Get a Head Start for Your Design Career with Dan Winer | Design Aloud 🎧

In this episode, we have an in-depth conversation with Dan Winer, who is currently a Head of Design at PandaDoc. Dan is an active member on LinkedIn with over 30k followers. With over 17 years of experience as a designer, he primarily assists others in their career growth by providing thoughtful, concise tips and tricks, whether related to tools or any form of communication.

Problem solving has like three depths. You have surface level: you’re completely directed, you are given a solution and you design the solution. The second level: you solve the immediate problem that you’re being given. And then third level is that you think very deeply about what the user needs. You really understand the motivation of the user.

Design Aloud Podcast | Season 03 Episode 05

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Episode details

🔍Dan Winer shares his extensive experience and expertise to offer practical guidance for individuals aspiring to excel in the field of design.

What can the listeners learn?

  1. Dan’s journey from Windsurfing to finding passion in Design.
  2. Fun side projects to feed creativity.
  3. Business understanding, effective communication and systems thinking.
  4. Storytelling and practical ways of improving both hard and soft skills.



Karthik: So thank you so much, Dan, for joining.

I am really grateful for this and I was very happy that you were very prompt with the response and I’m happy that we can do this recording. How are you doing?

Dan: Yeah, well, first of all, it’s a pleasure to be here and I’m really happy to be doing this and yeah, I’m doing well.

Karthik: Amazing. I’ve been following you for a long time on LinkedIn and I’ve really enjoyed your reposts, posts, comments, and it was always encouraging, especially for the new designers in the company, in the UX studio and they always, share things within the Slack group.

My first question to you is how do you introduce yourself without your name or profession? 

Dan: That’s a tricky one. Also being a little bit introverted, I’m not sure I would, but [00:01:00] maybe just talk about some things that I’m interested in. So perhaps I would just say: hey, I like surfing and, spicy food.

And, how about you? I don’t know. 

Karthik: I was trying to get warmed up with a bit more of interest, personal interest. And are you based in Tenerife? 

Dan: No, it’s a place called Tarifa. So it sounds similar, but Tenerife is one of the Canary Islands, and Tarifa is on mainland Spain, but it’s right at the southern tip of Spain. So facing Morocco. You can see Morocco from 30 foots, like just 15 kilometers from Africa. 

Karthik: That’s amazing. and do you have surfing spots there? 

Dan: Yeah, we do. so it’s also very windy. So we have a lot of windsurfing and kite [00:02:00] surfing. And these days people are doing a lot of wind foiling. So surfing like on a foil. And then we also have like just normal surfing, at this time of year is when it starts.

So in the summer, it’s completely flat and windy. And then in the winter, we have surfing as well. Yeah, and that’s basically why I live here. Because of all those: the conditions on the ocean and so just a great place for all those sports.

Karthik: Yeah. It’s a nice, nice thing to do. I wish I could do surfing. Did you have a dream job when you were growing up? 

Dan: Yeah, I did. Really anything to do with the wind surfing. So at one point I was hoping to be a professional windsurfer. I realized that that wasn’t really gonna happen I’m very very bad at competition.

I get very very nervous and I am always so, and I discovered this quite early [00:03:00] on in life when I was at school. I was competing in swimming and things like this, and I would always do much worse… the more pressure there was, the worse I would perform.

So I scrapped that idea, but I still wanted something to do with windsurfing. So my dad windsurfed and he got me into it when I was a little kid. And I actually ended up traveling around teaching windsurfing for about eight years before becoming a designer. So I kind of did a little bit of my dream job. 

Karthik: Wow. That’s very nice. how did you realize this moment? What was the moment when you realized that you were not doing well during competitions or tournaments, these things. I mean, how did that realization happen at such a young age?

Dan: It was because I did swimming competitions and I could swim quite well. And like the warmups and practice, I could see that I was kind of… you can kind of know how good you are on the team [00:04:00] in the warmups. But then when you translate that into like competition swimming, I was really terrible, like one of the worst on the team. And I was just so nervous like I would do a really bad start, or I would just like be so nervous that I couldn’t really swim properly and just be thinking about the competition. And also I didn’t… the feeling before the competition was so terrible.

I know for some people, like they get excited and it’s kind of like a good excitement. And for me, it was just kind of like nervous dread. So then I never competed. And also, even if I did some photo shoots when surfing for brands and even that, like the pressure of like somebody put a camera out and then it’s like, I couldn’t, I just couldn’t do any of the tricks. And camera goes away – And then I’m just back to normal again. 

Karthik: I guess it kind of translates to a really bad –  I wouldn’t say corporate job – , but just a bad [00:05:00] job where maybe you’re being micromanaged or just looked upon all the time and there’s a pressure on you and then eventually your performance dips. Maybe it’s kind of like that.

Dan: Yeah, I don’t know. I do know that when I’m like under pressure to work on something for a deadline, then I always just put it off until the last minute and then I do it all like right before the deadline. I don’t know if that’s related at all.

But something that it didn’t translate to is interviews. So Luckily, I don’t feel the same pressure and the same nerves for interviews and getting new jobs, which is lucky. I would have thought that it might translate to that, but thankfully not. 

Karthik: That’s nice. I think it, maybe it’s a sense of autonomy and. Doing it your way. 

Dan: Yeah. Absolutely. Yeah. Could be. 

Karthik: So, how did you go from, windsurfing to design? How did that switch happen? [00:06:00] 

Dan: Yeah. It’s actually quite related. So as I said, I traveled around for eight years. So, for eight years, I was teaching windsurfing, and I would travel around to different places. I would work and live in two to three places every year. And so it was kind of like the life of a nomad.

And then I came to this place where I am now, Tarifa, and I did two summers here. Then after the second… so I did one summer and then I went off to the Caribbean, worked the winter in the Caribbean, because you can’t work in the winter as a windsurfing instructor in Europe. And so then I came back here for the summer season. And then that second summer season, I was like, I just like had enough of traveling around and I felt like this is the place I want to live. and so during that second summer season here, I started studying online.

So by this point, I was actually managing the windsurfing school.[00:07:00] And then in the evening, night, I was studying design, and so at the end of the summer, my plan was just that when the winter came, I could use design to survive the winter without having to do, like, really terrible jobs, because normally, if I didn’t have, like, a winter job or off season job, I would end up doing, like manual laboring, building sites, gardening, work, stuff like that. Because I’m a high school dropout. So, at that point it was the only thing I knew how to do that wasn’t just manual laboring was windsurfing. Then I was like, okay, I’ve got to study something, and I’ve got to figure out how to stay in Tariffa off-season and not do like really crappy jobs for very little money.

So I started studying design online. At night. Whilst managing this windsurfing center. And I offered everybody who I knew that had a business, to do a website for them and mostly just [00:08:00] for free. I had a friend who was a professional kite surfer and he wanted like a website for his to get sponsorship. I was like, yeah, no worries. I’ll do that for free.

Another friend who had like a kite surf school and I did his website for free and then then I got contacted by a local company that imported surfing, windsurfing, kitesurfing products. And they wanted some help with that catalog. They wanted to put that catalog online. So they wanted a website for that.

And then a local estate agent, then they asked me to help them with their website and SEO and stuff. So then I just built from there. And that first winter I had these website projects and then the next summer came around and my plan had been to just carry on running the school.

But then I saw that I had so much work lined up and the money was better and I was really enjoying it. And so then I was just like, Hey, you [00:09:00] know what, I’m just going to stick with this. and so that’s what I did. And that was back in 2007 and has been going ever since.

Karthik: That’s amazing. But, I have a question. How did you come across design? in the first place when you were looking for things to study. 

Dan: Yeah, I don’t. I don’t know why exactly design. It just seemed like the thing that was right. I’d already always enjoyed drawing and art as a kid. My mom is an artist. She also worked as an art teacher for a while. I have a grandmother who’s an artist. So it kind of, I guess it was in the family, and I knew I didn’t want to be like a traditional artist, but I kind of just… I guess I had that sense for kind of the aesthetic and digital [00:10:00] design seems like the way to go. So, and it, it was, so, whereas my job.

These days are more around product design and UX design. When I got into design, it was very much for the visual aspect of it. Yeah.

Karthik: Yeah. I think it was on the rise because when I started my university in 2008, I never heard about UX or HCI or design. And when I finished it in 2012, that’s when I started, maybe it came to India a bit later. I don’t know.

Dan: When I started, I’d never heard of any of these things either. And really, it was just basically graphic design, but on the web for me. And just stumbled across UX design as I got a little bit deeper into it, luckily. [00:11:00] Read some books and found out about things like user testing and actually thinking about breaking down problems rather than just doing stuff that you thought looked good.

Karthik: That’s nice. This is a really inspiring story, to be honest, stumbling upon things and just enjoying it and loving it, then that becomes beautiful. 

Dan: Yeah, well, it was a different era back then. So I was the only web designer or webmaster or whatever we called it back then. Webmaster, I guess. I was the only one in my town.

So it was that I tend to avoid posts and advice to brand new designers who have never had a job yet because when I look back on what my experience was like, I don’t give advice because I think there’s really nothing applicable from what I did to what people are going through now. So I was just like, if [00:12:00] anybody wanted a website in my town, then they would just talk to me because I was literally the only person in town that could do websites.

And it wasn’t such a common thing back then to do these kind of deals remotely, you know, like the idea of, you know, you’re based in this small town in Tarifa, I’ll just get a web designer in Madrid, like people didn’t really do business like that, you know, without meeting each other and being face to face.

Yeah, just a huge advantage of just the timing. 

Karthik: Absolutely. Speaking of advice: what would you say is an ideal or optimal path for a designer? 

Dan: Become good at what they’re doing. Yeah. So one of the things that I always encourage is hard skills first and then soft skills. And it’s kind of seems obvious, but there’s so much advice floating around for designers that I think nothing is obvious anymore because, there’s, you know, there’s literally [00:13:00] like 20 different things that you should focus on. 

And at some point, you’ll want to focus on all of them. So, if you carry on being a designer for 10 years, then you probably want to hit all of those things. But the order in which you do it, I think is pretty important.

So if you are really just starting out in design, you’re in your first job, and you’re spending all of your time focusing on product strategy or things like that and you’re not an amazing visual designer you don’t have amazing technical skills for prototyping or things like that depending on what’s expected of you in the role then you’re going to really struggle because when you’re hired as a junior designer the first thing you got to make sure you can do is execute on a plan. So there’s probably somebody else has got a plan for you. You’re not expected to come up with the whole plan and the vision and the strategy that’s probably being done for you because you’re hired as a junior.

So [00:14:00] then what’s really fundamental is: can you take this plan that somebody’s given you and can you execute efficiently? Quickly something of that’s usable, visually appealing, clickable, you know, prototype that’s ready for user testing, things like that. Can you execute that quickly and efficiently, with high quality?

If you can, that’s an incredible asset for a company to have something like that. So I always encourage people to really concentrate on those hard skills. And if you look at a lot of – what design influencers are saying  – a lot of the messages, Figma, you know, UX design is not Figma, Figma is just a tool, stuff like that. And it’s like, yes, that’s true. But if you are just starting out and you’re not really good at Figma. Or, you know, if there’s some other tool that’s being used in your company, Sketch or whatever it is, then it could be that doesn’t really matter. [00:15:00] But if you’re not good at that hard skill of creating those designs, and let’s face it, to create the designs, you need to learn the tool.

So if you haven’t gone through those steps and you haven’t mastered that then Just ignore that advice, like get really good at at the tool, get good at the fundamentals of visual design, get good at prototyping.

It depends a little bit on what your role is. So if your role is more, you know, research-heavy, then obviously there’s a different set of skills. But typically like a junior product designer, you’d want to see those, those sort of hard skills in place first, right?

Karthik:  Yeah, I’ve observed in a lot of, let’s say interview challenges as well that they heavily focus on the tool itself, how people execute designs in the tool.

It’s not [00:16:00] essentially, focused on soft skills and it’s just, the process and, the way the candidate thinks, but I do get the point of having to master the tool in a sense, because even for me, when I don’t work, let’s say for six months in a project, especially in Figma, when I use other tools, actually, and whenever, when I go back to Figma, it’s quite hard to just be really efficient with the tool itself.

Dan: And I think that if you’re finding it very difficult to use that tool. And it’s taking, you have an idea in your head and it’s taking you a really long time to get that idea onto the artboard, it slows down your creativity, it reduces your ability to go through a bunch of different ideas before the kind of fatigue sets in [00:17:00] and you’re just, you know, you’re like, Oh, I’m just over this project now, like I’ve had enough and you’ve only had, you’ve only been able to express like one idea or two ideas.

Whereas, I’ve, if you know, I kind of compare this to touch typing, right? I can personally type really fast, and that’s really helpful for me because I can get my ideas out into a document really quickly before I’m just like, okay, I’m bored of this. Now I want to go and grab something to eat. I’ll do something else.

By the time that sets in, I’ve got many ideas out into that document and with design, it’s very similar. It’s like if Figma. Using Figma is like a real barrier to you. You don’t know any shortcuts. You don’t really know how to use it. You don’t know how to use autolayout. You don’t know how to do this.

But you have like five ideas in your head that you want to express. By the time you’ve expressed the first idea in Figma like you’re over it now. You’re like, okay, I’m tired. I’ve had enough for today. I need a break or whatever it is. [00:18:00] And so it really does help as well in your ability to express your ideas visually using the tool that the company expects you to use.

If you’re good at using that tool, the only way you get good at using the tool is just putting in the hours. So that means. In a lot of cases, that means doing projects for fun, or it means doing like projects on the side, and I don’t encourage people to just, you know, go completely crazy, work 16 hours and burn out. But I mean to be honest that’s kind of what I did when I was like starting out as a designer and I know a lot of people do that when they’re starting out. It’s you just want to be better than a lot of other designers, you want to be kind of not better than other designers, but you want to stand out and you want to be really good at design.

And part of it is just practice, practice, practice. And as you get better at using the tool. You’re also hopefully getting better at [00:19:00] spacing and typography and all that kind of stuff as well, as you are getting better at the tools should go hand in hand as, as if you’re being observant and also studying the fundamentals.

Karthik: Yeah. Yeah. It’s good to be really conscious when you are trying these things out on a daily basis. Sometimes it just becomes a pattern of usage that you kind of forget the small ones. Like you said, the paddings or the typography rules, et cetera. What do you think are the top five skill sets required for a designer?

Dan: Well, I mean, a lot of people are probably not going to like this answer, but I do think the visual design is probably right up there as one of the top skills you should master.

And I know there are a lot of UX designers that don’t really need visual design [00:20:00] traditionally, you know. So they are working more on sort of problem solving and research and maybe they’re doing wireframes and they’re not expected to do visual design. I think that the era that we’re in right now, though, that’s becoming less and less prominent that role. I’m sure it could just be my experience and my experience is always in the smaller startups and it could be that in very big sort of enterprise companies and like maybe in government roles, medical roles, I’m sure that’s still a thing. So I’m sure I have blind spots, but for me visual design is really key.

Understanding your users and the different methods to which you might understand users. That’s kind of like an umbrella statement: understanding users. So within that, it could be getting good at [00:21:00] interviewing users, getting good at like asking questions that are not leading questions that are not introducing your own bias. So that’s sort of like the art of interviewing users, being able to read data, being able to analyze data effectively. When you’re looking at, a funnel, are you segmenting it by, you know, the user base that’s actually applicable to this feature that you’re working on, you know, that sort of thing.

An understanding of how to analyze data and then, you know, thinking a little bit outside of the sort of standard ways. Are you looking at reviews in the app store? You digging through support chats, you know, just like really got trying to get the voice of the customer from different angles. So that skill set. Understanding users, definitely a big one.

Understanding the business that you work in. So understanding business in [00:22:00] general, I think is very important for designers, but also within that area is understanding the specific business that you work in. And, understanding if I design this screen better, what does that mean?

Like, an increased conversion rate here. What does that feed into? What’s the sort of business indicator, what is the business KPI that affects? So understanding really how your design fits into that business where you work, then I would say effective communication. Great. So this is super important for getting you a job as a designer, for keeping you in that job as a designer, for getting you a promotion as a designer, for helping your company understand.

Why you’re designing this thing and why it’s valuable. So it’s, it’s really, it’s design is communication and how [00:23:00] you communicate your designs and your thinking is really fundamental to your, to your growth of the design on your effectiveness. And then lastly, I would say systems thinking. So, I mean, this could be a lot of things.

So I’m understanding, you know, better, better systems. For working so better systems for, exploring problems, but it could also be system design systems. So, being able to design things in a way that’s consistent and scalable. So, yeah, those are my top five, I think visual design. Understanding users, understanding the business you work in, effective communication and systems thinking.

Karthik: I was curious about the business aspect. and especially from, since you mentioned that you work with a lot of startups, how do you negotiate the business value versus your design decisions? [00:24:00] because, right now in, at what I’ve observed at studio and elsewhere as well with young startups or early startups. It’s really hard for people to convince, let’s say the clients or the businesses. To take a step back and think about, long term business, goals rather than short term quick UI fixes or UI decisions that happen usually. So how do you balance that or negotiate that? 

Dan: Yeah. So I think there’s always a bit of like push and pull between design and business. Often design is talking about things that are like hard to quantify, you know, design quality and we should make this look good or for accessibility, like, you know, this is the right thing to do. And we struggled to convert that language into something that the business cares about.[00:25:00] 

There are two ways that you need to talk about this. There are either business opportunities or there are risks to the business, and it’s very good to just frame everything you’re talking about in one or both of those aspects.

So if we talk about instead of Quality of our design work we can talk about the risk to the brand by putting out Something that’s not consistent with the brand and, then you can start to talk about, okay, well, what happens if we. What is this risk to our brand? What is the domino effect of that?

and then so that’s a lack of trust. And if there’s a lack of trust, there’s going to be a lack of signups and there’s the word of mouth will reduce and et cetera, et cetera, or [00:26:00] with accessibility. The risk there is that you get sued in some cases, and the opportunity is that we have untapped market. So you need to try and quantify the number of users that might have impaired vision that are using the side that then won’t be able to find these CTAs won’t have a clear, path towards subscribing or whatever it is.

So always just kind of bear in mind what’s the risk if we Okay. Don’t do this or if we don’t fix this and what’s the opportunity if we do do this and yeah That’s the way I always try and think about it 

Karthik: Yeah, that’s a helpful tip To help a way to think yeah business opportunities and business risks. Can you share some tips and tricks for designers to get better? It could be like an early stage as well as like senior designers [00:27:00] 

Dan: Yeah, so I guess for the thing that I touched on earlier for hard skills. The time when I have learned the quickest is when I’ve been really excited about designing something and I’ve had a little bit of sort of creative freedom over the thing that I’m designing. And that has come a lot of the time from just designing things for free.

And it can be difficult, like if you’re working all day as a designer and perhaps the thing that you’re designing doesn’t really give you any creative freedom because perhaps you’re working inside a very mature design system, or it’s just like a boring, unappealing product visually, which a lot of designers is kind of stuck in that world where you’re working on something that’s just a bunch of forms for something enterprise. And it’s not that captivating for you.

I think in that situation, if you want to get better at your visual design and your technical skills, sometimes you just have to [00:28:00] design something for fun, something that you might not get paid for and not always don’t let everything you do be a transaction for money because often that kind of stifles all the creative design.

And some people will use perhaps their portfolio as an outlet for that. But if you’re early on in your career, you maybe don’t have a lot of content to put in your portfolio. So you can’t really it can’t be this sort of rich experience when you’re designing it. So what I did early on would be just design like websites for free for people. And I would continue to do that just because it was fun for me.

So now I’m 16, 17 years into my career, I’ve designed a lot of websites for people. It’s not my idea of fun anymore, but, for a long time, that really was my idea of fun. I would just, just love to design a new website for somebody.

So find that thing [00:29:00] that’s fun for you, whether it’s like designing a website or just an app that you would use yourself or a logo for somebody or whatever it is, an icon set, that you give away for free or you try and sell. But find something that you think would be really fun to design and just go and design that thing and then, it will help you get better design in a way that, if you’re enjoying it, it’s something that you find really fun. It’ll help you get better design and also might turn in something that you can put on your portfolio as well. So that’s kind of like the hard skills.

The soft skills… a lot of it is just being intentional. So sometimes just how you share your work. You don’t think of that as a skill, right? You think of doing the work as the skill and then all you got to do is just post the link in Slack and just be like, “Hey, I did this thing. Can you check it out? Give me some feedback.”

And it’s really just being intentional. It’s thinking about [00:30:00] how should I share my work? Are there frameworks out there? What kind of feedback do I want, and what should I communicate in order to get the feedback that I want? And so, just being really intentional about it.

Some of the stuff that I’ve talked about is when you share your work, make sure you provide context, so Where does this fit in if it’s something to do with onboarding like what is onboarding and why is it important? How do we define onboarding at this company? What’s the problem this work is trying to solve? What are the business opportunities that this redesign creates? What stage is this at? So is this … are we just getting ready to like hand this over to to engineering? So we’re kind of almost done or am I just at the beginning of the project and I just like just i’m gathering data and i’ve done some rough designs, but i’m open to All kinds of ideas.

So really just approaching these things very intentionally and understanding that as you [00:31:00] become more of a senior designer or you’re aspiring to be a senior designer, it’s not just doing that design bit that’s your job. It’s it’s everything now is part of being a better designer. It’s how you present your work. It’s how you share ideas with people. It’s how you give feedback. So have you ever studied how to give feedback? You know, like, do you have a framework for giving feedback?

So it’s like all these little things, which when I, at the beginning of the call, I said, you know, there’s like 20 things that you can get better at. I mean, there’s probably more than that, but that’s what I mean. Where it’s, it’s overwhelming. If as a junior designer, you decide that you’re going to get good at all of these things at the same time as you start your career, it’s just too much and you’re probably just be average at everything and never good at one thing, but as you become a senior designer, then you’ve really got to look into all of these different areas and try and, you know, [00:32:00] improve in all these different areas.

Karthik: I think probably it kind of, I could relate this, statement of not just doing the work, but presenting it with the podcast that I’m doing, it’s not just. It doesn’t just end with recording the podcast. I have to be very intentional about the distribution part of it as well. Like how does the marketing material look? How do I schedule it? What content do I need to write?

So I totally get the point of having to present your work and gathering feedback or using that data and then improving, iterating on whatever you’re doing. So totally get that. Does it kind of circle back to – I’m just curious – , does it circle back to having a mindset of systems thinking this idea of wholeness?

Dan: [00:33:00] I’m not sure. I mean, I guess if, you know, if you zoom out, there’s always a system there. So I think systems thinking is applicable to everything. So you could say that you’re getting good at requesting feedback is, you know, improving your inputs, improving your inputs will improve the outcome.

Could be, but I think for me, the big shift is when I realized that if I just keep studying how to be better at visual design or how to be better at using this tool there was going to be less and less return professionally for that. So there comes the point in your career at the beginning where there’s just a, you don’t know, you know, right at the beginning, you have no idea how to translate an [00:34:00] idea in your head into let’s say a prototype that is effective at solving the problem and also visually appealing and it’s interactive and somebody can click through it and they can understand this idea in your head.

Not just they can grasp this idea because they’ve just performed the whole thing in this interactive prototype you created. That’s an incredible skill to have right and most people on this planet cannot do that. They can’t take an idea and make it into an interactive prototype. So if you’ve never used the design tool before the return on investment is huge to be able to get you to that point. But at some point like you’ve been doing this for a few years, at some point you want to grow your career and you want to grow as a professional and what you’re doing is just trying to get better and better at that.

There’s going to be very like the return on your investment is very weak and then you start to think okay. Well, I still want to grow. [00:35:00] I still want to get better at stuff I still want to learn like what should I learn now? And then you start to realize that there’s a whole bunch of stuff that you need to learn to grow as a designer, but none of these things are really design-related.

So there’s this like shift that has to happen where you’ve got to spend a good part of your time studying things to be a better designer, but then not design things. And so that’s kind of the shift that I think has to happen to be a better designer. And you just got to know. You got to feel when the timing is right for that.

So, yeah, 

Karthik: So there’s no framework as such, like, okay, after two years, you need to start explore, expanding your skill set. So it just based on your work and your experience and you have this moment where you feel like I need to expand my skills. 

Dan: Yeah. [00:36:00] And I think you’ll kind of feel when it’s quite easy and efficient for you to translate that idea into something visual and interactive. And it’s like, okay, well, that was easy. But that’s kind of like the easiest part of my day.

Now, you know, stakeholder management is actually much more difficult for me or this colleague of mine who’s more junior than me like they really need my advice, I can accelerate like that. They’re not doing that well, and I know I can accelerate their growth and help them perform much better in this project and be a better designer. But i’m not really sure how to approach that situation, how to give them feedback in a way that’s going to be constructive and not piss them off.

So then you’re thinking actually that’s the more difficult problem for me to solve right now than, [00:37:00] taking an idea and turning it into interactive prototypes. It’s like, I’ve done that, done that a thousand times now. That’s actually really simple. It doesn’t involve a lot of complex decision-making for me.

Now, there’s all these other things that I’m expected to do and they’re much more complicated for me. And I haven’t studied how to do them and I don’t have a sort of a framework for how to approach them. So I think you just find over time that that shift happens.

And then I think what also happens to designers is there’s like a little bit of hesitation to just go out and learn these things because it’s like, well, I’m not here to learn how to give feedback. Like I’m here just to do designs and that doesn’t feel part of your job anymore.

So that can be a little bit of also a hesitation to really like step out of your comfort zone and start to learn things that maybe you were never interested in to begin with. But at some point you realize, well. I have a choice now. I either stay kind of stuck and [00:38:00] limited in my growth, or I learn these things and, they might not be the things that I necessarily find super interesting, but I know that if I don’t learn these things, I don’t dig into them, then I won’t grow as a designer and I’ll be less effective as a designer.

So you kind of have to embrace it. 

Karthik: Totally agree. And I feel like giving feedback or receiving feedback, learning how to give feedback, these skill sets, or let’s say doing fun projects on the side, like you mentioned. I think these kind of skill sets help doing the design itself with your client project, it kind of reflects back to your original work or doing the design itself. I think all these other skillsets kind of aid to your, the design, [00:39:00] skillset itself.

Dan:. Yep. Yeah. 

Karthik: I want to go to a very specific topic now, which is problem solving. 

How can we encourage designers these days to be better problem solvers?

And the reason I ask this is because I’ve observed a lot of designers where they’ve gotten accustomed to a lot of the standardized processes. And I think we touched upon this earlier. It’s hard for them to be creative when there’s a solid design system, or a solid standardized process that the client needs, and the deadline. How can designers become better problem solvers and think more creatively?

Dan: Yeah, sure. That’s a topic I like a lot. I recently gave a talk about this and so [00:40:00] the way I like to break it down is I think about solving problems or problem solving depths in like three depths.

So the very shallow surface level designer is not really solving any problems at all. They’re just being given a solution and you design the solution. So, “Hey, I want you to design a form. It’s going to have these fields and, the, you know, I want you to design it like this and this should be a radio and this should be a checkbox. And I want a button that says send.”

And so you’re given this sort of like product spec. It’s exactly what you need to design and you design it. That’s kind of like the surface level designer. And there’s nothing wrong with that because you get to really focus on visual design. Some people really enjoy that and specialize in that. And you become like a UI designer. And that’s fine.

And you know that those people typically if that’s the level you’re working at, they won’t be solving problems, but they will [00:41:00] get better and better at visual design and transitions and animations and stuff.

Then the next level down is what most of us aspire to. And this is really where most of design occurs or UX designer product design occurs, where you get given a problem. And so it could be, you know, Hey, the conversion rate on this form is pretty low. Can you do something about it?

And so nobody’s telling you what to design, they’re giving a problem. And so you go and look at the data and you design a new solution. Maybe you break the form up into three steps, and you try to remove some fields, and then you do some user testing, and you do some testing on the original, do some testing on the new design, you compare, and you come up with the solution.

And then there’s like a third level of design where you sort of, you really go to back to what the user is trying to achieve. So, like, what is the [00:42:00] user trying to achieve, and can I do something that removes this problem completely? So like they never even have to have this problem. So, in the case of the form like, can we just get them to use the product straight away?

When they want to save something, then we ask, Hey, you know, give us your email address to save your progress. And then they can save their progress. And then if they want to use this thing that they created again, maybe they can like fill out a few more details to Karen using it or something.

Actually, this long form that you’re asked to design in that first step, we didn’t even need it to get them to use the product and reach the aha moment because we can just save the product, the thing that they’re creating in local storage and then ask them to their email address to save it permanently.

So kind of an example where. You have surface level, you’re completely directed, he second level, you solve the immediate [00:43:00] problem that you’re being given. And then third level is that you think very deeply about what the user needs. You really understand the motivation of the user.

Hey, they just want to create this thing on my service and they don’t actually want to fill out a form. So let’s give them what they want and not make them fill out a form at all because that’s not what they want. That’s not what they’re here for. So there’s kind of like these three levels and the third level is this sort of designers innovation.

Karthik: Yeah, I was curious about this, innovation aspect of it. I feel like it’s a very alternate approach to What you usually think and how do you as a designer? Think about such solutions are to be innovative, one in generally, but also to when, let’s say you don’t have access to a lot of the users, what do you do in that case?[00:44:00] 

Dan: Yeah, so if you don’t have access to the users, I think it’s incredibly difficult because the way to use design as an innovation is to deeply understand the users motivation, like what they want from the service.

If you don’t understand that deeply, then you’re at risk of just guessing and creating something new, which is going to be difficult and costly and time consuming and you’re just doing it on a guess and then that will fail and then design, will be blamed for, you know, wasting all this money and you’ll be in a worse position than where you started from. And I guess to sort of answer the original question was like, how do you get better at problem solving?

Probably the most practical way is to have a set of questions to ask at the beginning of a project. [00:45:00] So something that I call a discovery framework. So for instance, you know, the question is, what is the problem for the user? And can you describe that problem for the user in their own voice?

So it’s not enough to just guess, can you go away and get the voice of the customer where they’ve expressed, they have this problem. So back to what I was talking about, the skill of understanding your users. Can you find some like interview transcripts where they talked about this problem? Can you see an app review where they express this problem?

Really bring the voice of the customer into this project right at the beginning. So that’s the first question. What’s the problem for the user? Can you describe it in their own words? Who has this problem? So do we know who the user is? And that could be, it could be demographics, you know, the typical stuff that goes into personas, [00:46:00] but it could be, could be something like users that have used the app for more than three months, typically have this problem or, users on their first on the first day or users on this paid subscription or, you know, it could, it could be anything, anything that helps describe the sort of user that would have the problem talk about how do we know it’s a real problem?

So how do we make sure that we’re not just guessing that this is a problem? Like, do we have some data to back it up? Do we have some, I don’t know, like a dashboard that That shows poor conversion rates, something like that. Why do we think the problem occurs? What assumptions do we need to verify about why the problem occurs?

So, you know, I think that the conversion rate is low because the form is too long. So now we have an assumption. We can create a hypothesis. If we had a shorter form, the conversion rates would be better. So now we have an idea of what to [00:47:00] go and solve. But we always have to remember these unless we’ve tested them.

We have real data. These are just assumptions. So we need to verify them. And before we invest too much. And never invest too much in unverified assumptions. yeah, so it’s just having a sort of, and also like, what’s the business problem. So either what’s, you know, back to that, like risk and opportunity, what’s the risk to our business. If we don’t solve this like, what’s the opportunity that we’re trying to uncover, by solving this?

Karthik: yeah. Interesting. and, and how do you validate usually these hypotheses just through usability testing? Or is there any other way where people can validate?

And the second part of the question is, I feel like these, these methods would take a really long time, if I’m not [00:48:00] wrong. Is there like a specific time frame that you recommend to validate certain hypotheses?

Dan: Well, I think it depends a little bit on the type of business that you’re working in. So if you are an agency doing client work, then probably your timelines are much shorter. With the environment that I work in, you know, it’s a startup, and basically everything is just running forever. So you then what it comes down to is the importance of the thing that you’re working on and the risk to the business of getting it wrong. So, sometimes if, and so for this, there’s a, I wish I could remember the researcher’s name, Jeanette Fruccello or something. She has this, matrix where you can understand like how much research is needed.

So [00:49:00] basically, if you imagine there’s like this quadrant and in the quadrant where it’s like low risk, high clarity. So we understand a lot about this problem, and it’s very low risk. Then you can just kind of move fast and, you know, not spend too much time on this research and experimentation. But then if it’s very low clarity and high risk for the business, you know, then you flip that around and really need to feel a lot more certain.

And then that’s where you do a lot of research, you do a lot of testing, maybe you release first to like a small group of people. But back to your question before, like, how do you measure, how do you test the hypothesis? And is it just usability testing? It could be a little bit usability testing. So you could, yeah have like the baseline. So you have a mock-up of the current form, and you have the new one, and you do usability testing. But it really depends as well how [00:50:00] rapidly you’re able to iterate in production. So this is a little bit down to your engineering capabilities. How quick they are, how quickly they’re able to move, whether you have the technology in place to like make a change, release it to like 1 percent of your users and get feedback.

So it’s like the engineering team, the capability to release to a small stream of users, but also the ability to actually measure changes and isolate those changes and capture that data. So it’s all like, all of that is very complicated. Not very complicated, but it’s all a sign of a sort of a more mature product when they’re able to do all of those things.

And then there’s also just experiments that people set up, you know, like a fake door experiment or something like that. So, yeah, so there’s all sorts of things. There’s also just getting people to, you know, sending out a form for people to fill [00:51:00] in. That could be a way to verify, a hypothesis that people want, people want product X, you know, you just send out a form saying, Hey, would you like to be on the, on the beta list for this, for this, feature?

And then you kind of get some data on whether people are interested or not. 

Karthik: Yeah, I think, especially I’ve observed in LinkedIn that especially for people who are trying to find a job, their first job, let’s say. I really admire when they kind of post their findings or designs and then just ask for feedback.

I think that’s also a really good way of one gathering feedback, but also seeing ways to improve your own design when you don’t specifically have access to a lot of the platforms at that stage. 

Dan: Yeah. No, I think that’s great. As long as they’re actually [00:52:00] posting a little bit of context and the link to the entire design.

And I’ve often given some feedback on stuff like that. If it’s just like two screenshots side by side, which UI is better, and you have to put in no context, then it’s yeah. 

Karthik: Yeah, absolutely. I agree. Yeah. And, when you spoke about business opportunities and the risks does storytelling or storyboarding, let’s say play a crucial role in these phases or in the whole problem solving phase, I’m asking this specifically from a very artistic point of view. 

Dan: yeah, I mean, for sure. Storytelling has a huge role in design. And I don’t know if you follow Jeff White on LinkedIn, but he has a whole course for storytelling for designers now, which I think is a good testament to how important this is as [00:53:00] a skill for designers.

It’s a skill that will help you get hired in the first place. So when you do a case study presentation, or even when just write a case study, you are telling a story there. So, and stories you know, as old as humanity, well, basically as old as our civilizations are older, you know, it’s storytelling.

And so, after all those years of telling stories, we kind of know what makes a good story and what the sort of key ingredients are. So I think it’s a great skill to learn just to be able to get a job. But also, as you said, when you’re talking to stakeholders, it’s great to be able to tell a story in a format that’s sort of captivating and is going to keep their attention if you want them to invest and see the value in this project that you’re working on for sure.

And I imagine for agencies, it’s, [00:54:00] you know, it’s absolutely critical to keep people engaged and motivated in this design work that you’re doing for them. Because in the end, what you’re doing when you’re designing for that client is you’re telling them a story about the transformation that their brand is going to go through.

And it should be an interesting story and not one, you know, it shouldn’t be a sad story or a boring story. It should be an exciting story with a happy ending. 

Karthik: Yeah. We went to a really nice design festival in Berlin. It’s called Forward. And there were a lot of agencies, they’re presenting their case studies and their work.

And it was really amazing to see how they told their stories in a very creative way. So I totally agree that it just captivates. And yeah, I think the point of it is to persuade or sell your work. 

And if you want [00:55:00] to get an interview, it’s very good to have the skill set. 

Dan: Yeah. So I was just going to add that sometimes the traditional storytelling format that you might learn when you’re a kid at school, where you do like an intro and then the main, part of the story, and then a conclusion can also work against you, especially, when you have like a research paper. UX researcher presents, you know, this sort of intro of like, giving you the context and here’s why we’re doing the research. And then it talks about the research itself and how we perform the research and all the details about it. And then at the end is the conclusion. And sometimes you really need to just break the script.

What I encourage instead is just put the conclusion, and the recommendations at the top so that people that want to read the rest, it’s just because they’re genuinely interested in how research is performed. But then most people that [00:56:00] accompany are just like, I just want to know what you’re recommending or, you know, what the conclusion was.

I don’t need to read all of this stuff. So I think you, you really got to understand there’s like a time and place for different story structures as well. 

Karthik: Interesting. That’s a very interesting thing. I’ve never heard of this. So, for example, by conclusion, you mean, let’s say, Hey, through my work, I increased the conversion rate by 12 percent for this particular feature in this product so that you put that on the top.

Dan: Yeah, exactly. So leading with sort of impact where it’s like, exactly. Like I said, this is the conversion, right? You know, before it was this now it’s this here’s a before and after visual. And then you get into sort of. You know, the context, how you did it, et cetera, et cetera, because, and this is, this can be good for portfolio case studies.

It can be good for [00:57:00] UX researchers because sometimes people will just skim and they’ll be like, okay, that’s good enough for me. and they don’t actually want to read the case study. They kind of. From that bit of data and, from that visual, maybe they got enough. It’s like, you know, that data and that visual, they can probably see, okay, this is, this is interesting.

So this person, was effective at increasing the conversion rate of onboarding. So they, they know a little bit about growth design. The designs look good. They, they understand the data that’s important. That’s fine. That’s enough for me to talk to this person. Or maybe they do want to read, you know, everything about the case study, but yeah, just kind of make it skimmable and also readable.

So like the two things on offer, whereas if you put all the conclusion, you know, the impact is at the end, like a lot of these design bootcamps that structure will tell you to do it. [00:58:00] Like if it’s all at the end, then you’re forcing people to read it. Whereas if you put at the beginning, you’re giving them the option.

It’s like, either you can get all the important stuff at the beginning and read it if you want, or you can just get the important stuff. 

Karthik: Absolutely. And apart from Jeff White’s course, do you recommend any other ways to master storytelling or learn more about storytelling? 

Dan: Well, I really liked the Minto pyramid.

So this is a little bit, that’s. Basically, what I was just talking about now is, that idea of putting that important stuff up front is the principle of Minto Pyramid and yeah, so it’s, it’s like you lead with the answer first. So you make your recommendations right away and then you support that with like key facts and insights.

At that’s kind of like the [00:59:00] next bit of the pyramid and then the base of the pyramid is you back up these key insights with like the detailed data, the analysis, the evidence and all that stuff. So, yeah, I guess I would recommend anybody that’s interest in this to look at Minto’s pyramid. This is.

Developed by somebody called Barbara Minto and, her writing on it is very interesting. 

Karthik: Lovely. Okay. I will, plug these links at the end. So we’re in the final act. Let’s see. Thank you for sharing the bits on problem solving. It was really useful. can you share some nice anecdotes that are I would say completely unrelated to design, maybe to do with your windsurfing or any of your adventures that can be an inspiration for designers to think about. 

Dan: So not an anecdote, but one of the [01:00:00] sort of quotes or chapters from a design book that I really like that goes back to that idea of design as innovation is from the book, I think it’s from “the design of everyday things”. And, there is this concept, this quote really from marketing is that, “the people don’t want to buy a quarter inch drill, they want a quarter inch hole.”

And so it’s this idea that is very effective in landing page design, which is, you know, don’t sell people the features, sell them the sort of the benefit or the outcome. So in this case, like don’t sell them the drill bit, sell them the hole.

You know, another way to look at this is like the great way that I’ve seen this expressed is like, you don’t sell Mario, the flower, you [01:01:00] sell Mario, the superpowers. If you played interesting, you’ve ever played Super Mario, you know it.

And it works for landing pages, but it. It doesn’t get at the, and it gets at the problem solving things. It’s like, Hey, you know, here’s your problem solved. You got a hole in the wall, you get superpowers, but it doesn’t get at that innovation, innovation point.

And, in the book, the design of every day things Don Norman has this quote, and this passage in the book where he’s talking about. But why would anybody want a hole in their wall? Like that’s not the, that’s still an intermediate goal. And you know, that’s not like the end goal that you just want a hole in your wall.

He says probably like maybe they want like bookshelves. So if they could have a bookshelf that didn’t require a hole in the wall, then that would probably be better. Like, you know, then they don’t have to have a hole in their wall or even like books that don’t need bookshelves. So, you know, digital [01:02:00] books.

So I really love that. That concept, where he took something that it makes a lot of sense, you know, don’t sell people to drill bits on the hole in the wall. That’s a fantastic concept for marketing something. And then he really shows you the power of understanding what users want, what their motivations are, and, and takes it further.

And it really talks about how innovation really stems from this deep understanding of our users needs. . 

Karthik: Yeah, understanding. Let’s say the psychographics of the users and. Asking the question of at what point did you think that you needed this, let’s say, tool or feature or whatever.

That’s a really good question to ask, to understand the underlying motivation. Good. Do you recommend any other books apart from the design of everyday things? 

Dan: Yeah, let’s go for [01:03:00] books on So two different levels. So, you know, I talked a lot about the importance of hard skills, visual design. So for that, I really recommend a book by Adam Danway and, it’s called Practical UI.

And that is a fantastic book, it’s just an amazing guide for your visual design. Then the other book, to go to a completely different level, is a book called When Coffee and Kale Compete. And I believe there’s a free version online somewhere as well, which is great. And this is about jobs to be done theory.

So this is more about how to make sure that everything you design relates back to, what’s called in jobs to be done theory. It’s called the [01:04:00] customer’s desire for transformation. So that sort of giving them the transformation they’re looking for.

So, you know, in that previous example. The transformation they’re looking for wasn’t a hole in the wall of transformation. They were looking for was like some beautiful bookshelves. 

Karthik: Right. Right. Yeah. Super. I will, thank these as well. Thank you for sharing these. Any other, initiatives or closing thoughts that you would like to share with the listeners?

Dan: No, I think covered most of it. You know, I guess if there’s one thing that I would like to kind of make clear is that although I recommend a lot of these sort of hard skills at the beginning, the visual design and stuff, ultimately, what I think design is about is creating that understanding of what your users, your customers, what they’re looking for. And finding the sort of most [01:05:00] innovative and transformative ways, to give them that solution and, you know, in ways that overlap with, business needs as well.

So, it’s that interplay between customer needs and the business objectives is what you’re aiming for. 

Karthik: Absolutely. And I really liked it when you said being intentional, I think it, it is a very underrated word. I think the intentional is really good and it makes you a bit more conscious of things. I think that’s needed to understand users deeply.

Dan: Yeah. Yeah. Great. 

Karthik: Amazing. Thank you so much, Dan, for this chat. I really enjoyed the conversation. Yeah. There’s a lot of highlights we can share from this podcast and yeah. 

Thank you so much. 

Dan: Oh, it’s a pleasure. Really fun. 



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Design Aloud is a podcast hosted by UX studio. Through this podcast, our goal is to spotlight UX and other disciplines that emphasise people and their needs in the realm of design.

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