How to interview your investor before they interview you
These are the questions founders should ask, but usually don’t… and later regret not asking.
Watch reactions more than answers.
A. MOTIVATION & INTENT
1️⃣ “Why does this opportunity personally matter to you?”
Look for:
✅ Thoughtfulness
❌ Generic answers
2️⃣ “What excites you and worries you about my business?”
Good investors see both highs and risks.
3️⃣ “Is this a financial investment or a personal passion project?”
You need to know if they are disciplined or sentimental.
4️⃣ “What would make you lose confidence in me as a founder?”
This reveals:
• toxic triggers
• expectations
• control tendencies
B. EXPERIENCE & STYLE
5️⃣ “What’s the worst investment you’ve ever made and what did you learn?”
Avoid anyone who has no failures.
6️⃣ “How do you support founders when things go badly?”
Look for calm, not control.
7️⃣ “How many investments did you write off completely?”
Zero = dishonesty.
8️⃣ “What kind of founder frustrates you most?”
You might be that founder.
Better know now.
C. CONTROL & GOVERNANCE
9️⃣ “How do you define your role post-investment?”
Words like:
✅ advisor
✅ guide
✅ support
Are better than:
❌ control
❌ steer
❌ direct
🔟 “When do you intervene in operations?”
The tone matters more than the answer.
1️⃣1️⃣ “Do you prefer board seats or observer roles?”
Good investors don’t need titles.
1️⃣2️⃣ “Have you ever replaced a founder?”
The answer tells you everything.
D. COMMUNICATION & CONFLICT
1️⃣3️⃣ “How often do you expect updates?”
Mismatch = friction.
1️⃣4️⃣ “How do we resolve disagreements?”
If they say:
“We’ll figure it out”
Run.
1️⃣5️⃣ “Have you ever had a falling out with a founder?”
If every founder was “difficult” —
the investor is the problem.
E. RETURNS & EXIT MINDSET
1️⃣6️⃣ “What kind of return makes you happy?”
If the answer is unrealistic —
so will the pressure.
1️⃣7️⃣ “What is your exit timeline?”
You don’t want surprises when they want out.
1️⃣8️⃣ “Would you support a profitable business even without VC-style exits?”
If not —
you’re just a lottery ticket.
F. INTEGRITY & CHARACTER
1️⃣9️⃣ “How do you behave when things don’t go your way?”
Emotional maturity shows here.
2️⃣0️⃣ “What do founders usually thank you for?”
If they list ego things —
pay attention.
G. CHEMISTRY CHECK
2️⃣1️⃣ “Can I talk to 2–3 founders you’ve backed?”
If they hesitate —
that’s your answer.
2️⃣2️⃣ “What would founders criticize you for?”
Self-awareness = safety.
2️⃣3️⃣ “How do you handle uncertainty?”
You live there.
They must survive there.
H. FINAL DEAL-BREAKER QUESTION
2️⃣4️⃣ “If you weren’t investing money, would you still mentor me?”
If yes —
you found a partner.
If no —
you found a cheque.
🎯 HOW TO USE THESE QUESTIONS
Ask:
✅ Casually
✅ Calmly
✅ Privately
✅ Early
✅ Directly
Do not interrogate.
Observe:
👀 Facial expressions
👀 Comfort level
👀 Defensiveness
👀 Evasiveness
👀 Blame shifting
👀 Ego spikes
Those are your real answers.
💣 FINAL WARNING
Money covers cracks — temporarily.
Character determines collapse — permanently.