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52 favorite interview questions from top design leaders.


Hear the responses we get when we ask design leaders, "What's your favorite interview question?"
LAST UPDATED: November 29, 2023

Listen: 52 favorite interview questions from top design leaders.

As most companies move forward with remote or hybrid hiring processes and accelerated deadlines, making the right match has become more important–and more challenging–than ever. Even carving out the time to prepare for those high-stakes interviews can be cumbersome, and over the past few months, design leaders in our InsideOut community have been actively looking for ways to make hiring easier, and better!

That's why we chose “What's your favorite interview question?” as our icebreaker for 9 recent InsideOut Design Leader Community roundtables! The questions that follow do NOT replace the mission critical work of digging down into a candidate's role, thought process and learnings from their work samples. But the reality is that while having exceptional design skills remains a vital factor in hiring the right designer, there are other, more difficult-to-uncover skills that can make or break a new hire's success.

All the following questions are answers to our icebreaker question, but to make them more valuable to you, I've broken them down into five areas leaders hope to uncover during interviews: Expectations, Resilience, Aspirations, Interests and Self-Assessment.

To uncover expectations:

  • What can we [company] do for you? 
  • If you're not here a year from now, why will that be?
  • Why did you join your current company and why have you stayed? 
  • Why do you want to work for the biggest [fill in the blank company type] in the galaxy? 
  • Tell me what you think this role is.
  • What was your most successful project and why? 
  • Tell me what you know about our company.
  • What will be your biggest challenge moving from your current culture to ours?
  • What do you need from a boss?
  • Do you use our brand/product? If not, why not? 
  • What should I do to keep you here?

To uncover resilience:

  • Tell me about a time you failed at work (the more embarrassing the better) and what you learned from it.
  • Describe a difficult situation and how you navigated it. 
  • Tell me a time when you had to persuade senior stakeholders to change their minds. 
  • What was your biggest “bomb” (that you expected to go well) and how did you learn from it?
  • Tell me about a time when you got bored with your job and what you did about it. 
  • What do you think is your superpower?
  • How did you impact and solve a situation?
  • Tell me about the most difficult person you've worked with and how you made it work?
  • If you could wave a magic wand and never have to do something at work again, what would it be?
  • What professional decision do you regret the most?
  • What did you accomplish in each of your roles?
  • What causes you stress?

To uncover aspirations:

  • What project did you do that made you say WOW – or made your boss say WOW? 
  • Show me a piece of work that you like best.
  • What are your 3 favorite brands and why?
  • What was your first job (ever)?
  • What is your sweet spot? If I had the perfect job for you, what would it be?
  • What's your favorite job and why?
  • What makes a GOOD vs. a GREAT designer?
  • What do you see future design trends being?
  • What do you want to learn here?
  • What would you do differently with our [product/service/platform]?  
  • A dream is something in your mind that you want but likely cannot achieve; a goal is something you're actively working on and likely can. What is a goal that you're working on today that most would consider a dream?

To uncover interests:

  • What do you enjoy doing outside of work? 
  • What are you most passionate about when you're not at work? 
  • Tell me something that is not on your resume.
  • What's the last cultural activity you did?
  • What's your guilty pleasure TV show during quarantine?
  • If design didn't exist, what would you be doing?
  • What are you passionate about at work (illustration, video, etc)?
  • If money didn't exist, what would you do?
  • What's on your Netflix queue that you haven't watched and why?

To uncover self-assessment:

  • If you were a tree, which tree would you be? 
  • What TV character are you most like and who would you like to be? 
  • Tell me about your sock drawer.
  • How do you organize your closet? 
  • What animal best represents you and why?
  • How do you function best (collaborator, independently, etc)?
  • What competitive sport (or other activity) have you participated in and what's your role?
  • Which of the following animals best describes your role in a team: Lion, Dolphin, Owl, Beaver?
  • Tell me about a time when you were sure you were right about something but then came to change your mind. 

Hope these questions help lead you to finding the perfect match for your design team. As you prepare for your actual interviews, prioritize what candidates really need in order to add value to–and thrive in–your group. And make sure you can clearly articulate the traits of the most successful designers you've hired. Crafting that picture for prospective employees helps them understand when they're not the perfect fit and saves you time later. Knowing what you really need can also open up opportunities for more diverse candidates!

By aligning during the interview on expectations, discovering true interests and aspirations, and testing for resilience and self awareness, you'll be starting off on the right foot. Shout out to our InsideOut community for sharing their favorite questions to help others succeed.

If you're a senior design, experience or operations leader of an in-house team and want to connect to others who share your unique challenges, let's talk. Our InsideOut community hosts virtual roundtables to support the learning, growth and sanity of our members, and I'm honored to get to facilitate those discussions.

We'd also love to hear YOUR favorite interview questions, so please share in the comments. Stay safe out there. Let's keep learning together!

This content was originally published on LinkedIn.

Additional Resources

Did you find the tips and strategies in this article helpful? Learn more expert tips from our expert team of recruiters by visiting these resources: