UX Design isn’t about building beautiful products for the sake of beauty itself, says Jon Daiello. We’re building something that solves people’s problems. “Design isn’t here to just manufacture,” Jon adds. “It’s here to help us understand what we should manufacture. That’s one of the big distinctions.”

In this episode of the Product Momentum Podcast, Sean and Paul chat with Jon Daiello. Jon is a UX Design Manager at Paychex, where he encourages his designers to “have your head in the clouds and your feet in the mud.”

Think of design as “a long-term investment,” he says, like retirement planning. “You don’t start a job and have your retirement built on day one. Design is like that; you’re looking into the future and asking, ‘What is my goal? Where do I want to go? What do I want this thing to be in the end?’ Design can really help you kind of tease out what that future could look like.”

Over time, within the team’s Agile process, you’re choosing the most important pieces to deliver, Jon adds. So the business case is understanding that Agile practices are not in competition with design; but that they’re inside the process and baked in in a way that works with design.

Catch the entire conversation to hear Jon’s practical tips for answering the ultimate question: what are we actually solving for?

• Get as many people involved as possible; workshops help.
• Be creative with time you have available – even just an hour here or there can be productive.
• Creativity blocked? Change your workspace. Try a different design medium.
• Simple design tools like paper & pencil help express design ideas quickly and cheaply.

Early bird pricing is now available as the ITX Product + Design Conference returns. Save the date: June 22-23 in Rochester, NY. Learn more.

Podcast: Play in new window | Download

Paul [00:00:19] Hello and welcome to Product Momentum, where we hope to entertain, educate, and celebrate the amazing product people who are helping to shape our community’s way ahead. My name is Paul Gebel and I’m the Director of Product Innovation at ITX. Along with my co-host, Sean Flaherty, and our amazing production team and occasional guest host, we record and release a conversation with a product thought leader, writer, speaker, or maker who has something to share with the community every two weeks.

Paul [00:00:43] Hey, Sean, how are you?

Sean [00:00:44] I’m doing great, Paul.

Paul [00:00:46] I am jazzed about the conversation we just had with Jon Daiello. He brings such a pragmatic approach to building a business case but also connecting empathetically for the human beings whose problems we’re trying to solve.

Sean [00:00:59] For sure. I loved his philosophy around design’s purpose not being to create, it’s about making things work better.

Paul [00:01:07] Yep.

Sean [00:01:07] I love that.

Paul [00:01:08] I think this is the first time we’ve also mentioned sidewalk chalk in an interview.

Sean [00:01:12] I think it is.

Paul [00:01:12] Lots of salient points, and I think my favorite takeaway is that you need to keep your head in the clouds and your feet in the mud.

Sean [00:01:18] Let’s get after it.

Paul [00:01:18] Let’s get after it.

Paul [00:01:22] Well hey, folks, and welcome to the pod. Today, we’re pleased to be joined by Jon Daiello. Jon’s a UX design manager with a passion for building strong designers that can create amazing experiences. His background as a product designer and front-end developer are used every day to foster innovative collaboration across multiple disciplines. He’s based in the lovely Dayton, Ohio, with his family, where they’re engaged in community activities outside of work, in his ample free time, I’m sure. Jon, welcome to the pod. Happy to have you.

Jon [00:01:49] Yeah, it’s great to be here. I’m happy to be here, Paul.

Paul [00:01:51] Awesome. So before the show, we talked a lot about investing in design systems within product teams and building sort of thought models to help bring some more agility, some more resilience to the practice. There’s been some criticism that there is a push to return to some waterfall practices or that design debt can be mitigated by a more lean approach. So just to get us started, can you tell us about some of the challenges that you observe on product teams that you work with in the way that design is framed?

Jon [00:02:19] Yeah, definitely. And this is not just, like, even my own experience, but I’ve found as I’ve talked to other like UX and design leaders in the industry, it’s kind of a pervasive flaw is that we kind of want to treat design almost like a manufacturing line sometimes. Like, we expect what the input is. We have known variables throughout all the pieces and parts lined up, and then you expect design to have the outcome that you want. And that’s a very linear kind of way of thinking. And design is traditionally and like psychologically a non-linear kind of way of thinking.

Jon [00:02:49] And when you treat design in a linear pattern, you actually lose all the exploration, all the opportunities, all the things that design can actually kind of stumble on and explore and understand, it’s really easy to lose that because you have already come to the table with what you think you know and what you think you want. And it really robs you of the opportunity that design brings to the table, which is that wide exploration, that ability to kind of deeply hone in on what a problem is and how do we understand it, and how do we actually craft something that really fits well with that problem, to really solve it and really bring your value proposition to the end user in a way that’s valuable?

Paul [00:03:27] Yeah. So I think that that kind of begs the question then, in this agile world where stakeholders and shareholders and board members and entrepreneurs are all trying to get things to market as fast as possible, how do we build a business case for design in this mindset?

Jon [00:03:43] Yeah. Long and slow. You know, because we really have this maybe misunderstanding of design that’s kind of culturally grown, it’s going to take some time to undo what we believe we know about design. And so I think one of the best business cases, like just to think about it, is it’s a long-term investment. Just like with your retirement, you don’t have your first job and you don’t have your retirement built on day one. What you’re doing is you’re looking out in the future and saying, “what is my goal, where do I want to go? What do we want this thing to be in the end? What do we actually want to offer? What do we want to do with it?” And having that big vision, design can really help you kind of tease out what that future could look like, start putting some visuals to it, start putting some early prototypes to it.

Jon [00:04:24] And then in that Agile process over time, you can start choosing what the most important pieces are to start delivering. So you can actually really understand if what you believe to be true about the future is actually true. Maybe you’re ahead of the curve and you need to wait until technology catches up. Or maybe what you thought you knew about the problem, you actually misunderstood, and now the problem is a little bit different than what you thought before. So I think the business case really is, you know, there’s lean practices, there’s Agile practices. They’re not in competition with design. They just need to make sure that they’re inside the process and baked in in a way that actually works with the design process.

Sean [00:04:59] Yeah, I think there’s got to be some kind of balance, right? So you need to get stuff built and that requires discipline and you need good designers for that, but you also need to have possibility injected into the equation. So you have to have some people thinking about, you know, what’s possible, what you called the wide exploration that has to be done to maximize creativity. So do you think that you have to create a divide in terms of your design teams? Like some people should be working on production and some people should be working on creativity? Is it everyone’s job? How do you find that balance on a team?

Jon [00:05:32] I think it really depends upon the skills of the people; it depends upon the makeup of your team. I’ve seen that divide where you have sort of the design UX strategy wing of people and they’re sort of feeding out these like long-term ideas and then you sort of have like a shorter-term team where they’re focusing more on the details, the implementation, or what the product’s going to look like in the next year or two. It’s definitely a way of doing it.

Jon [00:05:53] I prefer to try to get as many people involved in shaping that future as possible. So I really like to think about workshops you can run where the short term, you get a couple of people in a room, you hammer out what five years might look like. And then you bring another set of people and just continue shaping that over time. That way you get a really broad collaboration. You’re not sort of locked into any one person’s view. You really can start to sharpen the edges off of a really rough object pretty quickly that way. So, you know, my own preference is to get as many people involved as possible, but really keep it scoped on those short sort of stints of project to help tease out what that future will look like.

Sean [00:06:27] Yeah, I think that’s a brilliant answer. So your answer to the question is, well, everybody’s responsible for the creativity and the delivery.

Jon [00:06:34] Yeah.

Sean [00:06:35] So the way to do it is to segment the time up, like make sure that you’ve got some purposeful time, we call them workshops, and find the balance that way. I love that answer.

Jon [00:06:44] Yeah, and you know, that can be a challenge too, if you’re locked into like a traditional two-week Agile sprint module or, you know, if you’re doing that sort of sprint planning every few weeks, that cadence can be really difficult to inject that time. But even be able to find like an hour or two for designers to come together, workshop something out, and move forward, even that’s progress towards that sort of end goal. So you can kind of get creative with the time you have available.

Sean [00:07:05] Yeah. This, I think, goes back to the premise that more minds are always better, right? And we want as much creative capacity and thinking about the problems as often as possible within the limits of the business and getting things done.

Jon [00:07:18] Yeah, definitely.

Paul [00:07:22] Hey, folks, please excuse the quick break in our conversation, but I have some exciting news to share with everyone. Save the date. It is the ITX Product & Design Conference. We’re back, so mark your calendars. It’s going to be June 22nd and 23rd, 2023, right here in Rochester, New York. Also, back for this year’s conference to M.C. is the one and only Mike Bellsito of Product Collective. We’re going to have workshops, keynotes with industry thought leaders, opportunities to network with fellow product and design professionals. It’s just going to be a great environment and will be right in the heart of all the action during the opening weekend of the Rochester International Jazz Fest. We’re still working to finalize the speakers for this year’s lineup, but to give you a taste, last year we had Adam Lawrence and Mark Stickdorn, who were also guests on Episode 87 here of the pod. They talked to us about service design. We had Cindy Alvarez, the director of UX at PowerPoint and the author of Lean Customer Development, and she gave a workshop on conducting better customer interviews. And Holly Hester-Reilly was also there, who joined us on episode 33 of the pod. She shared a day two keynote on ways to leverage continuous discovery to become a high-growth product leader. So whether you choose the product track or the design track, there’s something for everyone. If you want to learn more, head over to ITX.com and there’s a link right at the top of the page. You can register to stay in touch and also check out the archives from 2022. All right, back to the conversation.

Paul [00:08:46] So I wanted to dig into your backlog. I’ve watched a bunch of your YouTube videos and read a bunch of your writing on how you approach this problem of UX, especially in a fast-paced product environment. You’ve alluded to heroes of the industry: Nigel Cross, Jesse James Garrett, and, you know, they have decades of foundation in this kind of thinking. So I wanted to get back to something really concrete, like what is a success metric? When you’re looking at a team, sort of a matrix product team with a product owner, maybe a Scrum master, developers, and a UX designer that’s supporting the vision, what kind of things come to mind when you’re looking at, how do you get through the day? And you just mentioned something that I think is really, really pertinent. It could just be an hour. We kind of have this idea that, like, in order to build the right design, it’s going to take months and months. But oftentimes some dedicated thought carved out deliberately can make all the difference in the world. What are some other things that you coach your folks around or your community around to help them think about what success looks like as a designer in teams like this?

Jon [00:09:49] Yeah, one of the things I think is most important for a designer is to grapple with both the idea of what is way out in the future to come, so, you know, Bill Buxton talks about like a designer who has their head in the clouds with their feet in the mud, right, that’s like the designer. Like, thinking about where can we go, what can we do, what’s possible, like way, way broad stuff that’s like kind of fringe. And this is where designers sometimes get the rap for, “you’re crazy; that’s never going to work.” Yeah, okay, maybe that doesn’t work, but we can learn from that and put our feet in the mud and say, “What can we do with it? Then what is possible?” So that’s something I really like to try to encourage designers to be able to create themselves is that ability to step out, go beyond the norm, try something you know is wrong, but still learn from it and bring it back into, alright, so what can we do with it that would actually work? And that ability to think creatively, but also, practically, at the same time, bouncing back and forth, that’s a huge skill.

Paul [00:10:44] I love that, “head in the clouds and feet in the mud.” That really speaks to product development overall. I think the product manager leading as voice of the user, an advocate of customers, and trying to build that empathy. And really, that’s what it’s all about, connecting with people’s problems and goals. And we’re not trying to build the most beautiful product for the sake of beauty itself. We’re trying to build something that solves people’s problems, right?

Jon [00:11:08] Yeah, absolutely. And I think that’s one of the big distinctions, is that design isn’t here to just manufacture. Design is here to help you understand what you should manufacture. And that’s really what we’re trying to do. We’re not trying to just make sure that we’re creating, but we’re also creating the best thing to express the best value possible. You’ve got a really clear value proposition; your product strategy is locked in; now all of a sudden design can come in and make that real for you. How does that express? What do the experiences look like? What’s the digital realm? What’s the entire customer experience wrapped around that? I think that’s the power of design and oftentimes it kind of gets locked into the final few stages of, like, the UI. But design is a far more broad discipline that we can apply not just to the UI, but to sort of that whole stack of thinking in between.

Paul [00:11:55] So what do you tell a designer on a team just starting out? The head in the clouds and feet in the mud analogy is great, and being able to parse between the strategic possibility and the tactical, “what do I need to get this user story complete?” What are some things that you do to help maintain that span of thinking? Because it’s got to take a toll over time.

Jon [00:12:13] Yeah.

Paul [00:12:13] Being stretched so broadly across that kind of thinking, what are some tools in your toolbox that help you support the teams that you’re on?

Jon [00:12:21] Yeah. One is just a simple pencil and paper. It’s the cheapest, most easy medium for any designer to start thinking about what could be. It doesn’t involve a lot of investment. It’s quick, it’s dirty, you can take that paper and throw it away. Even some of the like the most famous designers that, you know, Nigel Cross spent time studying, their first medium was always pencil and paper, just love, love that. But over time, then, you know, as you start to develop this, you’re going to get really disappointed really fast because you’re going to want to do these huge, big ideas that are world-changing, but you don’t have time and budget to do it all this year. You might not even have time and budget to do it in five years. So one of the things I try to build into designers is a patience that over time you can get there. What’s the most valuable thing we can focus on today that’s going to push us towards that end goal? So that head in the clouds is really important, but it has to be grounded in the world of reality or else, all of a sudden design is going to fail, you’re going to invest everything upfront and maybe you haven’t really fully vetted out the solution yet, so.

Sean [00:13:19] Yeah, I want to pull on that thread a little more about simple tools like a pencil and paper. You know, we have these really complicated, beautiful design tools available to us now, and I think the tendency is always just to jump right in and start designing it. So how do you take the time to actually sit down and sketch things out and find ways to banter with just simple tools?

Jon [00:13:44] Yeah. You know, with my background in design and actually coming through a design program and, you know, I was formally trained more in like visual and graphic design, but I always sort of was applying that to the world of digital because I knew, for me, that was where I wanted to go. And so over time, you know, if I see a designer or if I myself am really grappling with a problem and I’m working in a high-fidelity tool like Figma or Sketch or, you know, Adobe XD or something like that, that’s where we want to gravitate to. You’re absolutely right. But really quickly, we can get locked in because we’re stuck in that high-fidelity mode. So if I’m ever feeling like it’s not actually satisfying this problem, I know what I’m trying to get the user to and I can’t get there, I’m working with too much detail and I pull it back and I find a way to get a designer or team focused on something far more loose. So maybe it’s still a digital tool like Miro or FigJam or something like that, but they’re still getting away from that high fidelity to the really low fidelity, really rough, really crude where you can express ideas quickly because that’s really kind of the goal of sketching or something like that is to get your idea out there fast, get it out of your head, get it on paper, so it can kind of talk back to you. “Oh, yeah, that works’ oh, no, that doesn’t work; that was crazy.” So…

Sean [00:14:51] Yeah, along those lines, you know, you rarely hear about creatives having that aha moment while they’re sitting at their desk staring at the screen.

Jon [00:14:59] Mm-hmm.

Sean [00:15:00] When you said this, it just made me think about, you know, periodically just getting out of your normal pattern. So, like, sometimes I’ll just go to a coffee shop with a pen and paper and think about some of these problems. You can only do that really well, you know, with a pen and paper.

Jon [00:15:14] Yeah. There’s lots of different approaches to really invoking what you’re talking about, like, a creativity, like getting your mind to think creatively about a problem or a set of solutions in front of you. I wrote a really short, tiny book just recently, over the last year or two, on the topic of creativity, because I feel like a lot of us don’t know how to push it, like how do we invoke it? How do we make it go? So I just looked at like 13 different ways. And you’re absolutely right. You just listed like two or three of them, actually, in your answer, Sean.

Jon [00:15:41] Number one: change your workspace. Just get out of what you’re in. Like if you’re locked in, seeing the same thing over and over again, it’s not going to help you think differently. It’s going to reinforce your old patterns of thinking. Try a different medium. Like I recommend getting a giant piece of sidewalk chalk and go try and draw out your solution on a piece of sidewalk. Like, it’s a different sensation, it’s a different feeling. You’re going to smell different stuff, like, you’re just getting out of your normal flow to try to get different sensory input because that actually does have an effect on what we think about and how we’re perceiving our world.

Paul [00:16:10] Spoken like a parent of small children. I completely relate to that.

Jon [00:16:14] Absolutely. I have a giant box of sidewalk chalk in my garage. Love it.

Paul [00:16:20] Absolutely. I think there’s also a hidden benefit to pencil and paper because the word that’s coming to mind is confidence. Because once you have it sketched out in pencil and you can see where you’ve erased and you’ve got the edges around, when you take out that micron 0.7 millimeter and you start inking over it, there’s a confidence that comes. You can’t start with ink, you can’t start with the final. But once you have the skeleton and you’ve made all the mistakes, there’s something that comes from going over it and making it more permanent that you just, you can’t connect to if you start from that high fidelity mindset that you were talking about before. Because it really is a process that has to evolve and emerge over time. So I think that analogy holds up all the way down. It’s a really great way to think of it. Coming back to another story that you told us getting ready for the conversation, I’m curious if you could help us unpack briefly how you relate automotive design to UI and UX design. Can you maybe recap and share what that is and pull us into your mindset there?

Jon [00:17:19] Sure. So first of all, credit to Nigel Cross. In his book Design Thinking, he tells the story. So I just retell it with a little bit of emphasis. But one of the things that was really interesting is when Nigel Cross was doing sort of a psychological study on what makes really good designers, he pulled out this case study of Gordon Murray, who was working for Brabham at the time, and he’s really famous for a lot of different things, like, if you know of the McLaren F1 or any of the like the sort of like super, hypercar industry, he kind of was instrumental in that.

Jon [00:17:48] But when he was working on a Formula One team, they brought this new problem. Formula One said, “cars are going around corners too fast and the drivers are beginning to experience more and more g-force, and it’s not safe. So all cars can’t be less than six centimeters off the ground. They have to measure six centimeters off the ground.” So all the teams had gotten really good at like finding ways of getting the car lower to the ground so it would have more stickiness, they could go around the corner faster. And when a lot of teams started abandoning that, “just saying, all right, six centimeters, that’s it,” Gordon Murray set to work. Strategically, he knew races are won and lost in the corners. If I can keep my speed up through the corner, we’re good.

Jon [00:18:25] So he started taking a systematic approach to the car, figuring out, “what’s the actual problem we’re trying to solve for?” And he came up with this like crazy hydraulic solution where all the hydraulic fluid in the car was managed in a way that when the car got up to speed, it would actually settle down much lower than six centimeters. When you’re parked and it’s in the pits, measure six centimeters, no problem. But physically, you could see as it’s driving around the track, it gets lower and lower. And they were at points in corners down at one centimeter because they actually had the ability to think through the systems, the pieces at play, and they knew they had to measure at six centimeters, so they satisfied that rule. But with a lot of time, testing, development of new systems, they actually created an advantage, a strategic advantage of being able to blow the competitors away around the corners.

Jon [00:19:11] And it took time, right? It took exploration. It took kind of a wild, crazy idea to think about, “what if all the fluid in the car was managed in a way that would allow the car to settle in lower?” And that’s kind of the exploration that I really want to encourage, you know, product leaders and design leaders to think about is, “how do we actually get people to think in terms of that, those creative, systematic approaches that really allow people to come up with innovations and then figure out practically, does that actually fit with our strategy? Do we go down that road? How do we prototype and build a cheap test to figure out whether or not it’s possible?” Because that was really part of the whole process there. And yes, he did start with sketches; they’re in the book.

Paul [00:19:48] Absolutely. And that kind of speaks to the UX and product development industry, where compliance and security and accessibility and all of the things that we know are sort of the rules of the road, to stretch the pun, is imposing on the design system that the product will be felt through. But if we don’t take those as rules to govern us, but rather a fence to operate within freely, now we can start to not see them as roadblocks, man, I’m just stretching this pun as far as it’ll go, we can start to see them as ways to get creative about the problem and see them not as barriers, but as ways to actually get more competitive, as in the case of the hypercar industry.

Jon [00:20:25] Yeah, absolutely. I mean, these laws and these rules that governments are putting out to regulate our data and to keep us safe, those are important, those are good, and we want to uphold them. But you don’t need to bring a bunch of extra assumptions along with that. And that’s really where design and research can come in and really understand, “so what are we actually solving for?” Like, how do we actually preserve the goodness of what’s online and prevent what’s bad while still giving a very unique experience to your product that gives you that competitive advantage?

Sean [00:20:52] All right. Well, I’ve captured a bunch of things here, some great ideas from you, Jon. I’m going to summarize them in parts. I got a couple of key takeaways for the audience. You ready?

Jon [00:21:00] Yeah, go for it.

Sean [00:21:01] So first, design is a nonlinear thing because creativity requires wide exploration. Rigid process for the sake of rigid process has the potential to stifle that innovation and creativity. Second thing I think associated with that, to some extent, is how do we create the space for this exploration? And your one-word answer would be workshops.

Jon [00:21:23] Sure, yeah.

Sean [00:21:24] Getting as many minds as possible thinking about the problems, especially the minds that are closest to the problems, the ones that are working on it every day.

Jon [00:21:33] Yeah, absolutely. And it can be hard, you know, to wrangle a lot of people around a problem. But, you know, one of the tactics I’ve taken is, if I’ve got 30 people I want to be involved in a problem, you know, grab a random sample groups of small like 3 to 7 people, get them in a room, and then work through another 3 to 7 people. That way you can get those people involved without winding up with sort of, like, a gangly, hard-to-manage group. So there are definitely creative ways around that.

Sean [00:21:58] Love it. The third thing I captured was, “keep your head the clouds, but your feet in the mud,” which I think is a muscle. And that’s the key takeaway I got, is that design leaders, and all leaders, really, need to hone that skill and work that muscle. You got to find the balance.

Jon [00:22:13] Yep, you know, and some people are going to be better at one side versus the other, and that’s okay. And that’s where, like, good team composition can come in to really stretch each other and help grow both that crazy, high, Bill Buxton, “Where are we going? What could be possible?” with the mud in the messiness of reality.

Sean [00:22:29] I love it. And number four is that design’s purpose, contrary to popular belief in most of the language we hear about it, is not to create.

Jon [00:22:38] Mm-hmm.

Sean [00:22:39] It’s to make things work better. Which tied into something you said at the tail end. Like, purposefully taking a systematic approach to problem-solving can pay huge dividends. And I love that, I love that Formula One story. So that’s a great anecdote. Number six, we don’t need complicated tools all the time. Your point being, that they can actually stifle our ability to iterate if we are focused more on the tool than we are on the ideas. Change the texture. Change the things that you would normally do just to try to spark a little more creativity.

Jon [00:23:16] Yeah, absolutely. I think, you know, a tool wants to work a particular way. The more complex the tool, the more complex it wants to work. A pencil is a lead on a piece of paper, and so it tells you very little and allows a lot of freedom.

Sean [00:23:30] Simple. I love that. Great analogy.

Paul [00:23:34] So wrapping things up with their time together, Jon, what we ask most of our guests on the way out is just a quick take, what would you say your definition of innovation is? How would you define that word or concept, innovation?

Paul [00:23:47] Oh, man, that’s a great question. When I think of innovation, off the cuff, my response would be a new approach to solving a problem that creates a new kind of value.

Sean [00:23:59] A new kind of value. Interesting. Cool, you’ve mentioned a bunch of books. What are you reading now? What do you recommend for the audience in terms of books?

Paul [00:24:07] Yeah, in terms of the books, I always, always recommend Jesse James Garrett: The Elements of User Experience. It’s been around forever, but it’s still good today. I totally recommend that. Nigel Cross’s book Design Thinking. Love that one, one of the early books around how designers think. Currently, I’m reading a book by Joseph McCormick called Brief and it’s how to say more with less words. And it has been fantastic. I love it.

Paul [00:24:32] It is next on my reading list. I’m glad you mentioned that one. I look forward to it. Well, great ads and great conversation. Thanks so much for taking the time, Jon. This has been a blast, just kind of getting a peek inside your workflow, your mindset. I really appreciate it.

Jon [00:24:44] Awesome Paul, and awesome, Sean. I really appreciate being here. Thanks for inviting me. This is my hobby horse, so I’m always happy to talk about it.

Sean [00:24:50] Awesome.

Paul [00:24:50] Love it. Cheers.

Paul [00:24:54] Well, that’s it for today. In line with our goals of transparency and listening, we really want to hear from you. Sean and I are committed to reading every piece of feedback that we get, so please leave a comment or a rating wherever you’re listening to this podcast. Not only does it help us continue to improve, but it also helps the show climb up the rankings so that we can help other listeners move, touch, and inspire the world, just like you’re doing. Thanks, everyone. We’ll see you next episode.