Stop Asking How: Speed Up Your UX Job Search With This One Question

Sarah Doody (00:00.046)

What if tomorrow you had to apply for a UX job or you had to update your resume or add another case study to your portfolio or negotiate a job offer? Would your first move be to get to work and make it happen? Or would it be to open up Google or whatever you use and start typing in, how do I approach a UX job search? How do I update my resume?

How do I add a case study to my portfolio? How do I negotiate a job offer? If your default is how, then this episode is for you.

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.

all 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. Most UX and product people would do just that. They would default to asking how, but that’s actually the problem. When you default to asking how, that’s how you slow yourself down. Not because Google is bad, but because

you’re asking the wrong question entirely. So today I wanna introduce you to a concept that I cannot stop thinking about and once you hear it, you’re gonna start seeing the how trap everywhere and beyond just your job search. A couple of weeks ago, I grabbed coffee with a friend of mine who is a physical therapist. And oftentimes we get together and chat about businesses because at the end of the day, even though we’re in very different businesses,

Sarah Doody (02:11.127)

our problems are very much the same. And she told me about this book called Who Not How by Dan Sullivan and Benjamin Hardy. And the concept is that in business, oftentimes we focus on asking ourselves how. How do I market my business better? How do I hire people? How can I insert the blank there?

And the question we need to be asking is who? Because in business, our time is limited as entrepreneurs. And when we’re asking ourselves, how do I, that’s the problem. What we should be asking ourselves is who could do this for me? So for example, with marketing, instead of trying to figure out SEO, for example, and figure out how do I make my, in her case, physical therapy business,

show up in local search results, instead of asking that, what she really should be asking is who already knows, who is the expert in how to get local businesses to show up in Google search, right? So that then she could just hire that person instead of spending her time and energy probably doing a not so good job of it on her own by Googling how do I…

figure this out, right? So that’s the premise of who, not how. And when she was telling me about this, she said she sees this who, not how concept come up so often with her own patients at her physical therapy clinic, right? She said she sees patients spend months watching YouTube videos, scouring Instagram and Reddit threads, trying to DIY their own recovery, doing searches like,

How do I get rid of my back pain? How do I fix my shin splints and whatever the ailment is, right? But when they do this, when they try and DIY their own recovery, they’re slowing themselves down, right? And if those people would only just ask themselves, who can help me heal my back pain? Who can help me fix my shin splints? Those patients would be better, a lot faster.

Sarah Doody (04:36.909)

because they would have gone to an expert versus trying to DIY it themselves by piecing together information from the internet, right? So in our conversation, she turned to me and said, isn’t this the same for your people too, right? And I said, yep, it’s so true. Same thing for job seekers, right? So often you’re spending your time Googling and scouring the internet for how do I type

searches. What if instead of trying to do it on your own, you flipped that and started thinking about who can help me with my job search? Who could help me negotiate a better job offer? Who is the expert in resumes, portfolios, job interviews, whatever it is? So I started listening to the book Who Not How on Spotify and a couple of things came up for me. Number one is that this

how trap, it doesn’t just slow you down, but it costs you time, money, and frankly, momentum too, right? Even in my own business, there have certainly been times when I have taken the DIY approach and tried to figure things out on my own. Sometimes I can figure it out, but it takes me a lot longer than if I had gone right to an expert. And other times in my business, I have

bypassed the how do I step and gone right to an expert because over time I’ve learned number one the value of my own time as an entrepreneur but also the fact that when you lean on an expert a who if you will you are going to get that outcome faster more than likely and you’re also educating yourself so you’re not just getting the task done

but you’re leveling up your own skillset or at least knowledge because you are leveraging that person’s five, 10, 15 years of experience in that specific thing to help you pretty much leapfrog your knowledge, if you will, versus if you just started out trying to take the how do I do this approach. And another thing that’s come to me after listening to this audio book, I’m still actually in the middle of it.

Sarah Doody (07:04.391)

is that asking for help, leaning on other people is not a weakness. It’s actually how high performers really operate and really outpace their competitors. And as someone who loves to figure stuff out, this is always a tricky thing for me because I do enjoy problem solving and like the feeling that I get when I figure something out. But as a business owner, I also have to remember

There are many other things that I should be doing. So in trying to figure out something in my business, what is not getting done as a result of that? So kind of like the trade-offs, if you will. Another thing that’s come to me is that this is not about being lazy and outsourcing stuff to other people. This is about being really strategic with your energy.

and focusing on your strengths so you can reach whatever your outcomes are a lot, lot faster. So I wanna think about like how this how trap can keep you stuck in your job search. And maybe some of these ideas resonate with you. So are you, for example, spending hours trying to condense your 10, 15, 20 years of experience?

into a resume? Are you constantly Googling how to create a resume for a senior level UX person or a VP level UX researcher or whatever your scenario is? Even go to your Google history, it might be there right now, but I’m sure you’re probably starting to identify things in your own job search, your own career that you have been spending a lot of time trying to

how when you should be asking yourself who. Another example, are you currently trying to add another case study to your portfolio or maybe you haven’t touched your portfolio in five years because you were at the same company for five years and now you’ve been laid off or something like that. Is your first reaction to start going to Google or Claude or whatever you use and asking how do I?

Sarah Doody (09:29.807)

create an effective UX case study. How do I make a portfolio? How do I create a portfolio that people spend more than one minute on, for example? If so, you’re gonna end up with just an overwhelming amount of information. And then you’re gonna start to wonder, what information do I believe? What information is true? What information is clickbait, et cetera, right? And you’re gonna be caught in this how trap. Maybe you’re in that trap.

right now. Maybe you have interviews coming up or you have in the past and you can relate to this, but when you did secure those interviews, were you immediately Googling how to prepare for an interview, how to present projects in my interview, how to prepare for a whiteboard challenge in a UX job interview, right? All of those searches. Chances are you probably did one of those searches. And similar to the last example, you were probably stuck in this

just web of content that you were trying to untangle to figure out, wait a sec, I don’t even know what information to trust right now, because there’s so much of it, right? Instead, what would have happened if you asked who? Who could help me prepare for the job interview? Who could help me prepare for that whiteboard challenge or whatever it is that you feel like your weakness is?

when it comes to job interviews. So I wanna give you three actionable takeaways for this concept of who, not how. So takeaway number one is to do a quick audit of where you have been stuck, either in your job search, maybe in your career, maybe just in your day-to-day job. But take this moment to do an audit of where you’ve been stuck in how much.

for more than two weeks, let’s say, and make a list of all the things that you’re stuck in how mode for. Maybe it’s your job search and it’s specific things that you know you keep Googling or asking AI trying to get an answer to, yet you still are not making progress, maybe because you’re still searching for the answer or…

Sarah Doody (11:44.463)

You’re starting to implement some of this how-to advice you’re finding, but then you get stuck or you find a conflicting piece of information, right? So if you’ve been sitting on something for two weeks or more, that is really a signal that you don’t need more information. You need a who. And the length of this list that you create is data. It is a signal. It should be a yellow flag because

the more things that are on your list, it’s a signal that you’re stuck in this how trap and you really might need to think about who could help you with these things. All right, the second takeaway here is that I want you to match the type of things that you’re stuck in how mode with to a who.

So for all of the things on the list that you made in step one, that audit list of all the things you’re stuck in how mode for, I want you to think about what would it look like to then address each of those things with a person, with a who. So for example, let’s say you’re stuck on your UX portfolio and you’ve previously Googled, how do I make a portfolio?

How do I write a case study? How do I create a portfolio that is gonna land me interviews, et cetera? Number one, I would challenge you to go to Google or whatever you use and change that search so it says, who could help me with my UX portfolio? Who could help me write better case studies, et cetera? And compare that with the search results you get when you type in

How do I create a portfolio? How do I write a UX case study, for example? Because chances are those search results are going to be a little different. And another thing I would challenge you to do, and this might be easier if you’re using an AI tool like Claude or something, would be to follow up with a prompt along the lines of who could help me write a more effective case study and why should I trust them?

Sarah Doody (14:09.087)

or why are they the expert or what qualifies them to help me. That is going to help you start to find those people that might be the who of this whole who, not how philosophy. So something to think about, but take some of the things that are on your how list and start to just explore potential who’s or people that could

help you with this problem you are facing. Okay, and takeaway number three would be to go back and look at your list from number one, this how list, and think about that list through the lens of your time. So for everything on your list, ask yourself, how long have I been trying to get hired in user experience, get promoted in my product design job?

Finish my UX portfolio. Create a resume that actually leads to interviews, whatever is on your list. And in this third step, I want you to think about how long have I been trying to do those things for and how much longer can I afford to do it on my own? Because chances are there are things on that how list that have real consequences.

to not being finished, right? If your resume isn’t ready to go, you are not able to apply for jobs, right? If your portfolio is not ready to go, or if it’s kind of like half done, you maybe can get interviews, but you’re gonna be not prepared if you actually get interviews and need to talk about that project in the interview, right? So in this step, I want you to think about what would it mean if I could do these things

faster, right? And in this case, there’s like a tangible time component, but there’s also a money component too to getting hired, right? Because for every month that you stay stuck not being able to apply because your resume isn’t done, your portfolio isn’t done, and your LinkedIn hasn’t been updated in three years, every single month that goes by is a month that you’re not applying and a month that you’re not in your new salary.

Sarah Doody (16:36.687)

And that has a quantifiable impact, right? So to recap, number one, we wanna be auditing where you are stuck in this how mode. Number two, to explore the who’s the people that could help you achieve those things on your list in number one. And then number three, have a really frank conversation with yourself around

the time and consequences of continuing to take this how approach, meaning the DIY approach, and how you could potentially accelerate your timeline to achieving these goals if you had an experienced person, a who, on your side. Now here’s the thing, everything I’ve talked about today of course applies to a job search.

but this applies to frankly, everything on our lives. I spoke about how it applies to my business and my mindset as an entrepreneur. It could apply to your job if you’re currently employed. It can apply to hobbies that you have. Like for example, I have run marathons in the past and when I started out, I was Googling how to run a marathon, how to run a sub four hour marathon.

how to strength train for marathon running, et cetera, And I DIY’d my own training for my first marathon, but when I outsourced my training and found a coach, I took 20 minutes off my marathon, which was amazing, but could I have done that on my own? Probably not. So this who not how framework,

extends far beyond our job search. It truly extends to every area of our lives. One of the things that’s really stuck with me in this book is that the highest performers aren’t necessarily like working harder or researching more. They’re just better at identifying who can help them. They’re better at stopping themselves in their own tracks when they go down this how do i path.

Sarah Doody (18:54.415)

and they realize, wait a sec, should I be trying to do this or should I be finding someone else to help me with this, right? And that is a skill, that is a muscle, and I need to remind myself of this on a daily basis, let me tell you. But when you develop this skill, it compounds over time, right? And it becomes more second nature. And so I really encourage you to think about this concept of who, not how.

and where it might apply in your work or your life. So whether you’re job searching or not, this question is worth asking and that is, where am I spinning my wheels trying to figure out the how when someone out there already has this problem solved? All right, that’s it for today. Who, not how. That’s all I want you to remember.

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 will see you next time in another episode of the Career Strategy Podcast.