You have 20 to 30 minutes with someone who does the work you’re curious about. That’s not a lot of time, and the questions you choose will determine whether you walk away with real insight or polite small talk. These 12 informational interview questions are selected for what they actually reveal, with guidance on why each one works and what to pay attention to in the response.

What Is an Informational Interview?

An informational interview is a short, informal conversation where you learn about a role, company, or industry from someone who works in it. It is not a job interview. You’re not being evaluated, and you shouldn’t be asking for a job.

These conversations work because most people genuinely enjoy talking about their work when someone approaches them with honest curiosity. The format is simple: you ask thoughtful questions, you listen carefully, and you leave with knowledge you can’t get from a job posting or company website.

Most informational interviews run 20 to 30 minutes, whether over coffee, a phone call, or a video chat. That time constraint is exactly why question selection matters. You won’t get through a list of 40 questions, and you shouldn’t try. Pick five or six from the list below based on what you most need to learn, and let the conversation guide the rest.

One more reason to take this seriously: employee referrals consistently rank among the most effective hiring channels. Informational interviews are one of the best ways to build the kind of relationships that lead to those referrals.

1. What Does a Typical Day or Week Look Like in Your Role?

This question gets past the polished job description and into the actual rhythm of the work. It’s one of the most reliably useful questions you can ask because the answer is almost always more nuanced than what you’d find online.

What to listen for: How specific and animated is the response? Someone who describes their week with energy and detail is telling you something different than someone who sighs and gives a vague summary. Both answers are valuable.

2. What Were You Doing Before This Role, and How Did You Get Here?

Career paths are rarely as linear as they look on LinkedIn. This question reveals the real trajectory, including the detours, pivots, and unexpected breaks that actually shaped the person’s career.

What to listen for: Did they follow a traditional path, or did they come from a completely different field? If you’re exploring a career change or finding a career you love, hearing how someone else navigated that transition is invaluable.

3. What Surprised You Most When You Started?

This is where you uncover the gap between expectation and reality. The answer often reveals things no job posting or company website would ever mention: unwritten rules, cultural norms, or skills the person wished they’d developed sooner.

What to listen for: Pay attention to whether the surprises were positive or negative. Both tell you something important about what it’s actually like to work in this field.

4. What Skills or Qualities Separate the People Who Thrive From Those Who Don’t?

This question is far more revealing than “what skills do I need?” because it asks about differentiation, not minimums. You’re asking what separates good from great, not what gets you in the door.

What to listen for: Notice whether the answer emphasizes technical skills, soft skills, or cultural fit. If the person immediately talks about communication, adaptability, or resilience rather than certifications, that tells you a lot about what really drives success in their environment.

5. What’s the Most Challenging Part of Your Work?

Every role has friction. This question gives you a realistic preview so you can honestly assess whether those challenges are ones you’d find motivating or draining.

What to listen for: Are the challenges structural (long hours, bureaucracy, limited resources) or intellectual (complex problems, ambiguity, steep learning curves)? Structural challenges tend to grind people down over time. Intellectual challenges, for many people, are what make work interesting.

6. How Is This Industry Changing, and What Should Someone Entering It Know?

This question signals that you’re thinking beyond the next job and considering the longer arc of a career in this space. It also tends to produce some of the most candid, forward-looking responses.

What to listen for: Technology shifts, regulatory changes, emerging roles, and roles that are declining. If the person mentions specific trends, write them down. These are the kinds of insights that help you position yourself ahead of the curve.

7. What Do You Wish You Had Known Before Entering This Field?

This is often the question that produces the most memorable answer. It invites candor and reflection, and people tend to lean in when they answer it because they’re sharing something they genuinely care about.

What to listen for: Advice delivered with real conviction. If the person lights up or becomes more direct, you’re hearing something worth remembering.

8. What Does the Hiring Process Typically Look Like for Roles Like Yours?

This is where the conversation shifts from exploration to practical intelligence you can use right away. Understanding how hiring works in a specific field or company gives you a concrete advantage when you start applying.

What to listen for: Number of interview rounds, types of assessments, typical timelines, and any deal-breakers. If the person mentions that behavioral interview questions are a major part of the process, that’s a signal to start preparing for those now.

9. How Would You Describe the Culture Here?

Culture is one of those things that’s almost impossible to evaluate from the outside. A company’s careers page will always paint a rosy picture, but someone who works there every day can tell you what it’s actually like.

What to listen for: Specificity is a good sign. “We have a collaborative culture” is generic. “Our team does a weekly standup where anyone can flag a blocker, and people actually help” is real. Hesitation or vague deflection can be a red flag worth noting.

10. What Professional Organizations, Events, or Resources Have Been Most Valuable to You?

This question gives you a concrete next step beyond the conversation itself. Instead of walking away with only insight, you walk away with communities to join, publications to read, or certifications worth pursuing.

What to listen for: Recommendations delivered with genuine enthusiasm. If someone says “You have to check out this conference” or names a specific certification that opened doors for them, that’s high-signal information.

11. Is There Anyone Else You’d Recommend I Talk To?

This is the single most important closing question, and many people skip it because it feels forward. It isn’t. The person you’re speaking with fully expects this question, and it’s standard professional etiquette.

One conversation is valuable. A chain of conversations is how you build a real network. Each referral puts you one step closer to the people and opportunities that matter most in your target field.

12. How Can I Be Helpful to You?

This question flips the conversation from one-directional to relational. Most people conducting informational interviews are focused entirely on what they can learn, and they forget that relationships go both ways.

What to listen for: Even if the person says “Oh, nothing, I’m happy to help,” the fact that you asked changes how they remember you. If they do mention something, whether it’s sharing an article, making an introduction, or offering a skill you have, follow through on it. That’s how a single conversation becomes a lasting professional connection.

Questions You Should Never Ask in an Informational Interview

Not every question belongs in this setting. A few common missteps can undermine an otherwise great conversation:

• “Can you get me a job?” or any direct request for employment. This turns the conversation from learning into asking for a favor, and it puts the other person in an uncomfortable position.
• “How much do you make?” Asking about salary ranges for a role is fine. Asking someone to disclose their personal compensation is not.
• Questions you could answer with 30 seconds of research. Asking when the company was founded or what products they sell signals that you didn’t prepare.
• “Tell me about your company.” This is too broad to produce a useful answer and suggests you haven’t done your homework.

These mistakes all share a common thread: they signal that you’re there to extract value rather than to learn. The people who get the most from informational interviews are the ones who show up prepared and genuinely curious.

How to Make the Most of Your 30 Minutes

Having great questions is only part of the equation. How you conduct the conversation matters just as much.

Prepare five or six questions, not twelve. You won’t get through all of them, and that’s fine. Choose the ones that align with what you most need to learn right now, whether that’s understanding a career path, evaluating a specific company, or figuring out what skills to develop next.

Open with context. Briefly explain why you reached out to this person specifically. A sentence or two about what caught your attention about their background goes a long way toward building rapport.

Listen more than you talk. Aim for a 70/30 split, with the other person doing most of the talking. Your job is to ask good questions and then get out of the way. Research on active listening from Harvard Business Review reinforces this: the best conversations happen when one person feels genuinely heard, not interrogated.

Take brief notes. If you’re on a video call, ask permission first. Jotting down key insights shows respect for the conversation and ensures you don’t forget important details.

Send a thank-you within 24 hours. Make it specific. Reference something they said that was particularly helpful. A personalized note stands out far more than a generic template.

Follow up two to three months later. Send a brief update on your progress. Mention how their advice influenced a decision you made. This is what transforms a one-time conversation into a real professional relationship.

If your informational interviews are pointing you toward a new opportunity, the next step is putting yourself out there. You can also explore questions to ask during a formal interview to prepare for what comes next.