Fun Questions to Ask Designers
Twenty questions for a studio chat or a portfolio review that has run out of steam: the trend they want gone, the strangest client request, the font they defend, and the work they are proud of that never shipped.
The questions
Open any question for the note
What's a design trend you love, and one you wish would disappear?
Why ask it
A safe opener that still gets a real opinion, because complaining about a trend costs nobody anything. The trend they defend is usually more revealing than the one they hate, since it is the less popular position to hold.
What's the weirdest request a client has ever made?
Why ask it
Every designer has this story and enjoys telling it. Notice whether the punchline is the client's taste or the client's logic, because designers who mock taste and designers who mock reasoning work very differently.
What's your favorite typeface, and what do you use it for?
Why ask it
The second half stops it being a trivia answer. A designer who names a favorite and then describes exactly where it works, and where it collapses, is telling you they think in constraints rather than preferences.
What's a color combination that makes you unreasonably happy?
Why ask it
Concrete and easy to answer out loud, and it usually comes with a source: a football kit, a cereal box, a train ticket from 1974. The origin story is the interesting part, not the hex codes.
What's the most over-designed thing you've encountered recently?
Why ask it
Recently is doing the work: it forces a specific example rather than a general complaint about the industry. Answers about hotel taps, parking meters and airline apps come with an implicit theory of what design is for.
What's your go-to procrastination move when a project is stuck?
Why ask it
Half confession, half working method. Reorganizing layers, redrawing a logo nobody asked about, walking. Some of these are avoidance and some are how the problem actually gets solved, and designers usually know which is which.
What's the strangest place you've found something worth stealing?
Why ask it
Better than asking about inspiration, which produces a list of famous names. Expect car park signage, medical packaging, a bad menu. It shows whether they look at the world or only at other designers' portfolios.
What's a piece of work you're proud of that nobody ever saw?
Why ask it
Killed projects and unshipped concepts are where designers keep their favorite work. Being asked about it is unusual and welcome. Follow up on why it died, since that story is often about the organization rather than the design.
What software do you love, and what do you use only because you have to?
Why ask it
Workflow grumbles are specific and revealing, and the tool they resent usually marks a boundary in the job: the handoff, the client review, the print spec. Also a fast way to place where they sit in a production chain.
What's the most fun project you've worked on, and what made it fun?
Why ask it
The second half matters, because it is rarely the subject matter. Answers usually name a good brief, a client who decided quickly, or a small team, which tells you what conditions they need to do well.
If your work had a house style, how would someone describe it back to you?
Why ask it
Asks them to see their own work from outside, which many designers find harder than critiquing anyone else's. A crisp answer means they have a deliberate practice; a shrug often means they take whatever comes in.
What's a design rule you break on purpose?
Why ask it
The word purpose separates taste from carelessness. Listen for whether they can state the rule accurately first, because breaking a rule you cannot articulate is not a choice.
What's a decision you made that you'd undo if you could?
Why ask it
Easier to answer than a question about weaknesses, and it produces a real account of learning. Expect a typeface licence, a color that failed in print, or a layout that broke the moment real content arrived.
What kind of feedback actually helps you, and what just wastes a week?
Why ask it
The most useful question here if you will be working with them. Most designers have a precise answer, and it is nearly always about being told the problem rather than the fix.
What's a constraint you enjoy working inside?
Why ask it
Cuts against the assumption that designers want total freedom. One color, a fixed grid, a tiny budget, an accessibility standard. Watch whether the constraint they name is aesthetic or genuinely about the audience.
If you could only use three colors for the rest of your career, what would they be?
Why ask it
A playful constraint with a serious effect, since it forces a ranking rather than a list. The palette people pick under pressure is usually narrower and stranger than the one in their portfolio.
What would you redesign if nobody could stop you?
Why ask it
Reveals what they think is genuinely broken, and the choice tends to be either a public system or a personal irritation. Ask what they would keep, since the good answer is a repair rather than a demolition.
If you weren't doing this, what would you be making instead?
Why ask it
Nearly every designer has an adjacent craft, and the answer explains something about how they work now: carpentry, cooking, music, sign painting. It also tends to be the thing they do on weekends.
What part of your job would surprise people outside the field?
Why ask it
Invites them to correct a misconception rather than defend the profession. Answers often land on paperwork, file naming, arguing about margins, or how much of the work is persuasion rather than drawing.
What's the best thing anyone's ever said about your work?
Why ask it
A warm close, and the compliment they remember says more than the work itself. Notice whether it came from a client, a peer, or a stranger who did not know it was designed, since each means something different to them.
Talking Shop with Designers Without Annoying Them
Practical guidance for the conversation itself
How to Ask
Ask about decisions, not preferences
Why is that there gets a better answer than do you like it. Designers spend most of their day justifying choices to people who only react, so a question about reasoning reads as respect rather than critique.
Name what you are looking at
Pointing at a specific spread, screen or sign and asking about that beats a general question about their portfolio. Vague admiration is hard to respond to and usually gets a vague answer back.
Ask what the brief was before you react
Half of any critique dissolves once you know the constraint: the client's existing palette, a print budget, an accessibility requirement. Asking first also stops you from criticizing the one decision that was not theirs.
Separate the fun questions from a real review
If this is a portfolio review with a decision attached, say so, and do the assessment first. Mixing playful questions into an evaluation makes the whole conversation feel like a test with hidden scoring.
What Not to Say
- Can you make it pop, or make it more modern, without saying what result you actually want.
- My nephew does design, so I sort of get it. It lands as a comparison to unpaid amateur work.
- This should only take you a few minutes, right. You do not know, and asking implies you do.
- Asking for a quick logo, a favor, or free spec work in the middle of a friendly conversation.
- Suggesting a fix before you have asked what the constraint was.
- Debating whether design is subjective. It is the oldest and least interesting argument you can start.
- Asking which tool they use as a proxy for whether they are a real designer.
If You Want to Learn From Them
- 1Ask to see a project from the first rough to the final, including the versions that were rejected. The gap between them is the actual lesson.
- 2Ask what they would do differently with the same brief today, which gets you a critique they are willing to give.
- 3Ask them to talk you through a piece of work that is not theirs. People are far more candid about a stranger's decisions.
- 4Ask what they were looking at while they made it, then go look at that.
- 5Offer to be a test reader or user rather than a critic. Watching someone fail to find the button is worth more to them than an opinion.