Figure out what questions to ask your interviewer

Generic questions get generic answers. The best questions to ask in an interview come from understanding the specific role, the person you’re talking to, and what you actually need to learn before you can say yes to an offer.

This prompt walks you through all of that and generates questions tailored to your situation. It also tells you how many to prepare and which ones to lead with.

For background on what makes a strong interview question, see our guide on good interview follow-up questions.

Copy this into ChatGPT, Claude, or your AI tool of choice. Fill in the brackets.

I have an interview coming up and I need to figure out what questions to ask. Help me prepare questions that are specific to this role, this company, and this interviewer.

**The job posting:**
[Paste the full job description]

**Who I'm interviewing with:**
[Their name, title, and anything you know about them. Example: "Sarah Chen, VP of Engineering. She's been at the company 3 years, previously at Stripe." or "I don't know yet, just that it's a phone screen with someone from HR"]

**Interview format:**
[Example: "30-minute phone screen", "1-hour video call with the hiring manager", "panel with 3 engineers", "final round with the VP"]

**What I already know about the company:**
[Anything you've learned from research, previous interviews, the recruiter, or the company website. Example: "They just raised Series B, expanding into Europe, engineering team is ~40 people." Leave blank if you haven't researched yet.]

**What I'm trying to figure out:**
[What do you actually need to learn before accepting an offer? Example: "whether there's room to grow into management", "how much autonomy I'd have", "whether the team culture is healthy or if there's high turnover", "I'm not sure yet — help me think through it"]

**Instructions:**

1. Based on the interview format and who I'm talking to, tell me:
   - How many questions I should realistically prepare (phone screen vs. full interview vs. panel)
   - What types of questions are appropriate for this person's role (an HR screener gets different questions than a VP)
   - How much time I'll likely have for questions (estimate based on interview length)

2. Generate 6-8 questions tailored to this specific situation. For each one:
   - Write the question in natural, conversational language (not stiff or formal)
   - Explain in one sentence why this question is worth asking in THIS interview
   - Rate it as "lead with this" (strongest signal) or "backup" (good if time permits)
   - Suggest a follow-up question I could ask based on likely answers

3. If I provided company research, use it to make the questions specific. Don't ask "what's the company strategy?" when I could ask "how does this role support your European expansion?"

4. If I told you what I'm trying to figure out, make sure at least 2-3 questions directly address those concerns — but frame them in a way that sounds curious, not anxious.

5. Give me a game plan:
   - Which 3 questions to definitely ask (in priority order)
   - Which ones to hold as backups if the conversation already covers a topic
   - Any topics to avoid with this specific interviewer (e.g., don't ask an HR screener about technical architecture)

Important:
- Don't give me questions I could answer with a Google search. If the answer is on the company's About page, it's not a good question.
- Make the questions sound like something a person would actually say, not a script they're reading.
- If I didn't provide company research, tell me to go do it first — or suggest 2-3 things to look up that would make my questions better.

Tips

• Run the company research prompt first. The more context you feed in, the more specific your questions will be. Generic input = generic questions.
• Adjust for who you’re meeting. Questions for an HR screen are about logistics and fit. Questions for the hiring manager are about the role and team. Questions for a VP are about strategy and growth. This prompt handles that, but give it as much info as you have about the interviewer.
• Don’t memorize — internalize. Read through the questions a few times, but your goal in the interview is a conversation, not a recitation. If the interviewer already answered one of your questions during the interview, skip it and move to your backup.
• Use the answers in your follow-up email. Whatever they tell you becomes material for a specific, compelling thank-you message. See our guide on how to follow up after an interview for how to do this well.