Approach Job Hunting like a Design Challenge

How I interviewed and got my first Product Design roles

Interviewing for my first few product design jobs was a thrilling, yet challenging time for me.

Looking back, I remember feeling excited, determined, but also overwhelmed and intimidated by the lengthy interview process. There were so many questions swirling in my mind…

How many interview rounds are there? How should I present my portfolio? They say “product designer,” but do they mean UX, or visual, or research, or everything?

And of course, the worst…

I made it to the final round after weeks, but didn’t get the job… Arghhh, now what!?

Thankfully, through lots of trial-and-error and mentor advice, I was able to answer many of these questions. But more importantly, I started looking at job hunting as yet another design challenge. Once I applied design thinking principles to my job hunt, I had a lot more success, and even some fun.

If you’re new to product design, or making a career transition (as I did), I hope from reading my article, you can apply some of my strategies to your own job search. (And let me know how it goes!)

As always, if you have thoughts, feedback or just want to chat, feel free to reach out via email ( or meet up if you’re in San Francisco. Cheers!

My Story

After fumbling through my first few job interviews, I finally got to the last round with a mid-stage tech startup. And it actually went pretty well! From talking to the founder to presenting my portfolio and various 1:1 chats, each interview left me feeling more confident and more excited. I was exhausted. But, the end felt so near. I could finally. Stop. Interviewing.

Three days later, I got a phone call from their technical recruiter.

“I’m sorry. You know, the nature of startups… it’s very unpredictable. I hope we can keep in touch.”

She had been calling to tell me that they “lost headcount.” Whether that was true or just a coverup, I’ll never know. All I knew was that I was r-e-j-e-c-t-e-d. Sigh. I turned my phone off, collapsed into bed, willing my blankets to envelop me into a cocoon from which I would never emerge (I can be a tad dramatic, I know).

This wasn’t the first time I’d been left dry after weeks of interviewing and doing interview projects and presentations. I’d been rejected plenty of times, and by now, I had a nice little rejection routine: Pour myself a glass of Malbec… While simultaneously wiping the experience from memory… Then, after a satisfactory amount of moping had occurred, I would pick myself back up. Continue full steam ahead. Start to apply for more roles. Fill up my pipeline again, with the hopes that something would work out. Anyways, “it’s a numbers game!” several peers and mentors had encouraged.

But after this particular interview round, I finally realized this had become a faulty and costly strategy… Why would I continue doing the same thing again? Didn’t some famous person say the definition of insanity is doing the same thing over and over again, while expecting the same results?

So, I decided it was time for a new rejection routine. These were the new processes I came up with…

1. Approach interviewing like a researcher

At the beginning of my job hunt journey, one frustrating thing was the lack of resources for UX/product design interviews. After all, there are a ton of job interview “bibles” out there for other roles. Engineers have Cracking the Coding Interview; consultants have Case On Point. But there wasn’t a Product Design equivalent.

So I decided to create my own by documenting every interview experience I had into a Google Doc.

My Google doc of interview “research”

Like a good researcher, I began collecting key insights and learnings from each job interview I went on. I wrote down each question I was asked. And then the responses I gave. Then I thought about how I could improve them and wrote a “better” version.

As I continued to go on interviews, I integrated this retro system into my job hunt process. If I knew I had an interview scheduled, I would also “schedule” a retro for myself afterwards at the nearest coffee shop.

This served as a great “desensitizing” mechanism for myself. Usually, I would be anxiously overanalyzing everything that happened after the interview. With this new routine, I took the emotions out of it and made it a lot more objective and actionable. At the coffee shop, I would pull out my Google Doc, go into researcher mode and just document everything that happened. Then, I would reflect on how it went and if I could have said anything more eloquently or honestly. I knew I couldn’t change the past, but this process made even a “bad” interview still feel productive.

At a certain point, I had documented so many questions that nothing really surprised me, and my responses and confidence kept improving. I started to see patterns in what type of questions were asked and realized a lot of questions were just the same, but asked in a different way. I realized that a lot of whiteboard challenges fell into very similar categories.

My whiteboard challenge categories

In this way, I created a “living” interview guide that I still have today and keeps becoming more comprehensive and personalized for me.

A lot of people have asked me for this interview guide, and I’m happy to share it. But I also think the best thing to do is to build one for yourself. The act of building it is a great exercise in itself, and also you have the opportunity to make the responses and stories you tell your own.

2. Figure out the values that drive you to do good work

As I looked over my interview “research,” I quickly realized one key insight: I needed to figure out what values were driving my answers.

In the beginning, my answers were all over the place. I would just jump into whatever interview came up. I would deliver answers I thought seemed impressive or that I thought companies would want to hear. I also tended toward agreeable, safe answers that I hoped didn’t disqualify me. For example, “Of course, I can do graphic design for your email newsletters! Whatever you need!” Spoiler alert: I am not trained in graphic design.

For some reason, I couldn’t shake the fear that I needed to be able to do it all and that I had no experience. Like many UXers, I never studied “user experience.” I didn’t even study anything digitally related… For goodness sake, I studied textiles! In interviews, I always felt like my unconventional background was a handicap and didn’t want to draw attention to it.

Thankfully, I had some mentors who reminded me that my unique background was actually an asset and that despite not having UX experience — I did have work experience that I could draw upon to know what I need to do good work.

So, I set aside some time again to reflect and wrote out a list (I love lists!). I had worked in a variety of companies and teams since graduating college. For each job, I made a list about what I enjoyed and what was motivating. And then what I didn’t like or what was frustrating. Then, I started to synthesize these findings into what I valued in a job, a boss, a team, a company.

In the end, I realized you can easily judge job prospects by the external benchmarks: Attractive benefits, brand name, sexy industry vertical, fun perks… But ultimately, judging by what you value and what motivates you intrinsically is key.

Looking back on my own job history, it was the difference between waking up every morning and looking forward to the day, and hitting snooze, always thinking about the weekend.

3. Evaluate potential colleagues, bosses and work culture based on your values

One of my values was trust. Sounds a little vague, but what that meant for me was having trust with the team, trust between coworkers, trust with my design manager. From a design perspective, having trust meant having a fertile space for me to practice design, more room for creativity, more grace for failure, more opportunities to take risks and be bold, more space to be assertive, to be myself, to show my personality.

I knew that if I was going to be spending 50% of my waking hours somewhere, then I wanted to walk into a place where I could let down my guard to a certain extent.

At my current job today, my co-worker once said to an interview candidate, “It’s like we’re all cousins here!” Kind of a strange thing to say to the interview candidate. But as I was trying to stifle my chuckles at how weird that sounded, at the same time, I totally understood her.

In a well-known study by Google on work teams, they found that the most effective teams weren’t necessarily the smartest or most skilled, but generally just liked each other, trusted one another, and felt comfortable being themselves.

Trust leads to respect, which leads to stronger relationships, more willingness to be dedicated, more opportunities to be risky, more tendency to speak up about opinions, and thus, more thoughtful designs.

Unfortunately, it’s difficult to ask your potential colleagues point blank, “Does everyone here trust each other?” Instead, I began to ask more pointed questions. This was a big turning point for me, since before, I used to only focus on questions the company might ask me, spending very little time on questions I should ask them. But along the journey, I learned that was a waste of an opportunity.

A product designer friend of mine encouraged me, “You should be vetting them, just as hard as they are vetting you.” So, I started asking tougher questions. For example, is the team okay with failing together as much as winning together? Or is this a place where people are always pointing fingers, throwing each other under the bus, and constantly needing to CYA (cover your ass)?

I remember asking a product manager (who I currently work with now!), “What do you imagine an ideal working relationship between us to be?” She had a surprising answer, she said that we would have the “same brain.” Seeing my confused expression, she went on to explain that for example, if she went away on vacation, she would feel totally assured knowing that I could carry on the work, because we would be in sync with direction and priorities.

I really liked her answer, because it showed that she also valued trust and would consider me an equal product owner. Today, it’s pretty awesome to have this “same brain” play out as we both try to bring our product to life. By no means do we have the same opinions, but we do have a shared understanding of the product vision.

Another example that I constantly return to is when I started interviewing with my current boss. Before I had my final onsite interview, he offered me an opportunity to come into the office and run my presentation past him for feedback. I loved that! It was really cool that he had a transparent and supportive approach rather than a “prove it to us” cold approach to evaluating candidates. It also gave me an opportunity to show him how I take and implement feedback, which I value a lot in design process.

The fact that he offered his own time to give feedback showed that their culture would be open and collaborative, rather than the stiff, formal and silo’d environments that I had experienced in the past.

Tough questions reveal a lot about the company and team values. For me, my values were trust, collaboration, growth and diversity. Discover your values based on your own past experience and be convicted on them. Ask the tough questions. Don’t waste the last 5–10 minutes in an interview with some fluffy and safe questions. Vet your prospects as equally as they are vetting you — they will be impressed.

4. Take every interview you can get, but have a strategy

Sounds kind of contradictory once I said you should stand firm on your values… But take all the interviews you can get. I found this to be especially true if as a new product designer with less than five years of UX experience.

The benefit of taking every interview is that you get a lot of data. Instead of wondering in your head what type of roles, companies, teams would suit you, you just test it out IRL. When you take every interview, you also get a lot of practice. This way, when your dream job does come along, you’re fully prepared and your portfolio and presentation has gone through many iterations to get to a stellar point.

We’ve all heard of the “quantity over quality” study where ceramics students who focused more on output ended up making better pottery than students who tried to get it perfect once. Good design comes from iterating, and the same goes for job interviewing.

At first, this principle was a little controversial with other peers who were also job interviewing at the same time. We get a lot of contradictory advice. Some people are in the camp of thinking you need to “brand yourself” as a particular designer and only go after a certain vertical… For example, “I’m only interested in health tech or social impact tech and I’m only taking interviews there, because it aligns with my passions blah blah blah.”

Personally, I think that’s a little ridiculous and entitled to do at such an early stage of your career. It’s like the people who only go on a date if someone lines up with all 109 items on their perfect mate checklist. Uh, hello! You haven’t even had one conversation yet! You’re speculating and also have no idea about what you want! This is your first job! How do you know you want a mid-size Ed tech company for K-12 kids? (I’m mostly talking to my past self, here.)

Sure, you can have a vision. But just like with product design, at a certain stage, you shouldn’t jump straight to the solution. By taking every interview opportunity, I focused on learning and accurately assessing my needs and skill-level.

Take every interview you get at least in the early stages of your job hunt and then narrow it down to the ones that naturally fit you.

Side note: Practice, practice, practice! I noticed that some people don’t practice saying their answers aloud or giving a mock portfolio presentation, because they don’t want to sound rehearsed. I feel like the only way for me to not awkwardly stumble and fumble over my answers was to practice my spiel constantly. Practice during your walk, on the bus, in the shower! There are plenty of opportunities.

Although feedback and rehearsing can be excruciating, the more you practice, the less emotional it becomes. At this point, you already have a bank of questions from your self-created “interview guide” (Principle #1) to use for practice.

I think of it like physical exercise. Do a set of those questions like a circuit. Do each question 3–4 times like a rep. Do it everyday. It sucks in the beginning, but eventually strength training starts to feel good.

5. Build a support network of peers

Designers. We can sometimes get oddly competitive… And while competition isn’t necessarily bad (trust me, I love a little fun competition heh, heh…), it’s terrible when the job hunt feels competitive, rather than collaborative.

A design mentor of mine actually remarked that he built much of his network during his seasons of job hunting. Because once you start a job, you focus more on the relationships within your company. “So, you should take advantage of this time!” He exclaimed.

The friendships I made during this time surprised me, and in hindsight, makes me feel more grateful for this time… Today, I know I can call on one of these individuals if I need advice, a sounding board, or just someone to grab a drink with after a long day.

Make sure you have a good support system around you during job hunting. Sometimes, people don’t want to reveal too much about their job hunt, thinking it causes more pressure on them. But in my opinion, it’s way harder to do this process on your own. These friends can help you practice whiteboard challenges, interview questions, and rehearse presentations. They can listen to every God-awful rendition of the “Tell Me About Yourself” story.

Your support network also keeps you accountable to your personal values (from Principle #3) — you can ask them to remind you if a job doesn’t quite seem to align with what you want or need, instead of being tempted to take a job for the wrong reasons.

Get some people in your support network who are willing to challenge you and tell you the tough things that no one really likes to hear. I will never forget when someone said to me “My eyes glazed over during your presentation.” Ouch. But, okay!

Just like you should never design in a vacuum, don’t ever go through the interview process alone without getting feedback at crucial points. During this time, I reached out to tons of different types of people for advice. I looked up friends of friends, scoured LinkedIn and was pretty shameless about asking for feedback. This has led to invaluable insights, mentors, and a network I can rely on. In design, critique is the fastest route to growth and improvement. Same goes for the interview process! Also, make sure you return the favor.

Final thoughts

I’ve always thought the interview process is a lot like the design process. You iterate and iterate on it, making it better each time. You have a goal, constraints and many, many stakeholders to convince in order to get to a collective “yes.” Failures provide an opportunity to chew on the problem further and break through.

My job hunt journey followed a very similar route to the design thinking journey:

  • 1. Understand: What are your needs and problems? What do you need in a job? What problems have you encountered in the past when it came to job hunting and finding a role that best fit you?
  • 2. Define: Pinpoint your values and your vision. What is your “north star” that you can evaluate potential roles, teams and colleagues against?
  • 3. Generate: Take every interview possible, think of all the questions you could be asked, come up with many scenarios and types of responses
  • 4. Synthesize: As you go through interviews and practice, practice, practice, begin to crystallize your answers, your portfolio, your presentation and technical skills… ultimately you are the product.
  • 5. Validate: Get feedback from the interviews and from your support network. What worked and didn’t work? Was the “product” you created successful?
  • Iterate: Redesign the process as you go so it works for you.

One miraculous thing also happened once I reframed the job hunt process more like the design process… I started to actually have fun! It reminded me of why I decided to become a designer in the first place, because I actually love doing design and find it really fun. Shifting my mindset helped me take the pressure off and once I started to see job hunting as design I started to actually enjoy it.

Making the mindset switch might be all you need. Find ways to make the process fun and apply design thinking to unexpected parts of your life. It’s definitely easier said than done. However, the good news is that you have the rest of your life to keep practicing (unless you’re retiring early.) I’m sure I will be interviewing again at some point, in which I’ll have to re-strategize and relearn how to make the most out of it. Enjoy the process, enjoy your life!

Final thoughts, for real

At Weight Watchers (the company I now work at), I am constantly inspired by our users — many Weight Watchers members have struggled with body weight for all their life. Yet, they make a conscious decision to do something about it. They join the program, they try to figure out how to make the program a part of their life, they persevere, eventually reaching an “aha” moment in which they realize: there is no goal. You don’t reach your “goal” weight or ideal shape and then think, “Great, I made it. I’m done for life.” It’s a lifestyle change and requires constant effort and improvement.

Weight Watchers members realize that you’re always a work in progress. So you might as well come to enjoy the journey and the hard work that comes with it.

Similarly, the product design interview process has countless steps and conversations necessary to be had. And even when you get that offer, the process of improving your skills never really stops. Each day at my current job, I’m still trying to improve and get better. Just like living a healthy lifestyle, it’s an unending cycle for the rest of your life. Just as is becoming a better designer and getting better at interviewing.

I hope you are able to turn the pain into enjoyment and are able to be resilient through the many tough times. I’m sure I will continually be doing that myself.

Thank you, Alice Egan, Christina Chang, Lakshmi Mani, Rohini Bagrodia, Kenny Lopez, and Sophie Su, for reading my article and giving me feedback.

— Chrysan Tung

Currently product designer at Weight Watchers. I like design that is compassionate, research-centered and tells a good story. | @chrysantung