1. Tell me about the hardest conversation you’ve had with an employee or stakeholder.
Listen for: Direct but humane delivery, preparation, and a relationship that survived it.
Red flag: Avoided the conversation until it became a crisis.
Role-specific questions
2. Walk me through how you’d spot a problem in our books or our team before it’s visible.
Listen for: Leading indicators — burn variance, engagement dips, missed 1:1s — checked on a rhythm.
Red flag: Waits for the quarterly report or the resignation letter.
3. What’s a policy you’ve seen backfire? What would you have done instead?
Listen for: Second-order thinking about incentives, and a simpler alternative principle.
Red flag: More policy is always the answer.
4. How do you keep confidential information confidential in a small company where everyone talks?
Listen for: Specific habits — separate channels, need-to-know defaults, discretion under social pressure.
Red flag: Treats it as obvious and has never actually been tested on it.
5. Tell me about a time you pushed back on a founder or executive. What happened?
Listen for: Data-backed pushback, delivered privately, with the relationship intact either way.
Red flag: Never pushed back — dangerous in the roles closest to money and people.
Closers that work for any role
6. What does a great first 90 days in this role look like to you?
Listen for: Learning before changing, early small wins, and questions about how you’d measure them.
Red flag: Grand transformation plans before understanding the context, or no ambition at all.
7. What part of this kind of role do people usually underestimate?
Listen for: Lived-experience insight that only someone who’s done the job would know.
Red flag: Generic answers that could come from reading the job description.
8. What would your last manager say is the thing they had to manage around?
Listen for: A real weakness stated plainly, plus the compensating system they’ve built.
Red flag: A humblebrag ("I care too much"), or claiming the manager would say nothing.
Penroll writes these for your exact job post
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