Informational Interview Questions That Actually Work

Why do most informational interviews feel like a waste of everyone's time?

Because most people walk in with the wrong goal. They think the point is to seem impressive. Say the right things. Ask polished questions off a list they found somewhere at midnight.

That's not a conversation. That's a performance. And the person on the other end can feel it in about ninety seconds.

The whole reason informational interviews exist is because you can't learn what a job actually feels like from a posting. You can't learn what a company actually values from its careers page. You need a human being to tell you the truth, off the record, in their own words. That only happens when your questions come from real curiosity, not a script you copy pasted.

So let's fix the script.

What's the actual goal of an informational interview?

Not a job. Not yet, anyway.

The goal is information you cannot get anywhere else. What does a Tuesday actually look like in this role. What almost made this person quit in year one. What they wish someone had told them before they took the job. That's the stuff that changes decisions. That's the stuff worth thirty minutes of a stranger's time.

If you walk in hunting for a job offer, you'll ask defensive questions and get defensive answers. If you walk in hunting for the truth, people tend to give it to you. Most people are dying to be honest about their work. Nobody ever asks them.

What informational interview questions should you actually ask?

Skip the questions that sound like you're reading off a form. Ask the ones that make someone pause before they answer, because those are the ones worth asking.

Start with their path, not their title:

• What did you think this job would be before you took it, and what surprised you
• What's one thing about this industry that isn't obvious from the outside
• If you were starting over today, would you take the same path into this field

Then get specific about the actual work:

• What does a hard day look like here, not a good day
• What skill do you use constantly that nobody mentions in the job description
• What separates someone who's good at this from someone who's just doing it

Then get honest about the parts nobody puts on LinkedIn:

• What's the part of this job you'd never put in a job posting
• Who tends to struggle here, and why
• What would make you not recommend this path to someone

End with the question that actually moves your career exploration forward:

• Based on what I've told you about myself, is there someone else you think I should talk to

That last one is the whole game. A good informational interview isn't a dead end. It's a door to the next one.

How many questions should you actually ask in 20 minutes?

Four or five, max. Not fifteen.

This isn't a job interview questions to ask HR situation where you're checking boxes. This is a conversation. The best informational interviews feel like two people talking, where one happens to know more than the other. If you're firing off question six while they're still finishing question two, you're not learning anything. You're just performing curiosity instead of having it.

Let silence sit. Let them go on a tangent. The tangent is usually where the real answer lives.

How do you actually ask for an informational interview on LinkedIn?

Short, specific, and no ask hidden inside a compliment.

Something like: "I'm exploring a move into product design and came across your background. Would you have 15 minutes sometime in the next couple weeks to talk about your path into the role? I'd genuinely value the perspective."

Notice what's missing. No "I'd love to pick your brain." No vague "connect and learn from you." People say yes to specific, low-effort asks. They ignore vague ones because vague asks feel like homework.

Same logic applies to an informational interview email template. Say who you are, why you're reaching out to this specific person, and exactly how much time you're asking for. Fifteen minutes gets a yes. "Whenever you're free" gets ignored, because it puts all the work of deciding on them.

What if you're using this for a career change?

Then your questions need to work harder. You're not confirming what you already suspect about a field you know. You're testing an entire hypothesis about a life you haven't lived yet.

The best informational interview questions for a career change dig into transition, specifically:

• What did you have to unlearn from your last field
• What made you confident enough to actually make the jump
• What would have made you hesitate if you'd known it going in

Ask people who made the exact move you're considering. Not people who've always been in the field. The ones who crossed over remember the fear. They'll tell you what it actually costs, and what it actually gives back.

What happens after the conversation ends?

This is where almost everyone drops the ball, and it's bullshit, because the follow up is half the value of the whole exercise.

Send a thank you within 24 hours. Reference something specific they said, not a generic "great chatting with you." Then, and this part matters more than people think, actually follow up on whatever they told you to do. If they said read this report, read it. If they said talk to this person, talk to them. If they said apply now, apply now.

People remember who follows through. In a small industry, and most industries are smaller than you think, that reputation follows you into rooms you're not even in yet.

At Orbyt Labs we built our tools around this exact belief: the small, unglamorous actions, the follow up, the thank you note, the second conversation, are what actually move a career forward. Not the resume. Not the polish. The follow through.

What's the one thing to remember before you go in?

You're not there to be interesting. You're there to be curious.

The best informational interview question you'll ever ask is the one that makes someone stop, think, and say "you know, nobody's ever asked me that." That's the moment the conversation becomes real. That's the moment you get an answer worth having.

Your career deserves conversations that actually tell you something. Go have one.