Fun Questions to Ask an Interviewee
Light, revealing prompts to warm up interviews while learning how candidates think, play, and collaborate.
1What small hill are you willing to die on at work?
Click to see why this works
What small hill are you willing to die on at work?
Click to see why this works
Why this works
Shows values and taste with humor.
2Teach me something in 60 seconds—anything.
Click to see why this works
Teach me something in 60 seconds—anything.
Click to see why this works
Why this works
Tests clarity, enthusiasm, and presence under constraint.
3What’s a delightfully nerdy tool you love?
Click to see why this works
What’s a delightfully nerdy tool you love?
Click to see why this works
Why this works
Signals craftsmanship and curiosity.
4What’s the most fun team ritual you’ve been part of?
Click to see why this works
What’s the most fun team ritual you’ve been part of?
Click to see why this works
Why this works
Reveals culture-building instincts.
5If you had a personal 404 page, what would it say?
Click to see why this works
If you had a personal 404 page, what would it say?
Click to see why this works
Why this works
Self-awareness and playfulness combined.
6What’s a problem you enjoyed even after it was solved?
Click to see why this works
What’s a problem you enjoyed even after it was solved?
Click to see why this works
Why this works
Love of process, not just win states.
7What would your teammates tap you for help with?
Click to see why this works
What would your teammates tap you for help with?
Click to see why this works
Why this works
Community role and strengths branding.
8Pick a superpower you’d actually use at work.
Click to see why this works
Pick a superpower you’d actually use at work.
Click to see why this works
Why this works
Converts fantasy to practical priorities.
9What does a great day feel like for you?
Click to see why this works
What does a great day feel like for you?
Click to see why this works
Why this works
Chemistry with team rhythms and energy.
10What low-stakes hill did you concede and later celebrate?
Click to see why this works
What low-stakes hill did you concede and later celebrate?
Click to see why this works
Why this works
Signals flexibility and learning.
11What’s a recent micro-win you’re proud of?
Click to see why this works
What’s a recent micro-win you’re proud of?
Click to see why this works
Why this works
Finds intrinsic motivation and craftsmanship.
12If you renamed your job to something cooler, what would it be?
Click to see why this works
If you renamed your job to something cooler, what would it be?
Click to see why this works
Why this works
Personality and narrative sense.
Use with Care
Expert tips and techniques for getting the most out of these questions.