A friend of mine spent 47 minutes on a coffee chat last year and walked away with exactly one piece of useful information: the company had free lunch on Fridays. That’s not the person’s fault. It’s a question problem.
Informational interviews are genuinely useful when you ask the right things. I’ve seen them lead to referrals, job offers, and sometimes just a clear sense that a role or industry is not what you thought. But most people walk in with a list of questions that sounds thoughtful and extracts nothing.
This is a guide to questions that actually surface real information, organized by what you’re trying to find out.
What you’re really trying to learn
Before the list: it helps to be honest with yourself about your goal. Are you trying to figure out if a career path is right for you? Are you hoping for a referral? Do you want to understand what a specific company is really like inside?
Those are three different conversations. Going in with the wrong framing wastes the other person’s time and yours. A good informational interview isn’t about impressing someone, it’s an information transaction. You’re trading 30-45 minutes of their calendar for genuine career intelligence. Treat it that way.
According to LinkedIn’s Economic Graph research, a meaningful share of jobs are filled through referrals before they’re ever posted externally. So there’s a real upside to building these relationships well. But that’s a byproduct of a good conversation, not the explicit goal you should voice.
Questions about the person’s actual day-to-day
This is where most informational interviews die. People ask “What does a typical day look like?” and the person gives a polished PR answer. Here are versions that tend to get more honest responses:
- “What were you doing at 2pm on Tuesday?” (Yes, literally. It’s a great forcing function.)
- “What do you spend time on that you didn’t expect when you took the role?”
- “What’s a decision you had to make recently that was genuinely hard?”
- “What’s still on your to-do list from three weeks ago that keeps getting pushed?”
That last one is probably my favorite question in any informational interview. The things that get perpetually deprioritized tell you a lot about the real organizational values versus the stated ones.
Questions about the company or team culture
Culture questions are notoriously hard to ask well. “What’s the culture like here?” gets you the company values page. Better angles:
- “When a project goes sideways, what actually happens? Who gets in a room?”
- “Can you tell me about someone who was promoted recently and what got them there?”
- “What would I probably disagree with after six months here that I don’t know enough to disagree with yet?”
- “What kind of person tends to leave within a year?”
The promotion question is particularly revealing. If someone struggles to describe a specific person (not a type, a real person), that often means promotions are opaque, political, or rare. If they name someone quickly and can explain exactly what that person did differently, that’s a good signal.
Questions about the career path itself
If you’re trying to figure out whether a particular role or industry is worth pursuing, ask backward. Not “How do I get into this field?” but:
- “What do you wish you’d known before taking this path?”
- “What do people in adjacent fields think this job is, versus what it actually is?”
- “If you were starting over and wanted to get here faster, what would you do differently?”
- “What’s a skill that’s actually valued here but rarely shows up in job descriptions?”
I don’t have strong data on how these questions compare to more standard ones, I’m basing this on patterns I’ve seen work, not a controlled study. But the underlying logic is: give people permission to be contrarian and they usually take it.
The questions you probably shouldn’t ask
Avoid asking things you could easily Google. “What does your company do?” is a waste of their time and signals you didn’t prepare. Same with “Do you have any openings?” – it’s awkward early in a conversation and can make the whole exchange feel transactional in the wrong way.
Don’t ask for a referral outright in a first conversation. If the chat goes well and there’s a real connection, that often happens naturally or you can follow up in writing afterward. Pushing for it in the moment puts the person in an uncomfortable spot.
The Bureau of Labor Statistics Occupational Outlook Handbook is worth reading before an informational interview if you’re exploring a field, it gives you baseline salary ranges, job growth projections, and required credentials, so you can ask smarter second-order questions rather than asking for information that’s publicly available.
How AI can help you prep
One thing that’s genuinely useful: running through your planned questions before the actual conversation. Tools like Craqly let you practice live conversational prep, so you can test whether a question actually lands in a real back-and-forth or whether it sounds stilted when someone actually tries to answer it.
Some questions that look good on paper are genuinely hard to ask in a natural flow. Practicing them out loud, even with an AI, surfaces that before you’re sitting across from someone whose time you value.
Ending the conversation well
The closing question matters more than most people think. A simple “Is there anything you’d recommend I read or do before talking to more people in this space?” tends to get specific, useful answers. It also signals that you’re not done learning from a single conversation, which people generally appreciate.
Thank them with something specific. Not “Thanks so much for your time!” but “Thanks, the thing you said about promotion transparency is not something I’d thought to ask about before.” It shows you were actually listening and it makes a follow-up email feel less like a template.
Most people are more willing to help than you’d expect. The problem isn’t access, it’s usually that the questions weren’t good enough to give them anything interesting to say.