The 20 Best Informational Interview Questions (and the one networking mistake that can cost you your dream job)
Informational interviews are one of the best ways to get real insight into a career path while building meaningful connections.
In just one conversation, you’ll learn what the work is actually like, stay top of mind when opportunities come up in your favorite companies, and grow your network.
But so many people treat the interview as the finish line. It's not.
Skipping the follow-up is the single biggest mistake that can cost you your dream job.
Each interview will be a little bit different - if it’s just with an old family friend who works in your dream field, maybe it’ll feel more casual and you text them directly to set it up. If it’s with the CEO of your dream company, you’ll want to demonstrate that you can be professional and prepared, and the way in which you reach out to them should reflect that. Either way, the goal is the same: kind curiosity, authentic connection, and a conversation that leaves both of you excited to chat again in the future.
Depending on who you want to reach out to, it can be intimidating and scary to ask for a chat. But here’s a little-known secret: everyone loves talking about themselves. In most cases, they’ll be flattered that you chose them of all people to talk to at all. In some cases, you’ll need to send them a follow up nudge, or you may not hear back from them at all if they don’t already have a mutual connection with you. That doesn’t mean they were unhappy to receive your message; usually, it just means they’re very busy and have an overflowing inbox, so no need to take it personally. Shoot your shot!
And once you have your first one scheduled, take this list and make it your own.
20 Informational Interview Questions
Be sure to pick the ones that feel right for each unique person and each moment. Spoiler: #18 is the best of the best.
1. The Opener
Start by briefly introducing yourself, sharing your elevator pitch, and explaining why you were excited to connect with them specifically.
2. Can you tell me about your career journey and what led you to your current role? Did you always know you wanted to do this type of work?
People love talking about their own story, and this will give you new ideas for the various stepping stone jobs and experiences you can pursue to eventually get to a position like theirs.
3. What previous experiences have been most helpful in preparing you for this role?
This can reveal skills and experiences you may want to have yourself before taking on this kind of job.
4. When did you feel ready to take the next step in your career? Did you ever deal with imposter syndrome along the way?
Hearing that even accomplished people doubted themselves at some point can be so reassuring and empowering.
5. What did getting started in this field look like for you?
Everyone's entry point is a little different - use their answer to brainstorm how you can get a foot in the door.
6. What does a typical workday or week look like for you?
This is where the job stops being an abstract title and starts becoming something real you can picture yourself doing. Ask yourself, would the individual tasks be boring or fun for you?
7. What might surprise people about the day-to-day reality of your work?
Every field has a gap between how it looks from the outside and what it feels like from the inside.
8. In what ways has this role met your expectations, and in what ways has it been different from what you envisioned?
A great gut-check for your own assumptions about the field.
9. What are some of the biggest rewards of your position?
This helps you figure out if what excites them would also excite you. Think about whether the benefits outweigh the costs.
10. What are the most challenging or discouraging aspects?
Knowing the hard parts in advance is part of making an informed choice, not a reason to be scared off.
11. How would you describe someone who really thrives in this type of role?
A sneaky and effective way to assess your own personality & skill fit. Make a note of any relatable attributes to highlight in future job interviews!
12. What are the most important skills or experiences to build if I want to pursue something like this?
Take their advice seriously - they’re drawing you a customized roadmap from their own perspective.
13. What's one thing you wish someone had told you before you entered this field?
Often the most honest and useful thing they'll say all conversation.
14. Do you know others in similar roles, and have you seen different paths lead to this kind of work?
A reminder there's rarely only one ‘correct’ way in. Collect even more ideas for your own route.
15. If you could change something about your job or field, what would it be?
Not only can you brace yourself for these current realities, you can also thoughtfully enter the field with a fresh perspective on how to improve and heal these sticking points.
16. If you could go back, would you choose the same path or field? What might you do differently?
This is your chance to learn from their mistakes or regrets.
17. What other companies or organizations in this space would you recommend I explore?
They can point you in the direction of amazing workplaces you hadn’t even considered, and that can greatly expand your job search radius in this field.
18. Who else at your company or in your field do you think I should talk to? Would you be open to making an introduction by email?
This is the question that turns one conversation into three, five, ten, or more. And you never know who will tell you “well actually you might be interested in a position we haven’t posted publicly yet…”, so the more conversations the better. Don't skip this one!
19. Before we wrap up, is there anything else you think would be helpful for me to know?
Sometimes the best insight comes when you stop directing and just make space.
20. The Thank You
Always end by expressing gratitude for their time and insights. Simple and sincere - what they’ll remember most from this conversation won’t be the words you said, but how you made them feel.
Don’t forget the follow up.
Whether this was a warm intro through your aunt's college roommate or a total cold outreach to a stranger, the biggest mistake is the same: letting the conversation end and assuming it already did its job. It hasn’t yet.
Within the next week, send a message to thank them again for their time and insight, and explicitly remind them about question #18: "Thank you also for offering to connect me with [name] to learn more about [area of expertise]. I look forward to that email introduction whenever is convenient for you." That one line does double duty. It's your foot in the door with the next person in your network, and it quietly proves something huge about you: that you're dependable, that you follow through, and that connecting you to someone else won't come back to embarrass them.
Bonus points if you reference something you bonded over - wish them well on that upcoming vacation, mention the book they recommended, whatever made the conversation feel memorable and personal.
Skip this step, and the connection quickly fades. Send it, and you've just turned one conversation into a growing, thriving network.
Still feeling a little stuck?
No pressure, but if your brain is doing that thing where it spirals about your future at 11pm, a Career Clarity Call might save you a few sleepless nights. We’ve got you! Hop on a quick 30 min call with me for just $20, or grab a package of longer sessions for a deep dive into your next steps.
