Smart Interview Questions Every Entrepreneur Should Ask Before Hiring
Nov 12, 2025Hiring can either elevate your business or drain your energy.
As entrepreneurs, we don’t just need employees who can "do the job." We need people who can own the job. But how do you know if someone is the right fit before they start? Beyond resumes and rehearsed answers, there’s a better way: Ask smart questions that reveal attitude, mindset, values, and real capability.
This blog shares 21 powerful questions you can ask in your next interview, along with why each question matters. Plus, I’ve added a checklist of qualities to look for when you’re hiring.
Top Qualities to Look for in Your Next Hire:
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Right attitude (coachability, ownership, integrity)
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Communication skills (clear, respectful, confident)
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Relevant experience (but not blindly overvaluing it)
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Stability & longevity (no job-hopping signals)
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Learning mindset (eagerness to grow)
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Cultural alignment (fits with your team’s energy)
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Emotional maturity (how they handle failure & feedback)
21 Interview Questions That Uncover the Real Candidate
Here’s how to dig deeper than surface-level answers.
1. What do you know about us?
Reveals if they did any homework — and how serious they are.
2. What is unique about you? (Open-ended)
Tests self-awareness and confidence without arrogance.
3. What is 11 x 11? What’s 25 x 25?
Quick IQ and logical thinking check — especially useful for roles that need agility and number sense.
4. What are 3 characteristics you’ve taken from your parents that you’re proud of?
Shows values and how they view their personal growth.
5. What are 3 traits you’ve inherited that you're not proud of?
Honesty and vulnerability check — great for seeing emotional maturity.
6. Tell me 2 or 3 people whose lives you've changed. If they met you today, what would they say to you?
Reveals impact-driven thinking and emotional intelligence.
7. Why do you want to work with us?
Tests alignment with your company vision — not just “I need a job.”
8. What has been your most important challenge as a manager or in a team?
Leadership reflection and ability to assess complexity.
9. How have you delegated in the past? What’s the most difficult part of delegation for you?
Tests self-awareness in team dynamics and leadership potential.
10. What did you learn from your previous job?
Growth mindset check — what lessons they carry forward.
11. Who inspires you the most, and why?
Gives insight into their values and long-term vision.
12. Tell me something that’s not on your resume.
A great way to get authentic stories or hidden skills.
13. Tell me 10 things you observed in our office (or team).
Measures presence, attention to detail, and curiosity.
14. What was your best success story in your last role?
Helps you understand their definition of success and impact.
15. Tell me a story.
Open-ended — watch how they structure their thoughts and storytelling.
16. Ask me 3 difficult questions to make my life hard.
Tests confidence, creativity, and critical thinking — flips the power dynamic.
17. What are your 3 strengths and 3 weaknesses?
Classic question — but look for honest, not polished answers.
18. Tell me about your family — mom, dad, etc.
Get a sense of their upbringing and how it shaped their mindset.
19. How often do you lie? (Honesty test)
Surprising question — see how they handle discomfort and truth.
20. What went wrong in your life, and how did you handle it?
Resilience and problem-solving in real-life challenges.
21. Check their pressure level.
Not a question — observe their body language, tone, and composure throughout.
Bonus: Tips from Our Team’s Hiring Framework
From our internal Mastermind discussion, here are the 10 things we evaluate when hiring:
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Brief introduction + why they’re applying
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Skill test or knowledge demo
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Background & family questions
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Attitude
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Communication
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Past experience (relevant and transferable)
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Resume vs Reality check
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Stability and longevity
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Learning attitude
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Honesty and integrity
Final Thoughts: Hire for Heart, Train for Skill
It’s easy to get excited by a shiny resume. But real success comes from hiring people with:
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Grit over glamour
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Curiosity over credentials
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Ownership over excuses
If you're building a team, don't just hire performers. Hire partners in your mission.
And if you're a woman entrepreneur navigating hiring for the first time — you don’t have to figure it all alone.
π Inside WE Global Network , we support women founders in building strong, trustworthy teams and systems while growing revenue the smart way.
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