really like to do is also just kind of take the sketch, have it on the table, and then jump into like a code editor and already kind of try to start to assemble, sort of like the UI, to start to feel it. Because I kind of like know what good looks like. I don't necessarily need to draw it out, but I want to feel whether it also feels good. And the way we're building it, whether, you know, that kind of works back to the sort of like, designing just how it looks, but how it works and also, you know, how it's built.

• 16:06Speaker 00

  Yeah. Talk more about that, because I've heard other designers talk about that, like trying to get a sense for how it feels. And when you're trying to get a sense for the feel of something that you have designed, what are the steps that you're actually going through there to tell if it feels right?

• 16:21Speaker 01

  You kind of start to develop an intuition, especially kind of just interaction design, like what works, what doesn't, what's consistent with platform norms. And this goes down to like, when should a field, you know, blur or focus? Or when should a dropdown appear when you focus the field? Like, how does it interact with text with the keyboard? So respecting kind of like, you know, user expectations and standards that they, you know, are used to from years of computing, not re-aiming the wheel, but then also pushing the boundaries, right? That's kind of where I think this dance, this elegant dance, as a designer, as a builder, kind of comes in to really start to build something that just feels right, feels fun, feels novel, but still kind of familiar. And so that's when you really need to build within the actual medium.

• 17:06Speaker 00

  Yeah, that dance is always tricky, right? Like designing a thing that people are familiar with, while also wanting to kind of push the boundaries and innovate on something new and better. And but that requires education and, you know, changing expectations around how software should work. And obviously, AI is blowing that up in so many ways. What is that dance? Like, is that just your own kind of taste? And determining, you know, where to draw the line on consistency with existing norms versus trying new things? Or how do you think about that?

• 17:38Speaker 01

  Initially, it's maybe kind of like a taste. Do I like something? Or kind of rather, does it work for me? I always kind of say like, like is not a design word. It either works or doesn't work. And so that initial assessment might kind of lie with the designer. But then pretty quickly, because you built the thing, or like at least a prototype of it, you can actually distribute it over the web or over, you know, just kind of show someone on a laptop, your prototype and let them interact with it. And ultimately, I think users are the ultimate judge whether a design works or doesn't work. You know, one of the reasons why I think sketching on paper is so powerful is because the medium of paper affords you to do anything. You don't have any constraints at that point yet. Once you start to get into like a design tool or code, you start to kind of get like

• 18:23Speaker 01

  dragged down by sort of the constraints of the medium. Paper is this super flexible. It's like, it gives you just enough sort of like boundary, right? It kind of, the page focuses you within this sort of like, you know, within the page, you kind of get an idea out of your mind. It's not this infinite thing, so the constraint there is really good. But then within the page, it's completely unconstrained. Like, I can draw anything, right?

• 18:45Speaker 00

  Yeah, you're not limited to lines and rectangles and text.

• 18:48Speaker 01

  Hundred percent, exactly. And so I think, you know, a paper is super approachable for non-designers. Everyone can like doodle, right? It's a super approachable, it's very flexible, and you can really imagine anything on the page. And then you can take it, snap the picture or whatever, send it to an engineer or a designer to kind of like increase the fidelity of it. And so-

• 19:08Speaker 00

  Or upload it to AI now?

• 19:10Speaker 01

  Exactly. And so, you know, for a while, it maybe kind of seemed that sketching is, is like clearly we should just start this digital first, right? But what if now, you know, kind of like the value of a sketch actually becomes very important again? When you can skip that entire step, you kind of jot down an idea, you quickly sketch it out, you take a picture of it, you upload it into a design tool that then turns it into the real deal, you can skip everything in between, right? And so it really then comes down to what user problem are you solving? And is it sort of like an innovative approach to solving it?

• 19:41Speaker 00

  Awesome. Well, Rafael, thank you for joining us. It was super interesting to hear about your journey and your process here, starting with sketching. I think it's really interesting to see how your mind works when you're starting on a project, all the way through the completed thing, which is- You can feel the quality in the products that you have designed. And it's no wonder that there are millions of people that are using them today.

• 20:02Speaker 01

  Yeah, and my main message for the audience would just be to encourage more designers to become founders. It's been an amazing journey for me, partly also through Y Combinator. And then for existing founders to develop a design mind, because it's going to be one of the most important skill sets to rebuild the huge next-generation companies.

• 20:25Speaker 00

  Yeah, more examples of designers that can build the product to actually execute. So much power comes with that, and so I think you're a great example of that. So thank you for joining us today.

• 20:34Speaker 01

  Thank you so much.