Informational interview questions organized by what you're actually trying to learn.
Most lists just dump 20 random questions on you. These are organized by purpose — so a 20-minute conversation actually tells you whether the move you're considering is right.
What an informational interview is (and isn't)
An informational interview is a short, focused conversation — usually 15–20 minutes — where you ask someone already in a role, company, or industry you're considering how they got there and what they've learned. The goal is information, not a job offer. You're trying to make a better career decision, not close a deal.
It is not a disguised job pitch. If you secretly treat the conversation as a way to get hired, people can tell. They'll notice when your questions are really self-promotion, when you steer every answer back to your own qualifications, or when you end with 'so, are you hiring?' The problem isn't just that it's awkward — it burns the relationship. The whole point of an informational interview is to build a real connection with someone who might become a mentor, referral source, or advocate over time. Once they feel pitched at, that door closes.
Done honestly, informational interviews are one of the highest-leverage career tools available. They give you ground-truth information you can't get from job postings, help you avoid wrong turns before you've invested months, and create a network of people who know you by name before you ever apply.
How to ask for one
The best ask is specific, short, and respectful of time. 'Can we network?' or 'I'd love to pick your brain' are vague and easy to ignore. 'Would you be open to a 15-minute call so I could ask a few questions about [specific topic]?' works because it names the commitment, the topic, and the reason they should say yes.
Here is a full email template you can adapt:
Subject: 15-minute question about your move into [role/industry] Hi [Name], I'm a [current role] at [company or 'a [size] company in [industry]'], and I'm exploring a move into [target role/industry]. Your path from [earlier role or context] to [current role] stood out to me because [specific reason — one sentence]. Would you be open to a 15-minute video call so I could ask a few questions about what the day-to-day is really like and what you'd do differently if you were starting over? I'm free Tuesday or Thursday afternoons, but happy to work around your schedule. Either way, thanks for reading — and for sharing your experience so publicly. Best, [Your name]
And a LinkedIn version, kept shorter:
Hi [Name], I'm exploring a pivot into [target role/industry] and your background in [specific thing] is exactly the path I'm trying to understand. Would you be open to a 15-minute call so I could ask a few questions? Happy to work around your schedule. Thanks, [Your name]
The ideal ask names a topic, not a general desire to network. 'I'm trying to understand whether moving from engineering to product management at a Series B company makes sense' is ten times more likely to get a yes than 'I'd love to learn from your career journey.' Specificity signals that you'll respect their time and ask interesting questions.
The question list, by category
Pick 4–6 questions total for a 20-minute call, mixing categories based on what you most need to learn. Don't read them like a script — let the conversation breathe.
Role reality-check questions
Use these when you're trying to understand whether the day-to-day matches the job description — and whether you'd actually enjoy it.
- Walk me through what a typical Tuesday looks like in this role.
- What surprised you most about the job after you started?
- What do you spend more time on than you expected? Less?
- What would you tell someone who's considering this move but isn't sure?
- What's the hardest part of the job that doesn't show up in the posting?
Industry and company questions
Use these when you're deciding between companies, industries, or trying to read the room before you apply.
- How would you describe the culture on your team in three words?
- What's changing most in the industry right now?
- How do decisions actually get made on your team?
- What does success look like in this role six months in?
Career-path questions
Use these when you want to understand how people get into this role and what actually moves the needle in their careers.
- How did you get here — was it a straight path or a series of pivots?
- If you were doing it over, what would you do differently?
- What skills or experiences mattered most for getting your first break?
- What do the people who advance fastest in this field tend to have in common?
- What would you prioritize learning in the next 6–12 months if you were in my position?
'Who else should I talk to' questions
These are the questions that turn one conversation into a network. Don't skip them.
- Who else should I be talking to as I'm figuring this out?
- Is there anyone you think I'd especially benefit from meeting?
- Are there communities, newsletters, or events you'd recommend?
- If you were me, what's the one next step you'd take this week?
Free: Informational Interview Prep Worksheet
A one-page prep sheet with the request template, question bank by category, and a thank-you note template.
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What to do in the 24 hours after
Send a short thank-you note the same day. It should reference something specific from the conversation, not read like a form letter:
Hi [Name], Thank you for the 15 minutes today — your point about [specific thing they said] really stuck with me, and it's already changed how I'm thinking about [topic]. I'll follow your suggestion to [specific action they recommended] and will keep you posted on how it goes. If I come across anything useful on [topic], I'll send it your way. Thanks again, [Your name]
Then keep the relationship warm without being needy. The worst follow-up is 'just checking in' three weeks later with nothing to offer. The best follow-up happens 3–6 months later with something relevant: an article related to their work, a quick note that you took their advice and what happened, or a genuine congratulations if they get promoted or publish something. The goal is to stay in their mental map as someone thoughtful, not as someone who only reaches out when they need something.
If they offered to introduce you to someone, follow up within 48 hours with a short, forwardable blurb they can copy and paste. Make it easy for them to help you.
Frequently asked questions
Related networking guides
Turn conversations into a real plan
ClearlyPlanned's AI Networking module tracks every contact you make through informational interviews, with next-action reminders so relationships don't go cold. It also generates follow-up message templates personalized to each conversation — so you stay in touch without sounding like you're checking in.
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