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How to Approach Job Hunting Like a Design Challenge

Land your dream job — and learn a lot in the process

Chrysan Tung
Jan 12, 2018 · 13 min read
Photo: Hero Images/Getty Images

When I started interviewing for my first product design job, it was a thrilling but challenging time. I was excited and determined, but also overwhelmed and intimidated by the lengthy process. So many questions swirled around my mind: How many interview rounds are there? How should I present my portfolio? They say “product designer,” but do they mean UX, visual, research, or everything?

And, of course, the worst: I made it to the final round after weeks, but didn’t get the job. Argh! Now what?

Thankfully, through lots of trial and error as well as mentor advice, I was able to answer many of these questions myself. 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 was), I hope you apply some of my strategies to your own job search. (Let me know how it goes!) As always, if you have thoughts or feedback, or just want to chat, feel free to reach out via email or meet up if you’re in San Francisco. Cheers!

Background

After fumbling through my first few job interviews, I finally got to the last round with a mid-stage tech startup, and it 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 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,” she said. “You know the nature of startups—it’s very unpredictable. I hope we can keep in touch.” She told me they “lost head count.” Whether that was true or just a cover-up, I’ll never know; all I knew was that I was r-e-j-e-c-t-e-d. I turned off my phone and collapsed into bed, willing my blankets to envelop me into a cocoon from which I would never emerge (yes, I can be a tad dramatic).

Before, I overanalyzed everything that happened after the interview. This new routine removed the emotional component and made the process a lot more objective and actionable.

I had been rejected plenty of times, and I had developed a nice little rejection routine: Pour myself a glass of Malbec while wiping the experience from memory. Then, after a satisfactory amount of moping, I would pick myself up and continue full steam ahead. Apply for more roles. Fill up my pipeline in the hopes that something would work out. Several of my peers and mentors had encouraged me to think of interviewing as a numbers game.

But after this particular interview round, I finally realized my strategy was faulty and costly. Why would I continue down the same path? Didn’t some famous person say the definition of insanity is doing the same thing over and over while expecting different results?

I decided it was time for a new rejection routine. Here are the steps of the process I developed.

Step 1: Approach Interviewing Like a Researcher

At the beginning of my job hunt, I was frustrated by the lack of resources for UX/product design interviews. 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. I decided to create my own by documenting every interview experience in 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 wrote down every question I was asked, as well as my responses. Then I thought about how I could improve my answers, and I crafted better versions.

As I continued to go on interviews, I integrated this retro system into my process. If I booked an interview, I also scheduled a retro for myself afterward at the nearest coffee shop.

This served as a great mechanism for desensitizing myself. Before, I overanalyzed everything that happened after the interview. This new routine removed the emotional component and made the process a lot more objective and actionable. I knew I couldn’t change the past, but this process made even a bad interview 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 the types of questions interviewers asked, and I realized a lot of whiteboard challenges fell into very similar categories.

My whiteboard challenge categories.

Over time, I created a living interview guide that became increasingly comprehensive and personalized.

Step 2: Figure Out the Values That Drive You to Do Good Work

As I looked over my interview research, I had a key insight: I needed to figure out what values were driving my interview responses.

In the beginning, I was all over the place. I jumped into whatever interview question came up. I delivered answers I thought were impressive or that companies would want to hear. I also tended toward agreeable, safe responses that I hoped wouldn’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.

I couldn’t shake the conviction that I had to be able to do it all and the fear that I had no experience. Like many UXers, I’d never studied user experience. I didn’t even study anything related to digital—I studied textiles. In interviews, I always felt like my unconventional background was a handicap, and I didn’t want to draw attention to it.

I knew that if I was going to spend 50 percent of my waking hours somewhere, I wanted to walk into a place where I could let down my guard.

Thankfully, I had some mentors who reminded me that my unique background was actually an asset. Despite not having UX experience, I did have relevant work experience that I could draw on to know what I needed to do good work.

Again I set aside some time to reflect, and I wrote out a list (I love lists!). I had worked for a variety of companies since graduating from college, and for each job I made a list of what I enjoyed and what motivated me. Then I listed what I didn’t like and what frustrated me. I synthesized these findings into what I value in a job, a boss, a team, a company.

I realized that while you can evaluate a job prospect by the external benchmarks—attractive benefits, brand name, sexy industry vertical, fun perks—it is more important to judge according to what you value and what motivates you.

Looking back on my own job history, this was the difference between waking up every morning and looking forward to the day or hitting snooze and longing for the weekend.

Step 3: Evaluate Potential Colleagues, Bosses, and Work Cultures Based on Your Values

One of my values is establishing trust within the team, between coworkers, and with my design manager. From a design perspective, trust means having a fertile space to practice design, with more room for creativity, more acceptance of failure, more opportunities to take risks and be bold, and more space to be assertive, be myself, and show my personality.

I knew that if I was going to spend 50 percent of my waking hours somewhere, I wanted to walk into a place where I could let down my guard. At my current job, a coworker once told a candidate, “It’s like we’re all cousins here!” Although I had to stifle my chuckles over how weird that sounded, I totally understood what she meant.

Google’s well-known study on work teams found that the most effective teams weren’t necessarily the smartest or most skilled, but those that generally 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, as a result, more thoughtful designs.

It’s difficult, however, 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. Before, I focused on questions the company might ask me and spent very little time on questions I would ask them. That was a wasted opportunity.

Tough questions reveal a lot about the company and team values…. Don’t waste the last few minutes of an interview asking stale, fluffy questions.

A product-designer friend advised me to vet potential companies as hard as they were vetting me. So I started asking tougher questions, such as, “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 cover their asses?”

I once asked a product manager (who I currently work with now), “What do you imagine an ideal working relationship between us to be?” Her answer surprised me: She said we would have the “same brain.” Seeing my confused reaction, she went on to explain that if, for example, she went on vacation, she would feel totally reassured 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 try to bring our product to life. We don’t always have the same opinion, but we do have a shared understanding of the product vision.

Before I had my final on-site interview with my current boss, he offered me an opportunity to come into the office and run my presentation past him for feedback. I loved this transparent, supportive approach, which was a welcome change from the prove-it-to-us-cold method. This also gave me an opportunity to show him how I react to and implement feedback, which I value tremendously.

His offer to share his own time showed me that their culture would be open and collaborative, rather than the stiff, formal silo environments I had experienced in the past.

Tough questions reveal a lot about the company and team values. My values are trust, collaboration, growth, and diversity. Identify yours and stick to them. Don’t waste the last few minutes of an interview asking stale, fluffy questions. Vet your prospects — they will be impressed.

Step 4: Take Every Interview You Can, But Have a Strategy

Take all the interviews you can get. This seemingly contradicts the advice to stick to your values, but I found this to be especially important if you are a new product designer with less than five years’ UX experience.

If you take every interview, you get a lot of data. Instead of wondering what types of roles, companies, and teams would suit you, you can test things out. If you take every interview, you also get a lot of practice. When your dream job does come along, you will be fully prepared, and your portfolio and presentation will be stellar.

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

At first, this principle was a little controversial with my peers who were job hunting 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 go after a particular 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.”

Sometimes people don’t want to reveal too much about their job hunt because they feel like it creates extra pressure. But it’s way harder to go through this process on your own.

I think it’s ridiculous and entitled to limit yourself at such an early stage of your career. It’s like people who go on a date only if someone lines up with all 109 items on their perfect-mate checklist. You haven’t even had one conversation! You’re speculating, and you have no idea about what you want. How do you know you want a midsize ed tech company for K–12 kids? (I’m mostly talking to my past self.)

Sure, you can have a vision. But just like with product design, 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.

Be sure to practice, practice, practice your presentation. Some people don’t practice saying their answers aloud or giving a mock portfolio presentation because they don’t want to sound rehearsed. Don’t worry about this; practice! I had to practice my spiel constantly to avoid stumbling and fumbling. Practice during your walk, on the bus, and in the shower. There are plenty of opportunities.

By this point, you already have a bank of questions from Step 1 to use for practice. Think of it like physical exercise. Do a set of questions like a circuit, and answer each question three to four times, like a rep. Do it every day. It sucks in the beginning, but eventually strength training starts to feel good.

Step 5: Build a Support Network of Peers

Designers can be competitive. While competition isn’t necessarily bad, it’s terrible when the job hunt feels competitive rather than collaborative.

One of my design mentors built much of his network during his seasons of job hunting. He noted that it’s important to take advantage of this time, because once you start a job you focus more on the relationships within your company.

I am so grateful for the friends I made while interviewing. Today, I know I can call on one of them if I need advice or a sounding board, or someone to grab a drink with after a long day.

Make sure you have a good support system around you while you are looking for a job. Sometimes people don’t want to reveal too much about their job hunt because they feel like it creates extra pressure. But it’s way harder to go through this process on your own. Your network of friends can help you practice whiteboard challenges, answer interview questions, and rehearse presentations. They can listen to every god-awful rendition of the tell-me-about-yourself story.

Just like you should never design in a vacuum, don’t ever go through the interview process without getting feedback at crucial points.

Your support network also keeps you accountable to your personal values (from Step 3). They will tell you if a job doesn’t quite align with what you want or need, and they will talk you out of taking a job for the wrong reasons.

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

Just like you should never design in a vacuum, don’t ever go through the interview process without getting feedback at crucial points. I reached out to tons of different people for advice. I looked up friends of friends, scoured LinkedIn, and was shameless about asking for feedback. This 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. Make sure you return the favor.

Final Thoughts

The interview process is a lot like the design process. You iterate and iterate, 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 and break through:

  • 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?
  • Define: Pinpoint your values and vision. What is the north star against which you can evaluate potential roles, teams, and colleagues?
  • Generate: Take every interview possible, think of all the questions you could be asked, come up with many scenarios, and craft your responses.
  • Synthesize: As you go through interviews and practice, practice, practice, begin to crystallize your answers, your portfolio, your presentation, and your technical skills. Ultimately, you are the product.
  • 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 needed so it works for you.

Once I reframed the job-hunt process, I actually I started to have fun. Shifting my mind-set helped me take the pressure off. I love designing, and once I started to see job hunting as design I began to enjoy it.

Enjoy the process, and enjoy your life. Find ways to make the process fun and apply design thinking to unexpected parts of your life. This is definitely easier said than done. The good news, however, 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, and I’ll have to rework my strategies and learn how to make the most out of the process.

Final Thoughts (Really)

At Weight Watchers (the company I now work for), I am constantly inspired by our users. Many Weight Watchers members have had a lifelong struggle with their weight, but they make a conscious decision to do something about it. They join the program, they figure out how to make the program a part of their lives, they persevere, and they eventually have an “aha” moment in which they realize there is no stopping point. They don’t reach their goal weight or ideal shape and think, Great, I made it. I’m done for life. It’s a lifestyle change that 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, there are countless steps and conversations involved in landing a product-design job. And even when you get that offer, the process of improving your skills never really stops. Each day I try to improve.

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



I am currently a product designer at Weight Watchers. I like design that is compassionate, research-centered and tells a good story.

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

Product Designer @ WW (formerly Weight Watchers) — San Francisco, CA

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