3 Questions to Ask When Hiring Your Startup's First Designer

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@seejennydesignJenny Shirey

I help teams build better products. Find out more at www.jennyshirey.com

My first job as a UX designer was fresh out of grad school at a small startup with six people. It wasn't a great fit. I'd come from the world of print graphic design and had never designed a real-world digital software product. Even though I was enthusiastic, I had no experience to call on to know how to reconcile UX tradeoffs or convince the team why one design decision was better than another.
It's been years since this experience, but I’ve often thought about how startups like the one I joined can make sure they hire the best first designer for their needs. What should a startup look for to make sure their first designer will succeed?
Since leaving that first job, I've worked as a lead designer and design manager, and I've hired and mentored many designers at companies ranging from 500 to 10,000 people. I've hired people who were solo designers and observed their skills, and seen friends and former colleagues go on to be successful first designers.
Let's be honest: you're not going to find that elusive unicorn designer who can talk with users, lead brainstorming sessions, create flawless interactions, design gorgeous interfaces, do front-end code, AND mentor future designers. So which qualities should you look for and which are just nice to have?
While specific skills depend on your existing team and product, here are the questions I would urge all startups to ask when hiring their first designer.

Must-have #1: Do they have experience building a product from start to finish?

Your first designer will create the very first thing you give your customers (or at least, take what your team has already hacked together and make it more usable and attractive). They'll need to create initial designs based on often vague ideas, iterate on them based on feedback, create final high-fidelity mockups for the engineers to build, and QA the results. At large companies, you'll often have 2-3 different designers working on various parts of this process. At a startup you don't have that luxury, so you'll need to make sure the designer you hire has real-world experience in each of these areas.
Going through the process of working closely with a front-end engineer who is developing your designs is important, because it's during this phase that a lot of unexpected challenges will come up. Trust me: you will always find something in the design that doesn't work out as expected when you get into development, or will take too long to build.
Designers who haven't gone through this development and design QA process often end up frustrated or overwhelmed, and in the worst cases will refuse to consider tradeoffs. And unlike Apple or other large design-driven companies, early-stage startups don't have the luxury of making something perfect before they ship. You need a designer who can quickly figure out a good tradeoff between speed and quality; not every designer can do this.
So in addition to looking at the work a designer has done, how might you dig into their experience? Some questions to ask a potential hire could include:
  • Tell me about a product you made that shipped. How did you work with the engineers during the development process?
  • Have you ever had to redo your design because it would take too long to build?
  • What do you think about the phrase "done is better than perfect?"
  • Tell me about a conflict you had with an engineer based on something you designed. How did you resolve it?

Must-have #2: Can they deal with ambiguity and change?

Early-stage companies make hypotheses, find out they're wrong, and pivot. In the best cases, these decisions are made early before investing too much time in a feature, and are based on actual conversations and tests with users. Other times there's a tradeoff where the Head of Product has to decide whether to ship one feature or another because there's not enough time to build both.
Designers working on something from scratch often create designs that end up not shipping or have to be completely redone. Some designers can't handle this churn and will feel demotivated, even if the decision is based on a clear vision of the product's goals and users' needs.
In addition, the ability to create something without having it completely spelled out will be very exciting to some designers and terrifying to others. At this stage in my career, I love being involved from the birth of a product. I can help a product leader craft a hypothesis, figure out how to visualize it quickly, test concepts with users, and use the learnings to define the product in more detail.
But some designers don't want to or don't have the skills to do this. You need a designer who enjoys the fuzzy part and can start designing based on a prompt. It's the difference between stating "We need to design a way for students to keep track of all of their homework" versus "We need to design a bullet-list calendar with color coding which allows students to flag, save, create, and delete reminders." Of course when designing based on a prompt, there will be many details to figure out before shipping; look for someone who is excited to figure those details out with you.
Questions to ask a potential hire could include:
  • Tell me about a time you worked with a product manager to come up with a new product. How did you work together? (Look for a story about a partnership from early stages)
  • Have you ever had to throw away a design you were really excited about because the product changed? How did you feel about that?

Must-have #3: Are they able and willing to work fast and show messy, unfinished work?

It's hard for designers to show something that doesn't look good or lacks details, but it is necessary when time is of the essence. Of course the team needs to realize that finalizing design takes time; you shouldn't expect a designer to create and finish, for example, an entire onboarding flow in one day. But your designer might be able to put together an imperfect first draft in Figma so the team can look at it and figure out whether it's feasible. The ability to hack things together is crucial for first designers.
This is a harder question to answer and I would discourage using take-home design exercises to test designers in this area. Design exercises have many issues, including discriminating against people who don't have the time or means to do 8 hours of unpaid work. However, you can do an onsite whiteboarding exercise together; while it's not the same as digital design, you'll see how they think on the fly and how they react to questions about their design decisions.
You can also get a sense of willingness to show in-progress work from looking at someone's portfolio. Do they include sketches in their portfolio? Do they show iteration in their designs?
Questions to ask a potential hire could include:
  • (when looking at a portfolio project) How long did it take you to come up with the first version of this?
  • Tell me about a time you had to put a first draft together quickly to show a team. How did it go?

Traits that are nice-to-have

For your first designer, you'll most likely want a generalist—someone who can design a product that's easy to use and also make it look somewhat visually appealing. However if you find that you need more specialized help, why not hire a consultant or freelancer? Freelancers can help you with all sorts of things that your first designer might not have expertise in, including:
  • Recruiting users and doing user interviews or usability tests
  • Creating icons or illustrations
  • Defining an incredible visual style and brand guidelines
  • Leading design sprints
  • Creating motion design or vision videos
  • Hiring your next designer
I worry when I see startups posting a job ad for a designer who can do all these things, or who "has experience managing others" even though there's no one to manage yet. In general, I'd advise companies to only list traits on a job posting which you need someone to do in the next few months and which will be done often enough that it doesn't make financial sense to hire a freelancer to do them. Focus on the essential traits and remember that your second design hire will fill in the gaps that your first designer isn't as skilled at.
You also might want to hire a coach for your first designer while they get up to speed, particularly if they're a bit more junior or haven't been the only designer at a startup before. This can help open the field to more candidates, enabling you to hire more quickly, and also set your new designer up for success.
There's much more to say on this topic; I hope this gives you a good start! If you'd like to learn more, I'd recommend this article from Braden Kowitz which goes into detail about various skills (for example, when you might need a designer who excels in visual design versus interaction design). This article also has great advice from design leaders about how to hire designers.
Let me know in the comments if you'd to know more about any aspect of hiring. Or you can send me a message—I'm always happy to work with startups and help them get the design help they need!

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