Inside Shopify UX S2 EP03 | CEO and founder Tobi Lütke on UX at Shopify

An interview with UX Director Lola Oyelayo-Pearson and CEO and founder Tobi Lütke

Lola Oyelayo-Pearson: Welcome to Inside Shopify UX. I’m your host, Lola Oyelayo-Pearson, UX Director at Shopify. On today’s episode, I speak with founder and CEO of Shopify, Tobi Lütke. We’ll reminisce about some of Shopify’s previous designs, chat about the value of design systems, and of course, play a game of kiss, marry, kill. Let’s get into it. I am absolutely delighted to have Tobi Lütke on the show today for us to talk about all things UX, and I have been promised strong opinions and things that’ll definitely make the discussion interesting. So I’m gonna poke for all of those things. Thank you so much for being here, Tobi.

Tobi Lütke: Thanks very much for having me. I’m thrilled to be here.

Lola: Cool. So I want to go straight in with a question that’s just good framing because I think your external brand is very much the developer/CEO, getting into all the code, but you’re also very opinionated about user experience and design. So frame that for the audience. What is your ethos and philosophy around user experience?

Tobi: Yeah, that’s a big topic. So absolutely, in terms of my skillset, I’m an engineer. I’m extremely bad at designing things. I have some fun stories about early Shopify days that might be able to illustrate this, but I probably have been around the internet long enough. It used to be that one person actually did everything.

Lola: Yeah.

Tobi: I guess that’s where it started.

Lola: The full stack web developer that just did absolutely everything.

Tobi: It’s interesting, right? There was no such term but it was just like you did things on the internet. So that involved reasoning our own network protocols, deterministic stacks, and of course, engineering, but you did all of this for a very particular purpose which was so that people would get software one way or another. Especially in the 90’s. Actually, I heard someone frame the 90’s as the late 2000's.

Lola: The early 2000's?

Tobi: Yeah, the late 20th century or something like that. That’s a funny framing about this.

Lola: That makes me feel old.

Tobi: Yeah, yeah, yeah.

Lola: Yeah, I’m not a fan of that framing.

Tobi: Yeah, okay, cut this out. But I think it’s worthwhile to make it sound further away because it really is further away. Back then, every time someone did something it was basically the first time people got something. But you built for people. I grew up in Germany and my experience is also my parents also are not people who can design things but the nice thing about growing up in Germany in the 80’s and 90’s is that the products that people just had in their houses were largely designed by Dieter Rams and others.

Lola: Yeah.

Tobi: The nice thing is you go in a museum now and see these exhibits and that’s actually what a living room in Europe looked like during those times. So it was a time of terrible haircuts but also of really, really good product design. There’s a sort of metriality to these things that are just powerful and you’re surrounded by this. I encountered computers, wrote some basic and wrote some code, but clearly not the same kind of thought than interface. It was clear that there was potential to bring these principals into this world but that hasn’t happened. And so not wanting to spend too much time on this, I consider myself sort of a Toronto-raptors superfan of UX. I jump around and I see something amazing because I find every time it is such an incredible discipline because the most powerful thing that we’ve been working on in the last probably half century in the world of computing and software but none of it can be utilized to the benefit of people without actually making it sensible and approachable. And so the entire point is to make great UX, it supports that because you want to give people amazing abilities.

Lola: I absolutely believe that fundamentally. The tech should be designed around people, not for the tech’s sake. But UX does have this huge spectrum, right? One of the successful things we’ve done as a discipline is we’ve professionalized. So we’ve created it, we’ve made it a craft, we’ve made it so that there are qualifications, there are specific skillsets that you need, but then there’s this kind of other end of it which is still creative and subjective. So you were talking, essentially, about Bauhaus, design principles, which a lot of people love and there’s a lot of great deconstruction of it, but it’s also quite stark style and quite stark taste, and there are entire cultures that absolutely would hate that because it feels flat. So there’s this creative layer. So I’m interested in how you’ve seen that through Shopify. How are we balancing? Because we’ve had people on the episode talking about Hydrogen and Dev Docs and how opinionated and bold and specific the taste and the style that we’ve gone through is there, but still this kind of very functional and purposefully designed surfaces. So how do you rationalize those two things of designing for the user but also having a strong opinion that means somebody’s not gonna like it, right?

Tobi: Yeah. I think there’s a couple of different ways to get at this, but I think fun is one of those things. I think is a general criticism of Bauhaus. I like to figure out what’s behind things. So I love a story behind the object, usually a lot more than the object. Is the thing a product of deep thought? And if so, I think it’s something that should be judged as such. I think then there is a subjective layer of okay well, what’s it look like? And then how does it work? Is it intuitive, does it do the job well? And you have to put them all together, and I think people sometimes end up a little bit overemphasizing the quantifiable. Highly utilitarian is a very reductionist way of looking at things. So I think pure utilitarianism is not something my countrymen tend to be good at, but even there I would point out that the biggest exports of the German economy certainly are the cars and I do think they are very good examples of things that are not purely utilitarian. I think logistically from A to B, you can get everywhere a lot cheaper. There’s a lot of emotion underneath this, and I think the reason the cars that we are now picturing in our minds, why they do so well is because everyone who works on them knows this. This is not people cosplaying car builders. This is people who have an extraordinarily strong sense of who they’re building for and they tend to be okay with not building for everyone, and I think this one of the most key things which is just hugely important. I’m sure this is a topic that comes up over and over and over again.

Lola: Yeah.

Tobi: I’ve actually been looking for it, this is an essay which must be 15 years old. It was written by Kathy Sierra, given the time I forgot the name, but basically, it made a point which I think now is maybe better understood but was very new to me when I came across it for the first time. What she said is, she built this shortened diagram where there was love and hate on both the sides and it illustrated over the top that there’s a green zone close to both those things, and then there’s a very large piece in the middle called irrelevance. This is certainly one of those spiky opinions which very sensibly people would take another side on, but I do believe that. I think if you make something that anyone loves, some people also hate it, and I think actually the up sense of someone hating it is actually a sign that the thing you did might be somewhere in the middle and not fully committed to a particular vision.

Lola: Yeah, and I think this is a philosophy that I like to walk the line of which is it’s okay for someone to not like something as long as we’re not getting in their way. If they had to use it, it still works and it works really well. But you can have opinions about how something looks all day every day. I personally do really like pushing some of the work that we do at Shopify to not do … One of the things I was saying to my team is I care less about consistency than maybe I should as a head of UX because consistency assumes norming and I’m kind of thinking that norming is a bit boring, number one. I don’t want to work on stuff that has already been defined. It’s also not why I came to Shopify. But it also means that we’re not creatively expanding. We’re not trying new things, we’re not building and creating new paradigms, and trying to extend the possibility. But it does connect to something maybe more practical, which is the fact that we are seen in the world as being innovators in design systems because of how robust Polaris is and how powerful it is, and the fact that there’s a bunch of places you can go on the internet that look very Shopify because they basically just borrowed Polaris and that’s a good thing, but is it a burden for us? I’m asking that because I think it is, but I’m interested in your framing on that.

Tobi: Again, let’s unpack this. Everything is a mixed bag. There is no free lunch. Every time we do something, you also say no to something else and you have to be okay with that. Shopify’s very, very big software, I just checked, I think it’s something like 2.5 million lines of code in typescript just for the UX. The scale is sometimes just absolutely crazy. We could get an incredible amount of value out of a design system. The width of Shopify and all the screens it has and the teams.

The design system does something incredibly important which is that we put centrally a system together that then makes it easy for everyone to succeed. What it does is it raises the floor a lot, and this sounds like downside protection but actually, it’s incredible. For instance, when I open vs code into an admin project, even with my programmer art kind of thing, I can actually do something that people can then reason about, if this is valuable to you, that’s incredible. So design systems are incredible at raising thought. So where they can be problematic is if they lower the ceiling, and I think this goes right back into this conversation about how thoughtful are people when they build something, that we had earlier.

Especially when design systems exist, they feel like a set of constraints even though they aren’t. This is a fine line and actually, a line that requires constant adjustment inside a company. It’s actually not a line that comes from restrictions in code, it’s a cultural thing. It’s like what do you believe this system should do for you? Again, does it help you get started, or is it a setup that pushes conformity and sameness? It certainly looks like that’s what a design system would do and making it not do that is a constant conversation that I see teams having. I think this works well if you build your own design system because then you have all the people who understand the reason why it exists there. If you just adopt a design system from some other place, I think without understanding how complicated the cultural conversation can be, it might end up restricting you quite a bit.

Lola: Yeah, and I think we had a great conversation with Roy and Yesenia on one of the episodes and that was part of the conversation. It’s this idea of the ceiling going up and then floor going up. The design system helps us be mostly good, and a lot of things that you would otherwise have to think about are kind of taken care of. But then there’s this other thing which is how high is the ceiling? And how creative can you still be even when you use that? And I think it’s an interesting tension, and certainly my push at the moment is sometimes start the Figma file without the UI kit. Blank sheet of paper. Just do something that doesn’t feel like anything else yet because we can always pull it back, but start with a “what if” kind of question in your mind. And even given the breadth of some of the solutions we’re designing, like in my world we’re building financial products, the what if is not a Shopify competitor, it’s a financial product that exists in the world. Even just starting from a blank sheet of paper and say how do I solve this problem? And then I can work back how does this problem fit inside of Shopify later.

But it is something that I think we have to keep pushing at, that door that we’re okay with possibility exploration. And this is touching on the next subject because this is going to the sometimes part of that work means coming up with wild shit that is not buildable.

Tobi: Totally.

Lola: You said something to me in the chat, you talk about the Dribbblification of design where things are designed without hard constraints, and I feel like sometimes you should do that as a designer. Sometimes creatives need to let loose and shake off a boundary and do something that is way out there just to pull some good ideas into practical land. But I guess if you spend all your time on Dribbble, you’re probably getting way too much of that and not enough of the practical experience which is where designers get a little bit stuck. So unpack that for me. What is that Dribbblification of design as you called it?

Tobi: Okay, so this is something my co-founder Daniel, who you should have on the show as well, said a lot. What he said often is if you take 10 random people off the street and you ask them all their favorite color and you would then do an alpha blend on those colors, you would end up with mud brownish no one likes. Which again, you always end up coming to the same topic which is unfortunate because what you really should do, because every one of the individual colors that anyone picked would actually be a good solve, where the blend isn’t. So this is never a way to come at it, consensus decision making is in the way of making great things. At some point, I think the best projects, even though maybe not everyone is conscious of this, almost create a little bit of a democratic challenge to everyone about who cares most or who has the best sense of constraints and possibilities and for the highest ceiling, and then creates a thing that everyone just looks at this and says okay, that’s the way to go. And then everyone says okay, I’m gonna support you on your vision with everything else I got.

The best teams tend to resemble almost jazz bands a little bit more than other analogies. One person sets the key and the pace and then everyone else brings everything they know about their instrument and that’s actually fluid and changes depending on the style of music that’s coming. But it’s very fluid and improv, and I love that process. I think constraints can be good if they facilitate more of that creativity to happen. Because for instance, again back to our jazz analogy here, a constraint that exists in there is everyone says hey, from that time to that time, we’re gonna play music. That’s a constraint. People don’t think about it as such.

Lola: Yeah, we only have so much time, yeah. Or so many players in the band.

Tobi: Exactly. So anyway, what am I saying? Here’s the problem with Dribbblification as I see it, not a statement about Dribbble being bad, what I’m saying is you end up in a popularity contest but popularity contests will always be won by the thing that is least objectionable. Because again, it’s always gonna be a much smaller group of people who love something and it’s usually counterbalanced by someone who hates it, and that gets you a middling score. Again, if you blend everyone’s, get the thing that no one hates but more than 50% would like, it ends up doing better in design contests than a popularity contest, and the problem is, especially if you spent if then you spent a lot of your creative output making things and posting them, you will eventually work towards an audience, but you learn about what good looks like from an undifferentiated popularity contest rather than honing your own standards. And I think this is important.

People need to understand what great work looks like for themselves. This is something I always push with all the engineers I’ve ever worked with, and it’s something that we use a lot in Shopify, I actually learned a lot from UX world and jazz as I just said, I think one thing which really helps in the UX world is also learning engineering principles because every discipline is figuring out a lot of important things which then become relevant to everyone. So one thing I always push and always horrifies people is deleting code. The many very important features in Shopify-

Lola: Breaking things, basically.

Tobi: Yes. Well, not just subtracting things, but actually when we net new features we developed in such a way that we said this feature, the way we built this is we’re gonna start every single day from nothing and we ship it the day that the entire feature is going to be implementable in 24 hours or in a single workday. And this sounds surprising that this is an approach, but it led to probably some of the best code we’ve ever written and we worked as pair programming on these kind of things, and we kept the unit tests. But the point of this was the following: Almost all programming is not actually writing code. What you actually do is you’re building a model of a solution. You’re actually exploring the problem set deeply by trying to reflect it as a model in code and as an idea about UX and so on. So 90% of the work on a project is actually this building up of your mental model, using your creativity to find novel solutions to the same problem, and I think UX is that too. In fact, it’s actually kind of better in the form that your deliverable at the end of the day is something that everyone can reason about rather than just other engineers, and I think it helps everyone.

Lola: It is. It is. I think the thing that I would add to that is that the biggest difference for me between say like 2000’s UX and the 10’s and now we’re entering into, I don’t know what we’re calling them, the 20’s again, is how you marry up something that looks good with something that works really well. And so for me, the analogy that I like to use is imagine fashion houses. Your average person is not gonna go to a couture fashion show, but that couture fashion show and those highly opinionated, super random designs inspire in house designers in Zara and H&M and other brands, and they cultivate ideas that become part of clothes we wear every day and they’re very useful and they’re ready to wear type stuff, but the people who keep pushing the edges actually drag the rest of us with them as well. So in UX, it’s making space for yes, know what you’re building, yes, know how it’s being built, and actually even taking constraints from the engineering. So things like motion studies and looking at key interactions and stuff like that, but also giving yourself space to sometimes be a couture season or something like that. So like a couture season and just be like at some times I’m gonna do a runway show of just wild ideas, and that’s probably gonna trigger a bunch of small improvements or ideas in creative and lots of other places that people can pick up and build from in the depths of constraint land.

Tobi: I totally agree. I love this. I find it super important to just explore. Again, the way I’ve always done this, and this might be not relevant, is always by setting constraints. For instance, time limits. Today, I work only by using the mouse with my left hand or something like this, it sounds like a silly idea. But it’s interesting how that changes things, and you might end up winding up with some empathy for … My guitar teacher taught me once, I was complaining about lack of progress, he just asked me hey, turn around the guitar, play the fretboard from the other side, and I was terrible and he said okay, so did that feel harder to do than what you’re doing? And I said yes, and he said well, that’s exactly what it felt like the first time you picked up a guitar, so stop complaining about lack of progress.

It’s these kind of things that are just really useful, but then also, just do something completely different. Every single time you do, you will come back from that particular journey with something. The universe always conspires to make whatever you explored useful magically on the next project.

Lola: In some way, yeah, exactly. You will learn hard and then you will fold it in. So maybe on that question, what is our age? ’Cause I see different things. Sometimes I see that we’re 15, sometimes we’re 17, but Shopify’s like 17 years old or something, right?

Tobi: Yes. Yeah, it depends on we launched at 15 years ago and started as the snowboard shop 17 years ago.

Lola: Oh, 17 years ago, okay. So in the 15 years of official Shopify, what are some of the most spectacularly badly designed things that we shipped well intentioned but in hindsight you’re just like ugh? Either that didn’t work or that was ugly AF and why did we do it?

Tobi: Lots of things come to … You should go in the Wayback Machine to the first Shopify.com, it’s rough.

Lola: Wow, so you did this. You restored it the other day and I was looking, you had that project internally, like an old version of Shopify, and I was like oh okay, this is super interesting. Really cool to see but also like woof! in there.

Tobi: Now to be fair, sometimes we look at these through the Wayback Machine on things and we need to remind ourselves that we now have high DPI displays that didn’t exist back then so the horrible looking images.

So yes, we have internally bootstrapped a Shopify museum which is a version of Shopify as it was in the various years leading up to now, which is a very cool exercise because what you see is a lot of the bones are there. This is really important, especially in this context here. Shopify fundamentally is a very, very successful company now that got launched based on UX. I’m an engineer, but engineering was not the killer feature here. Shopify was not the first e-commerce software and the engineering side of the house came to the task bringing what it had and that was enough, but the new thing, the unlock, was it was the first e-commerce software actually designed for new brands to actually directly start. Everything else in the industry before it was to support existing businesses because that’s where the money was.

Lola: Yeah.

Tobi: Exactly. And try to get the existing retailers, and because we were kind of building this for ourselves and we wanted to start on it and not start a retail business first, and that just was a different set of constraints because suddenly we said okay, well, we have to make something that’s approachable to the people who want to reach for independence during their lunch break. The people who were thinking about plan B-

Lola: The side hustler dreamers, kind of thing.

Tobi: Exactly. And so we were forged in these fires. Our users are very different to everyone else, were people who didn’t know a lot about retail, they didn’t have a lot of time, didn’t have no money either, which some argued makes this a bad business, but that doesn’t matter because that was the mission, we’re building for them. And this meant that we would have to make something approachable which was extraordinarily difficult to do at the time, especially at those times before you got all the goodies, which we got since.

Lola: Yes, internet was harder then.

Tobi: Yes. But that’s what we launched against. The product was take the existing capabilities of the global world of supply chains and retail with all its warehouse location centers, ships, containers, and all these things, and making all that addressable through software, model that, and then put an approachable UX on top of all this insanity that someone can use to run a side hustle from. So it is a UX job, the whole company is. So I think this is why this has been such a primary thing, and I think this is also why we feel a little bit like … I would like to think of Shopify as being as intentional about this. We’ve been at the forefront of, people make fun of that tool now, but at some point, that was basically what is now, and suddenly it was the place where a lot of people brainstormed about hey, how does internet software looks like and how to make it better. So we were part of that mix and so I think we should continue holding onto standards of pushing this forward because the web browser’s an amazing thing that would never be allowed into anyone’s app store ever again. So making the best use of it is very important.

Lola: So you’ve kind of avoided my question though, and you said you had a bunch of examples of things that we didn’t do very well.

Tobi: Okay.

Lola: So at least one.

Tobi: Shopify.com Wayback Machine is super embarrassing.

Tobi: Let’s see … My business cards were terrible. I found some recently, it’s horrible. There’s some really dodgily designed things. Here’s what we did before design systems existed and the floor was easy to bring up. This is not a word of a lie, this is how it worked. At some point Daniel asked me to just stop cosplaying being UX person or designer and he would just make anything look good, and I should just do the programming.

Lola: So he kept you away from the design side?

Tobi: Yeah, yeah. But then I needed to hold him to actually making things good before they go out for shipping, and that’s been some spectacular failures along both lines as well. So we ended up where we agreed to do the following: There was a css class in our css files called eye cancer. It was absolutely terrible, it should never be used.

Lola: Okay, things that give you eye cancer, okay.

Tobi: Yes. It was pink and padding of 50 and a blue border.

Lola: Oh my god, it sounds amazing.

Tobi: Yes. So basically, I was supposed to put eye cancer on everything I’m doing, and then Daniel would get a message immediately and knew what he would have to do before something went out to production.

Lola: So this is like a tag on Tobi’s stuff so that it did not ship before it was actually designed.

Tobi: Yup. Before the days of code reviews and pull requests and all these kinds of things we didn’t have. So that was the way we worked together.

Lola: I quite like the idea of you doing rogue design shit and sneak it into production and having someone else come down on you and be like what the hell have you done?

Tobi: There was a famous case of me shipping something that’s still involved, sadly, this particular css class, and then having to run to the airport and being on a flight to Europe, and two things happened during this time. A, there was a downtime issue, and there was production code which… So both of us being because I somehow needed to ship to production before going to the airport and then there was a bit of a family intervention in early Shopify with shipping to production. Anyway, good times.

Lola: Keeping Tobi away from design. Okay, ’cause in today’s era, you do not stay way from design. You’re in our UX channels, you give a ton of really good feedback, sometimes it’s a bit like oh, Tobi hates it and people are like oof, what do we do? So how do you rationalize that old involvement in UX when you had Daniel as your buffer to today’s model where we’ve got hundreds of UX people across the company doing a bunch of different things, but you are very, very present sometimes in our creative work and shaping what goes out? Like would we be able to ship something that you didn’t like but you felt like it did the job really well?

Tobi: Sure, absolutely.

Lola: Okay.

Tobi: I don’t think my involvement is that much on taste and aesthetics, it’s on the consideration that went into it usually. I have two advantages. I generally have fairly high standards for myself and for the company which is useful. Lots of people have that, so that’s not my main contribution. My main contribution is uniquely I’ve seen all 17 years of this company and so I know the conversations leading up to the conversations, so I can help discover what’s behind things, and I know the merchants really well. I’ve talked with thousands and tens of thousands of them over the years. I know what they tell me about the early days. I have empathy because I sell myself, I’m a user of Shopify, so I have that perspective. So the thing I tend to give the most feedback on is when I see a category error around the empathy and mental state that the users might be in. You’re talking about building financial products, so this is very, very, very common in your space, but when you’re building a user interface, you’re building not just for … Sometimes I use baseball cards of people and some of them have a lot of context, but some of them often they talk a little bit more about socioeconomic things rather than actually what are they trying to do. What’s the job to be done, and especially on finance. The amount of anxiety is massive. Where you meet people, it needs to be clear to everyone who’s designing your interface because even today, we had a conversation in another forum.

We were talking about charts, and I’m trying to poke holes into people’s use of red, the color red. The color red is wonderful in the context of destructive operations, I think then that’s exactly what people actually should worry about, but if it’s like hey, in a week after, we’re recording this in the week after, like Black Friday Cyber Monday, so basically, there’s millions of Shopify stores right now which have a week over week growth number which is probably a reduction, and that is not hey, stop what you’re doing and pay attention to this number, that is just simply an occurrence. That has to do with their business. So empathetically, we are suggesting to people that they should be worried about something when they shouldn’t. So anyway, this is a random example of the kind of discussions I have with people. What I’m trying to say is that should probably be gray because it’s expected. Green is notable because something happened.

Lola: Yeah, yeah. Yeah, yeah, yeah. Colorblindness allowing.

Tobi: Yeah, yeah, of course.

Lola: I think what I’m hearing is the pattern. What is the pattern that’s being communicated here? Should you be worried about the thing that you’re seeing? Are you supposed to take action on it or not? And I think also speaking to the type of person we’re helping on Shopify, we’re not assuming a level of business nous or just literacy in finance and retail operations that means that they look at these things and just get it straight away, you have to just provide a little bit more of a step to get them to a healthier space. So I get that. Okay, we’re almost at time, but I want to do one crazy thing with you, Tobi, because you’re on Twitter a lot, you talk about Discord and Reddit. Kiss, marry, kill. Twitter, Discord, Reddit.

Tobi: Kiss, marry, kill?

Lola: Yeah, this is a CEO friendly version that’s not using a swear word, but you know what I mean, okay.

Tobi: Okay, so sorry. I need a reason for this. You’re giving me three things and I’m supposed to do three different things and this is an exclusive set, right?

Lola: Okay, so you’ve not played this game before?

Tobi: I think I need a stat solver for this, this is complicated.

Lola: Okay, no, no. So this is a great game. I just did it at a Burst last week and totally freaked my team out. But it is forcing you into a binary decision about each product. Which one would you kiss? So essentially, which one is the fleeting fantasy. Which one are you staying with in a long term relationship, in a sort of marriage? Which one are you killing? And it’s just a great way to draw out how you’re seeing these different services and the purpose that they serve for you, because you’re very active on all of them and I think people can find you in a bunch of places having various chats. So I’m just interested in how you see it.

Tobi: Sorry, it was Discord, Twitter, and?

Lola: Reddit.

Tobi: Reddit, okay. I would, hmm. Okay, I’d kill Twitter because Twitter I have the strongest emotion to.

Lola: It tends to bring out the strongest emotions in other people too, yeah.

Tobi: Yeah, I’d marry Reddit just because of the wonderful frivolousness and crazy that’s there but honestly, here’s the thing, these are Rorschach tests. It’s my filter bubble on Reddit is just very different from my filter bubble on Twitter. I think Discord is … I can’t decide if Discord is great UX or not, it’s this sort of hot mess that somehow always has these moments of delight in it. Maybe that’s how I sort it out, but that’s complicated.

Lola: So for me, my answer to that is I would also kill Twitter just because it has this impermanence where people basically shit statements and then run off and create controversy and it’s not a big deal. I’d probably kiss Reddit just because I feel like it’s great, but I find it’s like the precursor to what Discord is, which is much more community oriented, deeper conversations, higher quality sources. If I get something from Discord, I feel like I could probably trust it a bit more than Reddit and a heck of a lot more than anything I got off Twitter. So you kind of have this variance there.

And to speak to the design of the three, Twitter is probably the friendliest in terms of the user experience, but I have found that Discord and Reddit have been highly intuitive. My holy grail of design is you look at it and you can have all sorts of opinions, but everything you think you want to do is extremely intuitive, and so you’re basically learning with every single click. Every single action does exactly what you expect, and I kind of feel like Discord is nailing that. Reddit definitely is, but Discord is nailing that.

Tobi: I totally agree. I tend to call this approachability, but that’s probably not the right term. There’s this unfolding appropriateness of the UX that just kind of works in a way that just feels empowering. I talk a lot about it, I think the goal of a particular user interface should be to delight, and delight comes from-

Lola: That’s a controversial term in UX these days, you know. People are really wary of that.

Tobi: Oh, why’s that?

Lola: Because it speaks to frivolous. Does it actually drive purposeful, and if you start with delight, are you actually problem solving first? But I hear what you’re saying about delight being a part of how the experience is delivered.

Tobi: I think it depends on where you put delight. I would say I would only get into delight after the utilitarian values are done and after the thing is easy to reason about. Delight in the Discord sense comes from when you type a word that maybe you could use an emoji for, instead of putting some autosuggest thing, it animates a little icon in the bar and it clicks. It does the right thing but it over delivers. I think delight, I might use this differently than what people want to currently, but to me it’s just like you take the expectations and then minus experience or do it the other way around, just so I have a positive number, and whatever the difference is the delight factor. It’s an out performance. It’s almost like a display of mastery over the task that can only be achieved by the teams that so fully understood it that they ended up being able to spend the little bit of extra thing just to outperform what even reasonably well versed people in the tool would ever expect of the team. So I like that.

Lola: Yeah, it’s great but it also makes me think of the Kano model. I don’t know if you’re familiar with that.

Tobi: No.

Lola: So the Kano model is like this old manufacturing concept of there’s exceeding expectations, meeting expectations, and then under delivering on expectations, and over time, the things that exceed will eventually become the expectation, and then the things that are the expectation will eventually go below, and so it pushes you to say if you’re reaching for the top, you’re actually having to fight to stay there because continuous improvement mindset about what is an expectation and what’s that other level that you’re gonna go to, because today’s expectations are tomorrow’s whatever kind of thing.

Tobi: Yeah, it’s funny because this is a concept that clearly comes from old manufacturing but philosophers have been talking about this for thousands of years. But you encounter this in even just life experience, I know the term of a hedonistic treadmill. It normalizes to that.

Lola: It normalizes to the next thing.

Tobi: Yeah, the ambient experiences. So I think this is a very real thing. This is an interesting thing about standing up a Shopify museum. What was killer UX in 2006 is hilariously … The entropic damage that has been caused there is incredible, and that’s just a sign that our standards have evolved with again, people just moving forward. But this is an entire other conversation. So by the way, I’m reverse engineering, but I think delight actually ought probably to be treated with contempt here because I think stated outside of the context of that, it’s the cherry on top after everything. After you’ve found the Venn diagram of all the stake hold requirements of the interface, finding the perfect spot in it is the delight thing, but if that’s not clear, then people will over optimize for appearance potentially or more importantly, go into the biggest trap of all which is wanting perfection. This is where everything goes wrong because again-

Lola: That’s never going to happen.

Tobi: Even if you try to hold yourself to perfection, and even if you actually ship something so far ahead of where everyone else is, this very thing about the hedonistic treadmill of design will outpace you so much because everyone is gonna be faster, yeah.

Lola: Exactly, exactly. Thank you so much, Tobi. Okay, last thing. Gimmick, for the episode. So we’ve got here a chatterbox which I hope you can see. You have four options. Do you remember these games? Did you play it as a kid?

Tobi: Vaguely. I know the shape. I’ve never played a game with the shape.

Lola: There are questions in here, there are one of eight questions and we’re just gonna play it. So first I need you to pick either the cart, the rocket, the lettuce, or the banana.

Tobi: I take the cart, clearly.

Lola: The cart, okay. C-A-R-T. Okay, you have the numbers three, four, seven, and eight, pick one.

Tobi: I’ll take eight because everyone usually picks seven, right?

Lola: Well, I learned from my team that actually that means I gotta do another round. So it’s like one, two, three, four, five, six, seven, eight. Okay, now you have one, two, five, and six.

Tobi: Okay, I’ll go with one.

Lola: Okay. Question number one is, let’s go here. Oh, what design book are you currently reading? And maybe if it’s not a design book but it’s design adjacent or interesting it might be good to know what are you reading.

Tobi: Yeah, I’m reading a book called Crafting Interpreters, which is about designing programming languages, which is actually also design but probably doesn’t qualify. Which design book am I reading? I’m not reading one sadly right now.

Lola: Okay. What is that designing technologies book? What is it about?

Tobi: Crafting Interpreters it’s a book that got recommended by one of our internal teams that’s Ruby. I find programming language design to be a fascinating part because again, it’s at this intersection. I’m insanely excited about everything that gets more out of technology to power human minds or human journey. Shopify is literally that. But I have this subplot of I find this programming language design to be fascinating. I’ve built some myself including Liquid which powers Shopify. So every couple of years I get back to this topic, but the book is just kind of neat because it discusses the pros and cons and gets at it with a little bit more computer science rigor than I have because I never studied computer science.

Lola: Yeah, nice, okay. That’s one for our UX audience to maybe go look and see if we’re interested in.

Tobi: The technology world was right to reject status quo. Computers are so net new that we’ve had to reinvent everything, but we now understand them so well that we actually really have to go back through time and learn from the greats in all the different disciplines, because every discipline automatically is this long quest which discovers a set of a very few universal truths that then just come back in these new and novel ways. Sometimes it’s just faster to just, because the greats in these other fields just actually told us what they discovered in their books and biographies, and it’s just a good life hack to go to them, figure out what a set of problems, figure out how they solved it, and then see if it applies.

Lola: Yeah. This is kind of how I use Asimov books because there’s probably a bunch of stuff in there as well. Tobi, thank you so so much for this conversation. This has been really good fun and interesting for our audience to hear about your perspectives on UX and yeah, I’m excited to see what other stuff we can do at Shopify that’ll keep folks interested in us and our mission. Thank you.

Tobi: Awesome. Yeah, yeah, please. It’s a really fun company, we are building awesome stuff, and it’s a fantastic place to spend a couple years surrounded by amazing people like Lola and team, and working on really, really important things that just help millions of small businesses reach for independence and sometimes make huge contributions to their local economies and all these kind of things. It’s a good place and we really value this work, and have sometimes interesting conversations and sometimes uninteresting conversations.

Lola: This is definitely an interesting one.

Tobi: Christopher Alexander is the name. I’ll send you the name of the book.

Lola: Ah yes, we’ll get the book link in. Thank you. Thanks for listening to Inside Shopify UX. Check out more from our team or find out how to join us by visiting ux.shopify.com. Inside Shopify UX is hosted by me, Lola Oyelayo-Pearson.

Jen Shaw: Produced by Jen Shaw.

Isabelle Hamel-Caressi: Assisted by Isabelle Hamel-Caressi.

Michael Busse: Edited by Michael Busse.

Alisha Giroux: With art and graphics by Alisha Giroux.

Dani Chavez-Zackerman: Dani Chavez-Zackerman.

Trevor Silvani: And Trevor Silvani.

Matt Griffin: Music by Silent Quiet Spaces.

Lola: Make sure you’re subscribed to Inside Shopify UX for next week where we’ll be finding flexibility in complexity.

Show Notes

• Lola Oyelayo-Pearson
• Tobi Lütke
• Polaris design system
• “Physics of Passion: The Koolaid Point” by Kathy Sierra
• Wayback Machine Internet Archive
• Kano model: a theory for product development and customer satisfaction developed in the 1980s by Professor Noriaki Kano, which classifies customer preferences into five categories.
• Crafting Interpreters by Robert Nystrom
• A Pattern Language by Christopher W. Alexander, Sara Ishikawa, and Murray Silverstein; with Max Jacobson, Ingrid Fiksdahl-King, and Shlomo Angel