When I talk with candidates, I’m not trying to trip anyone up or see who’s the most polished. I’m trying to understand how someone thinks, how they assess fit, and whether they’ve actually pictured themselves in the role.
These are three questions I almost always ask, plus a couple more that often come up. I’ll also share a bit about what a strong answer looks like.
1. Why are you interested in this role, and why do you think it’s a good fit?
This isn’t about enthusiasm or loyalty to the mission (though those matter). I’m listening for whether you understand this role, and whether you can connect it to your experience in a concrete way.
Strong answers usually:
Reference the actual responsibilities of the role
Draw clear lines between past experience and future contribution
Avoid being generic enough to apply to five other jobs
For nonprofit positions, I’m also listening for whether you feel a strong connection to the mission
2. What parts of this role do you think will be most challenging for you?
This question makes some candidates nervous, but it’s not a trap. I’m not looking for perfection or self-criticism. I’m looking for self-awareness. Everyone has something they can get better at. If you don’t think you do, then you don’t have the self-awareness I’m looking for.
Strong answers show:
Realistic understanding of the role
Ability to name growth edges without underselling yourself
Thoughtfulness about how you’d approach learning or support
Red flag answers tend to be either “nothing” or challenges that suggest the role hasn’t really been understood.
3. What questions do you have for us?
This one matters more than candidates often realize. Your questions tell me how you think, what you prioritize, and whether you’re treating this as a mutual decision.
Strong questions often focus on:
How success is defined
Team dynamics and decision-making
What’s changing or evolving in the role or organization
You might consider asking about a program or initiative that you saw on the organization’s website. This signals that you’ve done your research and have a genuine interest in the work.
No questions means you haven’t thought about it. Asking only about salary, logistics, or PTO usually signals that you’re not engaged with the work itself.
Two More Questions That Often Come Up
4. What would success look like for you in the first 6–12 months?
This helps me see whether a candidate can translate a job description into real impact. The best answers show an understanding of priorities, pacing, and what “doing the job well” actually means.
5. What kind of environment helps you do your best work?
This isn’t about preferences being right or wrong. It’s about self-awareness. For example, if you know that you work best in an environment where you have dedicated quiet time each day, that shows me you’re a reflective person who wants to be set up for success. Those are the types of people I want to work with.
The bottom line:
Good interviews aren’t about having perfect answers. They’re about clarity, self-reflection, and showing that you’ve thought seriously about the role — not just about getting an offer.
If you can answer these questions honestly and specifically, you’re already ahead of most candidates.
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