Most candidate questions are either generic ("What's the culture like?") or transparently flattering ("What do you love about working here?"). Both produce useless answers. Here's the version that produces signal.
Specific over generic:
Bad: "What's the team culture like?"
Good: "When was the last time the team disagreed on a major decision, and how was it resolved?"
Operational over aspirational:
Bad: "What are your goals for this role?"
Good: "What does success look like 90 days in? Specifically, what would I have shipped or changed?"
Hard questions over comfortable ones:
Bad: "What's the biggest opportunity here?"
Good: "What's the most common reason hires in this kind of role haven't worked out before?"
Manager-specific:
"How do you give feedback to your team, what's your default mode?"
"When was the last time someone on your team disagreed with you publicly? How did it land?"
"What's the part of your job you find most frustrating right now?"
Company-specific:
"What does the next 18 months realistically look like? Where might it not go to plan?"
"How does the senior team operate when there's a disagreement on strategy?"
The closing question that always works:
"If you were starting this role today, what would you want to know that I haven't asked?"
These questions feel uncomfortable to ask. That's why they work, most candidates don't. The hiring manager remembers the candidate who asked the harder question.
What questions do you ask?
— Dr. Hosney Adel