The framework to ace the UX whiteboarding exercise with Ray Gonzales

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The whiteboard exercise is a hot topic when it comes to UX hiring. Part of it is solving it, and part of it is managing the nerves while doing that. Ray Gonzales, Lead UX Designer at Zappos, a veteran of whiteboarding exercises, walks us through his thinking process behind administering this exercise as a hiring manager. Then, he switches places as Filippo puts him through an impromptu whiteboard exercise. Next, Ray lays out the very effective framework he uses to approach these exercises and then dives into it, coming out on top!

Do this 50 times, and then by the time you get into your interview, hopefully this will just be muscle memory. Because once you step in that room, and they ask you that question, at least for me, I know every single time, my mind goes blank for about five minutes. And then I realized that my mouth is moving, I’m saying something, and now I got to put pen to paper. So practice definitely makes perfect. Build that muscle memory.


Ray Gonzales

Lead UX Designer at Zappos


00:00Introduction 02:24Why live exercises? 05:15Past exercises Ray administered 06:50How to handle spec work 09:02What makes a whiteboarding exercise successful? 14:51The framework in practice 16:40Design a travel app 17:20Who am I designing this for? 18:48Why a travel app? 23:00Using interviewers as stakeholders

Behind the mic

Ray Gonzales smiling

Ray Gonzales

I find interactivity fascinating. It’s a conversation between myself and other folks I will probably never meet. Granted, it’s a very abstract conversation and limited in scope, but the end result is hopefully helping those folks to achieve something more. Beyond user interactions, my interests in design are wide ranging. I enjoy typography in all its form as well as photography, illustration, and pop/internet culture. I dabble in various forms of creativity, such as photography, silk screening, cooking, exploring, and playing guitar. I believe it is important to explore other creative avenues to inform and improve my own work.

Filippo Lovotti's with an intrigued look

Filippo Lovotti

In case you missed my barely audible accent, I was born and raised in northern Italy, near the Milano area, and moved to the USA a decade ago. I started venturing in the realm of pixels and websites during high-school, but at the time, I had no idea design would become my career, my biggest passion, and such a vital part of my life. Nowadays, UX design, strategy, and mentoring take up most of my days. And I love that. When I’m not behind a screen or recording podcasts, you’ll find me drawing with pen and ink or training at a local park for my next Highland Games competition.

Show notes

Ray and Filippo discuss the infamous whiteboard exercise.
First, Ray explains that this exercise helps validate whether a candidate can make sense of a problem and back up their design-thinking claims or not from a hiring manager standpoint.
Ray also mentions that this type of exercise highlights the attitude of the interviewers toward helping and supporting the candidate, which could be an indicator of the kind of experience one could have once hired.

Regarding spec work, Ray believes that it’s not ethical; however, you have to make your own choice as a candidate. If this is your dream job, would you be ok with this unethical practice if it leads to great things?

“Let’s cut to the chase,” says Filippo “what makes a whiteboarding exercise successful in the eye of the hiring managers?”. From the hiring manager’s standpoint, understanding who you are trying to hire is critical – so as a candidate, showing your thinking process becomes the key to the entire experience.
Also, another equally important component comes back to the same good ol’ practice, practice, practice.

Filippo then puts Ray through an impromptu whiteboarding exercise. The prompt is simple: design a travel app.
Ray lays out a quick framework based on asking the right questions to develop any kind of ideation phase on top of.


Watch with Closed Captions


Ray Gonzales 0:00

I think maybe the first thing that you should consider is like asking questions from these folks who are giving you this whiteboard exercise, right? Ask questions, try to uncover more. In fact, if you can try to come in with a framework,

Filippo Lovotti 0:12

this is the industry of UX season two, beside the UX hiring Jordan, we talk to the experts to bring you the strategies, the thinking process, and the reasoning behind the hiring decisions in the UX job market. Let's dive into the episode.

Filippo Lovotti 0:49

Hello, you wonderful you exerce Welcome back to another episode of the industry of UX. I'm your host, Filippo Lovotti. Murray. Glad to be here with you today. So we have covered a lot of great topics so far in season two, one of the hot ones that is brought up very often is the whiteboard exercise. I know we talked about it in the past, but we have not done an appropriate deep dive yet. So today, I brought my colleague Reagan's Alice, lead UX designer at Zappos, to go over the infamous whiteboard exercise. Okay, here is how this is going to go down. In the first part of the episode, we talked about what a successful whiteboard exercise looks like. In the second part, I actually put Ray through an impromptu whiteboard exercise. And he did really well and all that despite a vague and generic prompt I gave him so kudos to Ray Ray also lays out a great framework that he uses to tackle this type of exercise. So if you struggle with finding the right approach under pressure, or want to improve your whiteboarding skills, just keep listening. Let me know what you think about this episode, by tweeting at industry UX. No offense to Android users. But if you have an iPhone, give us a five star rating and review on Apple podcasts. It helps us produce a better show and bring the podcast to a bigger audience. Okay, on to the conversation with Ray.

Ray Gonzales 2:24

All right, so just to recap, the question they asked was I've ever done a live exercise? And why do i do live exercises?

Filippo Lovotti 2:31

Yeah, you can ask your own questions and answer them too. That's awesome. I'm just sitting here.

Ray Gonzales 2:39

And I interview myself. That's what I do exactly. Pretty. is this important? No, no. Okay. Anyways, so Yeah, actually, I have administered a couple of different live exercises. And it really depends on the type of role that we're looking for. And the type of traits that we're looking for as well. Right, but the skills, the soft skills, and whatnot. I was thinking if I should go into like talking about the specific exercises that I've gone through, but I don't think it's that valuable at this point. But yes, no, I have definitely run some live exercises. And the reason why you'd run those live exercises are a couple of different things, right? You know, just looking at a person's portfolio, it's a little difficult to gauge how easy it is it might be to collaborate with them, and what exactly it is that they did, because just showing your portfolio of work, you can easily hide amongst a big group, and it would be difficult to tell exactly what you've done. And then furthermore, it helps to validate the skills that this person has presented in their portfolio. If they say that, oh, yeah, they're a master at this thing. You know, you might be able to challenge them and really validate and understand and gain confidence on that thing that they say that they are a master of. And if they're not a master of it, you know, you can understand, okay, well, what level do they actually sit on? And is that something that I can work with? Is that something that that can grow? Or is that something that is like a complete blocker for this position?

Filippo Lovotti 4:02

So it's a almost an exercise in validation, as a hiring manager of the skill set and the contribution that they bring that they will bring to the team?

Ray Gonzales 4:13

Yeah, no, definitely. It's definitely that gives you greater confidence. And then I think on another level, too, it just kind of helps you to better understand this person. Yeah.

Filippo Lovotti 4:22

How much of a culture fit are they are when I say culture fit? I don't necessarily mean, that is the one thing you care the most about. But definitely, if they are a brilliant jerk, that's going to be a harder sell for them.

Ray Gonzales 4:38

That's true. Yeah. I mean, if they are brilliant jerky should hopefully be able to find that out through this exercise. And I guess thinking about it from the candidates point of view as well. There is that same value, right? Like you can understand like, Oh, well, is this person actually trying to work with me or is this person I don't know, just acting like a brilliant jerk or whatever it is that you might Trying to check for red flags around?

Filippo Lovotti 5:03

Exactly. I know that you self censored a few seconds ago about what exercises you have administered as a hiring manager. And then you said maybe that's not relevant. But I'd actually want to dig deeper into that, like, Can you bring just up one of those exercises that you have administered in the past? Just to give an example of something that you found valuable in testing or challenging on the spot?

Ray Gonzales 5:31

Yeah. So two of them come to mind for me, I think that are pretty common. So one of them is like a critique of an app. And you could take this in a bunch of different directions. So let's say, all right, I'd like you to critique this specific app that I have on my phone. So that's one direction you can go. The other direction that you can go is something like, oh, okay, can you tell me about an app or a web or a service that you found that shows bad UX? And can you tell me why it's bad UX? So those are like some of the more common exercises, specifically in terms of like, whiteboarding exercise, because you could argue that that's maybe not necessarily whiteboarding. For me, it was around. Gosh, I don't quite remember all the details of it. I think it was like design a banking app for an ogre, I remember what it was. But essentially, it was like designing a banking app to make it easy to just withdraw and to exchange money with maybe a friend. And then like, somewhere in the middle of it, I would also make a twist and say, Okay, well, you know, we've just discovered that, hey, we have to actually design this thing for kids. How would you approach that?

Filippo Lovotti 6:40

So what advice would you give to a candidate or to a UX designer that is applying for a job, and they are moving through the hiring process, and they are asked to participate in an exercise where they have to critique or they have to do some level of exercise, where that the app or the website or the product of the of that company is actually critiqued? And the subject of the feedback? What would you tell this candidate, this UX candidate that feels that maybe sees this for the first time?

Ray Gonzales 7:13

Gosh, man, that is, that can be sometimes difficult. And it really depends, I guess, on the situation, right? If you're applying for your dream job, and they asked you that, you're like, Huh, okay, maybe I should just go. On the other hand, if it's just like, Well, you know, this is just the job, perhaps that might give you a little bit more leverage as to like, what you might be able to do here. But I think in general, I think there's a couple of things to keep in mind, one, you know, stay courteous and stay polite, right? It's not an opportunity here to like, show other folks that, hey, you're knowledgeable about like, UX, and the ethical practices that go with it. And of hiring rather, you may be, what you might be able to do is say, like, Hey, I, I don't know if I feel comfortable critiquing or going through this exercise here. Because this exercise here seems like it might have some direct alignment with your current business. And what that does is that that alignment might create some biases, there's information that you know, that I won't have access to. And so the path that we might be able to go down in terms of what we can explore might be rather limited. So I'd prefer if we could choose something that is not related, at least to the business, but is potentially related to the problem or the skill set that you're trying to better understand. So that's one way to go about it. If they still push on it. I think, ultimately, that's up to you how you want to continue there, because there is an aspect of now I'm providing free work to these folks. But then there's also the other aspect of what is this opportunity worth to me, there's a it could very well lead to some very good things could also lead to some very bad things. I don't know a you know, you'll

Filippo Lovotti 8:58

have to make that judgment call when you're there. Let's just cut right to the chase. What makes a whiteboard exercise successful from a hiring manager standpoint?

Ray Gonzales 9:11

Great questions. So, you know, in my mind, the things that makes whiteboarding exercise successful for hiring managers are a few things, one, a deep understanding of what it is that they really want in terms of hard and soft skills. You know, if they don't understand that, then they're shooting in the dark. They're not really asking the right questions from the candidate to is that, you know, they create a friendly environment. I think, as a hiring manager, this is not like a confrontation. This is not me, trying to show you that I'm better. This is not me trying to like impress on you how cool this company is. But rather, this is me trying to do my best to draw out your creativity, your thinking. And so from that perspective, right, like, the way that they should be approaching these interviews is that Oh, Okay, well, I want this person to feel as comfortable as possible. I want them to be not nervous, I want them to understand that this is a conversation, not a critique. Unless, of course, you know, they're asking for critique, in which case, then that's a little bit different. And then finally, I think the last part is, at least from a hiring manager is that practice makes perfect is that I've definitely been in situations. And also I, I've created those situations myself as well, where I wasn't quite ready for interviewing these folks. And because I wasn't quite ready, I didn't really understand what I was getting into interviews would start, the candidate would stumble, and I would stumble along with them, or even worse, the candidate would do amazing. And then I would stumble, and then we wouldn't really uncover anything. And so just being prepared, and going in there, understanding what it is you're asking for, I think all of those things, helps to set up a more successful exercise.

Filippo Lovotti 10:58

Absolutely, especially the preparation is a big one, because the candidate expects you to be in a way it's understood that you are a competent interviewer or a competent, yes, the hiring managers because the candidates are already coming in. Nervous, like, regardless of even if you are calm, relatively calm, you're still in an interview setting. So it's really hard to be as calm as when you're walking to the ice cream store about to get your two scoops of your favorite flavor. It's not like that. It's a follow up to that. As a hiring manager, though, what are you looking for in terms of what are the check boxes, the mental check boxes that you're trying to check when you're administering a whiteboard exercise? Because I think that new UX, UX designers or candidates that apply for these jobs, I think it would be good for them to understand, what are the things that you need to hit on and uncover for your exercise to be successful in the eye of the hiring manager? There is another question about don't fake it, meaning, how can we set them up for success right now, if you had a couple of just a couple of minutes to explain no duties, things equals, your exercise is going to likely go very well, regardless of the problem that they are asking to solve for, or the prompt that they gave you. Yeah.

Ray Gonzales 12:27

So I think there's a couple things that candidates could do. I think practice is definitely one of the bigger ones practice makes perfect. Do this 50 times, and then by the time you get into your interview, hopefully this will just be muscle memory. Because once you step in that room, and they asked you that question, at least for me, I know every single time My mind goes blank for about five minutes. And then I realized that my mouth is moving, I'm saying something, and now I got to put pen to paper. So practice definitely makes perfect. Build that muscle memory. I think another thing to think about as well is like to understand the company, and the culture, right, depending on the company that you're applying to, they are looking for something specific. And they're also trying to solve like, specific sorts of problems. So if we take Amazon, for instance, they're going to be solving a lot more like e commerce type of problems. Whereas let's take a banking app, right? Chase, they're going to be concerned about different types of issues, security, trust, making sure that your money, you never mistakenly like dropped your money somewhere that you don't intend to. So there's like some things to consider there. And then finally, like, you know, think about what exactly it is that roll is asking for more and more, I think organizations are looking for designers that can sort of bridge the gap and think about different aspects of the business. Right. So the business itself, the technology, the product, right? So there's going to be questions about Okay, well, with this problem that I'm asking you to solve? Are we asking you to solve the right problem? Are we asking you to solve it for the right person? Does it actually add value to the company? And then like, can we actually build this thing with the technology that we have? So you know, thinking about those things and the breadth of things that you'll need to consider before you actually start going into a design? I think maybe the first thing that you should consider is like, asking questions from these folks who are giving you this whiteboard exercise, right? Ask questions, try to uncover more. In fact, like if you can try to come in with a framework, I think, given the whole like mind going blank, when someone asks you a question, at least for me, I find a framework to be very helpful. If I know that I always have to start with these questions or with this type of thinking, definitely helps to, you know, clarify where else I should go next. And also help me to understand the things that I might be forgetting or missing out and not have that framework.

Filippo Lovotti 14:48

Alright, let's test that framework. So for the next few minutes, I don't know we don't have a lot of time left, but for the next few minutes, I'm going to be your hiring manager or newer Going to be my candidate.

Ray Gonzales 15:01

Oh, man. All right, fingers crossed that I get hired this time.

Filippo Lovotti 15:06

So I'm very biased against you, just I know, right out of out of the bat. Alright, so let's talk about it. So if I were the hiring manager, you are the candidate. Let's start by understanding that we don't have a whiteboard in front of us. So you're not going to be designing. But I want to understand I want to show folks how you can, there is a lot of preparation work before you actually go up to the whiteboard. And you are probably one of my top five best question askers that I've ever met in my entire life, including in Italy. So you like internationally, you are my, definitely my top five, it's kind of hard to rank you because you have some fierce competition, but you're definitely my top five. So folks, if you need to understand, if you need some lessons on how to ask questions, raise your go to is amazing. So with that said, So now that I've set the bar really, really high for you. So what if I asked you to design a travel app? You have, you know, normally we'll give you an hour or 30 minutes, whatever it is, but if you had to design a travel app,

Ray Gonzales 16:28

Alright, that's it, just jumble up.

Filippo Lovotti 16:30

Okay, the smallest possible prompt that I can give you.

Ray Gonzales 16:33

Okay, great. Should I like, sort of verbalize what I'm trying to, like, think about and okay. Alright, so, but just thinking about, like this exercise for here of design a travel lab, right? It's incredibly ambiguous, you could just immediately start going into and designing Okay, well, it's going to have a login screen right here is going to have this other thing. And then now you're going to get to the flights. And try to figure that out, however, that if you think about it from the hiring managers perspective, like that's not necessarily what they're looking for, they'd probably have something in mind in terms of the business, they probably have something in mind in terms of who they're trying to solve this for, that would benefit the business. So perhaps you might want to start, they're like, Okay, well, like, you know, who am I designing this thing for?

Filippo Lovotti 17:21

So this is for, we are gearing up to reopen everything, after the pandemic, so or we are gearing up to get ready to open at some point in the next year to year and a half. So we want to build this app so that when people are finally able to travel more freely around the world, they have a new experience that takes in consideration maybe countries that have different rules and different your travel limitations. Maybe they were carried over with COVID. So we want to make sure that we covered that we want to make sure that we have a fresh new experience for people coming out of the pandemic grow.

Ray Gonzales 18:05

So as you can see, just by asking that question of who am I designing it for now, we've suddenly added a bunch of constraints here. Right? We're thinking about, okay, post pandemic, folks, we're thinking about, like, different parameters or limitations that you might encounter in different places. And so this will start to give you information about Okay, well, this is a constraint for sure. It's like, well, we have to expose this information to these customers, we have to expose like, or make sure that that they're meeting this criteria in order to actually travel to this place. Yeah. So you could also have easily just gone to the first question of like, why a travel app? And considering that if your first question was like, Who is this for? And now they tell you that it's about COVID, you can simply ask that question. Like, why I travel a lot for COVID.

Filippo Lovotti 18:48

Something necessarily a travel app for COVID is a travel app for our life after COVID which is going to be a little bit different than traveling before COVID. Before we could go everywhere, didn't really have limitations other than these, or vaccinations that maybe if you went to some places in Africa or some parts of the world, but after COVID there might be some limitations when it comes to vaccines there to be condition limitations when it comes to travel. Also, there might be limitations, we want to make sure that we can we have a way to tell people you know, places that tells or cities or locations or traveling options that are safer than others, even after COVID when it comes to the CS or the possible spread of some leftover COVID. Okay. Okay, cool. So, in this way, when, by the way, I'm pulling all this out of my ass, just so you know. So I'm spinning it out right now. So it could be like a traveling app for health conscious or like for maybe for that type of person.

Ray Gonzales 19:57

I'm writing this down on Though I guess I don't necessarily need to this is just a force of habit. Okay, anyways, so, you know, we've started to ask questions about, like, who this is for and why this is important for the business a little bit right now, there's a lot of questions that we can go down. So for example, like one of the questions that I might be able to ask is like, Okay, well, is there a specific audience in mind? Because you said, pandemic, folks, is this limited to a specific region, us, you know, Japan, India,

Filippo Lovotti 20:27

us, right.

Ray Gonzales 20:29

And there you go, you'll you'll start to understand, okay, a little bit more about this. And then maybe you might also ask questions about like, what are the constraints that we have to work around? So there could be legal constraints? And you might ask about that. And there also might be technological constraints to it's like, Okay, well, for this travel app, are we targeting like a specific platform? Or is there a certain type of technology that we have to go through,

Filippo Lovotti 20:51

we want to stay primarily on iOS at first, because according to our survey, folks, that people that use R Us are just not the right demographic that we we want, which is like younger demographic at 18 to 35, health conscious, very well knowledgeable when it comes to news. And they also tend to be more conscious travelers. That's what we have determined.

Ray Gonzales 21:23

Okay. And so now you're starting to get, you know, a lot more information, given your current knowledge about COVID, about how people react to it, how you know, what the current medical recommendations are, now, you could start to think about additional questions that you might layer on there. Although there is one thing to keep in mind is that you have a time limit, you know, you got to keep track of the time limit. So, at a certain point, if you feel like you have enough information, you can start to say, Okay, well, you know, I think I have enough information here to go off of, and then now you start to move on to the next steps of whatever it is that you're doing for the whiteboard, right? So that could be the ideation portion that could be listing out what your assumptions are, because you're definitely going to make assumptions. And actually, that those listing out and vocalizing those assumptions would be very helpful in terms of at least like shortcutting some of these questions because, at the beginning, I could have just skipped over the part about asking who this is for and just said, Okay, well, I'm gonna make the assumption that this is for a post COVID world where people are very concerned about COVID. And then just skip straight to other questions that I thought might be more pertinent to ask. Yeah, just from there, and you know, just always make sure that you're keeping track because I think you can easily fall into a trap of asking questions for 30 minutes. And then after 30 minutes, you have a you have a list of questions to show for your work, but probably also looking for other things too, like, Alright, how do you approach actually like designing How do you approach collaboration in design? And, you know, how do you go about like solving certain patterns and whatnot. And really, again, that depends on what that role is, and what that company values.

Filippo Lovotti 22:56

So I think we can stop there with the with the exercise. So two things that I wanted to also highlight is how you have basically you use me, the hiring manager as a stakeholder almost as a, in a way, either researcher slash user, and you basically, when you have some inconsistencies, or confusion, you just turn to me for more information. And this is something that I see a lot of folks they forget, is that, which is if you are in doubt, the hiring manager, whoever is giving you this whiteboard exercise is there to answer those questions. In fact, it's great if you pepper them at first, at the beginning to get you started. If you ask them a lot of questions about the problem, they're solving for the user, use them as a stakeholder, as if they were there just to help you build this thing, which is something that you did without even it's almost second nature to you. And then the other thing that I want to highlight twice, because you already brought it up is the set of assumptions that you're working with. So you basically are listing out a set a set of assumptions that our company comprised by, you know, the answers that you've been given, just to basically exactly cut a line in the sand, or like, not cut, but draw a line in the sand and say, Okay, that's it, I want to maybe go through a flow or like a user flow, or I'm going to start with how my wheeze or whatever type of thing that you want to draw out. It gives you enough information so that the hiring manager knows Okay, these are the limitations or not limitations, but the assumptions that they're going to start with working with and that really makes them understanding what headspace your, your app and then last thing that you wanted to say is that how good you were at vocalizing everything that you were thinking and why you were doing, what you were doing and the thinking process that you were going through now and I understand that you were emphasizing that because this is a podcast, you're not actually showing it. But at the same time, it's really important for you as a candidate to speak out what's in your, in your mind, because as a hiring manager, I can't read your mind. So I won't understand what's going on in there. Because that's what I'm looking at what specific as high as a hiring manager, when understanding what the way you think and the way you process information. And so if you just are quiet the entire time, and you just are like, you're quiet, most of the time you just ask question, get the answer and do something. But you're not telling me how you're using that information, or you're processing and and how that information is potentially even birthing or generating more questions, then I, it's hard for me to evaluate that. And you're basically leaving me with making up my own mind on about what I'm seeing, you're not, you're not driving the narrative anymore, I'm actually filling the gaps, and me fiddling with stuff that you don't like. So that's also really a reality.

Ray Gonzales 26:08

But it's going to also add that like, you know, just through this display that we had here, it also shows the importance of preparedness, both for the candidate and the hiring manager. Because as the hiring manager, you're going to get peppered with all of their questions, right. And like, okay, I mean, if you're comfortable pulling things out of your ass, then cool. But like, if you're not very good at thinking on your feet, then you may want to come in prepared, at least with like a couple of constraints or a couple of different things that you think that most candidates would be asking for. In addition to that, as a hiring manager, I think it's also important to understand like, when those candidates are struggling, and that the struggle isn't necessarily a sign that they aren't a fit, but rather, it could be a variety of things, right? It could be that they're nervous, it could be that they just blanked out, like I do, you know, it could be a number of things. And so you got to come in prepared to prompt the candidate, right? Like, if you see that they're stuck on that very first part, you can start to ask open questions like, Okay, well, perhaps we can start by, you know, thinking about Alright, well, what is the current situation of our world right now, this is a post COVID world. And so, you know, what do you think are going to be the important things for a travel app in a post COVID world.

Filippo Lovotti 27:25

I hope you enjoyed the episode. If you are interested in any of the resources we mentioned, all the links are on the opposite page of our website, the industry of Thanks to Ray for coming on the show. And thanks to Julian at podcast edition for the audio engineering work. If you have any feedback about the episode or the show, let us know by tweeting at industry UX. If you really want to help or say thank you from the bottom of your heart, please leave a five star rating and a review on Apple podcasts. It helps us climb the charts and bring our show to a bigger audience. Lastly, but not leastly. Thanks for listening and I'm looking forward to talking to you next week.