Questions to ask during the interview process
When I was younger, my entire interview prep energy went into thinking about the questions I was going to be asked… and whether I’d be able to answer them.
My older brother would tell me, “No, this is a two-way street. You should also be trying to gauge if this company is a good fit for you.” But it took me years to get there. Now, there is just no way I am signing an employment contract before I have answers to specific questions.
In fact, even the answers recruiters refuse to give me are part of the puzzle. They often highlight red flags that might otherwise be conveniently swept under the rug.
I use the following questions to determine whether the role, team, and company will support my well-being, creativity, and growth. Some of these questions are non-negotiable.
Psychological safety
Nope, not just another trendy buzzword. Very much the foundation of trust, in fact. If it is not safe to speak up, ask questions, or make mistakes, no amount of talent or productivity will protect you. These questions help reveal whether the workplace encourages honesty or actively deters it.
- How is feedback typically given here?
- Is it culturally acceptable to disagree with a manager or push back on a request?
- What happens when someone raises a concern?
- How are mistakes handled?
Workload and pacing
Job descriptions are often written to sound clear and well thought out in ads, but once you’ve signed on, you may very quickly realize they’re simply unsustainable… and there’s no plan B. Enjoy the impending burnout.
Ask these questions to get a sense of whether the company’s expectations are fair and realistic, and what happens when things inevitably get a little too busy. And yes, this is very much about reading between the lines: answers often reveal how much your time and energy (read: health) will be valued at a workplace.
- What does a typical week look like?
- How is workload prioritized when there is too much to do?
- How do you make sure part-time roles stay within the agreed time boundaries?
- Whether full-time or part-time, how was workload for this role scoped out?
- What happens when deadlines start slipping?
Role clarity
You cannot meet expectations if they are constantly shifting or never properly defined in the first place. These questions help ensure the role has been properly scoped and will not change overnight just because it suits the organization’s purposes.
- Is this a new position or a backfill?
- What are the top priorities for this role in the first three months?
- Who defines the scope of the role, and does that ever shift over time?
- How do you fight against structural ambiguity to help keep your employees’ work clear and meaningful?
Leadership and growth
Strong leadership is more than delegation. It’s about offering direction, support, and a clear sense of purpose. These questions are designed to help you find out whether the people leading the team actually lead—and whether you will have the space to grow without having to constantly advocate for yourself.
- Would you say your leadership approach leans more transformational, transactional, or something else entirely?
- When a team member makes a reasonable request to improve their work, even if it meets resistance, do you tend to back them up?
- What kind of support can I expect as I settle into the role?
- What does growth or development typically look like here?
Tools and logistics
The tools a team relies on (along with the ones they avoid) can tell you a lot about how smoothly the work flows. Is there an actual system, or is everyone improvising? These questions help uncover whether the company is serious about clarity and efficiency, or if navigating chaos is just part of the job.
- What tools are in place for project tracking and communication?
- What creative software or platforms does the team use regularly?
- Are there any tools the team finds frustrating or limiting?
- Are there tools or technologies (such as AI) that the organization has chosen not to adopt?
Availability and flexibility
Contrary to corporate opinion (at least in some circles), boundaries matter. These questions clarify how much flexibility the team offers, whether workload spills into personal time, and how the company handles pressure without overstepping. They are also great for gauging how much trust leadership places in its team.
- What are your expectations around availability during the week?
- How is time off handled when things get busy?
- What is your remote policy?
Conflict and culture
As much as we’d all like to avoid them, disagreements do happen. What matters is how they are handled. Can people disagree in a way that still leads to a constructive outcome? Are concerns taken seriously? Is “culture” just a buzzword or something you can actually feel?
In my experience, culture is a concept all too often used to gaslight employees. It’s important to determine from the outset whether you’re signing on with a company that values a human-centric approach… or if it’s all talk. And you know what they say about talk.
- How do you handle disagreements within the team?
- Can you share a time when someone spoke up about an issue, and how it was received?
- What is something someone did here recently that really aligned with your company’s values?
Onboarding and integration
Onboarding should strike a careful balance between clarity and autonomy. If there’s no structure at all, you’re left piecing things together through trial and error (and good vibes, apparently). But if the process is too rigid or overly scripted, it may hint at a workplace that values conformity over individual thinking.
What you’re looking for is a thoughtful, human-centered approach: structured enough to support you, but flexible enough to let you find your footing.
- What does the onboarding process look like?
- Who is responsible for onboarding me?
- Is there a structured plan for the first few weeks?
- Will I have a dedicated point of contact or onboarding buddy?
- What kind of documentation or internal knowledge base do you currently have?
Creativity and ownership
Creative roles walk a fine line between freedom and structure. These questions help you understand whether you are being hired to genuinely bring ideas to life, or just to execute someone else’s vision—or worse yet, work for a micromanager who doesn’t even actually have a vision.
Asking these questions should also give you a sense of what already exists and what is off-limits, so you can determine how much room you will have to explore and contribute to the vision.
- How much creative autonomy does this role offer?
- Are there brand guidelines or visual identities already in place?
- What kinds of creative decisions require approval, and from whom?
- How open is the team to experimentation or unconventional approaches?
- Can you give an example of a time a creative idea shifted the direction of a project?
- What is something you are hoping this person will elevate, not just execute?
Organizational maturity
Especially helpful if you are joining a startup, scale-up, or a team in transition. These questions help uncover whether basic foundations exist—or if you’re expected to thrive on chaos, high-fives, and team lunches (and ultimately burnout).
- How would you describe the current phase of the organization or team (early growth, transition, stabilization)?
- Are there any major changes happening right now (new leadership, reorgs, etc.)?
- What processes are already established, and what is still being figured out?
- Is this a role that requires building from scratch, or are you stepping into an existing system?
Retention and turnover
How long do people stay in the organization? This is such an important metric. If turnover is high, it is worth understanding whether that is due to growing pains, leadership changes, or something more sinister.
When I ask these questions, I am trying to see whether an organization values long-term investment in its people—or cycles through them like the next smartphone.
- What is the typical tenure on this team or in the organization overall?
- Has there been a lot of turnover in this department recently?
- When people leave, do you conduct exit interviews? If so, have any themes come up?
Collaboration and team dynamics
It is one thing to work on the same project, and another to work well together. These questions reveal how people interact day to day, and whether collaboration is truly valued… or just a company buzzword that sounds warm and fuzzy.
- How do teams collaborate across functions (design, development, marketing, etc.)?
- Are roles clearly defined, or is there a lot of overlap?
- How do team members support each other when someone is overloaded?
Autonomy and trust
Whether you are a strategist, creative, or technician, autonomy is often what makes or breaks the role. Will the environment empower you to do your best work, or is micromanagement lurking around the corner?
- How is progress tracked? Through outcomes, hours, or check-ins?
- How do you balance autonomy with accountability?
- What does “ownership” mean in this role?
- Are there approvals required for day-to-day decisions?
Final thoughts
Obviously, there is no world or timeline in which you will be able to ask all of these questions. But many of them are questions I wish I had asked sooner.
It is worth coming back to them to clarify what’s being asked of you and to protect yourself. Ultimately, this is about building the kind of work life you want.
Save this list for your next interview, and feel free to share it with someone who might need it.
This post was co-written with ChatGPT to refine ideas, structure arguments, and enhance clarity.