Michael Riddering on Navigating Startups, Launch Days, and the Future of UX

Alex Smith: Design Leader Insights is brought to you by Fuego UX. Fuego UX is a leading UX research, strategy, and design consultancy. Hey, Michael. Thanks so much for joining the show today. 

Michael Riddering: Yeah. Thanks for having me. It's been fun. 

Alex Smith: Yeah, for sure. And to get started, can you give us a little bit of context and insight into your journey in UX design? 

Michael Riddering: Yeah. So I was actually like a founder turned designer after many years of designing every day. And maybe kind of actually turning back into a founder. I'm not even really sure to be honest, but I've spent the vast majority of my career, either working on my own startups or doing design for different startups. Most recently, I spent the last few years as the Founding Designer for Maven. So I've been thinking a lot about education as of late.

Alex Smith: I think that's an interesting topic that is not a typical journey of a lot of leaders that have joined the show. Which is super interesting. I think I have a few questions around this. How should maybe a founder listening who's not design savvy, someone just looking to start a business, think about design is the first one I'll ask.

Michael Riddering: I think that the best way that a founder can set up like an early designer for success is by really just like inserting them as high up the value chain as possible. So I've worked with different types of founders and some of them are like very prescriptive, basically like. Just design this thing, just make it look pretty kind of thing. And I've worked with others who very much so invite design into like the early stages of the conversation when you're still trying to figure out what even should we do. And so if you basically try to create design as a role where they're not just solving problems, but you're actually tasking design with the responsibility of finding the right problems to solve and getting people excited about solving those problems in the beginning. I think that is like a good measuring stick where you're not just going to create like a more healthy culture, but I think you're going to ultimately design a better product. 

Alex Smith: And understand the users better from the get go. And then I think the flip side of that, which you touched on a little bit is, a lot of designers now, a lot of designers I talk to, are burned out and they're like, I want to go to, I want to go to something new, something small. Like, I think it's, it's a great idea for a lot of reasons. And I think it's also a risk because there's a lot of founders that don't understand design or they don't, you know, have any maturity in their design. Or what advice would you give to those designers who are hungry to join a startup? 

Michael Riddering: You know, I've actually been asking a lot of people this question and the advice that I've even been getting is pretty clear. And that is people at the top startups look for designers who have built something from scratch.

They have some kind of a side project. They've launched something into the market. And it's a scary thing to do, but it's also so exhilarating. You're going to learn so much. Like, I'm a big, big believer that everyone should have at least one launch day under their belt. Like, put something on Product Hunt and just feel the rush kind of thing. Like, who cares if it flops? Showing that you can go from zero to one on something. And then also be able to take those next steps, like learn from the market's response, what worked, what didn't work? What were those iterations that you made after launch day? Like if you can bring something like that to the table, it's going to, it's going to mean so much more than any resume, than any portfolio website, even like having that under your belt, I fully believe is the best way to get noticed by the top startups today.

Alex Smith: I think, you know, from our unsubstantiated, you know, we haven't done a ton of research on this, but just the pulse in the market, a lot of design teams are now reporting the product in B2B. How, as a designer, are you encouraging designers to learn product management traits or learn what products up to, or go be a PM for a little bit, or are you saying, hey, let product on this design, do this. It's kind of changing. At least that's what I get a sense for. How do you think about that?

Michael Riddering: I'm always going to be a champion of more generalist designers who don't really put too much weight on the typical box that we think of as like the roles and responsibilities of a product designer. So yeah, like I wrote a lot of PRDs and like really started thinking about different product requirements. And I think there's a level of like the management piece that I don't, I wouldn't say that I did a ton of but early stage thinking through the scope of a project and the right questions to answer and where we need to get aligned as a team before we're even really getting too far into Figma at all, like very much so I think that is, it just sits right in between like maybe like a designer and a product owner and it's like totally on the table and up for grabs for design in my opinion. And oftentimes I would like contribute pretty heavily in that part of the process. Man even beyond managing product on a specific project, I think it's so important for design to have an opinion on like higher level product strategy and like where you think the product roadmap should go and why and a big part of that too like that is very much so just like my experience, but I think oftentimes you get the opposite advice so I'll talk about it really quickly is like people, you know, you'll hear people talk about like you know, don't put too much weight on your competitors, just stay heads down and execute kind of thing. And I obsessed over the competitive landscape for years. I mean obsessed. I had a notion database with every single product. Not only that was in the competitive landscape, but like tangential to it. And it was filtered and broken down perfectly. I had all over the flows documented. I had subscribed to all of the, like, founder updates from every product in the space, and I read every single word of them. I got investor updates from products in the space. Like, I, in many ways, positioned myself as the keeper of the competitive landscape, even more so than the founders to an extent where the founders would come to me and say like, hey, what do you think like X product is doing? Like what, where are they headed kind of thing. And you can start to identify opportunities and create this lens that you can even view specific projects through, because you know, these companies that are. Considering this kind of surface area as a part of their value proposition, here's how they attack it. And here's like how we can do something that is unique or more opinionated or something that is like more specific that these other companies have to create like more of a generic blanket use case for. I think having that level of understanding is like such an easy way that any designer out there can develop the product sense, but also give credibility to their voice whenever they do weigh in on product strategy. 

Alex Smith: Yeah, I love that advice. I mean, I think competitive research should be key to all user research, which designers should be doing. We've talked about this a little bit but it's a question I always ask. What is like some, some key advice you have for new designers entering the field today in, in a frankly difficult market.

Michael Riddering: I actually think that we radically underestimate the value of strong visual skills in today's market. Like if you're looking for a role, the fact is nobody's going to look at your case studies unless you check that initial box of like, okay, this person demonstrates the ability to execute on like basic visual fundamentals. They know how to use typography. They know how to use layout. They know how to use spacing, contrast, all of this stuff. If you can't do that, I think, I think it's going to be tough. I think it's going to be really, really tough because there are people that can and that also have the same case study caliber as you. So like, don't overlook that is my first piece of advice that I just have to say, even though it's like not that novel, it's like, I have to say it. I think design can be so easily paired with other skill sets. And so thinking strategically about like, what's a unique intersection that I can create for myself. You know, even just two skills, just two skills or something else that I compare with design where I can position myself and create some kind of a narrative about myself or why I am a unique candidate and it could be almost anything like we've talked a little bit about product management. I think that counts like demonstrating that like, Hey, I can, I can wear this hat and move this kind of needle for the company. Technical skills are another big one. Like if you can write basic front end code, it's a really big deal. Especially if you want to get a role at a company that is either a startup or like some of the top product teams, I think actually do have more of their designer's code. I literally just got off a call with the team at Notion and that was a requirement for all of their early designers because that's just something they believed in. And so it's like that is a way to make yourself more unique. There's also this like marketing lens too, where if you can create basic, basic visuals, graphics videos that you can use to market a product, I think that's like a really underestimated skill set for designers. Like when I was almost at every company I've ever been at, I made all the marketing videos. Like we were going to make a product announcement and some kind of like a go to market strategy. Like I'd create some kind of a simple prototype and Figma and take a screen recording of the two things, turn it into a GIF and give it to the person that's writing the email, like little things like that. I think that maybe the high level takeaway is just like find something that you can sell yourself on that again, exists outside of that typical box of what a designer should do. And I think it's like a really, really easy way to differentiate yourself in the market. 

‍Alex Smith: Michael at the end here, I want to kind of touch on your own podcast that you have. Where can people go to find that and kind of what, what are you talking about on there?

‍Michael Riddering: Yeah, so I'm really kind of just focusing almost all of my attention on this right now. If you go to dive.club, this is where I'm hosting all of the different episodes where I'm trying like you to just interview designers who are moving the needle at like the, the, the teams that we all look up to, right, whether that's like a notion or a linear and trying to find unique stories around craft or even just like design systems at scale, or what does it look like when you're the first designer or second designer at this like high growth startup? What does that actual journey look like? How are people learning and growing? It's definitely supposed to be educational in nature. Like I love learning. So I try to find people that I can learn from and hope that others can as well. 

Alex Smith: Love it. Yeah, I'll definitely check that out. And thanks so much for joining this series.

Michael Riddering: Yeah, absolutely. This has been really fun. Thanks for having me on.