Informational Interview Questions Worth Asking
Informational interviews — short conversations with people doing work you want to do — are among the highest-value activities in a career change. But most people waste them: they show up with no questions, ask generic things Google could answer, or accidentally turn it into an awkward job pitch.
The questions are the whole interview. This guide gives you a practical question bank organized by what you actually need to learn — the day-to-day reality, the skills that matter, how people broke in, and the advice they would give — plus how to request, run, and follow up on the conversation.
Keep it to 20 minutes and never ask for a job — ask for insight. Ask about a typical day, which skills actually matter, how they broke in, and what they would do differently. Research the person first so your questions are specific. Send a thank-you within 24 hours referencing something they said.
Before you ask: the request
Find people through alumni networks, LinkedIn (second-degree connections are ideal — a mutual contact makes yes much likelier), professional communities, and friends of friends. Target people one to three years ahead of you, not CEOs; they remember the transition vividly and have time to talk.
The request message should be short and specific: who you are in one line, why them specifically (reference something real — their career path, a project, a talk), and a small ask — "Would you be open to a 20-minute call? I'm exploring a move into X and would love to hear how you approached it." Specific flattery plus a bounded ask gets yeses; vague long messages get ignored.
Research before the call. Read their LinkedIn profile, skim anything they have written, note their career path. Your questions should prove you did homework — "I saw you moved from teaching into UX research; what translated?" beats "So how did you get into this?" enormously.
The question bank: day-to-day reality
Start here, because job descriptions lie by omission. "Walk me through a typical week — what does the work actually look like day to day?" "What proportion is meetings versus focused work?" "What surprised you most about the day-to-day versus what you expected?" "What is the part of the job nobody warns you about?"
These questions reveal the texture of the work — the parts no posting mentions. Listen for energy: what lights them up versus what they tolerate. Their answers tell you as much about fit as any self-assessment, because you are hearing the unfiltered reality.
Ask about the hard parts directly: "What is the most frustrating part of the role?" People answer honestly when asked with genuine curiosity, and the frustrations are often the most useful data — every job has them, and you want to choose yours.
The question bank: skills and breaking in
Skills: "Which skills do you actually use most — versus what the job postings emphasize?" "If you were hiring for your team tomorrow, what would you screen for?" "What is something you wish you had learned before starting?" The gap between posted requirements and real requirements is where career changers find their opening.
Breaking in: "How did you personally get into this field?" "What did your first year look like?" "For someone coming from [your background], what is the most realistic entry path you have seen?" "Are there adjacent roles that are easier doors in?" People's own paths are data; collect several and patterns emerge.
Credentials: "How much do certifications or degrees matter in hiring here, honestly?" "What would you do instead of a degree if you were starting over?" These questions save people months and thousands of dollars — ask them before enrolling in anything.
The question bank: advice and next steps
"What would you do differently if you were making this move today?" "What is one thing I should do in the next month?" "Who else should I talk to?" That last question is gold — every conversation should end with one or two new names, and warm introductions compound into a real network.
"Is there anything I should be reading, following, or learning right now?" gives you a curated curriculum from someone inside. "What questions should I be asking that I am not?" invites them to share what your outsider perspective misses — often the most valuable answer of the call.
Never ask for a job or a referral in an informational interview. It breaks the implicit contract and makes everything before it feel transactional. If they offer to refer you or pass your resume along — which happens often when the conversation goes well — accept graciously. Let it come to them.
Running the call and following up
Open by restating the deal: "Thanks so much for 20 minutes — I have a few questions about your path into X, and I will keep us on time." Then ask your best questions first, in case time runs short. Take notes; it signals respect and gives you material for the thank-you.
Manage the clock visibly: "We have about five minutes left — one last question." Ending on time is a courtesy they will remember, and it makes them likelier to say yes next time or introduce you onward. Do not run over unless they explicitly invite it.
Within 24 hours, send a thank-you referencing something specific they said — "your point about stakeholder management being the real skill changed how I am thinking about the transition." Then act on their advice and tell them: "I took the course you suggested — thank you." Few things build a relationship faster than showing someone their time mattered.
Common mistakes that waste the opportunity
The biggest mistake is asking questions Google answers: company size, basic job description, salary ranges from a posting. Every generic question spends their goodwill on nothing. Your questions should require a human with experience — judgment, trade-offs, surprises, advice. If a search engine could answer it, do not ask it.
The second mistake is the stealth job pitch — steering every answer toward "so are you hiring?" It puts the other person in an awkward spot and poisons the well for genuine advice. Trust the process: insight first, relationships second, opportunities eventually and organically.
The third is poor logistics: running over time, bad audio, no notes, no thank-you. These sound trivial, but informational interviews are auditions for your professionalism — the person is mentally noting whether they would introduce you to colleagues. Nail the basics and the introductions follow.
Frequently asked questions
How do I find people for informational interviews?
Start with alumni networks and LinkedIn second-degree connections — a mutual contact dramatically raises yes rates. Professional communities, friends of friends, and people who create content in your target field also work well.
How long should an informational interview be?
Ask for 20 minutes and keep it. Short enough that busy people say yes, long enough for real insight. Ending on time is part of the impression you make.
Can I ask for a job or referral?
No — never in the informational interview itself. The deal is insight, not opportunity. Referrals often come voluntarily when the conversation goes well; let them offer.
What if someone says no or does not reply?
Normal — expect a 20–30% yes rate on cold asks. Do not take it personally or follow up more than once. Thank anyone who declines politely; circumstances change.
Educational content only — not professional advice. Talk to a qualified professional about personal career or education decisions.