50 Questions to Ask in an Informational Interview (That Actually Impress)

Why Your Questions Matter More Than Your Resume

Here's a counterintuitive truth about informational interviews: the person you're talking to will remember how you made them feel, not what you told them about yourself.

Asking thoughtful, specific questions signals three things:

1. You've done your homework (you're not wasting their time)
2. You're genuinely curious (not just looking for a favor)
3. You think critically (you'd be good to work with)

Generic questions like "What does your day look like?" signal the opposite. They tell the professional you couldn't be bothered to prepare, and they've answered that question a hundred times.

The questions below are organized by category and designed to spark real conversations — the kind where the other person leans in, shares stories they don't usually tell, and walks away thinking "I liked that student."

Career Path Questions (The Door Openers)

Start here. These questions get people talking about their favorite subject — themselves — and reveal insights you can't find on LinkedIn.

1. "What's the most unconventional part of your career path?" Everyone has a story about a detour, a surprise, or a lucky break. This question surfaces it.

2. "Was there a specific moment or conversation that changed the direction of your career?" This is more interesting than "How did you get into this field?" because it asks for a story, not a summary.

3. "What were you planning to do when you were my age, and how does that compare to where you ended up?" Shows genuine curiosity and often leads to surprisingly honest answers.

4. "If you had to start your career over today, knowing what you know now, what would you do differently?" This question gets the advice they wish someone had given them — which is exactly the advice you need.

5. "What's a skill you developed early in your career that still pays dividends today?" Practical and actionable. You can start developing that skill immediately.

6. "Who was the most influential mentor in your career, and what made them effective?" Reveals what good mentorship looks like and subtly signals you value mentoring relationships.

7. "What was your biggest career mistake, and what did you learn from it?" People rarely get asked this. It creates vulnerability and trust — the foundation of a real relationship.

Role and Industry Questions (Show You've Done Your Homework)

These demonstrate that you understand the industry at a basic level and want to go deeper.

8. "What's the most common misconception people have about your role?" This surfaces insider knowledge you can't get from job descriptions.

9. "How has your role changed in the last 2-3 years, and where do you see it going?" Shows you're thinking about trends, not just today's job market.

10. "What separates the top performers on your team from everyone else?" This is the cheat code. They're telling you exactly what to optimize for.

11. "What's a problem your team is trying to solve right now that you find particularly interesting?" Shows genuine intellectual curiosity about their work, not just the job title.

12. "How do the different teams or departments interact in your organization?" Reveals org dynamics that matter for actually doing the job well.

13. "What's something about your industry that's changing faster than most people realize?" Gets them to share forward-looking insights. Shows you're thinking strategically.

14. "What does success look like in your first year in a role like yours?" Much more useful than "What do you do day to day?" because it tells you what actually matters.

15. "How do you stay current in your field? What do you read or follow?" Gives you a reading list from an insider and shows you want to keep learning.

Culture and Team Questions (Understand the Human Side)

These questions help you assess whether you'd actually enjoy working somewhere — which matters more than the brand name.

16. "What keeps you at this company? What would make you leave?" Bold, but it gets honest answers about culture and satisfaction.

17. "How would you describe the culture of your team in three words?" Forces them to be specific instead of giving the company PR version.

18. "What's the most rewarding project you've worked on recently, and what made it rewarding?" People light up when talking about work they're proud of. That energy is contagious.

19. "How does your company handle failure or mistakes?" This tells you more about culture than any Glassdoor review.

20. "What does work-life balance actually look like in practice on your team?" The word "actually" signals you want the real answer, not the recruiting pitch.

21. "If you could change one thing about your company's culture, what would it be?" Shows you're evaluating fit, not just chasing a name brand.

22. "How does your team celebrate wins?" Reveals whether they have a recognition culture or a "just do your job" environment.

Advice and Guidance Questions (Get Actionable Help)

These are the questions that turn a nice conversation into a career advantage.

23. "Based on what I've told you about my background, what gaps do you think I should address before applying to roles like yours?" This is the most valuable question on this list. You're asking them to coach you. Most people are happy to do it.

24. "If you were hiring for your team right now, what would make a candidate stand out?" They're literally telling you how to get hired.

25. "What's one thing I could do in the next 30 days to make myself a stronger candidate for this field?" Specific, time-bound, actionable. Shows you're serious about following through.

26. "Are there any certifications, courses, or experiences that you think are genuinely worth the investment?" Gets you past the generic "learn to code" advice into specifics.

27. "What would you recommend I read, listen to, or follow to better understand this industry?" Builds your knowledge and gives you conversation starters for future networking.

28. "Is there a particular project or experience that would make my resume stand out for roles in this field?" Direct and practical. They'll tell you exactly what to go build or pursue.

29. "What's the best way to demonstrate interest in this field beyond just applying to jobs?" Opens the door to creative approaches — writing, speaking, volunteering, open source, etc.

Company-Specific Questions (When You're Targeting Somewhere)

Use these when you're talking to someone at a company you want to work at.

30. "What's your company's biggest competitive advantage, and is that changing?" Shows business acumen and genuine interest in the company's position.

31. "How does your team decide what to work on? What's the prioritization process?" Reveals how much autonomy you'd have and how decisions are made.

32. "What's something about working here that surprised you when you first joined?" Gets the unfiltered truth about the gap between expectations and reality.

33. "How does your company invest in employee development? Are there internal mobility opportunities?" Shows you're thinking about growth, not just landing the first job.

34. "What does the interview process look like for roles on your team?" Directly useful intel. They'll often share specific tips.

35. "Is there a type of candidate your team has struggled to find?" If you match that description, you've just learned you're in demand.

Deep-Dive Questions (For Longer Conversations)

When the conversation is going well and you have time, these questions create memorable discussions.

36. "What's the hardest decision you've had to make in your career?" Creates a moment of real human connection. People rarely get asked this.

37. "How do you think about risk in your career? Are you more of a calculated risk-taker or do you prefer stability?" Philosophical but practical. Their answer reveals a lot about how they think.

38. "What's a trend in your industry that most people are either ignoring or getting wrong?" This is the question that makes them think. It signals you're looking for insights, not platitudes.

39. "How do you approach building relationships with people more senior than you?" Meta-networking question. You're asking them how they networked their way up.

40. "What's a book, talk, or idea that fundamentally changed how you think about your career?" People love sharing their intellectual influences. It also gives you great follow-up material.

41. "If you could go back and give yourself one piece of career advice at my age, what would it be?" Classic for a reason. The answer is almost always different from what you'd expect.

42. "What do you think will be the most important skills in your field five years from now?" Shows you're playing a long game, not just looking for the next job.

Relationship-Building Questions (The Follow-Up Fuel)

These questions create natural reasons to stay in touch after the conversation.

43. "Is there anyone else you'd recommend I talk to?" The most important question you can ask. A warm introduction from them is 10x more valuable than a cold outreach.

44. "Would it be okay if I reached out again in a few months to share how things are going?" Gets explicit permission to follow up. Almost everyone says yes.

45. "Is there anything I can help you with? I know I'm early in my career, but I'm happy to help however I can." Reverses the dynamic. Even if they decline, the offer is remembered.

46. "What's something you're working on right now that you're excited about?" Gives you follow-up material — you can reference this in your thank-you note.

47. "Are there any events, communities, or groups in this field that you'd recommend I join?" Expands your network beyond this single conversation.

Questions to Avoid (And What to Ask Instead)

48. Instead of "What do you do?" — ask "What does a typical week look like when things are busy versus slow?" (More nuanced, shows you understand work isn't the same every day.)

49. Instead of "How much do you make?" — ask "How does compensation typically progress as you advance in this field?" (Gets you the trajectory, which is more useful than a single number.)

50. Instead of "Can you get me a job?" — ask "Based on our conversation, what do you think would be my best next step?" (Lets them offer to help without feeling pressured.)

How to Actually Use These Questions

Don't bring a printed list of 50 questions to your coffee chat. That's an interrogation, not a conversation.

Before the meeting:

1. Pick 8-10 questions that are most relevant to this specific person
2. Write them in your notes app, not on paper (you'll look at your phone naturally)
3. Prioritize the ones you can't answer through Google

During the meeting: 4. Start with 1-2 career path questions to warm up the conversation 5. Let their answers guide your follow-ups — the best questions come from actually listening 6. Save the advice/guidance questions for the second half when rapport is built 7. End with a relationship-building question

After the meeting: 8. Send a thank-you within 24 hours referencing something specific they said 9. Follow up in 2-3 months with an update on how their advice played out 10. Introduce yourself to anyone they recommended you talk to

The Hidden Goal of Every Informational Interview

The questions you ask matter. But the real goal isn't to collect information — it's to build a relationship with someone who wants to see you succeed.

When someone spends 30 minutes answering your thoughtful questions, they're investing in you. They want that investment to pay off. That's why referrals happen naturally from good informational interviews — not because you asked for one, but because they genuinely want to help someone who showed up prepared, curious, and respectful of their time.

The students who build the strongest networks don't have the best resumes or the most connections. They ask the best questions.