If U Seek: When the UX Playbooks Meet Reality

Christopher Nguyen joins If U Seek to talk about UX playbooks, product judgment, design habits, and what experienced designers learn when frameworks meet real product work. For a conversation about the UX ideas, methods, and industry habits that start to look different with experience tune into this episode.
Christopher is the founder of rectangles.fm and he helps designers shape their craft, careers, and calling through education and media. Previously a Head of Design, he has worked with startups and companies like Google, Nike, and 21st Century Fox. His path through design gives him a practical lens on the frameworks designers inherit, the judgment they build over time, and the advice that does not always survive contact with reality.

Listen for Christopher’ thoughts on revisiting design sprints, over-researching, momentum, permission-seeking, AI, taste, and why phrases like “just have empathy” need to become more actionable to help teams make better decisions.

You can find If U Seek on Spotify, Apple Podcasts, or YouTube Music.

Preview

What’s in this episode:

• Why design sprints can be useful, but not always as a fixed process

• How teams can over-research when they are avoiding difficult decisions

• Why momentum matters in the early stages of product work

• How asking for permission can quietly limit designer growth

• What AI may reveal about judgment, taste, and design craft

• Why “empathy” can become too vague to be useful in real UX work

• How designers can move beyond playbooks and make better decisions based on context

Transcript

[00:00:00] Christopher: So I don't know if this is a UX advice, but I, I, I typically hate the term empathy because it feels like everybody just says, "Yeah, you just gotta have empathy." And, and that word to me is sort of the umbrella term for you just gotta do something fuzzy or like whatever, right? So it, it's kind of like non-actionable, and I think that gets plastered everywhere, and it's not actually that useful for folks where you just kind of throw out like, you know, "Empathize," or like, "You gotta just have empathy for the user

[00:00:33] Nikol: What we seek shapes what we build.

[00:00:36] Nikol: This is IF U Seek by Useberry. Hello, everyone. Welcome back to IF U Seek by Useberry. This is Nikol Fotaki, and with us today is Christopher Nguyen, founder of UX Playbook, and he runs Rectangles.fm, a live stream and newsletter. Chris has, uh, had a somewhat unconventional path through the world of design, from rising to a head of design role early in his career to building a platform around sharing practical lessons from real-world product work.

[00:01:08] Nikol: He's spent years reflecting on what actually helps designers improve and what ideas don't always survive contact with reality. Today, I'd love to have a slightly different conversation. Uh, I think every experienced designer reaches a point where they start questioning some of the rules they learned early on.

[00:01:27] Nikol: So I'd love to explore the ideas our industry tends to take for granted, the ones you've changed your mind about, and what experience has taught you that the playbooks often can't, Christopher. Welcome to IF U Seek.

[00:01:43] Christopher: Thank you very much for having me. Excited to have this conversation.

[00:01:48] Nikol: Thanks so much for being here.

[00:01:50] Nikol: So I, I'd like to start with some of the methods and frameworks, uh, because they can be useful, uh, but only when they're helping us think rather than just giving us, uh, steps to follow. Is there a framework, uh, or method you used to swear by that you barely use anymore? And do you think we sometimes become too attached to processes instead of following, you know, or focusing on the underlying thinking behind, behind them?

[00:02:21] Christopher: So to that answer or to that question, yes and yes. So the, the first c- sort of method and framework I used to swear by, um, is the design sprint or the sprint book, right? The five days, um, fuzzy big idea at the beginning and then at the end of the day, or at the end of the week, sorry, uh, proto- prototype with your test results, right?

[00:02:46] Christopher: That was something that I loved because as a new designer coming into the field, it felt like that was that playbook, that blueprint, and I was like, "Oh, this is really good." And it took, like -- It's still a great book, and the designers who wrote it and built the framework took pieces of, like, product strategy, business thinking, and o- obviously design thinking and kind of mashed it into one.

[00:03:09] Christopher: And obviously they went through the reps of going through Google Ventures and building that, um, you know, body of knowledge and experience and really battle tested it. However, when I was sort of using it, um, sort of later in my career, I found that- You could customize a lot based on the problems and context and resources required.

[00:03:32] Christopher: So I used to swear by it. Um, I still think it's very valuable for someone that, um, just got into the field or learning how to do these types of collaborative, facilitated, you know, product development exercises, you know, with, with a group of people together. However, um, yeah, I've since like changed what I do when I do it, depending on, again, context, experts in the room, if you're the participant and the facilitator at the same time, or, you know, how big is the problem, how fuzzy and hairy is it?

[00:04:06] Christopher: Um, and you know, there's lots of mix and match stuff that I do. Uh, this was with not just my own teams where we did like the, you know, three-hour sprint, for example, or, um, with clients where we would potentially stay with them for three days, not five days, but, uh, put in our own spin and activities based on what, uh, outputs we wanted and what we found valuable, uh, from that session and, and client knowledge.

[00:04:37] Christopher: So, um, yeah, so, so that's it, right? Th- so the first sort of thing I don't, like barely use is the full design sprint process. What I do is, you know, remix and improve based on my context and situation. Uh, but to your, you know, follow-up point question of do I think we get attached to processes, I actually think for probably about a decade when design thinking was, uh, really popularized by like folks like IDO and, and, and the D school at Stanford, yeah, of, of course.

[00:05:15] Christopher: Like we-- that's kind of how the consultants sold design on, you know, boardrooms and, uh, these kind of like C-level conversations. So yes, it was a way to, for them to understand, therefore, like the whole industry sort of inherited this kind of like being attached to process, how good is your process, therefore, uh, your output and your delivery.

[00:05:38] Christopher: But I think we're in that moment of change where processes are getting reinvented. Uh, so I think folks are becoming non-attached to it at the moment because there, there's so much new things. Um, but yeah, we ha- we had been stuck in it, but I don't think, uh, no longer is that the truth. Mm.

[00:06:02] Nikol: Mm-hmm. Yeah, and I, and I think, um, okay, process is helpful when it creates clarity, of course.

[00:06:09] Nikol: Um, but it can become limiting when the process starts to matter more than the actual problem. And, um, yeah, and I think, uh, I'd like to go into this, uh, place a little bit more. Uh, like what happens when the process meets the reality of product work? Is it possible to over-research, let's say, a problem? And have you ever seen teams use research or process as a way to delay perhaps making a difficult decision?

[00:06:42] Christopher: Yeah, I think it is definitely possible to over-research a problem. And again, like most designers will tell you, it depends on what the problem is, right? Um, so it depends is a huge thing. But have I seen teams, um, like kind of delay because they needed to go through a process? Absolutely. Uh, I have always been in a startup environment, but as soon as I move to corporate, I see all sorts of, uh, interesting delays and excuses because, like, this needs to be done before we need to do this.

[00:07:16] Christopher: So, uh, I'll, I'll tell you what we used to do, uh, in some organizations that I used to work with and in some of my teams. You know, we used to swear by having thorough personas through lots and lots of interviews before we proceeded. Like, really try to understand the, the customer, and also, uh, another healthy thing we did was just rounds and rounds of testing.

[00:07:40] Christopher: And I think we had the luxury because we were, um- again, kind of like we had the infrastructure, but I think the reality of when I started working on my own is different, right? I'm a very small team. I'm building things for myself, uh, and I'm, you know, uh, I've only got to answer to myself. So I didn't really figure that out until I was doing it for myself.

[00:08:08] Christopher: It was my own time, my own money, where I actually was like, I ... The value of getting the product out there basically as soon as possible, uh, with real users, with real feedback, the people paying you real money to use the thing, that is often way more valuable than, uh, what I call, like, a simulated, uh, testing environment, when often it doesn't really yield the most practical results.

[00:08:33] Christopher: Like, it's like kind of asking that question, "How much would you pay for this?" And it's just like, don't ask that question. Uh, right? Like, if you wanna find out how much someone would pay for it, there's, like, a landing page test or actually have someone pay for it, right? And test through actually going through that process.

[00:08:52] Christopher: So I think, you know, research is one of those activities that, um, you don't just do at the beginning and you're kind of, like, done with it. Often it's like, get something out there and you learn more through continuous testing at every stage, uh, if the customer can actually touch the product. So I, I think, you know, over-researching can definitely, uh, hold some team back because, like, they'll never figure out, like, if they're 100% confident.

[00:09:26] Christopher: I, you know, like, I don't think we will ever think about i- if it's 100% confident, but definitely see that in, in some of the teams that I've worked with.

[00:09:35] Nikol: All right. Real quick before we jump back in. You know how product teams are always trying to move faster and research teams are trying to move smarter?

[00:09:46] Nikol: Well, Useberry actually helps you do both. It lets you run quick remote user tests, and honestly, they're just as easy to run as they are to share. No bottlenecks, no endless waiting around, and definitely no

[00:09:59] Nikol: more guessing. It's just research that moves at the speed of product. Check it out at useberry.com.

[00:10:09] Nikol: Because at some point, uh, I guess the work has to move from learning into actually deciding. And, uh, and that line is not always obvious, uh, which brings us to judgment, uh, especially in moments where the usual UX wisdom doesn't quite fit the situation. Um, so what's a situation where you've deliberately gone against conventional UX wisdom because you knew it wasn't the right approach for that context?

[00:10:42] Nikol: And, um, what gave you the confidence to trust your judgment?

[00:10:48] Christopher: I, I think, um, what I've learned is that, um, every project needs a mo- like, needs momentum. So that's really typically when I go against conventional wisdom. Like, you know, w- I, I think we're kind of taught with like, "Oh, don't just go off your assumptions," or like, "Really understand the users and their problems and their needs and their environment and their situation, and then test, test, test, test again."

[00:11:15] Christopher: But like, yeah, like those stuff might be true, but what I prioritize, especially at the beginning of projects, uh, when you're working in small teams, that small wins really matter. 'Cause a lot of projects just die even before meaningful things are decided and worked on. So the beginning is all about, uh, momentum building.

[00:11:39] Christopher: Like, whether you're working in an org, whether you're working with- on, by yourself, or whether you're working with a bunch of friends, like everybody wants to feel progress. So it's like, I think at the beginning, that's kind of my approach now, where it's always like momentum, momentum, momentum. So again, like what I was saying earlier, like you're much likelier to learn something if you can move really quick.

[00:12:05] Christopher: Uh, and because you learn something earlier, that builds momentum, that builds sort of your judgment for better decision-making. I think what gave me confidence is just screwing up 100 times. And, and where, and it literally, I don't think I've had, uh, I, my last job was in 2020, so between then and now, uh, I've had countless of projects that failed, you know, tried to raise money, um, went to an accelerator, did a bunch of things, started companies and stuff, and y- you know, that gives you confidence when you've kind of screwed up so much.

[00:12:45] Christopher: And so m- you've wasted so much time, you know, uh, you've potentially burned bridges with friends that you started projects with. Like, all of this stuff is just like, I think it's experience at the end of the day. Um, you don't exactly know when, um, your judgment is like the best, but you are confident that you have to just keep moving.

[00:13:09] Christopher: Um, and you know, that sort of like, there's always decisions, like, in the road, but I would con- I would prefer to move quicker, build momentum, and then sort of let the obvious things come through, and then, uh, and then hopefully from there, my judgment is better than it was previously.

[00:13:31] Nikol: Uh, yeah, and I guess that's also one of the harder parts of design, um, when the situation needs something else to actually know when to, uh, follow the rule or not follow the rule.

[00:13:43] Nikol: Mm-hmm. Um, and, uh, that idea of judgment also leads into growth because experience doesn't always, uh, turn into better judgments automatically.

[00:13:57] Christopher: Mm-hmm.

[00:13:58] Nikol: Uh, so why do you think some designers, let's say with 10 years of experience, feel like they still have one year of experience repeated 10 times? Have you noticed habits or mindsets that quietly limit growth even for the very talented people?

[00:14:17] Christopher: Yeah. I, I think the first one is m- potentially a symptom of asking for permission or feeling like they need to ask for permission. Um, that's typically not what I do, and that's why I kind of prefer startup experience, where you get to try a bunch of stuff, and usually there's l- very little oversight to what you're doing, so you can go ahead and just kind of mess up with a bunch of small experiments.

[00:14:49] Christopher: However, if you're coming from, like, potentially a more traditional design background or more of a corporate environment, um, i- i- in parentheses, I never fit in in corporate environments, but so i- because there's so much structure, because, you know, there's, uh, roles and responsibilities clearly defined in some sort of career ladder.

[00:15:11] Christopher: So, like- I think that one is, uh, interesting, and I think if designers could, you know, ask for permission less or just don't feel like they need to, or ask for forgiveness versus permission. So that one is, I think, a, a real thing, uh, and it also comes up in different, um, educational systems, different, um, cultural sort of, uh, environments.

[00:15:41] Christopher: You know, whether you're working in Australia, England, and the US, they are also very different, right, i- in terms of asking for permission and, and culturally. Um, so that's one. The other, i- on the same lines, is also kind of waiting for someone else to tell you what to do next versus solving a problem that you see exists.

[00:16:03] Christopher: This happens with sort of more, like, junior designers. I know you, you're speaking about, um, more experienced ones, but I, I think I still see it in more experienced ones where they, they potentially might lean on the product manager or the CEO for, for more business, quote-unquote, orientated decisions, whereas they could potentially make some recommendations, suggestions based on what they already know and their depth of knowledge in the field.

[00:16:30] Christopher: Like, you don't, you don't need someone to tell you to do that thing where you could just do it and then show them the result, and if it was wrong, hopefully it's not life-changing, um, and you can kind of reverse that decision. I, I see that a lot. And then The, I guess the third one, uh, if we're speaking about designers with, like, 10 years of experience and it feels like they've had that repeated the same one year, is potentially they're staying somewhere too long where- Mm

[00:17:01] Christopher: that environment just feels like that. There's, there's not enough nurturing or there's no systemic way for them to sort of continually improve, and this is more anecdotal, but it, it's kind of what happened in my career where I found that soon as I felt a bit stagnant and I felt like, uh, I couldn't grow anymore, the best option for me was always to move somewhere else, to new inputs, new experience, new things to work on, new problems.

[00:17:32] Christopher: Um, and that really helped me. So yeah, staying somewhere too long where it's, like, too comfortable where you're just kind of, like, resting and vesting, I think that's a Silicon-

[00:17:43] Nikol: Yes ...

[00:17:44] Christopher: Valley shit, yeah, where you're just chilling and it's just like- Yes ... okay, that's good for some, but it doesn't necessarily kind of, uh, potentially propel you unless you're in one of these, like, really fast-moving companies like Lovable, Anthropic, right?

[00:18:00] Christopher: But not, that's like the .1%, and, and most of us are probably staying somewhere for far too long, and we should really seek for new challenges.

[00:18:11] Nikol: I'm also thinking, like, um, t- time alone does not necessarily create the growth. Uh, as you also mentioned, it's, uh, actually reflecting on yourself, uh, what you need, uh, perhaps feedback and, uh, the kinds of challenges, uh, someone is exposed to.

[00:18:30] Nikol: So perhaps, yeah- Mm ... you need to move on to another experience, let's say.

[00:18:34] Christopher: Mm-hmm.

[00:18:35] Nikol: Um, and, and I think, uh, that becomes especially relevant now when the tools around design are changing so quickly. Um, for example, AI. AI is changing the way we work, uh, but beyond productivity gains, do you think it will expose who understands design deeply and who was mostly following a playbook?

[00:18:59] Nikol: And, and if that's true, what becomes more valuable for designers and researchers to cultivate, uh, over the next few years?

[00:19:09] Christopher: Yeah. Um, this is an interesting question. Yeah. Mm, I think on the surface, like to potentially the end user, they might not know or care if the, you know, the people working behind the product understands that deeply.

[00:19:28] Christopher: But for folks within the organization, like the folks you work with day-to-day, they, uh, obviously there's a, there's a hiring bar, right? So you're like, "Okay, well, I see your work, but let's talk to you," and then be like, "Oh, okay, you don't know as much as, uh, your work says." Okay, so for consumers, they might not care, but for us who are building product, we probably do.

[00:19:52] Christopher: And I think this is interesting because if it does expose designers, uh, especially within the hiring process or researchers in the hiring process that they don't understand this and they're just following some playbook, then I think over the next few years what folks should focus on instead of ring, instead of following a playbook, if there is one, 'cause arguably there potentially isn't, uh, because we're reinventing so many things, then it becomes, uh, to the point that we mentioned earlier, um, how do you curate and hone in the skills of judgment, right?

[00:20:32] Christopher: What is the right thing to build? Uh, that's hard in itself, what, like, you know, the right thing to build, or framed differently, what do we think is the best bet? Um, and I think, um, the company Basecamp, uh, Jason Fried and David Heinemeier Hansson have this really interesting process called, um, Shape Up, and they frame every project that they work on for at least six weeks, um, a bet because that's what it is.

[00:21:04] Christopher: They don't know if it's right, but they're willing to put resources behind it, and that framing, because the words that we use matter, uh, really helps shapes what the team thinks about what good judgment is. 'Cause bets don't work out, some fail, some big wins, some 10Xs, some 100Xs, whatever it is. So that sort of curation of judgment, um, uh, that I think would always be valuable even before AI, but potentially even now just because of the executional loop is so much shorter.

[00:21:37] Christopher: So it's like, well, can you make good judgment consistently, uh, uh, right, when you're working with these tools and when you're leveraging these tools? And then, um- In terms of like kind of, yeah, I, I think there's, there's one interesting piece here is like Will it expose folks who don't understand their craft deeply?

[00:22:06] Christopher: And it might, um, and let, let's just say it does, 'cause I, I could, I could argue for both, but let's just say it does. Yeah. Then what are the, like, ramifications of it, right? When, when these tools, uh, can be launched by literally anyone on, on very few tokens, then, uh, it means that potentially they don't know what they're doing, uh, and maybe it might affect, uh, their customers.

[00:22:35] Christopher: It could, uh, increase churn. Uh, and then does that mean that necessarily people who do think of their craft deeply would win, uh, because of these ramifications? That's not necessarily true if, if craft is the only thing that matters when you're building products. Um, but what I do know is that if there is good judgment, and th- this word that, uh, I'm not sure if you mentioned earlier or, or, or one I've been thinking about, uh, and is a huge buzzword now, is like taste, right?

[00:23:09] Christopher: It's, it's like, it's not necessarily following a playbook. It's not necessarily following what the consumers might want. Uh, it's not necessarily following some sort of even logical thing that they're doing, but it's, like, interesting. It's opinionated. It's, um, has some emotion behind it. Uh- Mm-hmm ... so, like, I love products like these.

[00:23:35] Christopher: I've always loved products like these. So I think that again, um, however you define that word taste in, in product building and, and design, uh, that would be so much more. I think it's just- Um-

[00:23:50] Nikol: Mm ...

[00:23:50] Christopher: potentially how you describe it is like, how does it stand out from the rest? What's different? What's the differentiator?

[00:23:55] Christopher: How does it feel emotionally, uh, and what resonates with the end user and the end customers? So that's gonna be huge. Um, could there be a playbook for it? Maybe. Mm. Um, but you definitely do need to have an element of, uh, craft to, to even k- kind of, uh, have taste show up and, and hard to be faked over a, over a long extended period of time.

[00:24:22] Christopher: Probably easier at, you know, on the surface, but not easier when someone's, you know, spends like 20 hours a week in your tool. I, I think, yeah, that's kind of the l- line I, I would say.

[00:24:35] Nikol: Yeah. I, I think, uh, taste is kind of like the, the fingerprints. It's kind of, it's different for every person. Yeah. Uh, a- and that really makes the actual difference of what's going to launch at the end of the day.

[00:24:50] Nikol: Um, yeah, and, well, UX has so many phrases, you know, that sound true because we've heard them a thousand times. Uh, some of them are useful, of course, because, uh, yeah, uh, it's a, it's a given. Uh, but some become a kind of a industry wallpaper. You know, the everyone sees them, nobody really look at them anymore.

[00:25:18] Nikol: Um, so what's a piece of UX advice that gets repeated so often that people have stopped questioning it- Mm ... but that you've found isn't actually that useful? And, uh, was there a particular experience or project that made you rethink it?

[00:25:38] Christopher: So I don't know if this is a UX advice, but I, I, I typically hate the term empathy, uh-

[00:25:45] Christopher: because it feels like everybody just says, "Yeah, you just gotta have empathy." And, and that word to me is sort of a, um, a umbrella term for you just gotta go to do something fuzzy or, like, whatever, right? So it, it's kind of like non-actionable, and I think that gets plastered everywhere, and it's not actually that useful for folks where you just kind of throw out, like, you know, "Empathize" or, like, "You gotta just have empathy for the user."

[00:26:14] Christopher: Like, I don't ... I'm not saying don't be empathetic. I'm just saying that doesn't help, and that is definitely plastered everywhere on every wall, on every, on every book cover, w- whatever, right? And, um, w- Is there an experience ... I mean, yeah, uh, in terms of, like, experience of, like, actually, I, I think it's actually more than just a couple of experience.

[00:26:44] Christopher: I think just people just say it to the point where it means nothing. I think what is potentially better is, um, maybe, like, something like sympathetic. Like, I can, I can feel what, you know, uh, you're going through, but, but I don't know exactly know. So I can feel something like it, where then it's like, okay, well, I'm in the head space of trying to help you.

[00:27:18] Christopher: But, like, if I'm just empathetic, I feel like that is not very actionable. But regardless of, you know, the verbiage, 'cause I know, you know, words matter, it still is like, what's the more tactical way to frame empathy, uh, that designers and UX professionals can then go and do something about it, right? This is

[00:27:47] Christopher: I don't know what the answer is. I ... But, like, I, I just think that we need to get past that, of, like, very surface umbrella term. Let's just kind of go deeper. Maybe it's like that, you know, the, the five whys, right? Or, or whatever, or something that is, like, just way more useful and, and tactical so we can kind of, like, strip away this kind of fuzzy term that potentially you just tell, like, your CEO or your product manager or whoever, uh, and they'll then look at you like an alien anyway.

[00:28:17] Christopher: So it's like, let's just get a bit more practical here, guys.

[00:28:22] Nikol: Uh, empathy. That's a y- that's a buzzword everywhere, I think now, in every industry. Uh, in marketing also, uh, it's one of the top words also that, uh, that's been, that's been used. Um, great point. Uh, thanks so much. I think this is also a good place, uh, to wrap up.

[00:28:46] Nikol: Uh, uh, great advice. Uh, thank, thank you so much, uh, for joining us today, Chris, and, uh, uh, for sharing your, all your perspective with us.

[00:28:56] Christopher: Absolutely. It was fun. I could talk for ages, so- ... uh, thank, thank you for allowing me to come on.

[00:29:02] Nikol: Uh, we'll also link to Chris's work in the show notes, so be sure to check those out.

[00:29:07] Nikol: And to everyone listening, thanks to tuning in to another episode of IF U Seek by Useberry.

[00:29:16] Nikol: For more exciting content, follow us on our social channels. Your reviews mean the world to us, so don't forget to leave one. And of course, hit that subscribe button to stay updated on our latest episodes. IF U Seek is a platform for discussions and personal insights. The opinions presented by guests are independent and do not represent the official position of the host, Useberry, or our sponsors