How I hire designers

How quickly can I get to know you and what are you capable of?

Darrell Estabrook
8 min readSep 20, 2018


Life is about relationships. Friend and friend. My wife and I. Parent and child.

Yet, when we consider a business or employer relationship, we must merge the humanity (that is, emotional to rational) with the reality of the transactional (labor for benefits). It can get a bit weird if it’s unbalanced—all humanity and you can become undisciplined in driving measurable results. All transactional and you can have a lifeless, stick-no-carrot work experience.

When hiring designers, it can seem like you’re entering an added turmoil of nebulous ambiguity. What do you mean by Designer? was the implied question by the recruiting services I spoke with early on in my hiring role. Are these the designers you’re looking for? they seemed to ask as they sent me resume after resume.

So, I came up with a framework resulting in a team of passionate individuals doing top-notch work in experience design for our firm. I emphasize our firm because the type of talent I look for is intended to propel our company forward. The criteria which makes a strong candidate for us may not make a strong candidate for you. Yet, the principles of our approach may be helpful in your case.

I reviewed multiple hundreds of resumés and portfolios, and conducted dozens of interviews to get the team we have. Here’s the process.

I reviewed multiple hundreds of resumés and portfolios, and conducted dozens of interviews to get the team we have. Here’s the process.

1. I defined the core aptitude of our future designer

Let’s put the label “designer” aside and focus on what’s observable.

At the end of the day, this person should be master of one thing. What is that for your company?

Since I grew the team for a technology consulting company who builds digital products, these designers need to be part of cross-functional teams. They need to be able to work in an agile software development environment. They need to be able to understand how to turn an idea into something tangible. They need to be able to command the digital medium and make strong design choices and articulate their rationale.

Of the unending list of desirable qualities in a candidate, the one thing I found striking and unique among our company’s roles was the ability to communicate visually. I saw that a mature visual designer will always research a problem, but a mature researcher will not always be able to communicate visually. In addition, splitting a designer between deep customer research activities and visual communication activities (or front-end coding activities) waters down the quality output of both activities. I wanted focus.

So, I called what I was looking for Design Chops. Namely, how well do you command the medium using typography, color, composition, photography, and language to create a strong experience and fulfill a business purpose? This is a ready-made ability the candidate needs to have on day-one, not something that we invest in schooling from the ground up.

2. I want to see evidence of your aptitude

I wish it were as easy as typing “amazing designer” in a job board and getting a list of candidates that fit my requirements. Labels are pigeonholes, and what we really want is never bundled neatly into a single phrase. I go to the source.

If you claim to have aptitude in an area, then show me what you’ve done with it.

Generally speaking with any position, this is the story you can tell about what you’ve done. The better you can show actual work speaks volumes about your credibility and future work. Even a series of photos or a narrative is helpful — anything which tells me the story of your aptitude and how you used it in a particular situation. Back in the day, a well-structured resumé did the trick. Today, we’re dealing with cross-functional teams and complex digital products.

For me, looking for design chops requires a portfolio. I don’t have the time to do deep research into the background of every person. While I do look around the web, the portfolio is a way for me to get to know you quickly. What you decide to put into your portfolio is a part of your thought process.

That’s valuable to me.

So make your portfolio about the work you’ve had a hand in, as well as about you and your philosophy on design. This is a relationship you’re building.

I find it remarkable the number of folks claiming to be digital designers who don’t have any work to showcase. Even if you are a student, I want to see your student work. Surely if you are passionate about this profession, you can back up your claims with evidence.

The candidates with portfolios that demonstrated design chops were also ones that explained their work. Some explained more deeply than others (some even had case studies). Telling me the problem you were trying to solve, your involvement in the project, and even the challenges you had all help paint a picture of you.

3. Perfect fits don’t exist, so I consider potential

We’re a digital product shop, and we’re looking for people that can start designing digital experiences on day-one. But your portfolio demonstrates your print design chops. Is that a show-stopper?

Not necessarily. It simply means you’re on a spectrum of how you’ve applied your design chops compared to where we need you to deliver. I’m always weighing the strength of having a candidate that can deliver exactly what we need with what investment it will take to mature them.

Of course, sometimes we need to fill a position where only an experienced candidate will do. Yet, I found having design chops takes the experience-gap out of the equation. The person can focus on applying their aptitude in a new medium, and I can focus on mentoring over schooling.

The real question is back to the candidate: are you even interested in digital software work? I’ve had a few prospects kindly decline, and that’s fantastic. This is a relationship we’re building, so let’s be clear about what we can each give to it.

With design chops assessed…

4. Let’s meet!

What you bring to a face-to-face conversation reveals your personality on all sorts of levels.

This is our first 1-on-1 meeting. I want to see the “you” you’re bringing to the table. You should want the same of me.

I won’t take a phone interview unless it’s an ultimate last resort. With video chat technology these days, you can have a face-to-face conversation within a click and a half. If you’re in town, I want to meet you in person. We should see each other. This is a relationship and we’re painting a picture of how it’s going to work.

Sure, there are standard questions to ask in an interview, but I also want to converse. Let’s talk about design.

How did you get started? I see the world of design this way, how do you see it? What was your favorite project? Oh nice, tell me more about that aspect of it. How did it challenge you? What kind of teams have you worked with? Interesting, this is how we work. Here’s the design role and what it’s accountable for. What drives your passion for design?

As we talk, I’m fitting you into the virtual project team in my mind. I’m asking questions to draw out your strengths and weaknesses. I want to hear about your past, and hopes for the future. In the end, this conversation is another assessment of where you fit on the spectrum of professional maturity. I need to arm myself with a rationale for the cost of training versus day-one self-sufficiency, but I also have to ask: Do I want to work with you? You’re asking the same thing of me.

If the meeting goes well, there may be other conversations, but ultimately a decision.

But sometimes we need more.

5. Spec work is aptitude-in-action

Much flack is given about spec work, but it need not be. In fact, the label is intended to paint it negatively. Rather, we call it the design challenge.

The design challenge should be viewed as another type of assessment tool. It’s used for a specific purpose at a specific time.

The reality is you may have a lot a great qualities, but at the end of the day you must deliver refined designs which solve problems as strongly as possible. And at the end of my hiring day, I need to have enough certainty to trust how you will perform.

We are about to invest in you with more than just a paycheck. It’s an investment of mentoring time as well as developing our brand. We want to give due diligence to your application given the importance of this position.

So what might trigger the need for a design challenge?

  • There may be multiple candidates in a hiring cycle with similar qualifications.
  • There may be some gaps in the portfolio between what you did (restrictive past design situations) and what I think you can do (open sandbox).
  • It’s still not clear from your interview what part you played in your past work.
  • I need to directly observe your thought process from beginning to end.

While the design challenge is about gauging your level of mastery with the medium, it’s really about revealing how you think through solving business problems.

Do you play it safe with your design, or do you push it in key areas? Do you see opportunities within the challenge and invest effort into exploring them? Can you articulate the drivers behind your design choices? Do you have a vision for the future?

I’m amazed how this challenge reveals and augments the aptitude already inside someone. In some cases, candidates have simply restyled the challenge while others have reinvented the expereince. Again, this is not only about aesthetics but also about your keeness to identify a need and solve for it.

Sidebar: Creating an effective design challenge

While the design challenge is not a direct client situation— nor should it be—I want to simulate the ingredients realistically enough. I want to set a purpose, see how you respond, and then critique the difference.

So, I created a one page creative brief I give to candidates with this process:

Find a website not designed to our quality standard.

This is the only thing which is real. Everything else in the brief I describe inthe site is fiction.

Define the purpose of a new homepage

I set out 1–2 objectives on how this new homepage should drive the business.

Describe the business challenge

I invent a customer-oriented problem for the business in which this website could potentially solve.

Describe the people running the business

There is a personality behind every business. Call it the brand, call it personas. I describe the atmosphere of this business created by the people that work there.

Describe the aspect of the business they are known for

This is the key service or product they offer. Their uniqueness. Their value proposition.

The ask is a redesigned homepage. Anything else is up to the candidate. More deliverables does not mean better. Appropriate communication is far more important.

So, there you have it. Hiring is an act of design itself. Each person’s talent and voice adds to our brand. I’m not only designing the Design team, I’m designing a brand reputation. My goal is to always push deeper into delivering excellence with the people we hire, and that will take a lot of conversations.

There’s no shortcut to a great relationship.



Darrell Estabrook

I'm an award-winning UX Product designer specializing in simplifying complex B2B applications and helping companies level-up their UX design practices.