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Hey and welcome back to a new week!

It is easy to spend an entire interview trying to prove you are right for the job, then leave without knowing whether the job is right for you. This week, I am looking at how to make your questions count.

Start with what matters to you, research what is already available, and use the conversation to clarify the doubts that could change your decision.

In this issue:

  • Your Design Interview Is a Two-Way Street: Research, useful questions, and judging whether the opportunity fits.

  • Joe’s Portfolio: A (Design Engineer’s) portfolio that’s outgrown junior level showing us how it’s done.

♥ THE TOOL I TRUST FOR MY IDEAS (INCLUDING OPEN DOORS)

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Your Design Interview Is a Two-Way Street ↔️

When you really want a design job, it is easy to treat every interview as a test you need to pass. You prepare your introduction, practise your case studies, and think about how to answer the difficult questions. Most of your energy goes into helping the company decide that you are the right person.

Then someone asks whether you have any questions. You ask about the culture, hear that the team is collaborative, and leave hoping you made a good impression. But what did you actually learn about the job?

An interview is a two-way street. You are being evaluated, and you are gathering the information you need to evaluate the opportunity.

If something about the role worries you, or there is a condition you need it to meet, this is your chance to ask. Your questions can also show preparation and design judgment. But you should leave with information that is useful to you, especially as a junior whose next environment will shape how you learn the job.

Build a question bank, then do your research

Earlier this year, I shared my general guide to design interviews. Preparing questions is one part of that preparation that deserves more attention.

Keep a reusable bank of things you want to know about an employer: the work you would own, the feedback you would receive, how decisions happen, working arrangements, growth, and anything else that matters to you. Include conditions that would make a role a poor fit.

Group those questions by who is likely to know the answer: a recruiter, the hiring manager, or a future teammate. Then, before each interview, try to answer them yourself. Read the job description, careers page, and any public team pages. Look at what the company has already told you.

If you have several interviews and this sounds time-consuming, use AI to help. Give ChatGPT or Claude your question bank and the relevant pages. Ask it to find answers, include the source and supporting passage for each, and mark anything it cannot establish as unknown. Check the evidence before relying on it.

You are looking for what is already answered, what is partly answered, and what still needs a conversation.

Asking something stated plainly in the job description can make it look as though you have barely read it. Missing a detail buried in a presentation three links deep is understandable. Nobody expects you to uncover every public sentence, but your questions should show an effort to understand this particular opportunity.

If the careers page says designers work in cross-functional squads, asking whether they work with engineers will not get you very far. You could ask: “I saw that designers work in cross-functional squads. How are decisions made when the designer, PM, and engineer disagree?”

The research gives you a starting point for something the public information cannot answer. It also makes your interest specific. Saying you really want a job tells the hiring manager little about why this role makes sense for you. A considered question shows that you have thought about the work, while helping you judge whether you would actually want to do it there.

Put your doubts and deal-breakers first

Before choosing your questions, ask yourself: what am I uneasy about here? What would I need to know before feeling comfortable accepting this job?

Maybe the description celebrates being “always on,” and you are worried about working hours. Maybe an earlier interviewer described repeated changes in company direction. Maybe the team promises autonomy, but you suspect that means working without feedback or support.

Those concerns belong at the top of your list. So do conditions that are critical for you even when nothing has raised suspicion. If predictable hours or an experienced design manager matters a great deal to you, find out what is actually available.

Check whether the information you already have answers the concern. Often it will be too specific for a public page. Ask directly, giving enough context for the person to understand what you need to clarify:

  • Working conditions: “The job description mentions supporting launches outside normal hours. How often has that happened recently, and what is expected of this role?”

  • Company direction: “You mentioned that the product focus has changed twice this year. What is the current priority, and how does this hire fit into it?”

  • Ways of working: “In the previous conversation, I heard that I would be the only designer in the squad. Who would I get design feedback from, and how regularly?”

You are asking about something you noticed, without treating your suspicion as fact. The answer may reassure you, reveal an acceptable trade-off, or confirm a concern. All three are useful outcomes.

If nothing specific has worried you, check for warning signs you personally care about, such as routinely unpaid overtime, unclear expectations, or a lack of support. You do not have to wait for a hint to ask about a condition that matters to you.

Keep questions relevant to the role, company, industry, and people. Get the information you need rather than hoping every important problem will reveal itself between the lines.

You may only get two or three questions. Make them count.

Do not plan around a long conversation at the end. Recruiter calls can leave more space for questions, but a hiring-manager interview or case-study presentation can easily run long. Extra time depends on everyone being able and willing to stay.

If you only get two or three questions, prioritise unresolved concerns and conditions that could change whether you would accept the job. General curiosity can come afterward. Keep a few backups in case your priorities get answered during the interview.

Make each question focused enough to produce a useful answer on its own. Most companies will say they value feedback. If their team page mentions critiques, ask: “I read that you run regular design critiques. Could you walk me through a recent one and what changed afterward?”

That gives you more to work with than a broad question about culture. Perhaps experienced designers review work regularly. Perhaps critiques are still something the team hopes to introduce. Those are different environments.

If there is room for a follow-up, use it. But you may not get three more turns to reach the detail you actually needed, so make the first question count.

Ask the person who can actually answer

A recruiter may know the reporting line, process, salary range, and working arrangements. They may know very little about how designers and engineers resolve disagreements. A future teammate is more likely to describe that from experience.

With a hiring manager, focus on expectations, support, priorities, and decisions. With a designer or engineer, ask about the daily experience: how work moves between people, where it gets difficult, and what they wish a new colleague understood.

Build on earlier conversations too. “The hiring manager mentioned that designers join engineering planning. What does that look like from your side?” gives the next person a useful starting point.

If location, compensation, working hours, or another requirement determines whether you can take the job, clarify it early enough to avoid investing in an impossible match. You do not need to earn the right to understand the basic conditions.

Listen for detail, honesty, and consistency

Pay attention to how comfortably people describe the work, including its difficulties. “Our research access is inconsistent, so designers currently join support calls while we improve recruitment” gives you a real constraint to consider. “We are very user-centred” tells you much less.

Specificity does not guarantee a good environment, and one vague answer does not prove a bad one. Someone may be nervous, new, or the wrong person to ask. Give them room to clarify.

Across the process, look for a coherent picture. If the manager promises close guidance but teammates say nobody has time to review work, that deserves clarification. If people consistently describe a messy situation and explain how they are handling it, you can assess the trade-off more confidently.

Questions can arise naturally during the conversation too, when the format allows it. Follow the conversation and respect the time. If there is no room left, ask whether you can send a couple of questions afterward or cover them in the next stage.

Leave with more than a feeling about your performance

Afterward, write down what you learned. What work would you do? What support would you have? Did the answers resolve your concerns? What still needs clarification?

Separate what someone said from what you hope they meant. “They plan to hire a design lead” is different from “I will have an experienced design manager when I start.” That distinction can matter a great deal.

You may still choose a role with uncertainty, limited support, or compromises. People have financial pressures, location constraints, and different opportunities available. Better questions do not remove those realities. They help you make the decision with a clearer understanding of them.

I want you to prepare strong answers and give yourself the best chance of getting the offer. I also want you to reach that point knowing whether the job can give you what you need.

Your questions deserve real preparation. The answers may shape far more than the rest of the interview; they may shape your next few years of work.

🏗 I’VE BUILT A LOT WITH LOVABLE - NOW IT’S YOUR TURN

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  • Describe the business, get the real product

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  • Keep going, or try the next one

Discount of $5 applies to first month of any paid plan. You need to sign up via this webpage in order to claim the discount. The discount applies to new and returning users without an active paid plan. Terms apply.

Portfolio Showcase: Joe Parker-Rees

Joe Parker-Rees is a London-based multidisciplinary designer working across product design, design engineering, brand, and visual design.

His portfolio brings those disciplines together through work that feels carefully considered, from complete applications to smaller interactions. There is breadth here, but also a consistent attention to how things look, behave, and fit together.

Muesli, an iOS app he designed and built himself, makes that particularly clear. Let’s take a closer look at that project, the experiments around it, and two ways Joe could make the portfolio stronger.

That’s it for this week—thanks so much for the support! ♥️

Do you want your own portfolio reviewed in-depth with a 30-minute advice-packed video portfolio review? Look no more. I do offer these as an async service you can book directly with me here.

Keep kicking doors open and see you next week!
- Florian