Leading Designers At Square, Dropbox, And Flipboard On How To Land A Dream Job

Six mistakes designers make in interviews with startups, and how to avoid them


I continue to be excited by the number of startups that value design and create wonderful environments for designers to learn and grow. At the same time, designers are realizing the right startup can be an amazing place to hone their skills, build great products, and impact the world in a big way.


Unfortunately, time and again even experienced designers fail to present themselves in a way that meets the bar of these top startups. So, we went out and asked our partners from Bridge, a design education program that connects experienced designers with top startups, for some advice. They shared their thoughts on what mistakes designers make when interviewing and how to correct them for the best chance of landing a dream job.

Understand the Company and Problem Space

“Designers spend so much time creating beautiful work and preparing their portfolio very thoughtfully; they shouldn’t forget the importance of having prepared questions as well–related to our customers, products, team or anything else that shows considered thinking beyond their presentation,” says Chris Heimbuch, director for creative operations at Square.

When I interviewed designers at Facebook, I and the Facebook design team would often ask interviewees to suggest product improvements–and we took a blank stare as a sign that the candidate wasn’t thorough, lacked insight, or quite simply didn’t care enough.

Don’t just learn about the company you’re interviewing with; do a bit of research on the problem space it works in, too. If you’re interviewing at Facebook, know how to talk about social networking. If you’re interviewing at Pinterest, be conversant in visual bookmarking. “When I talk to a designer, I’m expecting to feel enlightened,” says Marcos Weskamp, head of design at Flipboard. “If that person truly and deeply cares about the problem space–not just the product–then it will be really easy to go deep into a constructive session on what’s been done right in the product and which areas need improvement.” Good designers don’t just know what a company’s doing. They have ideas for how to take it a step further. “Every candidate we ended up hiring is because they had a very particular point of view on the product that no one else in the team had,” he says.


Don’t Interview For the Title, Interview For the Role

“Good designers often go for the wrong job, probably because it’s open season on traditional design titles,” says Nate Kerksick, design director at “As what might seem like a given, applicants should understand the common meaning of the role they’re applying to and then pull out all the stops to demonstrate mastery of the role’s expected process and results. For example, product designers should convince me that they know how to plan a useful and desirable product. Communication designers should show me they know how to be persuasive.” What’s more, different companies have different expectations for jobs with similar titles, so make sure you ask what’s expected of the specific role you’re interviewing for.


Make–and Practice–Your Portfolio Presentation

“It’s crucial that candidates put together a formal presentation of their work,” rather than just showing the online portfolio they’ve already submitted, says Jonathan Lieberman, director of product design and user experience at One Kings Lane. “Not only does it give the designer control over the narrative, but it is another opportunity to showcase their command of color, composition, and typography.”

As tempting as it is to think your design will speak for itself, make sure your talk is just as polished as your visuals. “Rehearse your portfolio presentation, don’t just wing it,” says Soleio Cuervo, head of design at Dropbox. “This is a big time commitment for the team coming to watch you tell your story. Not only will you tell a better story, but it also shows that you understand the importance of being ready and prepared.”

Show Your Process, Not Just the End Result

“The most important thing a designer submits in an application is their portfolio of work,” says Kerksick of “Oftentimes these portfolios show just the result, which doesn’t tell me much. Projects that challenge me with a problem; take me through the ugly, messy process; then inspire me with their solution–those are impressive.”


Other designers agreed: Interviewers want to see how you think and work, as well as what you can do. “It’s critical to show the iterative nature of the design process from early tears and cross-functional brainstorms to sketches, wireframes and high-fidelity designs,” says One Kings Lane’s Lieberman. “What is most interesting to me is not the end result, but hearing a designer articulate why some of the early concepts failed and were discarded.”

How you explain your choices along the way is a signal to interviewers. “We care a lot about the ‘why,'” says Dropbox’s Cuervo. “You should have good answers about why you made the decisions that you did. What were your constraints? How many iterations did you actually go through? Why did you end up with this solution?” And whenever possible, let your interviewer experience the process firsthand, he adds: “Don’t show me a slide show of final screenshots. We’d love to see a working product.”

Own Your Mistakes

“One of the biggest mistakes I see people making is throwing their previous team under the bus when discussing past design decisions,” says Stephanie Hornung, lead designer at Asana. “It’s fine to say that if there were no constraints you would have done things differently. But when a designer talks badly about a PM or engineer, it says to me that they don’t recognize that everyone has different goals as part of their job. To be a successful product designer you need empathy, creativity, and the ability to see the big picture. All of that comes out in how you talk about your team.”

Interview the Interviewer

This is good advice for any job, but it’s especially important for design roles given all the different ways companies produce products and structure design teams. When candidates don’t have plenty of questions, “it’s a signal that someone doesn’t have a strong interest in what we’re doing,” says Square’s Heimbuch. “There’s a lot to find out about how our group coordinates with the rest of the design organization and with the structure of the company at large. Ask questions like: Are you guys doing your own product design? What influence or exposure do brand designers have on the product design?”