Questions to Ask Designers
Questions for a conversation with a working designer, suited to a coffee chat, a mentoring call, or a portfolio review. Written for someone learning the craft rather than someone hiring.
The questions
Open any question for the note
What did you work on this week?
Why ask it
Far better as an opener than asking about their process, because it produces something concrete and unrehearsed. It also shows you the unglamorous middle of the job that portfolios never contain.
How did you get into design, and would that route still work today?
Why ask it
The second half is what makes this worth asking. Many designers came through paths that have closed, self-taught into agency work, or from print, and they will tell you plainly if their own route is no longer available.
What does a normal day actually look like, hour to hour?
Why ask it
Most people are surprised by how little of it is designing. If the honest answer is three hours of calls and two hours in a file, that is worth knowing before you choose the career.
Which part of the job did nobody warn you about?
Why ask it
Usually one of three things: the amount of persuasion, the amount of writing, or how much work never ships. Whichever they name is a gap in how design is taught.
What do you do first when a new project lands on you?
Why ask it
Watch whether their first move is opening a design tool or talking to someone. The answer is more revealing than any description of a process, because it is a habit rather than a theory.
Where do you go when you are stuck on something visual?
Why ask it
Expect specifics: a shelf of books, a folder of saved work, going for a walk, or starting again at a smaller size. This is practical, immediately borrowable, and rarely written down anywhere.
How do you get to a decision when there is no data and everyone has an opinion?
Why ask it
This is the actual condition of most design work. Listen for a mechanism, a bet framed narrowly, a decision-maker named in advance, rather than an appeal to good taste.
Is there anything in your portfolio you would not put there now?
Why ask it
Designers are usually candid about this, and the reasons teach you a lot: work that photographs well but failed, work that was mostly someone else's, work that no longer represents them.
Which project got the most pushback, and how did it end?
Why ask it
The ending matters more than the conflict. Ask specifically whether the design shipped, was watered down, or was killed, and what they would try differently against the same resistance.
How much of your week is designing versus talking about design?
Why ask it
The ratio shifts sharply with seniority, and people rarely mention that when giving career advice. Ask what they gave up as the meetings grew and whether they wanted the trade.
What do you do with feedback you think is wrong?
Why ask it
The useful part is what they do next: ask what problem prompted it, offer two options, or hold the line with evidence. Designers who simply comply, or simply ignore it, both have stories about why that stopped working.
How did you learn to talk about money, whether pricing or a raise?
Why ask it
Nobody is taught this and most designers learned it badly first. Expect a specific mistake with a number attached, which is more instructive than any general advice on the subject.
What tool did you move away from, and what did that cost you?
Why ask it
This gets at how they hold their skills: as investments or as habits. The answer often includes what carried over and what turned out to be tool-specific rather than real ability.
Who taught you the most, and what did they do differently?
Why ask it
Naming a person forces something specific: how they critiqued, how they showed unfinished work, how they handled being wrong. Generic answers about mentorship carry nothing you can use.
What do people early in their careers overrate, and what do they underrate?
Why ask it
The pairing is what makes this productive. Common answers overrate tools and trends and underrate writing, follow-through, and asking about constraints, but hearing their version tells you what they see going wrong around them.
How do you keep working on days you have no interest in it?
Why ask it
Professional practice is largely this. Expect something mundane, a lowered standard for a first pass, a fixed start time, doing the boring layout first, rather than anything about inspiration.
Which of your skills have stayed valuable, and which have become obsolete?
Why ask it
This is the closest thing to a forecast you can get without asking for predictions. The skills they name as durable are usually about judgement, communication, or typography rather than software.
How do you decide whether to take a job or a project?
Why ask it
Listen for criteria, not just enthusiasm: who the decision-maker will be, whether there is a real problem, whether they will get to see the work used. These criteria are usually built from a bad experience.
What would you do differently in your first five years?
Why ask it
The regret is almost always specific: staying too long somewhere, chasing polish over placement, not writing things down, avoiding the business side. Ask what it would have cost to fix at the time.
If I want to get better at this, what am I probably not doing?
Why ask it
Better than asking for general advice, because it invites them to look at you rather than the field. Bring work if you can, since the answer improves enormously when they have something to point at.
Getting real answers out of a designer
Practical guidance for the conversation itself
Set the conversation up properly
Ask for a specific amount of time and honour it
Twenty-five minutes with three questions gets accepted far more often than an open request to pick someone's brain. Ending on time is also the thing that makes a second conversation possible.
Name what you have already read of theirs
Referring to a particular project or piece of writing changes the register immediately. It also stops them explaining basics you already know.
Bring work if you want feedback
Advice given in the abstract is generic by necessity. Two or three pieces, with a note on what you were trying to do, produces far more specific answers than any question about career strategy.
Follow-ups that open an answer up
- What did you try before that?
- Who disagreed, and what did they want instead?
- What did that cost you in time or in credibility?
- How would you do it now?
- What would have to be true for the opposite choice to be right?
- Is that particular to where you worked, or general?
What to avoid
Asking for a design philosophy
It produces the answer they use in interviews. Asking how they decided one specific thing gets you the same information in a form you can act on.
Asking them to review a whole portfolio in a first conversation
It is hours of work presented as a favour. Ask about two pieces, and ask a narrow question about each.
Turning it into a request for a job
If you want a referral, say so plainly at the end rather than steering there gradually. The indirect version is obvious and it retroactively sours the conversation.
Asking about trends
Trend talk dates fast and most working designers find it dull. Their reasoning under constraint is the part that will still be useful to you in five years.