What I learned from 200 design interviews

Dave Senior
Playground Inc.
Published in
7 min readJul 30, 2018


I’ve been on the frontlines of interviewing all sorts of designers to help us make digital things. Personally, I’ve hired 40 design team members (so far) and I’m still not sure if I’m doing it right. Although there’s been substantial change in both the industry and what people think about design — my approach to hiring hasn’t changed very much over time.

We get the opportunity to work on some really cool stuff. Playground Inc. is trusted to design the flagship experiences and applications, take on large UX organizational tasks, and create comprehensive design systems for Fortune 500 clients and consumer brands across North America. We’ve thankfully managed to surround ourselves with designers who have not only been capable, but have excelled.

For context, we’re a 20 person design company that receives 5 unsolicited resumes a week and upward of 40 when were actively hiring for a role. Do we have a secret? Probably not, but either way — here’s our approach after 9+ years of meeting people:

All designers are multidisciplinary. Even if they don’t know it yet.

For the past 9 years, we’ve seen tools change, we’ve seen new roles emerge, and we’ve seen silos created. Good designers have the ability to learn, adapt and grow alongside this constant change. We’ve never hired anyone who specializes in information architecture or wireframing. We’ve also never hired someone exclusively for UI design, illustration, or motion graphics. Same goes for research, design thinking, or design strategy. We believe these are tools. Tools that can be learned, developed, and nurtured. To us, IA and wireframing are ways to articulate plans and design solutions. There are certainly people who are really, really, good at a particular discipline, but for our team — the most value is added when we don’t box designers in.

We focus on the current strengths of a person, their potential and the things that got them in the room with us in the first place. If someone is interviewing at Playground, chances are they’ve done a little bit of everything — even if they can’t articulate it. We try to pull it out of them with thoughtful questions. We have a ‘learn by doing’ mindset here, so it’s crucial to be around the right mentors in order to find where they will add the most value. We want our designers to develop their craft with an open perspective on the different tools available to make that craft stronger and more dynamic.

2. Stop hiring for fit — what will they add?

Cultural fit isn’t a thing

Hot take: Cultural fit is bullshit. Do they think like you? Do they act like you? Do they look like you? Do you immediately get along after a few interviews? In my opinion, all of these things constrain your ability to truly evaluate a person. We think of new team members as additions to the culture. What emerges should be a net positive for everyone here — but how can you measure that during an interview?

When we hire, we specifically think about what someone adds to our already dynamic team. We embrace differences in experience and personality. We want to be challenged and shown different perspectives on the world. We also welcome differences in expectation of work. For example, someone coming from a high pressure advertising or startup environment typically brings a unique perspective if given the right opportunity. Someone who is an empathetic thinker will teach others to ask better questions. Someone who prototypes in code, will shepherd others looking to learn. Empower people to bring something new to the organization, let go and allow the culture to emerge and evolve in unexpected positive directions.

3. Skip the resume. It’s not about their experience, but how they’ve gained it.

Who is you?

This may be controversial, but I only give resumes a quick glance. I want to see their work. If they have demonstrated they have the raw skills, they’ve got an interview.

We ask a lot of questions that hopefully encourage storytelling.

Here are some questions I’ve asked in the past:

  • How did you find design? Did it find you?
  • How did you get here?
  • How do you learn?
  • What type of designer do you want to be?
  • What are you most excited to work on?
  • To you, what’s important about the internet, technology and people?

Our industry moves so fast. If your portfolio looks and feels contemporary — that’s probably a good sign that you’re able to keep up. Past experiences can be so deceiving. They may not apply to the context of our organization or our expectations of a designer.

What I’m most interested in is how they afforded themselves those experiences? Did they teach themselves design until they had enough spec work for someone to hire them? How did they get their first design job? Did they learn from being on a team with other designers or were they a Lone Ranger? Why do they care about design? How do they learn about it? What are their first memories of getting started? Who are their heroes? Who do they learn from daily? The probes are specifically about the designer’s framework for learning and growth.

In my experience, even the most shy person will become comfortable if they’re talking about a topic they truly care about. Sometimes it’s one story, or the mention of one person that provides a clue into whether they would be a good hire or not. Find out if they care about their craft and determine if they have developed a framework for learning. Additionally, find out how they developed their design taste. There’s plenty of time to teach them new applications or processes later — so long as they have the desire and ability to learn.

4. Be transparent

During our first interview, I’ll do 3 things. Learn about the person, sell them on Playground, and tell them what to expect next. When learning about the person, we find out what their goals are, the context of their previous work, and how Playground can help them in their career journey. We’re first collaborating to understand if this is the right role for them.

The first meeting is typically with someone like me. The second is with our Creative Director, Ryan Bannon. The third meeting is with the team they will be working with everyday. During these three conversations — we’re able to find out if they are curious, if they love their work, and if they are going to work well with others. No interview is longer than 90 minutes, and most are shorter than 60. After each one, our internal team debriefs together.

5. Enough spec work

We’ve tried wireframing exercises and asking problem solving style questions. We’ve even tried a ‘solve out-loud’ type of approach in the past — but nothing has been as consistent in identifying great designers as learning about how someone learns. We allow our candidates the appropriate space and time to walk us through their work. From there, we will be able to ask how they’ve made decisions, how they asked questions, and what level of experience they have within our specific context.

Our work changes with every new client or challenge we take on — so we look for the drive to dig deep, understand nuance, and be flexible. That’s really it. From their portfolio, we should see evidence of that type of thinking and evidence of raw skills.

It’s our job to figure out if they have the raw skills, that’s the stuff we work on before inviting someone into the interview. Once that’s out of the way, let’s get to know each other, what excites us, what motivates them to keep up and push themselves. Whiteboarding and homework exercises usually lack context and are often solving unrealistic problems. On a project, we would never have a designer solve every problem by themselves, with limited information, in a short timeline — so why is that expectation during the interview? We are looking for team members, contributors and inspiring folks to learn from everyday.

Lesson Learned

This may seem obvious but the people who actively work on design every day should be reviewing candidates and the ones conducting interviews.

Know the candidate you are talking to before the interview. Take some time and do your research. Appreciate that this may be a big deal for them. Try to identify some unique questions that prove you give a shit about them. This goes a long way in helping build respect and trust. Never show up cold or unprepared.

Build lasting relationships. Perhaps the person isn’t the right fit today — but they could be someday. This is the perfect opportunity to give constructive advice and help them develop into someone we’d kill to have on our team.

Much like Sway, we don’t have all the answers. Being an agency has given us the unique privilege of working with a lot of different people, nourishing growth and practicing design in almost every context imaginable. This approach has worked well for us (so far) but we’re no strangers to insight-based iteration and change.

Marco Rogers shared his thoughts recently on hiring engineers for startups and we saw a lot of parallels. While our techniques are different, the human centred hiring insights stayed the same. You don’t know what you are hiring for, and get the whole team involved, always debrief and skills are to be nurtured.

I’m curious, how do you hire designers? Does it look anything like our process? From your perspective — what’s the single most important question to ask? Let’s talk about it.



Dave Senior
Playground Inc.

Partner at Playground, Co-Founder of Burstn. Fan of new things, basketball and making stuff.