Questions to consider if you’re approaching a role as a Founder or Operator
Founder / Operator Thinking
They want someone who can build, validate, and iterate quickly.
- Tell me about a time you took an idea from zero to launch.
- How do you evaluate if a new idea is worth pursuing?
- What’s your approach to MVPs? Can you give an example of one you built?
- Walk me through your first steps if given a raw idea today—what do you do in the first 48 hours?
Customer Discovery & Validation
Your ability to talk to users, test hypotheses, and iterate is central.
- How do you conduct customer interviews to get useful insights?
- Tell me about a time customer feedback changed your approach.
- How do you balance speed and quality when validating a concept?
- Describe a time you built something that didn’t work—what did you learn?
Execution & Hustle
They want doers not strategists alone. Prepare to show how you get things done.
- Describe a time when you had to figure something out with little guidance.
- What’s the scrappiest thing you’ve done to move a project forward?
- Tell me about a time when you handled multiple roles in a project.
- Give an example of how you navigated a legal, ops, or regulatory hurdle.
Team & Leadership in Unstructured Environments
You’ll need to recruit, inspire, and lead without clear authority.
- Tell me about a time you recruited or assembled a team from scratch.
- How do you influence people when you don’t have formal authority?
- What’s your approach to hiring co-founders or first hires?
- How do you maintain momentum on a project when things get hard?
Self-Awareness, Drive, and Culture Fit
- Why do you want this role specifically at XYZ?
- How do you stay motivated when working independently or remotely?
- What are you world-class at? What are you still working on?
- What does “no job too small” mean to you, and when have you lived it?
Bonus: Sector Curiosity & Trends
- What’s a space or industry you think is ripe for disruption?
- If we gave you $500K today to test an idea, what would you build and why?
- How do you stay current on trends in technology or startups?
