My Favorite Interview Questions (and What They Actually Reveal)

I love a good interview, not just because it’s a chance to evaluate someone’s skills, but because it’s a rare opportunity to glimpse the heart of what motivates someone, how they think, and how they show up in the world. Over the years, I’ve developed a few go-to questions that consistently lead to rich, revealing conversations. These aren’t your typical “what are your strengths” questions. They’re designed to surface intrinsic motivators, self-awareness, and values alignment.

Here are my favorites, how I use them, what they tell me, and when I reach for each one:

"When you were little, what did you want to be when you grew up, and how does that show up in what you do today?"

What it reveals: This question gives the person you're speaking with an opportunity to talk about their childhood, which naturally uncovers what they care about most deeply (at least in my experience). It shows what they were intrinsically drawn to before external expectations crept in. It tells you what they admire, and gives them a chance to recall simpler times. This question has never returned void. I always walk away with something we relate on, and it typically gives me a fun talking point to reference in future collaboration. It's also just fun and low-stakes.

When to ask it: First 1:1s, icebreakers for large or small groups. For large groups, use a sentence prompt to ensure everyone gets a turn to share.

"Where do you believe the [insert industry] is falling short?"

What it reveals: This one reveals where a person directs their passion and sometimes even their rage. Both are valuable when evaluating for mutual fit. Before you ask it, be clear on the kind of answer you’re looking for and make sure it aligns with your team and company goals. Also, know what red flag answers sound like. I’ve found this question can uncover underlying motivations that would have been in direct conflict with team values.

When to ask it: When interviewing a potential new manager, a peer you’ll work closely with, or anyone whose personal values you want to better understand.

"Tell me about the last time you received constructive feedback that resonated and how you acted on it."

What it reveals: The framing of this question is key. You're not asking what they usually do with feedback. You're asking for a specific, recent example. That makes it harder to default to the “ideal” answer and forces them to tell you what actually happened. It also reveals how long it’s been since someone gave them feedback that truly landed and whether they were able to meaningfully change how they show up as a result. If someone cites an example from six years ago and struggles to name how it changed them, they’re probably not a fit for any team that values personal accountability.

When to ask it: Every interview. Every time.

Bonus tip: When interviewing C-level executives, ask for the last instance of constructive feedback that came from a direct report or lower. That answer alone will speak volumes.

Final Thoughts

Great interview questions do more than check boxes. They invite someone to reveal who they are. These questions help me get under the surface in a way that’s meaningful, human, and often pretty fun. Whether you're hiring, onboarding, or just getting to know someone better, I hope you find them as powerful as I have.

Let me know if you try any of these and what they reveal for you.