Because interviews aren’t auditions, they’re collaborations to see if both parties work well together.

I’ve prepped for over 40 design interviews in the last decade. From early-stage startups to Big Tech, from IC to leadership roles.

And if there’s one pattern I’ve noticed? The most revealing moments aren’t during the whiteboard challenge or design critique.

They’re when you flip the script, and start asking them some real questions.

Most people treat interviews as one-way evaluations. But the best ones are mutual. The questions you ask show what you value, what you’re solving for, and whether you think like a partner, not just a potential hire.

This is a curated list of the most valuable questions I’ve asked (or wish I had) — grouped by theme, with context on what to listen for and how to read between the lines.

Questions for your hiring manager

Use this round to uncover expectations, leadership style, and your long-term fit in the team.

What does success look like in the first 3–6 months of this role?

• Do they have clarity on your role from day one — or are they hoping you’ll figure it out for them?

• Look for specific outcomes: launching a feature, improving a metric, unblocking a workflow. Vague answers like “make impact” or “just get settled in” can signal unclear expectations or poor onboarding.

What are some of the trade-offs you’ve made in the design org recently?

• Good leaders know design doesn’t happen in a vacuum, it’s shaped by constraints.

• You want to hear about decisions that involved prioritisation, resourcing, or speed vs quality. This tells you whether leadership values transparency and whether they invite designers into tough decisions.

What are the expectations from design and how are they measured?

• Every org says design matters. This question tests whether they’ve defined how.

• Look for answers that tie design performance to business outcomes like adoption, engagement, retention, etc. If metrics aren’t defined, that may reflect either early-stage chaos or a lack of investment in design.

Where do you see opportunities for design to be more influential?

• Design leadership isn’t just about what is. It’s about what could be.

• Their answer reveals whether the team is expected to contribute to business strategy or just polish the UI. It also gives you a read on what kind of influence you’d be able to build.

How involved is design in roadmap and prioritisation?

• This helps you understand where decisions actually happen and when design gets to shape them.

• “Design is involved from the beginning” is ideal, but probe with examples. If design is mostly brought in post-brief, you’re downstream.

Where do you see this role evolving over the next few years?

• You’re not just joining for the job, you’re also joining for the journey.

• Look for clarity on how scope might grow, new skills you’d be encouraged to develop, or future leadership opportunities. If the role is seen as fixed, it may not be set up for growth.

How do designers grow once they get in?

• It’s one thing to get hired. It’s another to keep levelling up.

• You’re listening for structured feedback loops, levelling criteria, mentorship, and performance reviews. “We just promote when it feels right” is not a growth plan.

Can you tell me about the design org structure and career ladder?

• The org chart reveals power dynamics and the ladder reveals growth design.

• This tells you how many IC levels exist, how design interacts with cross-functional leaders, and how promotions are earned. A flat org isn’t always a red flag — unless it’s paired with a vague ladder.

What’s one thing you’d change about how design works here?

• Self-awareness in a manager is gold. This question brings it out.

• Listen for humility, insight, and a desire to improve. If they say “nothing really” or deflect, that’s either a lack of reflection or fear of being honest.

Your manager will set the tone for your success and growth in the company. "People don't quit jobs, they quit bad managers”, so choose wisely.

Questions for your future teammates

Use this round to understand culture, collaboration, and the lived reality of design inside the company.

What are some problems the team is trying to solve right now?

• You want to know what you’ll walk into on your first Monday, not just what’s on the roadmap.

• Their answers reveal whether the team has focus or is spread thin. Look for a balance of ambitious goals and practical challenges. Bonus if they’re excited about what they’re working on.

What’s your typical day like at the company?

• The answer to this tells you more than any company values deck.

• You’re listening for rituals (standups, crits), autonomy, and work-life balance. If there’s no “typical” day, ask what the last three days looked like — you’ll get a clearer picture.

How do design, product, and engineering collaborate? What’s still a work in progress?

• Aspirational answers are nice. Honest ones are useful.

• You want specifics — not just “we work well together.” Probe for how ideas are prioritised, who gets the final say, and how conflicts are resolved. If design always “works around” others, take note.

What do you like most about your role?

• This tests for authentic connection to the work.

• Listen for enthusiasm, ownership, or learning. If they pause for too long or give a generic answer, that’s signal in itself.

What’s something you’ve learnt here that surprised you?

• A great question for surfacing hidden strengths or unexpected gaps.

• The answer can reveal a lot: maybe they were surprised by how collaborative leadership is, or how broken onboarding was. Either way, you learn something you wouldn’t from a job description.

What’s harder here than it should be?

• Every org has friction points. The good ones talk about them.

• This can surface real blockers: broken tools, unclear direction, or process churn. If people dodge this question, that’s a red flag too.

What kind of support do you look for from design leadership?

• This is how you find out what’s missing in the current setup.

• Are people asking for more coaching? Better resourcing? Clearer vision? You’ll also learn what’s expected from someone more senior joining the team.

What do you love most about the design culture here? What’s one thing you’d change?

• Culture is rarely perfect. That’s why this dual-question works.

• Honest answers here give you the vibe beyond ping pong tables and what values are actually lived, and where the culture still has growing up to do.

Questions for company leadership OR HR

Use this round to map business strategy, leadership thinking, and whether this company is future-proof.

What are some key bets the company is making in the next 12–18 months?

• You’re looking for signal, not spin.

• Look for specificity: entering a new market, doubling down on a vertical, launching a new product line. Vague phrases like “growth” or “optimisation” aren’t enough.

Where do you see the biggest opportunities for design to drive impact?

• This frames design as a multiplier and not just a support function.

• You want them to reference business-critical areas where design is integral: conversion, onboarding, retention, trust. If they struggle to name any, design might still be seen as ornamental.

How is the company leveraging AI?

• Are they reacting to hype or reimagining their product?

• Ask how AI is influencing strategy, not just tools. Bonus points if they’re thinking beyond efficiency and toward differentiated experiences.

What does inclusion look like on the ground — in hiring, teams, and leadership?

• DEI theatre is easy. Proof is harder.

• Ask for examples: how they write job descriptions, how inclusive design shows up in process, how diverse voices are included in decision-making. Numbers are good. Stories are better.

How does the company uphold its values across a diverse and distributed team?

• Culture doesn’t survive by accident.

• Listen for deliberate practices, not just Slack emojis. How do they onboard? Handle conflict? Make people feel seen across timezones?

What does career growth look like for senior designers here?

• Is the only way up out?

• You’re looking for clear paths to Staff or Lead roles, not just managerial tracks. Ask how many designers have been promoted in the last year and what helped them get there.

What’s one thing you’d change about how design works here?

• This reveals what leadership knows and what they’re still figuring out.

• If they’re aware of friction points, great. If they’re acting on them, even better.

What are you most excited about in the next year?

• Optimism is contagious or conspicuous by its absence.

• Their answer tells you whether this is a company with momentum… or just inertia.

Ask like a partner, not just a candidate

Whether you’re applying for your first design role or stepping into design leadership, remember that interviews are mutual. You’re not just trying to get hired, you’re trying to make sure you’re joining a team, a manager, and a culture where you’ll thrive.

Asking better questions won’t just help you evaluate them. It will also help you show up as a designer who’s thoughtful, strategic, and intentional about your craft and career. The kind of person they’ll remember and want on the team.

Until next time, ✌️!