UX Hiring Insights Dan Maccarone on Thinking Over Tools & UX Career Reinvention

Dan Maccarone (00:00.288)

I always say, I don’t care. I’ve hired people who didn’t know Figma or or back in the day, Audner Grapple or whatever. I don’t care about the tools. Like we can teach you the tools, but if we can’t teach you how to be deductive and how to be, I think, strategic, you can be a better strategy. But like, if you don’t have that analytical mindset, I think that’s what I need. And I think part of that is being able to have a really frank and honest and friendly conversation. Like, I want to learn from the people who

come and work with me. I don’t want them to just learn from me.

Sarah Doody (00:34.296)

Hey, I’m Sarah Doody, a user researcher and product designer with 20 years of experience. In 2017, I noticed something a little ironic. UX and product people, despite being great at designing experiences for other people, often struggle to design their own careers. That’s why I created Career Strategy Lab and this podcast to help you navigate your UX job search, grow in your current role, and avoid skill and salary plateaus.

in a chill and BS free way. So whether you’re stuck in your job search or wondering what’s next in your UX career, you’re in the right place. Dan and I have known each other since about 2011 is my guess. Dan started his career in around 1999 as an information architect and worked at companies including Razorfish, New York Times, and a lot more.

And about seven years into his career, he co-founded Charming Robot, which is a product strategy UX design branding studio, you could say, where he worked with clients including Hulu, Rent the Runway, Foursquare, Blade, like Uber for helicopters, Wall Street Journal, and more. And now Dan does a lot of fractional product officer work for early stage startups. He also has a podcast, which maybe I’ll come on some day.

Story in a bottle, side note, Dan is also a red wine connoisseur. And he’s owned bars, he still owns bars, I think. He also wrote a book called The Barstool MBA. And similar to many of you and myself, Dan had kind of a roundabout way into user experience and actually has a master’s in journalism. Dan, I leave out any important facts about you?

Dan Maccarone (02:26.606)

Wow, mean, just hearing that is overwhelming, maybe, but I, you know, I’ll take that to start. I actually, currently have three bars just to set the record straight around the East Coast. Sure. If you’re in Boston, I have a bar called Small Victories, which is in Southie. Still have Fool’s Gold in New York, which we’ve had for almost 12 years now. That’s in the house and streets. Wonderful, wonderful craft beer and whiskey bar. Then in North Carolina on Oak Island, we have a bar called

of Oak Island and it’s kind of a good beach bar, live music kind of thing. Kind of remote, but it’s a great place if you’re on vacation.

Sarah Doody (03:02.958)

Well, I’ve never been to North Carolina, so if I’m there, I will go there. But I can totally vouch for Fool’s Gold, and I just love the name as well. Thank you. I thought, I was trying to think, how did we ever meet? And my memory is a little vague, but I think we met because you were doing a talk at General Assembly on that original place on 23rd Street, I think, about Rent the Runway. And I was working at this startup, and I thought,

I need to go there, hear Dan speak, become friends with him so he can talk some sense into the people at the company I was working at.

Dan Maccarone (03:37.518)

Are we allowed to mention the name of the company? I remember the company very well. Yeah!

Sarah Doody (03:41.27)

Yeah, it started as AdKeeper, like A-D-K-E-E-P-E-R, and the concept was that people wanted to save banner ads on the internet, like they clip coupons. And they raised $40 million, so I thought they have to know something that I don’t. And so I went there, and it was interesting. It obviously doesn’t exist anymore, but yeah, that’s how Dan and I met.

Dan Maccarone (04:06.222)

That sounds right. I forgot that the GA talk was before the ad keeper talk, but that makes sense now. Yeah, I always thought that was a crazy idea, the idea that you wanted to save banner ads. But I didn’t know you wanted to come and meet me and befriend me. We obviously became friends. I mean, I’m flattered.

Sarah Doody (04:23.31)

I think in the back of my head, I was like, this guy sounds really smart and maybe he can help talk some sense into these people at my company. I didn’t own the company. worked there. then it didn’t work. No, they tried to do a few pivots, but you know, it didn’t work. But Dan and I also created the curriculum for and taught General Assembly’s first 12 week UX program, which was

in 2012, which is insane to think about. That was so long ago.

Dan Maccarone (04:55.212)

I know. And I don’t know how much you want to talk about this, but there was certainly some problematic aspects of that. Some of it were on our side. mean, it was the first time we were really developing curriculum. And I think we were almost like a pilot program. And then I think there were some issues with it in terms of the education aspect and the idea that everyone had to pass the course, even the people who were not particularly great at it, which is not a knock on them. They’re wonderful people. Not everyone’s great at UX. And I’m like, I would be a terrible programmer.

So, you know, I think that there’s, some interesting learnings I thought from that, that first course that we did.

Sarah Doody (05:28.374)

Yeah, we can totally talk about that. think, you know, they approached, I don’t know if they approached you or I, or I can’t even remember, but we sat down and created this 12 week curriculum around everything in UX. And I don’t think when you and I started it, we imagined that we were going to generate 100 % ready to hire people that could like go into a company and save the day.

And towards the end of that, I think we realized, no, that’s what they were kind of wanting to pitch at least.

Dan Maccarone (06:03.03)

Yeah, yeah, think the way that the way I think we designed the course, it was almost like a survey, right? Of all the things, a survey course of like all the things you should know about UX and touching on, you know, each of the pieces, right? Because you and I are both generalists and which I love is which, you know, the idea that like we can do a little bit of everything. And so we taught it that way from everything from user research to wire framing to kind of documentation to to all these different things. And then we brought in a bunch of guest speakers who I was very proud of the people we got for that those 12 weeks.

But yeah, if I were thinking about how to do that now, I would actually still keep the idea of a survey course and then I would create specialization branches off of it, which I think you and I talked about at some point. But GA basically said, you need to get these people career ready so that when they leave this, they have a certificate of UX expertise in their hands and they can go to companies and be like, all right, I’m now a senior level UX person, not even a mid level or entry level, which I thought was…

incredibly ridiculous because, you know, we as you said, we’ve been doing this for a long time. And like, I mean, even I remember when I started, I thought I knew everything and boy, did I not to kind of climb the ranks of that is a really about experience in in doing it and learn and like learning on the job. And I don’t think anyone’s ready for that on day one, even even with what I’m sure was magical teaching on our part.

Sarah Doody (07:24.942)

Well, I like that you brought up this topic of generalists because I think, you know, you and I are both amazing generalists. So to both of our horns here. But I think that’s what the market really needs right now. We’ll probably get into that in a second. But if I were to redesign UX education right now, it’d be very similar to what you described. And I think it’s very similar to like becoming a doctor. think there is.

this survey element where you have to learn a little bit of everything. And then we need to go deep into a lot of other topics, right? Because in order to be a successful UX person, you need to have a pretty broad understanding. And then if you choose, depth in some areas.

Dan Maccarone (08:11.842)

Yeah, what I also think, know, why I was really happy with the people we brought in to speak at the class, and this goes beyond just learning things about user experience and the different pieces of UX. It’s also understanding all the other pieces that go into building things, right? From design and branding to development to content to marketing, like all those things need to work together to create great products.

I think when we silo ourselves into our individual component of the vertical we’re in, whether it could be UX, could be design, whatever, we are ignoring how these things kind of get woven together in the course of not just the process of creating it, but also in the end product, if there is an end product. My world, we’re never done building, right? But that, think, is often ignored in UX education. Like, if you, as a UX person, can speak to…

the language of design or speak the language of development or understand why, when and why marketing is important. It’s not always important free product, but at some point, and then, you know, bring the respect that those other, you know, verticals deserve to the table. All of a sudden that collaboration becomes so much easier and even when UX is done and you need to fix something during development, there’s an easier conversation to be had there. And I, you know, I think that some of something that often is left off the table when we’re trying to get UX jobs or.

even like just work within our teams. Because at a lot of agencies, we don’t do this at Terminal Robot, but certainly seen at other agencies where everything like UX is over here, design is over here, know, engineering doesn’t come into the picture until later and you’re like, well, that’s kind of just create a mess. Even 2026, which you think we would have solved these problems in product process, but certainly seen everywhere still that it’s problematic.

Sarah Doody (09:56.854)

Yeah. You, you touched on a few topics that I think are popular with people who are already in UX and that’s really around how do you continue to develop these, I even hesitate to say soft skills because I think understanding business, understanding a little bit of marketing, understanding a little bit of development. And as you said, like how all these things come together, how, how would you suggest that someone go about like sharpening

those skills if maybe they currently have three, five, 10 years of experience and they’re trying to get to that next level, whatever that level is for them.

Dan Maccarone (10:35.392)

It’s a great question. No, and I think it’s because the industry is always changing too, right? And I don’t mean just the UX industry, I mean the tech industry, you know? And so to me, it’s about constantly making sure you’re continuing to educate yourself, educate yourself on the technologies that exist and how they’re used, you know? I mean, the obvious example right now would be AI, right? A few years ago, it was blockchain.

Sarah Doody (10:36.79)

An easy path to that, you know?

Dan Maccarone (11:04.342)

You know, and even though like on the blockchain side of things, it didn’t affect the front end all that much. It certainly affect how you thought about developing something or what security looked like. And so, you know, it’s, really important to, I think, read or watch or, or listen to podcasts or whatever from people who have different angles. Or you know what, like my favorite way of doing it is finding people I can grab a beer with or have a coffee with and just pick their brains. I mean, I do that all the time still. I have a friend of mine who’s a, another UX person who’s

was pretty well known. And he and I have a weekly, no, we have a monthly coffee chat over Google Meet where we just talk about how technology is evolving and how it impacts our jobs. He works at a Fortune 500 company running a huge UX team. I obviously do not. But those kinds of things where you can find people to just shoot the shit with, I think become really even much more impactful than just reading articles here and there though.

that certainly is worthwhile doing. So that’s how I kind of do it myself. And I think we all need to be doing that, whether we’re year one or year 10 or year 30. But because everything moves so fast and products are made so fast and I think are also failing fast, it’s easy to get out of touch, especially when we get into our own little realm of whatever job we have. And that, I think, often creates a lot of ignorance as to the kind of

perspective we could gain by looking at things outside of our own bubbles. Does that answer the question?

Sarah Doody (12:36.118)

Yeah, well, and I think too, you know, just the nature of what you’ve done running an agency and being a chief product or a fractional chief product officer, it kind of forces you into this kind of mindset and habit of the education of you as a UX person will never be over because you have clients coming to you, you have, you know, fractional product officer.

people coming to you and they all want to know like, how can we put AI into our product? Right? Or I remember years and years ago when the Apple watch came out, remember you, you a charming robot were designing something for the Apple watch and I hadn’t done anything, but it was like, you just kind of were thrown into the deep end because the market forced you to.

Dan Maccarone (13:21.71)

Yeah, it goes back even further than that. you think about, I remember years ago in like 2000, it was 2000. What was it? WAP? Was that what it was? The mobile, like mobile technology? Yeah, like I remember doing a product. I didn’t know anything. I had to buy a special phone just to be able to get a WAP enabled phone to work on a like eBay type product for text based navigation on a phone. By the way, it was a terrible idea and it failed spectacularly, but it may raise a lot of money.

But like those kind of things, you know, the iPhone came out and all of a sudden we had to think about how do you design for an iPhone or a smartphone? And we always want to be one step ahead of that, right? Like I think everything that we do at Charming Robot especially, but this is true back when I was at Hard Candy Shell, which is my company before Charming Robot, we were like, how do we keep up with this? it’s like making the effort to reach out to people and say, hey, can we maybe do that? Even if we don’t do it for a lot of money.

Let’s just build something so we know how to do or build it for ourselves. And that happened for sure with the iPhone. happened with the Apple Watch. It happened when we worked on VR stuff in the mid teens. It happened with blockchain starting probably in the late 2000 teens and into early 20s. And now it’s happening with AI. And I have this constant fear of becoming a tech dinosaur, especially as I get older. so constantly learning and keeping up with a beat on what’s going on. And then also evolving.

your role, right? Like mentioned the fractional chief product officer role. Like that’s something I’ve now been doing for I think three or four years. It’s still part of the timing robot world, but I come in myself and help startups. And that even itself is an education because I never technically run product for anyone before I launched products, I’d evolved products, but only on the agency side. So even that was an education. I talked to a bunch of fractional people outside of product who are fractional CTOs, CMOs, know, BFOs and

learned a lot about how that works and what it means to do that so I can form kind of my own perspective on it. So it’s like always, I don’t want to say it’s always reinventing yourself, but it’s always trying to be a little bit ahead of where everyone else is so you can kind of be the expert in the room, whatever that means when you’re called to task on it. Luckily, fingers crossed, keep getting, me and the team keep getting called to task on it, but that’s an important part of it though, right? Because I’ve also worked with, and I don’t mean an insult to anyone.

Dan Maccarone (15:44.226)

with people who are kind of mid-level UX, people who have no desire to kind of rise through and they kind of want to kind of stay here and be steady, which is, that’s great. Except that if you’re not keeping up, you’re going to find yourself in a bad situation because the people who are keeping up are going to rise in their careers and keep their jobs. And it’s a scary industry right now. You know, I mean, there’s a lot going on, a lot and changing. And I think people are very, not to be negative. I hate being negative, but.

I do see a lot of people worrying about their own jobs in UX and I know you talked about this a lot of time, a lot, like that if you’re not keeping up, you’re gonna lose kind of whatever grip you have on where you stand in the industry. You know what I mean?

Sarah Doody (16:25.728)

Yeah, Scott Galloway, you’ve probably listened to some of his podcasts, but he is often asked about the impact of AI on, you know, just our careers in general. And he says, and I’m paraphrasing, like, AI is not going to take your job, but someone who knows how to use AI will. And I think it goes so nicely with the idea of reinvention, keeping up, et cetera, because when companies and teams are trying to do more with less resources,

It’s the people that have a broader skill set, maybe actually depth in a certain industry or types of product or something that they’re gonna wanna go with. But you mentioned something that I think is important to touch on and it’s your own kind of career reinvention and it’s happened a couple of times, but this most recent one, I think it would be interesting to dive into that a little bit because I forgot to say at the beginning,

Dan is also an amazing user researcher and Dan and I have traveled the country, far and wide, had lunch at random places all over on our research trips. But I really think there’s so many elements of user research that we can apply to our careers. And I’m curious, in hindsight, when did this kind of rumblings of a reinvention start and how did you know?

you know, that maybe you should act on it. Because I think a lot of people listening maybe are at some fork in the road as well, and either they’re scared to act or they just don’t know what to do. So can you share more about what that kind of moment or chapter was like or is like, I guess?

Dan Maccarone (18:05.678)

Do you mean for the current one or in general in my career?

Sarah Doody (18:08.908)

Well, the current one, or if there is another one that you really want to talk about, like we can go back further than, you know, the last six years or something. Because I know like even the pivot, the pivot from, you know, working in-house at like Razorfish and New York Times and stuff, there was the pivot to then start agencies. So that could be an interesting angle too.

Dan Maccarone (18:29.678)

Sure, maybe I’ll start with recency and work backwards. Okay. So the fractional chief product officer work really started in, right around kind of the end of COVID when, you know, my team went, my team totally went dispersed in 2019. So we were ahead of the game, you know, if you will. But what I noticed is that, first of all, I’m really bad at being bored. I can get, like, I get in trouble when I get bored. And so I…

was like sitting there and I’m working on projects and I’m kind of like, okay, I feel like I’m repeating myself and I don’t like repeating myself. I don’t feel like that’s helpful to the way my, at least my head works. And so I was like, what’s missing in my career? Where can I apply my skillset? And one of the things I realized, and I was talking to my COO about this era, who you know, Sarah, and I was like, what’s different? And the thing we realized is that like, you over the course of at least Charming Robot’s history, nevermind everything before that,

we’ve probably launched a hundred products, right? Let’s say, let’s probably give or take, we’re at a number. And some of them are very, very successful, which is always lovely, but we’ve also seen some spectacular failures. And sometimes those failures are because of founders, sometimes it’s because of product market fit, sometimes it’s because of unforeseen things. But what I realized in that moment was like, where can I be helpful? And I was like, I can be helpful because I’ve seen, maybe not everything, but I’ve seen almost everything. I’ve seen good things and bad things about founders, and good things and bad things about…

products and B2B and B2C and whatever. And I was like, I think I want to go and like be more involved in those things. And I don’t want to get a full-time job because I love running my team. But I think if I framed it the right way, I could go in and be like, I want to be more long-term with these companies and like see it through, you know, however long that means. I kind of still think I have an expiration date after like 12 or 18 months in a company. Because I think when you get to that like series B area, like I’m not good at scaling on that side.

But, and was another thing is like realizing kind of your limitations and where you fall on things. I would be really bad working at my friend Patrick who works at Workday. Like I’d be really bad at that job and he’s really good at that job in the US world. So I kind of like, need to do this to help founders and also to take on projects in a deeper way that I’ve been industry. And then at the same time, you know, there’s obviously technology stuff going on at the time, blockchain, LAA, AI. And so part of that is my own like need to not be boring. And part of it is trying to push myself

Dan Maccarone (20:51.982)

further and see where I find a breaking point, I guess. But if I go back further than that, like you mentioned like when we started Hard Candy Shell and later Toming Robot, that was a frustration part of my life. Like I was at Razorfish and there’s some brilliant people who worked at that company, this was 20 years ago. And I loved a lot of the people, but I hated the process. When we were working on Hulu, one of the things that, and I’ve talked about this a lot, that was really frustrating was that

people were making decisions based on how much they were getting paid for the project, not on what was gonna be the best product to create. And after that happened, I was just like, and we actually ended up luckily kind of rescuing that project. My friend Kevin and I, you know, by having the team whittle down and then kind of doing a very quick sprint to get Hulu launched, I realized like, I’m not driven by money. And so I’m just driven by like creating things I can be proud of. And I found at the time that

I couldn’t be successful doing that at a big agency. Other people can, but I couldn’t. So for me, I was like, I need to do this on my own. And I kind of had wanted to do it for a while and I don’t think I was ready. And when the Hulu thing happened, I was just at a frustration point and my friend Kevin and I were like, both like, gotta do this together. so neither of us knew how to run an agency, but we were like, you know, we’ll figure it out.

And I’m a big fan of like, we’ll figure it out. That’s true when we’re making a product, it’s true in my own life, you know, whatever. And so I think those, those, those kinds of points of reflection are when those things happen. Same thing happened at Hard Candy Shop. I left it after four years because I found the culture of the company wasn’t what I wanted it to be. You know, I felt like we had, we had, and this has, this has been well documented by Kevin and I, like our egos went through the roof because we kept hitting home runs. Like we went lunch to Tulu and then the Wall Street Journal and then Foursquare and rent the runway and learn best. And it was just like, this like.

I mean, it was great run, honestly, but it didn’t really help our egos. And I think we became quite arrogant and that arrogance trickled down into our team members. And it became a very, I think, I would say, dissonant place to work. And I was like, I don’t want to be that. I don’t want to be an asshole. I want to help people. And so when we started Charming Robot, was a point of, with my friend Chris, I was like, let’s take all the arrogance away. Let’s leave our egos at the door and really focus on

Dan Maccarone (23:10.958)

just the things we can create and make great stuff and hopefully partner with, you know, team members on our side who can kind of share that that kind of point of view and with founders or with big companies who can share that point of view too. The founders of big companies think, eh, you know, sometimes you got to do things just to do them. But for the most part, I think our team has really shared those values over the past 15 years or so, 14 years or so.

I’m really proud of that fact. I think that that’s something that helped really like invigorate my spirit into the world of UX. That was definitely down in a bad mental state right before that.

Sarah Doody (23:48.108)

Yeah, I think this idea of being curious about yourself and noticing, like you said, when you are bored or frustrated or sensing you don’t like how egotistical you’re becoming or something, right? I I left a company when I realized everyone here is so negative and so at each other’s throats. I literally don’t want to be in this environment anymore. And I think it’s so easy to be kind of just in the

day-to-day routines and habits that we get stuck on. And sometimes you just need to put the brakes on and like do some research on yourself, you know? True. Like this is, we do this whole part of Career Strategy Lab where the first thing people do is go do some user research on themselves to then figure out like what from their past roles do they want to continue doing, stop doing, what traits, what values, et cetera. And then once you identify that,

Dan Maccarone (24:25.982)

Yes.

Sarah Doody (24:45.152)

you can go find that job that maybe more aligns with your values or pivot from a specialist to a generalist or something. as being someone who I should have said this at the beginning, Dan and I worked together for a long time. worked at Hard Candy, or no, I worked at Charming Robot for a while. I was like a consultant. And I definitely see that kind of value alignment. Like it was not egotistical at all. It was really, let’s make cool shit.

with other really talented people and have fun while we’re doing it, you know?

Dan Maccarone (25:20.974)

We try to have fun at least. And the thing about it that I really appreciate from, I I love working with you and I love working with the other people on the team. And one of things I don’t know, it’s not really the secret to the company, but it’s something that I could never have predicted, but I’m very excited about is that even when people leave, and they do leave, you know, whatever, they come back, you know? The people who’ve been working at this company from day one are still a part of the company, you know, even when they’ve gone and…

taking other jobs and kind of had their fun there and they come back and we get to work and play together again. that what’s great about that is they bring a new set of knowledge to the table too, right? And someone goes and like goes to a big company or goes to a startup and then they want to come back and hang out. Like we’re like, great. Like what have you learned? Like, can we look, what we take from that? And like apply it to whatever we’re working on. And that’s the, that’s the best, you know? And, and that, that, that kind of friendly atmosphere, like again, you can’t create a culture. You can’t force a culture. It has to come of itself.

And I look at to the people who have been a part of that, yourself included, and think to myself, that’s part of what makes the work successful is when you have other people there who share those same values and who want to collaborate. And this goes back to speaking the language, right? Like I have people who are great brand people. I’ve learned so much about brand from the people who I work with at Charlie Rebut and who are on the design side of things and the brand strategy part of things. think that that’s true even when we brought in social.

you know, marketing people and that’s something I did not know a lot about years ago and now I do. And it’s just, it really makes us all better. You know, we all become lift, lift up and become smarter by, by listening to each other. As you do and use a research, listen, you don’t go in with a thesis. You come in with a kind of a blank slate and the sense of like what you’re, you want to learn. And then you talk to people and, and that kind of ends up creating the story of what, what the right solution is. And I think that’s kind of how we do things internally and externally too.

Sarah Doody (27:14.838)

Yeah, yeah. I want to stay on this theme of applying user research to parts of our careers because you made me think of a question I wasn’t going to ask you, but we talked a little bit about values alignment and identifying your values, and then in your case, creating values for your agency. And so for someone that might be thinking of the job they’re going to take next or launching a job search this week or something,

and maybe they have an idea of kind of the culture and values that they’re looking for in a company, how could they go about like figuring out if that company is a match? Do you have any tips that you’ve kind of implemented even with deciding which companies maybe you work with on a fractional product officer basis? Like how can they kind of vet and do research around is this company, know,

collaborative or egotistical or value, I don’t know, socially conscious or whatever it is.

Dan Maccarone (28:11.502)

I mean, if the company exists already as opposed to a startup, think there’s certainly research you can do online to learn about that. you know, a lot of the questions I would ask, and I would ask this when I’m talking to a founder about working with their company is, you know, how do they look at the role in terms of the bigger picture? Is this something where like, you expect me to kind of create the stuff and come back to you with it? Is this something where we’re meeting?

you know, every other day and whiteboarding together, you know, is this something where we get to do user research? You know, do value user research? And if you don’t, that’s not gonna be, want to work with, you know what I mean? I just, I mean, I just walked away from a project where I was really excited about it. It was a good civic journalism project. was like some, something’s still up my alley and I walked away and my team walked away. It wasn’t just me. four of us had walked away from it because we were doing user research and they literally just were like, yeah, but the research doesn’t.

validate our thesis. And I’m like, no, it’s like if your thesis is here, the research is here. Like you’re not this far apart. And they’re like, well, we’re just going to build what we want to build and we’re not going listen. And I was like, then we’re not your people. I think that when you’re looking to, and by the way, that’s not to say you guys have to agree with me on this. Like everyone should have their own perspective. But I think that when you’re asking the questions about how does this whole team work together? Is it a water flow, waterfall process?

Design’s over here and UX is over here. And if that’s okay with you, then great. For me, I’d be like, is there, like how often do design and UX and engineering meet together? Like are they having conversations? Like is engineering involved in the planning process? Like I would ask that question because if they’re not, then we know where those failures are going to happen later on down the line. Very predictable. I think like, if it’s a founder you’re talking to versus a big company, I would ask them what their knowledge is. Like what, do they know what they don’t know? And that’s not a direct question I would ask, but it’s more about like,

What’s like, do you work with, how are you thinking about working with your CTO? How are you thinking about working with, you know, myself or where are you, when are you bringing marketing in? When does, you know, cause I think marketing is often brought in too early, not an insult to marketing. It’s that we got to give them something to market. And so like, we can’t get to a certain point, you know, let’s, like give them some context. so, and I’ve watched people, you know, bring in PR and marketing, you know, when UX is just starting and I’m like, boy, I see that mistake and how that’s going to work. And how much does the founder, you know,

Dan Maccarone (30:32.494)

trust and this is how you have to get through other people. Like how much do they trust the input versus always just going with their gut or what they think versus what the data says, you know? And then the culture thing is a tough one because I think it’s really hard to judge a culture when you’re interviewing for a job because you just as much as they’re interviewing you, you’re interviewing them and everyone wants to be on their best behavior. But I always do ask questions about that. I’m like, so how do like, do people hang out up to work? Like not that that’s important, but it’s interesting to find out or like, you know,

How much are you, you I had bosses and I do ask this like work life balance. I believe in work life balance. I don’t believe people should work 18 hour days, whether it be a startup or a big company because you get burnt out and the work suffers. And I like, I would not want to work. And I have worked with founders who were, or CEOs who were like, nope, you’re here. You got to be here at 8 a.m. You got to stay until seven or eight. And I’m like, I did that shit in my twenties. And I’ll tell you what, it wasn’t worth it. It was, I was passionate about it.

And that’s the last thing I’d say is passion. If you really believe in the thing you’re working on, I can’t stress that enough because your work will suffer when you’re not excited. Not that every day is going to be glorious. It’s certainly not, but like if you have a North Star that you’re like, yeah, I believe in this, could be a big company and just believe what their mission is and the problems they’re solving. could be a startup that’s just getting off the ground. Like the problem you’re solving, it doesn’t feel worth it to you. Then that’s something I know for me, like I would, I’ve learned how to walk away.

in a much better way than I did probably 15 years ago. But it was a hard lesson to learn. But the delta on happiness, which I think is so important, has changed significantly because…

Sarah Doody (32:11.394)

Yeah, yeah, I’m going to have to quote you like this, this thing that you said, you know, your work will suffer if you’re not excited. And I think it’s so true. I can think back to people I’ve worked with and you could tell they just kind of cranked out the deliverables and were kind of painting by number and not thinking, not getting creative. They were just kind of going through the motions. And yeah, that’s why I think we also see a lot of people discussing burnout in UX and product and this kind of like.

sub conversation happening of like, how do you leave UX and leave product? And it makes me really sad because I think there’s so many products that need help and we have all this amazing talent just wanting to walk away. And I think it’s not an issue with the industry. I think it’s probably kind of a misalignment of where they are currently working. I don’t know for sure, but that’s my hunch.

Dan Maccarone (33:05.44)

Well, I think that there’s that’s probably true, but I think there’s also a very Unfortunately, the pendulum has swung the other way when it comes to understanding of UX like there was a point maybe ten years ago where I think maybe even less than that where there was a better understanding of what UX brought to the table and I’m finding that in this day and age just through colleagues that I’ve talked to I haven’t seen this as much from my own experience, but from friends of mine in the world of UX I do hear that like there’s a lot of like well, you know

What is UX really mean? It reminds me of the 90s or early 2000s. Can’t we just do this in design? Now that we have AI, an AI can just come up with the right platform or the right flow or the right UX for this. It’s like, well, no. You still need a human touch there to a certain point. It’s a bad thing for our industry that that’s the case because the education around not how to be good at UX, but what UX means and brings to the table is sadly, I think, going…

not going away, but it’s becoming a little bit more inaccessible to people.

Sarah Doody (34:06.574)

So I love this topic of what UX brings to the table. And I’m curious, when you’ve been hiring and you choose the path here, whether it’s for Charming Robot or if you’ve helped some of the companies you work at hire, what did you look for in candidates to see what they bring to your table?

Dan Maccarone (34:30.016)

So I’m probably better at speaking to how I hire people who work with me. Great. I’ve talked to, I have had clients where I’ve hired their CPO or their head of UX. And it’s so funny when they ask us to do that. But I do think that when I’m looking to hire people, it’s a few different things. And you’ve met, I think, a lot of the UX people I’ve hired over the years.

I think the common trait in them is one of the things you said earlier, is curiosity. Like, I really want someone who is genuinely curious and wants to learn. Like, we talked earlier in this conversation about we’re never stopping to learn. Like, those are the kind of people I find fascinating. You know, I have my own probably stupid bias around, like, kinds of people I like to work with. Like, I love people who have experience in the humanities, you know, people, whether it could be theater or journalism or history or philosophy, because I think that there’s a

a part of that of your brain that creates an understanding of humanity that’s important when it comes to UX, whether it be research or creating wireframes or whatever. Now that is a by by side. There are plenty of great UX people I know who come from like programming backgrounds and engineering backgrounds and those and I have no issue with those people. They’re great, but they tend to work on very different kinds of products than I want to work on. And that’s, that’s why or that work well for what showing robot does. But that like that, that aspect of understanding humanity is so important.

I always say, I don’t care. I’ve hired people who didn’t know Figma or or back in the day, Audner Grapple or whatever. I don’t care about the tools. Like we can teach you the tools, but if we can’t teach you how to be deductive and how to be, I think strategic, you can make it better at strategy. But like, if you don’t have that analytical mindset, I think that’s what I need. And I think part of that is being able to have a really frank and honest and friendly conversation.

I want to learn from the people who come and work with me. I don’t want them to just learn from me. And so whatever they can bring to the table. Like I just hired this person who I met at UGA where I lecture down there every now and then. And she had just graduated with a master’s in journalism. And that’s not because I’m biased against people with journalism degrees, just to be clear. She’s just whip smart. And you know, she’s like 25, 26 years old. And I was just like, oh man, here’s someone who really wants to do this, who really wants to like ask the right questions, who will push back. And by the way,

Dan Maccarone (36:52.226)

someone who’s 20 years younger than me, so she can probably bring things to the table that I will never think of because of how she uses technology and what she grew up in. I want people who bring perspectives like that that are different than mine. And are different than my teams, not just me, it’s like everyone. Like you’ve mentioned before, like we all work together on this stuff and that’s what I want. The hard skills are easy to teach, it’s the soft skills that are hard.

Sarah Doody (37:14.828)

Yeah. No, I love how you said, you you don’t care about the tools and you can teach tools. And I think it’s such an important point to emphasize because it’s so opposite of what we see in the industry right now, the obsession over tools. Right. And I mean, I’m in the same camp as you. mean, we can teach the tools, but if you, if you don’t know how to think, if you don’t know how to interact with AI and write a good

prompt and give it the right context, et cetera, it’s not going to create a prototype in 20 seconds that’s going to be usable. And so one of the things that

Dan Maccarone (37:51.15)

Can I add one more thing, Sarah? I’m sorry, can I one more thing this? Sorry. The other thing I think is really important is what do you do that’s not UX? What are your hobbies? Everyone at Charming Robot has something they do outside. I don’t really care if I find that interesting or not. That’s not the important thing. It’s that you have something else that you do that I bet the passion you have for that can be the same kind of emotion you can bring into work. And maybe that thing you do outside,

You can even apply sometimes, you know, in the most strangest of ways. I always encourage people to not just have a life outside of work, but like do something you love. Like, I don’t care if it’s reading books or, you know, making paintings or it doesn’t even have to be artistic. Just like, something.

Sarah Doody (38:35.628)

Yeah. Okay. I’m going to reveal my podcast episode that’s coming out in two weeks from the recording of this, but it perfectly aligns with what you said. So there’s this trend of career minimalism where people are kind of doing the bare minimum. And I now have coined this phrase career maximalism, because I think sometimes when people put too much into their career, especially their identity,

It makes them not great at their job because they take everything personally and their whole identity is wrapped up in it. And so part of this podcast episode says like, you need to form your identity outside of your job. And this was all kind of inspired by this Reddit thread about why do so many UX people wrap their whole identity in their jobs? I can send it to you later if you want, but I think it’s so important because,

I’m really, I need to write a book about resilience or something, but I think when you have something else in your life, like for me, it’s skiing or yoga or marathons, right? And then when I’m in a meeting, you know, or a decade ago when we were working together and like certain problem clients would say stuff, it’s like, okay, like I didn’t take it so personally, you know, because I have an identity outside of my job. Yeah.

Dan Maccarone (39:58.99)

I couldn’t agree with any more. I love that career maximalism. That’s a good phrase. I might steal that from you.

Sarah Doody (40:05.678)

Okay, well, two weeks until my episode goes live so I can will. Then I can link to it.

Dan Maccarone (40:10.766)

Yes, you need your AEO juice, not your SEM juice.

Sarah Doody (40:14.922)

It all works together though. That’s true. Career maximalism. Coming soon. Trademark.

Dan Maccarone (40:22.966)

Love it.

Sarah Doody (40:24.666)

I know, I know, you know, I interviewed Patrick actually a while ago and I’ve interviewed a lot of hiring managers and people involved in hiring. Of course, we talk about portfolios, resumes, etc. I think you bring really interesting perspective about what happens in the interview. And you said, you know, I love just have a great conversation with people. So are there any other questions that, you know, you kind of rotate through as you’re trying to just get to know someone?

figure out if they’re a fit, et cetera, that maybe aren’t kind of standard questions that are on the list of interview questions that float around all the time.

Dan Maccarone (41:04.046)

Oh man. Or topics like… I, okay, I, as you know, am probably the most unorthodox interviewer because I don’t follow any of the standard protocols for this. If I had a better HR department, I’d probably get in trouble for it. And that’s not because I do anything wrong. I just tend to do all my interviews over drinks or coffee. Yeah. More often than not drinks. Doesn’t have to be wine. And that is probably my, like…

the thing I do that’s different because I don’t want to sit there in an office and try to talk about someone like, by the way, this is no offense to anyone who put together an amazing portfolio. I will be happy to look at portfolios, but what I really want to do is have a conversation to help understand how you think. And so we’ll kind of talk about all sorts of things in terms of know, someone’s past projects and we’ll talk about, you know, what their role was in that, which is always important. And I would love, I love asking about like what, you know,

Let’s have an honest conversation about what went wrong, but like not just like that standard, like what could you do better? What is like, what’s your best trade or worst trade? It’s more like, what did you see? What did you, like what, are you looking for something new? Like what, other than maybe needing a job, which is a reason, but like what, like what is different there? but I find that like when you’re having honest conversations over coffee or drinks, topics come up that don’t normally come up in a conference room. it could be anything, right? You know, it’s like how people treat staff at a bar or wherever, or

Cafe like I want someone who understands how to be empathetic to those people because that means you understand how people In the world in the real world are who aren’t aren’t in our little UX bubble or tech bubble. Yeah I Love I love like those kind of things, you know when we talk about user research Part of you the research isn’t just asking questions is observing right? It’s watching how people what people actually do versus what they say and that’s why taking the interview outside of the conference room and into the real world can really kind of

say a lot about that person. So that’s kind of my take on it. It’s about reading people and that’s, know, for better or worse, something that like oftentimes when people get to me, they’ve gone through a few other people or I’ve met them like when I met you, like I met them at a talk or something. So they already kind of have an interest. But yeah, that’s probably my way of thinking about it. It’s not, there’s no specific method. It’s about really just understand the person.

Sarah Doody (43:27.832)

Well, and I think, you know, knowing as much as I do about who you’ve hired in the past and things, a lot of those people have come through referrals from people that you currently or previously worked at. So there’s been somewhat of like an initial stamp of approval by people that you very, very much trust because you’ve worked with them.

Dan Maccarone (43:45.868)

Yeah, that’s very true. Yeah. Yeah. Luckily.

Sarah Doody (43:49.358)

Okay, I have so many questions, but I got to limit myself here so we can get to some of the questions from people. One of the things that many UX people listening to this may want to do is go down that freelancer consultant route. What are like two, maybe three quick tips that you would have for anyone that is thinking about trying to go down that path?

Dan Maccarone (44:13.65)

don’t, no, I think, I think, I think that, well, if you’re starting your freelance career, don’t, and I know this is antithetical to how we think about working, like, don’t be a stickler for your rate to start. Like just get work, like, you know, find something to work on, by the way, make your own thing, especially now that we have things like vibe coding, like why not? Like find a problem that you want to solve and just make a sample product. that if someone has to see it, you can walk through every, every thought.

pieces of thought process. That doesn’t mean you need to be a designer, need to be a developer, certainly not these days on the development side. like, just find things to work on and I think the revenue part of it can come as you get more experience. And as you show that you actually have a freelance career. But I say that thing about the rate thing because I think sometimes we get so caught up in what we’re worth.

by the hour and I don’t believe in charging by the hour, I never have and it’s something I really hate. It’s about like, can you be proud of this work and can it be a stepping stone to something else? And when I find people get so wrapped up in the money part of it, they forget about the fact that they need to deliver quality work. And if you deliver quality work, you’re gonna get referred by that person to someone else and then someone else and then someone else. And that’s how you build a career, not by just charging absorbed.

crazy rates and I’m not bitter about it anyways. just like, I did it. Like I was a freelancer and I loved being a freelancer. It was one of my favorite times of my life. It was a freeing time of my life. But I took on projects from $500 to $20,000, you know, and sometimes the $500 projects were just fun, you know? And so I think that that’s the best part about freelancing is you can pick and choose yourself.

Sarah Doody (45:57.132)

Well, and you say it’s one rate today and the person that knocks on your door tomorrow gets another rate. That’s obsession over rates, I’ve done it in my career too. And it’s such a waste of time because it’s going to change even multiple times in the day. So don’t worry about it. Exactly. You get an inquiry in the morning and then you get an inquiry in the afternoon and you may not say the same rate.

Dan Maccarone (46:23.79)

Yeah. And I think sometimes it’s like, I’m not afraid to ask people for their budget. Like when I was freelancing or now, like it’s like, if they have a budget in mind, sometimes I’m so excited to work on something. I’m like, all right, you only have this much? Let’s figure out what that looks like. And then I guess the corollary to that is be creative in how you think about your deliverables. So a project that’s, let’s say, random numbers, someone paying you $20,000 worth, they probably want X, but if they only have $10,000, you say, well, how do I reduce these deliverables, but still get you what you need?

to get you to that next step or how can I collaborate with your designer or your engineering people or whatever. But those kinds of things can make you happier, especially if it’s something you want to work on. And if someone you can see, by the way, early on that they could be a problematic client, well, you might want to raise that rate a little bit because there’s like a problematic client tax, you know?

Sarah Doody (47:10.22)

Yep. Yes. Yes. Just like a service fee at a hotel or something or the Airbnb cleaning fee, right?

Dan Maccarone (47:17.294)

That’s right. They’ll never know it’s there, but there’s a reason why there are people you charge a little bit extra for.

Sarah Doody (47:22.574)

in white, white ink, it’s there. Yeah. Okay. I want to go to some of the questions here because Colleen loves the name of your companies. So congratulations on the amazing names. I always love Charming Robot. Katie said, how would you recommend asking for those kinds of state of the industry coffee chats that you said? I keep hearing no to a lot of inquiries for like pick your brains. So which ones do you say yes to?

Dan Maccarone (47:52.728)

Well, first of all, I think I may have learned this from you Sarah. I don’t know if this is true. Maybe it someone else. I think when someone asks you whether they can pick your brain or can you mentor me or whatever, those are generic questions that don’t spark any particular interest. I I do think it’s helpful when someone has clearly done a little bit of research on you because it shows that they’re interested in what your perspective is as opposed to just a person, a random expert’s perspective. But I also think coming with intention is important. So what do you want to talk about?

Like, do you want to talk about, you know, how I could better use AI as a UX person? And like, and I think it has to be a two-way street. What can I get out of it? No, I don’t mean that selfishly. I remember years ago, I hired this woman, Claire Marine, and Claire Marine came to the GA Talk and she afterwards, she’s like, hey, you know, I’d love to like meet up for coffee. She’s like, I’m working at a marketing company, doing UX. I don’t think it’s the right kind of UX. I’m really interested in working in product. And I just want to understand like how, what is the difference?

in that working experience or something like that. was something very specific she asked me. We met up for coffee and I literally hired her like on the spot. It was one of those things, like, but that’s not what I should say everyone should expect. But like, but she was so deliberate in what she wanted to talk about and what her particular problem was as opposed to what do you think about product design? It’s like, I’ve written articles on that. You can go read that, you know, but like you want to have a talk about it.

I think that’s what, it can be like, and don’t take someone’s time. Don’t ask for an hour, ask for 15 minutes, ask for half an hour. Chances are if it’s a good conversation, it’ll either last longer or you’ll have a follow-up conversation. I’d say that. then I think intent and goals maybe, not the goal should not be let me get a job, but it should be something a little bit more like I think tangible or reachable.

Sarah Doody (49:38.988)

Yeah, I mean, you and I are in the same boat. get all these very generic questions and similar to you. like, did you not even Google me? Like, did you not put portfolio and Sarah into Google and see what came up? And one of the things I do as well is I, in the email, will say, do you have time for like a 30 minute chat? Or if it’s easier, you could answer questions over email, you know? So give them an option because for some people, 30 minutes of their time on a calendar feels like very stressful.

Dan Maccarone (50:10.89)

And I hate, mean, while it makes me disgusted to say this, like you and me, Patrick also, all very, very Googleable people. you know, I mean, that was never an intention I had, but I know that people have Googled me. It’s there. Like, hey, take advantage of it, you know?

Sarah Doody (50:25.654)

Yep, yeah, no, we joined Twitter like way back in the 2000, below 2010 era. Okay, Nicole said, I’ve been hearing a lot of predictions that fractional is the future for senior tech expertise in UX people, I guess. What are your thoughts on that?

Dan Maccarone (50:33.322)

Yes. Yeah.

Dan Maccarone (50:45.12)

I have a lot of thoughts on this. I’ll limit them to a certain amount. Okay. I believe in Fractional, think, especially for early stage companies where to hire someone like, you know, who has senior level experience, has been doing this for a long time, it’s almost impossible because they’re so expensive, even if you’re giving them equity. think that, to let number one. Number two is, I don’t think Fractional is right for everyone. I think that you have to have a career that allows you to, or that has allowed you to

kind of fractionalize your brain across multiple projects. So like, and I’ve talked to Patrick about, when we say Patrick, by the way, we’re talking about Patrick Nieman. we wanted to do a little bit. Yeah, he’s great. He’s a great, brilliant guy. But like, and he and I talked about this when he was in New York a few weeks ago, when we were having drinks and like, was like, you know, he goes, don’t want to do that. Like I, he’s a big company guy, you know? And that’s awesome. Cause I’m not, but people who worked at like GE or Chase or big company for years.

Sarah Doody (51:24.59)

We’ll link to his episode.

Dan Maccarone (51:42.156)

I don’t think they’re as good at fractional because I don’t understand how to compartmentalize their time and to be almost as efficient as you have to be in the startup world. So that’s number two. And number three, think that kind of piggybacking up that I think there’s a certain place you have to get to in your career to be ready to be a fractional person. Someone I talked to recently was asking me, she was, think like, you know, maybe in her early thirties. I don’t know exactly, but she was like, I’m thinking about taking this fractional CPO role. And I was like, listen, you’ve been doing

UX and product work for like five years. I honestly just don’t think you’re ready to do that yet because you haven’t seen enough to really understand what it takes to manage multiple CEOs. It’s not just about the work, it’s managing the CEOs, managing up, managing down, hiring right, hiring. Like I love being a fractional person with a right-hand person in the company. So someone who’s like right, you know, I don’t like to say below me because it sounds insulting, but like right there who can like do a lot of the day-to-day that I can’t do because I’m working on three companies. So I think those three things

can make a great recipe for success in fractional. And that’s not just doing product, it’s true in technology or marketing or whatever. But the other thing I’ll say is that not all fractional gigs are the same. Some I’m running the product team and really in the weeds on. And some I’m a startup whisperer to the founder where I talk to them a couple times a week and they’re going a little bit slower in their journey. Or they’re great, they’re great CEO and just need advice. The size of the project.

depends on what the needs are. That took me a little while. It took me like a year or two to really understand how to come in the right way and forget about the money part of it, though that also took me a little while to figure out. But to come in the right way and be like, okay, this is how I can help you versus I know everything. I’m your CPO now and let me just do my thing. Sometimes that’s the right way to do it, but that’s my take on it.

Sarah Doody (53:29.26)

Yeah, yeah, I think it requires a lot of user research, right? Like not just before you say yes to the company, but even, you know, from day to day trying to figure out what are their needs, how have they shifted, et cetera. And I think too, one of the benefits of working with multiple companies at the same time is like the, the muscles, I guess, that you develop in managing up, managing down, et cetera. And that cross, I don’t know how to phrase this, like the, the learnings that you can apply across all those companies.

Dan Maccarone (53:58.55)

Yeah, there’s one other thing I’ll add. by the way, there’s an article I wrote on Medium about this. I’m not trying to plug it, other than if you’re interested in fractional, it does break it down pretty, pretty well. that it’s fractional is a two way street too. So you need buy-in from the company that they are okay with you being fractional. And because when I think of fractional, you are not a consultant, you’re not an agency, you’re not a freelancer. You are a part of the team, generally a C level suite, you know, ELT part of the team.

Everyone has to buy, especially the CEO has to buy into the fact that even though you’re not a 40 hour a week employee, you are just as part of that team as anyone else. And that has to be communicated across and down through the channels because if that buy-in isn’t there, the relationship will fail. I mean, I was at one place where they asked me every week, the CEO would be like, so when are you coming on full time? I’m not coming on full time. I’m here as a fractional CBO. I believe in the company, but you don’t want me full time. I would not be good at that. This happened again recently at a company I’m running product for.

where I’m replacing myself, which is great. And I’m training that person who’s going to replace me. And then she’ll take my place in like four months. So excited about that. But that buy-in is so critical. And boy, when I’ve made the mistake of not getting that, it just turns out poor.

Sarah Doody (55:08.022)

Yeah, yeah, it just turns into chaos and slack, I’m sure, and just lots of drama and you’re not a drama guy.

Dan Maccarone (55:17.748)

No, other than my theater.

Sarah Doody (55:19.335)

OK, what’s your take on companies that want candidates to do some assignment in the interview process?

Dan Maccarone (55:25.742)

hate it. I hate it so much. It makes me so angry because again, this is why I talk to people over, hey, how you doing? the dog’s here. This is why I talk to people over drinks. I hate it when people, because it’s asking me for free work. And sometimes they’ll use that work. I have a friend of mine who was recently interviewing for a head of product role and he had to spend two weeks on a deck that was outlining product strategy. I’m like, dude, that’s what they’re hiring you to do. They should be able to have a conversation with you to understand that.

In your past works, it’s like when you’re pitching a client too. I also don’t believe in doing design work for pitches. Cause I think it’s, I don’t know your strategy. I don’t, I haven’t done a deep dive. I’m not going to come up with the right solution. That’s a ton of time I could be spending working on things that will pay me. I may not be money driven, but I do like making money. And so, you know, it’s like, like you’re, high me for my brain and you’re hiring me for all the work I’ve done before this. If I’m not the right fit, that’s okay. But asking me to do work upfront to me is it’s insulting, not just anyone anyway. And I would never ask it of anyone who works.

with us. I just think it’s rude.

Sarah Doody (56:26.508)

Yeah. I noticed some companies like Help Scout are paying people for these. that is, I guess, a step in the right direction. But I think too, like, if we can’t understand people through conversations and if they have a portfolio, a portfolio, I mean, it just, feels like, I don’t know, kind of a cop out, like a little bit lazy on the company’s part to request that they do these free work, essentially.

Dan Maccarone (56:53.824)

Yeah, I totally agree. It happens too often in our industry on all sides. The one thing, hell will say, to be a total hypocrite. I know a lot of people do this on the engineering side, where they ask them to do it. And I’ve talked to lot of engineers about this, and it’s basically expected at this point that that’s part of it, because it’s trying to identify your skill sets as a coder. And I actually kind of see why that’s valuable in a way that’s not valuable in a UX designer.

because of the just the, I don’t know, the way that those rules work and the way that programming works. think that there’s something we said to like making sure you can actually do that. Again, it’s not about the tool, it’s about how you do it. But I kind of understand that. I’ve talked to CTOs about it too, and just different perspective, but I do forgive that one.

Sarah Doody (57:40.962)

No, it’s like, if I was a CTO and I asked someone to write some code, like there is an element of being able to look at code and know like, did they think through that right? Did they use like variables or whatever versus like repeat the same code blocks over and over? So yeah, I see a reason for that. Especially if they just let them do it real time during the interview versus give them a three-day homework assignment or something. All right.

Dan Maccarone (58:04.472)

Yeah, exactly.

Sarah Doody (58:06.882)

The last question, let me try and paraphrase it here. So Tostri was doing a UX research project with a product team and towards the end they said, we’re not going to be able to incorporate these findings. And I hope the dog’s okay. It’s okay. Okay. So the team that this research was done for has said, we’re not going to be able to re-integrate the research findings.

So as a researcher, how can I identify early problematic stakeholders and how to handle them? Like what is the canary in the coal mine, you know, even thinking through past clients that you’ve had and maybe yellow flags that you didn’t see or ignored.

Dan Maccarone (58:48.776)

You’re not going like the answer to this question. OK. But I’m going to be honest about it because I’ve been in this situation before. If people aren’t going to listen to research, they’re not going listen to research. And it’s unfortunate because it can be a waste of our time to create it. It’s a waste of the people’s time that we’re talking to. And ultimately, think what’s going to happen is for most people who are not listening to the research and not listening to data, they’re ultimately going to fail out their jobs and probably not

you know, last very long. could be true of founders starting something new. It could be true of people who are executives at companies. Years ago, we were doing research for Newsday, which is a newspaper on Long Island. The person who was our client was also a good friend of mine. I’d worked with her for about a decade at that point, maybe a little less than that. She had a thesis as to what she wanted to do to build all these kind of products within the Newsday environment.

And we did focus groups. as Sarah knows, I don’t love focus groups. But in this case, we got some really good recruits and had conversations over three or four nights with all types of people. And two things were very clear in this situation. One was that no one wanted the things that this person wanted to build. Like zero people. Like nothing resonated. But the other thing that came out of that research was a very, very clear opportunity for Newsday. was like, was one of the, it just doesn’t happen in research often, but it was one of those things where like,

It was so clear that they should make this thing and everyone wanted it. And we weren’t even asking about it. It just kept coming up again and again. So I’m in the middle of this research in this focus group and I got a message on my computer from my client who’s behind the wall, you know, in the one-way mirror. She’s like, get back here right now in all caps. And like my friend and I who were doing the focus group were like, this is very unorthodox, but okay. So we get back into the room where she is with all her

team members and their team members like cowering against the wall and cartoonish like I felt like smoke was coming out of her ears. She’s like, this is terrible. They don’t know they don’t want anything we want to build. And I’m like, no, that’s that’s true. They don’t but it’s not terrible. Like don’t build it. You can build this thing. She’s like, but it’s on our roadmap. And I’m like, yeah, but your roadmap is flexible. And this other thing is a thing you should build. And she’s like, this is terrible. This is disaster. Like this research is useless. And I’m like, okay, it’s not well, they built what she wanted to build. And she got fired.

Dan Maccarone (01:01:08.308)

So because it didn’t work. I think at some point, you have to, like you and I have done this, Sarah, like you make the argument, you make the argument as best you can, you try it from different angles. use quotes from people, you know, do everything you can to get it across. But ultimately if people want to put their fingers in their ears and don’t want to listen, like they’re either not the right people to work for. I hate to say that. Or, you know, you maybe have to gather more data. One other thing I’ll tell you from that, this one did work. About maybe a couple of years after that, that Newsday thing.

was looking with another company and they wanted to do user research and we do ethnographic studies. We talked to like 16 people. Now after like the first six or seven, you get the same stuff and you find the story you gotta tell. Went to this company, gave the findings and it was very obvious that we had to design as part of this. Like our designs, we did A and B test stuff and it won, like everything won like 99 % of the time. They’re like, well, you only talked to 16 people. That’s not enough people. You need more research. We’re like, okay. So we did a survey.

AB testing the same designs is 8 % of people pick the one that we put together. That’s not enough people. Now you’ve only talked to 116 people. We got to talk to a thousand people. Okay. So do a survey with a thousand people will AB test this. Well, in that case, 920 people voted for ours and 80 and at some point there’s a tipping point and they did finally agree like, okay, I guess you’re right. But, that’s not to we’re always right, but in that case it was like, guys, you gotta just go with it at some point and test it in real in the real world. So yeah.

Sarah Doody (01:02:35.116)

Yeah. Yeah. Show me the data, right? mean, data me the data. Yeah. Exactly. My last question for you, and it could even just be one or two words, is thinking back to Dan from 25 years ago, what is one piece of advice you would give yourself?

Dan Maccarone (01:02:39.627)

Exactly.

Dan Maccarone (01:02:52.622)

Don’t be so fucking arrogant. Don’t so fucking arrogant. Don’t be so fucking arrogant. Because I would say 1999 through 2010, I mean, I was very lucky to have made some great things and had a lot of success. But I think that like, it was alienating to people, even friends of mine who I worked with when I started like developing that and thinking that I was better, not better as a human being, but better at the job than some of my colleagues. And I think that was a huge mistake because

missed opportunities to learn from them and to listen to them and see what their point of view was. I really wish that I’d look back on that and luckily I prepared most of those relationships. it wasn’t always the best person, especially when I was younger. my 20s, my early 20s, I thought I knew everything and I really just didn’t.

Sarah Doody (01:03:42.862)

Yeah. I mean, I think there’s the ability to be humble and still be a hard ass when you need to be, you know? And I think I say that with the most like respect to you because I think I’ve never known egotistical Dan, or at least I never felt that, but you are very convicted about your values and

what you believe is right or wrong for product, et cetera, and you’re not afraid to say that. And I think that is something that just takes time to develop, right? And you have to practice it over and over and over, and it gets easier the more you do it. But I think both of those can exist at the same time.

Dan Maccarone (01:04:26.382)

I call it finding your UX voice. Another article I recently wrote. And that voice will evolve over time, which is a great thing as we all evolve over time. And the inputs you get to help change that are great. And I think that it took me a while to find the right voice and that voice is much more in tune to what I’m like today. But yeah, I think you put it the right way.

Sarah Doody (01:04:47.118)

Hey there, I just wanted to say thanks for listening to this episode all the way to the end. If you’re looking for links or resources mentioned, visit careersstrategylab.com slash podcast to find this episode details and the details of the hundreds of other episodes. If you’re looking for help with your UX or product job search, you may want to consider checking out my program, Career Strategy Lab.

where I help UX and product people just like you navigate unexpected challenges in their careers, whether that’s a layoff, trying to get promoted, or getting hired without applying to hundreds of jobs. To learn more about that, just go to careerstrategielab.com and click UX Career Coaching at the very top. That’s all for today, and I’ll see you next time in another episode of the Career Strategy Podcast.