The Design Interview Challenge

If you spend any time reading or discussing design hiring the subject of design challenges will inevitably come up. I’ve experienced design challenges both as an interviewee and an interviewer.

As an interviewee, many of the interview challenges I participated in left me feeling uneasy. From the conversations I’ve had with design peers who had design interview challenges, this isn’t an uncommon feeling. Few of those I spoke with had anything positive to say about their experiences.

As an interviewer, I’ve participated in interview loops with both take-home and live whiteboard design challenges and saw how they could be helpful windows into a candidate’s thought and design process. I also saw how even with the best intentions they could easily go off the rails without careful handling.

So when I reached the trial phase of my Automattic Product Design interview, I have to admit that I entered into it with trepidation but also with curiosity and an open mind because it was unlike anything I had participated in before.

How Automattic’s Trial Works

First, a little background on the interview process at Automattic.

Since Automattic’s an entirely remote company without an office headquarters for people to interview in, the hiring process isn’t a full day interview loop with people on site. Instead after moving on from an initial screening interview with someone on the hiring team, candidates participate in a trial where they work on a project and use the same tools that that everyone at Automattic uses to communicate and work together.

The trial process is something that’s been in place for a number of years, and if you’re interested in learning more this article in the Harvard Business Review goes into more depth about it.

My Design Trial

My design trial kicked off with a post by Mike Shelton on my trial WordPress site, where I received my project brief, background on the project, and resource links as well as the criteria through which I’d be evaluated. I was told to expect my trial to last two to six weeks depending on how much time I could put into it per week. Two to six weeks seems like a lot, but knowing that the trial wouldn’t be limited to a short period of time like a single weekend or 24 hours was a relief. I was still working a full-time job which limited the time I could spend working on it to some nights and most weekends.

The other benefit I found for the extended timeline was that it better reflects a typical timeline for a product design project and allows for iterations and feedback. During my trial I went through a research phase as well as two design iterations based on feedback from designers on the team. Being able to get feedback from some of my future colleagues really set Automattic’s hiring process apart for me. Other take-home design challenges rarely give time for the interviewing designer to get feedback and make improvements like they normally would working with a team. As a candidate, being able to get a feel for the culture of critique and feedback at a company is incredibly important and can be challenging to do during a typical interview process. And I wasn’t just able to get a feel for how designers collaborated. Since I had access to other team’s projects I could read through their history and see how different cross-functional teams interacted with one another, which typically you don’t get to figure out until you’ve been working at a company for awhile.

As my design trial moved forward I was continually impressed with how freely information was shared with me. When I had a question or needed more information I found the team really opened up and was quick to get back to me. With “I will never pass up an opportunity to help out a colleague, and I’ll remember the days before I knew everything,” and “I will communicate as much as possible, because it’s the oxygen of a distributed company,” as part of Automattic’s company creed, I probably shouldn’t have been surprised by this. However, in past interviews I had sometimes felt like the company and people I interviewed with were holding cards close to their chest making it difficult to understand how things really were behind the scenes. It was great to see that the company’s values were not only deeply held, but that they were actively being practiced.

What I Learned

After coming out on the other side of the design trial process, I found it to be a great opportunity to not only get a feel for what it would be like to work with an entirely remote team, but to also understand how people worked together, how they communicated and how true the company’s values really were. So in the end, my feelings towards design challenges have changed. I now believe that when done right, design challenges can be just as valuable and insightful for the interviewing candidate as they are for the interviewing company.

Photo by Jack Hamilton on Unsplash


By Megs Fulton

Product Designer @ Automattic