Article · 15 min read

40 Startup Interview Questions to Ask Potential Hires

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A ready-to-use question bank grouped by the traits that separate a generalist first hire from a specialist: adaptability, comfort with ambiguity, initiative, and balancing big picture with detail. It hands you the two questions that matter most here, no-playbook problem solving and working outside the job title, so you can screen for range instead of resume.

  • Ask 'describe a time you completed a project without clear instructions or a playbook' to test comfort with ambiguity directly.
  • Initiative and ownership questions ('a time you took initiative to solve a long-standing problem') surface end-to-end shippers, not task-takers.
  • Range questions probe how a candidate balances big picture and detail, the tell of someone who has genuinely worn multiple hats.
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The question it answers

  1. Should my first hires be generalists or specialists, and how do I tell the difference in an interview?

Read with it

  1. A serial founder makes the exact call you should make for your first seats: hire generalists until product-market fit, because... Mean CEO (STARTUP POV) Essay · 14 min read Generalists vs. Specialists: Which Should You Hire First in Your Startup? Violetta Bonenkamp
  2. Written for Indian founders hiring right after a seed round, it argues your first employees should be hustlers who can figure... Quartz (qz.com/india) Article · 8 min read A Guide for Early-Stage Indian Startups to Lure the Right Talent Quartz India
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