Informational Interviews: How to Ask, What to Learn
Job postings lie by omission. They tell you the requirements and the perks, but nothing about what the work actually feels like day to day, which skills matter versus which are listed out of habit, or whether people in the role are happy. You can read a hundred articles about "a day in the life of a UX designer" and still not know if you would like the job.
Informational interviews fix this. A 20–30 minute conversation with someone doing the work gives you ground truth that no job description provides: the real frustrations, the real entry paths, the real day-to-day. They're also the single highest-leverage networking activity for career changers, because they build genuine relationships instead of transactional ones. This guide covers how to ask for them, what to ask in them, and how to follow up so the relationship continues.
An informational interview is a short, curious conversation — not a job ask. Request them with a specific, low-pressure message; prepare 5–7 questions about the reality of the work; listen more than you talk; and follow up with thanks plus one thing you learned. Do ten of these before committing to a career direction and you'll make a dramatically more informed decision. They don't guarantee referrals, but they often produce them naturally.
What they are (and what they definitely aren't)
An informational interview is a conversation where you ask someone about their work, their field, and their path — with the explicit understanding that you are not asking for a job. That boundary is what makes people say yes. The moment it smells like a stealth job application, busy people decline.
This matters especially for career changers, because you have the most to learn and the most to gain. You're not just collecting contacts; you're doing field research. Ten conversations with working data analysts will teach you more about whether the field fits you than any bootcamp landing page. You'll hear which skills actually get used, what the boring parts are, how people really broke in, and what they'd do differently.
The format is simple: 20–30 minutes, video call or coffee, you ask questions, they talk. You are not pitching yourself. You are not handing over a resume (unless they ask). You're a curious person doing homework, and most professionals find that flattering rather than burdensome — provided you respect their time.
How to ask: the message that gets yeses
People say yes to informational interviews when three conditions hold: the ask is specific, the time commitment is small, and the reason is genuine. Your outreach message should hit all three in under 100 words.
The structure: who you are in one line, why them specifically in one line, and the ask. Example: "Hi Maya — I'm a former teacher transitioning into instructional design, and I came across your post about onboarding programs at fintech companies, which is exactly the space I'm exploring. Would you be open to a 20-minute chat about your work? I'm trying to understand the field before I commit to it, and your perspective would be genuinely helpful."
Why them specifically is the load-bearing sentence. Generic "I'd love to pick your brain" messages get ignored because they signal mass outreach. Reference something real: their career path, a project they mentioned, a talk they gave, a post they wrote. It proves you did thirty seconds of homework, which is thirty seconds more than most.
Where to find people: LinkedIn (alumni of your school, people with your target title at interesting companies, fellow career changers a year ahead of you), professional Slack communities and Discords, and your existing network's second degree — "do you know anyone in X?" is one of the highest-yield questions you can ask friends. Aim for a mix: some senior people for perspective, some recent entrants for practical entry-path detail.
Questions that get real answers
Prepare 5–7 questions, but treat them as a safety net, not a script. The best informational interviews feel like conversations, and the best questions are the ones that invite stories rather than facts. "What's your typical day like?" gets a generic answer. "What's the part of your job that surprised you most?" gets a real one.
Questions that consistently produce useful answers: What does the first year actually look like for someone entering this field now? What skills matter most day-to-day versus what job postings emphasize? What's the most frustrating part of the work? If you were starting over, what would you do differently? What would make someone a bad fit for this work? That last one is gold for career changers — it helps you rule things out, which is just as valuable as ruling them in.
Also ask about them, not just the field: how did you get into this? What was the hardest part of the transition? People love talking about their own path, and for career changers, these stories are the practical playbook — they reveal the actual doors, not the advertised ones.
Listen more than you talk. Take notes. And watch the clock — ending at 25 minutes when you asked for 30 makes you the person they recommend to others. The people who run over are the people who don't get second conversations.
After the conversation: the follow-up that builds relationships
Send a thank-you within 24 hours. Make it specific: mention one thing they said that changed your thinking. "Thanks for the time today — your point about portfolio pieces mattering more than certificates completely changed my study plan" beats "Thanks for chatting!" by a mile. Specificity proves you listened, and being listened to is memorable.
Then — and this is the part most people skip — close the loop later. If they suggested a course, take it and tell them what you thought. If they mentioned a skill to build, build it and share the result. A follow-up three months later saying "I took your advice, built the project, and just landed interviews — thank you" turns a one-time conversation into a genuine professional relationship. This is how informational interviews become referrals: not by asking, but by becoming someone worth referring.
One thing never to do: ask for a job or a referral in the thank-you note. If the relationship develops and an opportunity comes up, they'll offer — or you'll have earned the right to ask months later. Leading with the ask burns the exact goodwill the conversation created.
Frequently asked questions
How many informational interviews should I do?
There's no magic number, but ten is a good target before committing to a new direction. Fewer than five and you're still working from anecdotes; beyond fifteen or so you hit diminishing returns unless you're exploring multiple fields. Quality beats quantity — ten thoughtful conversations beat thirty rushed ones.
What if no one responds to my messages?
First, check your message against the formula: specific reason, small ask, genuine tone. Response rates vary, but fellow career changers and alumni typically respond most. If you're getting silence, try warmer channels — ask existing contacts for introductions rather than cold-messaging strangers. And keep the ask to 20 minutes; "quick chat" without a number feels open-ended and gets declined.
Should I do these before or after I start retraining?
Before, ideally — or at least in parallel with early exploration. Informational interviews are cheapest when they can still change your direction. Many career changers discover through these conversations that the role they imagined differs from the reality, or that an adjacent role fits better. Ten conversations now can save you six months of training for the wrong target.
Is it okay to ask someone at a company I want to work for?
Yes — just keep the boundary clean. You're asking about their work, not angling for a referral, and most people understand the difference. If the conversation goes well and they later mention an opening, that's their call. Never open with "I'm hoping to work at your company" — it reframes the whole conversation as a job pitch and makes people guarded.
Educational content only — not professional advice. Talk to a qualified professional about personal career or education decisions.