20 Questions

Fun Questions to Ask Designers

Creative and playful questions to explore a designer's process, inspiration, favorite work, and the stories behind their creative decisions.

1

What's a design trend you love, and one you wish would disappear forever?

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Why this works

Invites strong opinions and reveals their taste and aesthetic values.

2

If you could redesign anything in the world, what would it be and why?

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Why this works

Opens space for imagination and shows what they think needs fixing.

3

What's the weirdest design request a client has ever made?

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Why this works

Invites storytelling and bonds over the absurdity of client work.

4

What's your favorite font, and why does it spark joy?

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Why this works

Gets nerdy about typography and reveals their design philosophy.

5

If your design style were a movie genre, what would it be?

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Why this works

Playful analogy that helps them articulate their aesthetic.

6

What's a piece of work you're most proud of that no one ever sees?

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Why this works

Highlights passion projects or hidden gems that didn't make the portfolio.

7

What's the most over-designed thing you've encountered?

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Why this works

Invites critique and shows what they think is excessive or unnecessary.

8

If you weren't a designer, what creative field would you be in?

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Why this works

Explores adjacent passions and how they see their skills translating.

9

What's your go-to creative procrastination activity?

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Why this works

Humanizes the creative process and acknowledges that everyone procrastinates.

10

What's a design decision you made that you'd change if you could go back?

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Why this works

Invites reflection on growth and what they've learned over time.

11

What's the best piece of design advice you've ever received?

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Why this works

Surfaces wisdom and lessons that have shaped their practice.

12

If you could collaborate with any designer, living or dead, who would it be?

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Why this works

Reveals influences and who they admire in the field.

13

What's a color combination that makes you irrationally happy?

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Why this works

Gets specific about aesthetics and what resonates emotionally.

14

What's the most fun project you've ever worked on?

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Why this works

Highlights joy and what kinds of work bring them the most satisfaction.

15

If your design aesthetic were a season, which would it be?

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Why this works

Another playful analogy that helps them describe their style.

16

What's a design tool or software you love, and one you can't stand?

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Why this works

Gets technical and reveals their workflow preferences and frustrations.

17

What's the strangest place you've found inspiration?

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Why this works

Shows that creativity strikes in unexpected moments and places.

18

If you could only use three colors for the rest of your career, what would they be?

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Why this works

Fun constraint that forces them to articulate core palette preferences.

19

What's a design rule you love to break?

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Why this works

Reveals their rebellious streak and where they push boundaries.

20

What's the best compliment you've ever received about your work?

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Why this works

Ends on a positive note and shows what validation means most to them.

Talking Design with Designers

Expert tips and techniques for getting the most out of these questions.

How to Engage

Show genuine curiosity about their process, not just the final product.
Ask follow-up questions that dig into the 'why' behind decisions.
Share your own reactions and observations—designers love feedback.
Be respectful of their time and creative energy.

What Not to Say

'Can you make it pop?' without explaining what that means.
'My [relative] does design, so I kind of get it'—no, you don't.
'This should only take you a few minutes, right?'—it won't.
Asking for free work or 'quick favors'—design is labor, not magic.

Learning from Designers

1
Ask to see their design process from concept to final.
2
Request book or resource recommendations to learn more.
3
Attend design talks, exhibitions, or portfolio reviews with them.
4
Follow their work and celebrate their wins publicly.

Find Your Perfect Questions

Search our collection of thoughtful questions for any conversation or situation