Conflict and repair
Aim for specifics from their past, not hypotheticals about their character.
- Tell me about the last time you were genuinely angry at a colleague. What did you do in the following 48 hours?
- When we disagree and neither of us convinces the other, what should happen?
- Do you get louder or quieter when a conversation gets tense?
- What does an apology from you look like?
- Who ended your last serious working relationship, and what did they say about you on the way out?
- When I've upset you, will you tell me that day, that week, or never?
- What's a criticism of you that you've heard more than once?
- How do you want me to raise something you're doing badly?
- Have you ever stopped speaking to someone you worked with?
Power and decision rights
Write the answers down. Verbal agreements here evaporate exactly when you need them.
- Which decisions are yours alone, which are mine, and which are both?
- If we're deadlocked on a hire, who breaks the tie?
- What spend amount requires both of us to agree?
- Who is CEO, and what does that actually change day to day?
- How do you feel about being overruled in front of the team?
- If an investor prefers dealing with one of us, how do we handle it?
- What would make you go around me rather than through me?
- Which single decision would you refuse to compromise on?
Money, equity and fairness
If any of these feel premature, that discomfort is the reason to ask now.
- What split do you think is fair, and what is that based on?
- Should equity reflect past work, future work, or risk taken?
- Are we vesting, over how long, and with what cliff?
- What happens to equity if one of us leaves in month six?
- How many months can you personally survive with no salary?
- What salary do you need for this to be sustainable for you?
- Are you keeping consulting or contract work? How much?
- What would we do if one of us needed to take money out early?
- How would we handle a small acquisition offer that suits one of us and not the other?
- Do you have debts, dependants, or commitments that change your risk tolerance?
Commitment, pace and ambition
Different answers are fine. Assumed-identical answers are not.
- What outcome would make this a success for you — a number, not an adjective?
- Would you rather own 20% of a large company or 60% of a small one?
- What does a normal working week look like for you in six months?
- What are you not willing to sacrifice for this?
- How long do you give this before you'd call it?
- What would you do if we failed in month nine?
- Is there a job that would make you leave?
- What are you doing this for, honestly — money, proof, curiosity, freedom?
Values and moral trade-offs
Concrete dilemmas beat abstract values every time.
- Would you exaggerate traction to close a round we badly need?
- A supplier undercharges us by a meaningful amount. What do we do?
- We can cut a corner on privacy for a big customer. Where's your line?
- Would you fire a friend who's underperforming? When?
- How do you handle a customer complaint that's our fault and expensive?
- What's something the industry does routinely that you think is wrong?
- Would you ever pay yourself before paying the team?
Blind spots and self-knowledge
The gap between how someone sees themselves and how others do is the most predictive answer on this page.
- What will I find hardest about working with you?
- What do people consistently misread about you?
- When you're stressed, what changes in your behaviour first?
- What part of this company are you worst suited to?
- What did your last manager or partner want you to change?
- What's the least flattering true thing about how you handle pressure?
- If this ends badly, what will your version of the story be?
- How would you know if you were the difficult one?