Design System Interview Questions

Successful design systems are finely tuned to the organization they serve. At the beginning of every client design system engagement, we spend a great deal of time learning about our client’s culture, politics, products, tools, and workflows. Sure, we’ll get links to decks, GitHub repositories, and Sketch libraries, but these artifacts don’t really tell the story of how digital products get built at the organization. For that, we need to talk to people.

We kick off our engagements by interviewing a large cross-section of stakeholders across an organization. We’ll line up mostly one-on-one interviews but also sometimes do group sessions (say, with a product scrum team), and conduct a slew of 30-45 minute interview sessions over a week or three.

Three stylized question marks

My friend and colleague Josh Clark often takes the lead on this part of the engagement, and he truly is a master interviewer. I’ve learned so much from him about being an active listener, a tactful questioner, and (in many cases) an empathetic therapist.

Here are the kinds of questions we ask:

  • Name and title
  • How long have you been at the organization?
  • Can you give a brief background of your time at the organization?
  • What are you working on now? What are your priorities?
  • What’s a day in the life look like?
  • Can you describe your current workflow?
  • What aspects of the current workflow are working really well?
  • What aspects of the current workflow do you think could be improved?
  • If you had a magic wand and could change one thing about how things work here, what would that thing be?
  • What tools and technologies are you using? What about these do you like and is there anything that could be improved?
  • How do you hope the design system will help?
  • What about the design system makes you nervous or apprehensive?
  • What does success look like? Fast forward a year from now, things are humming along and everyone is thrilled with the design system. How did that happen?
  • What’s going to sink this ship? Fast forward a year from now and the design system initiative is a total failure. Why did it fail? 
  • What do we need to know in order to operate successfully in your organization?
  • What questions should we be asking you that we aren’t?

It’s worth noting that we very often don’t get through all of these questions. It’s also worth noting these aren’t blanket questions, and we’ll cater our questions to who we’re talking to. A VP of product and a junior engineer obviously have different perspectives, so we want to tune our line of questioning differently. And as Josh likes to say,  the interviews are about discovering what you don’t know—and often that means uncovering the real questions as you go.

Here’s a breakdown of these questions in more detail:

Intro

It’s obviously a good idea to start with some friendly introductions, but you can quickly get down to brass tacks.

  • What’s your title?
  • How long have you been at the organization?
  • Can you give a brief background of your time at the organization?

What we’re trying to do here is get an understanding of who the person is, what their position is, how much sway they have, and also how much history/context they have.

Work and workflow

  • What are you working on now? What are your priorities?

Here we’re trying to get a sense of what this person is up to and what they care about. From leadership, we’ll tend to hear about big incentives and where they’re trying to go as a digital organization. From practitioners, we’ll here about the latest and greatest product work.

  • What’s a day in the life look like?
  • Can you describe your current workflow?
  • What aspects of the current workflow are working really well?
  • What aspects of the current workflow do you think could be improved?
  • If you had a magic wand and could change one thing about how how things work here, what would that thing be?

These questions help extract current state of affairs and some of the frustrations that are leading the organization to reach for a design system to help with.

Tools and technologies

  • What tools and technologies are you using?
  • What do you like and are is there anything that could be improved?

These questions help us understand how teams have arrived at their present tools and technologies setup, and where they want to go from here.

Design system hopes and fears

At this point in the interview, we’ll briefly introduce the design system initiative. “So as you likely know, we’re helping establish (or improve) a design system to [lay out benefits]…”

  • How do you hope the design system will help?
  • What about the design system makes you nervous, apprehensive, or skeptical?

Here we’re taking a lot of the prior conversation and framing it through the lens of the design system initiative. How could a design system alleviate those frustrations and get everyone to a better place? But also, what makes the interviewees nervous about this whole endeavor? It’s absolutely critical for the design system to tackle these skepticism and apprehensions head on. This in my opinion is the biggest key to design system success.

Outcomes

  • What does success look like? Fast forward a year from now, things are humming along and everyone is thrilled with the design system. How did that happen?
  • What’s going to sink this ship? Fast forward a year from now and the design system initiative is a total failure. Why did it fail? 

What kind of outcomes does the interviewer want to see? But what are the biggest threats to success? “What’s going to sink this ship?” is my absolute favorite interview question because it gets to the heart of the work to be done.

Anything else?

  • What do we need to know in order to operate successfully in your organization?
  • What questions should we be asking you that we aren’t?

As outside consultants it’s important for us to be able to successfully navigate a company’s culture, and it’s great to hear tips from people on the inside. This is also an opportunity to ask a catch anything that we didn’t cover and gives them an opportunity to get anything else off their chest.

Now what?

Once we’ve conducted the interviews, we being the hard work of synthesizing themes, pulling quotes, and preparing for our kickoff workshop where we will discuss and prioritize outcomes with the project stakeholders.

One last thing worth mentioning is that these interviews can be conducted by an internal team, but I’ve found that this work is one area where coming in as a hired consultant is especially beneficial. We’re asking questions because we truly don’t know the answers, and because we’re objective outsiders interviewees are more willing to open up and aren’t distracted by where we sit in their org chart or if we have ulterior motives.  So if you need help, just reach out!

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