A hiring process only tells you something if both sides are asking intelligent questions, not just answering them. Here’s what we’d put in front of a client, and what we’d put in front of a candidate.
A job interview is really two evaluations happening at once, but most processes are only made for one of them. The client asks the questions, the candidate answers them, then asks something polite about culture on the way out. In scenarios like this, neither side gets what they actually need.
We’ve sat through thousands of these conversations from both sides of the table, in the placements we run every week. Here’s what we’d actually play it, either side.
If you’re hiring
Skip the portfolio walkthrough – you can do this yourself before the interview. Anyone can narrate a finished project; the interesting answers come from asking about the thinking underneath it. “Walk me through the decisions behind this project, not just where it ended up” separates people fast, and “what’s a project that got close but never happened?” is often more revealing than anything that made it to a case study.
Test taste directly, because it’s the hardest thing to teach and the easiest thing to fake. “Tell me about something you saw recently that you thought was brilliant, and why” does more work than any case study. So does the harder version: “show me something you think is bad design, and explain your reasoning.”
Look for a problem-solver, not a problem-spotter. “Tell me about a brief that was boring or limiting. What did you actually do with it?” filters for people who bring solutions when the work is truly challenging, and “what’s a bad idea you’re glad you said out loud?” tests for real imagination over safe execution.
Finally, check they can lose an argument. “Tell me about a time when an idea didn’t land, and how you handled it” is one of the best filters we know to spot arrogance dressed up as confidence.
If you’re the one being hired
Ask about ownership before you ask about culture. “What does creative ownership actually look like here, day to day?” tells you whether you’ll be originating work or executing someone else’s brief, which is one of the biggest reasons we hear people leave a role.
Ask the progression question directly, not politely: “Where did your last three promotions come from?” A vague answer, or a long pause, tells you everything you need to know. So does “how long has this team been together in its current form?”, since frequent restructuring is one of the clearest instability signals there is.
Ask about fairness, not just the number. As our founder Dan puts it: “money keeps people polite, fairness keeps them loyal.” So ask what actually drives pay decisions here, and whether responsibility and recognition tend to move together.
On flexibility, ask for the honest version, not the written one, with something like “What does hybrid actually look like for this team in practice?” Don’t just glance at the written policy.
If you’re feeling especially brave, you could ask: “what would make someone leave this role?” It’s disarming enough that most people answer it honestly, and the answer is usually the truest pitch, or warning, you’ll get in the whole interview.
The pattern underneath all of these questions is the same. You’re not tricking anyone or trying to trip them up. You’re just being clever about getting past the rehearsed answers.
Polish is easy to produce now, on a portfolio or in an EVP deck. Thinking, taste and honesty about what a job is actually like are still only visible in conversation.
