Design Leader Insights - Dan Winer's Approach to Effective Communication in the Workplace

October 30, 2023


Alex Smith:   Design leader insights is brought to you by Fuego UX, a UX research, strategy and design consultancy. Hey, Dan, thanks so much for joining the show today. 

Dan Winer: Hey, Alex. Pleasure, yeah happy to be here. 

Alex Smith:   Yeah. Awesome. And as we get started, can you give the audience a bit of context on your journey in UX? 

Dan Winer: Sure. So I've been designing since around 2007. I started out doing print design and then websites and also along the way, a lot of graphic design, flyers, things like that. Fell in love with doing web design, got my first product design job, probably around 2009, 2010. And then, yeah, ever since that I've worked at small startups and became a design manager around 2015 and. Been doing that ever since. At the moment, I'm head of design for a company called and it's an e-commerce related app for loyalty. So mainly Shopify stores, but also Wix and big commerce. And so we have a loyalty program, which shoppers interact with. So we have millions of shoppers using it. So we have the shopper persona to think about. And we also have like the admin area for the merchants. So like a B2B side of it, which they are our main customers. But having to think about these two personas and create interfaces for both is really awesome. And it's kind of a good challenge. 

Alex Smith:   I want to dive into that in a second, but I want to also touch on the fact that you're doing this all from Spain, one of my favorite countries in the world. And I think it's super cool that you designed your life around a place you want to be, which is Tarifa, which I've been to, a little coastal town.

Dan Winer: That's awesome that you’ve been here. So I've always worked from home. I've actually never worked in an office. The way I ended up becoming a designer was because I was basically in love with Tarifa and I wanted to live here all year round. My kind of origin story is a little bit different. For eight years I was teaching windsurfing and I was traveling around the world teaching windsurfing. And eventually I got tired of being a nomad. So not a digital nomad, but I was just like living in maybe like three different countries a year. And it was, it was kind of a dream for a while. And it's what I set out to do was pay my way around the world by teaching windsurfing and discovering all these different places. And then I ended up in Tarifa and I was just like, okay, this is, this is the place. So I borrowed some money to do a course in design and the course was, like, Photoshop HTML, CSS, PHP, MySQL, like, all of this like, Dreamweaver, stuff that, like, now is completely irrelevant, but was basically just, like, everything you could imagine related to websites and I was really enjoying it and making, making more money than I had done previously. So yeah, I was hooked and I was just like, okay, now I'm just going to do this.

Alex Smith:   Makes a lot of sense. Let's switch gears into one of your side projects, which has a ton of followers and you know, a lot of good advice and content about moving up in your career. Let's touch on those. 

Dan Winer: Yeah. So, I guess the theme around a lot of what I write is that early on in your career, you kind of need to be able to execute on ideas and it could be somebody else's ideas, but you need to, you need to be able to use the tools. You need to be able to use Figma. You need to be able to design a prototype. But then eventually if you're just sort of executing on other people's ideas and just doing, doing what you're told and producing mockups that won't be enough for you, right? That's good enough to perhaps get you a job and to perform at that job for a while. But if you want to get paid more, have you know, change your title to mid or senior designer, there's going to be more expected from you. And a lot of that's going to be around how you plan your work and communicate your work and show the value of what you're working on. And so that's the kind of stuff that I focus on. And in my writing, I try to give the same sort of tips that I would give to somebody that I would be mentoring or managing to help them become a more senior designer. Like one practical example is you're sharing your work, you've got this prototype, you know, various screens that you've linked together and you're ready for feedback and a junior designer, and also myself, you know, a few years ago, the way you typically do that is just say, hey, I've been working on that thing. Tell me what you think. Like a little kind of coaching tip I would give for that is instead of just chucking it out there and hoping for feedback, and it's going to be a bit hit and miss because you don't know if the person that looked at the prototype really understood what it is and what it's for and what kind of feedback you need. How about some context? So let's say this prototype is for onboarding. How about you define what onboarding is? So like we define onboarding as the moment when the merchant installs our app until they've had their first shopper redeem points, for example. Let's say that's the definition. And we think onboarding is really important because it's the way that they launch their program and it's the way they understand the value of what we provide them. You know, some context like that. So tell people this area in the app, like, what is it? Why is it important? Explain what the problem is for the user. So what is this problem that you're trying to solve? Explain maybe some of the goals of the redesign. So by doing this redesign, we hope to increase launch rates, or we hope to optimize the program settings or whatever it is. Tell the audience what your goals are. Consider a video walkthrough of the prototype. So people might just click around and just feel a bit lost. Maybe. It's better for them to just watch you talking through it. Show people what you tried already and why you rejected those. So the things that didn't make it into it and then tell people the kind of feedback that you're looking for. So is this just like a real blue sky thing? And it's just, hey, I'm just open to completely new ideas. Or has this been through some review cycles? And it's like, I'm just about to do some user testing, just tell me if you spot something that's really like a glaring error? So that's just like taking one example. Like, how do you share your work? And you can see that like between the just hey, what do you think to that sort of structured approach. Not only have you, what you've done is you've shared a lot of knowledge with the people that are going to look at your designs. So now it's not just, it's not just a one way thing where I want something from you. It's like, hey, I'm giving you all of this context and knowledge about this area of the app that I've been digging into. So now you have more information, you have more knowledge about it, and now I'm asking something from you in return. But not just that, it's also setting you up for presenting case studies, maybe for an interview in a much more structured way. So it has sort of like a compounding effect. 

Alex Smith:   I love that. That's gold. Like context, context, context. Pretty quickly if people are applying that level of advice that you're giving them, they're going to be asked to lead, right? Like if someone's actually doing everything you just mentioned, they're going to be seen as like, Hey, this, this is a leader right here. They just explained everything to every team and broke down silos.

Dan Winer: I think the only post I've written about it is a post on why It was like a post saying why you might not be cut out for this or why you might not want to be a manager. And because a lot of the sort of reasons why we get into design, they sort of disappear once you become a manager and you start to wonder occasionally, like, why am I doing this? Like, I got into design to, for those moments where it's like headphones on and I'm in a Figma and I'm just really enjoying like creating this thing and then I'm hooking it up and I'm playing with the interactions and, and then you don't really get that anymore. And so then you start to wonder, like, did I make the right decision and I've spoken to a lot of managers and they all kind of have this, this moment where they're like, oh no, did I make a mistake? And a lot of managers end up going back to becoming ICs. And also something when I first became a manager, I did the same thing. So I became a people manager. I did it really badly. And then I wanted, I went back to being a product designer. And the thing that I did really badly as well was, sort of trying to manage the end of the process. So have you got this thing ready? Like, is it on time? Does it meet the requirements? And not very much of the sort of player coach thing. So the player coach analogy is great. So if like, you're not really coaching your players and you're just worrying about how they perform, like on the pitch, obviously it's going to go badly. Once the game starts, like, they should be ready and they should be supported and up to that point. So that's the kind of concept I have now, which is like, when designers are working on something, I'm assuming that they are prepared and they know what's expected of them and they're going to do a great job. Because it's all about supporting and preparing them for that up front and not like chasing the results at the end. So that's kind of the shift in mindset that I've had that really has helped me enjoy this role where it's, you know, it's more about the success of the people that you're managing and being more like a coach and less like a manager.

Alex Smith:  I love that. Well, thanks so much for chatting, Dan. Where can people go to find more? Where would you point people to find more or connect with you? 

Dan Winer: Yeah. So my writing on LinkedIn, of course, I'm pretty active there. And also I am starting to write some sort of longer form information or guide about design careers. So that's a There's a wait list to sign up. And that's really like a whole kind of structured approach to effective communication and planning out your career. And there's going to be some guidance on preparing for interviews and building your personal brand as a designer, all kinds of things like that at the end of every section. There's some ideas for something that you could add to your personal growth plan. So I'm trying to make it really actionable and a sort of resource that you can use to put together a personal growth plan for your design career.

Alex Smith:   Cool. I'll check that out. And thanks so much for the chat today. 

Dan Winer: Cool. It was a pleasure. Nice to chat to you, Alex.