Every job I've gotten in the past six years started with an informational interview. Not an application. Not a recruiter reaching out. A 20-minute conversation with someone doing work I found interesting. I've done over 60 of these, and they've completely changed how I think about career development.

What an Informational Interview Actually Is (and Isn't)

An informational interview is a short, informal conversation where you ask someone about their career, their company, or their industry. That's it. You're not asking for a job. You're not pitching yourself. You're learning.

This distinction matters because the moment someone senses you're treating it as a back-door job interview, they'll shut down. I learned this the hard way when I asked a VP at a fintech company for an "informational chat" and then spent 20 minutes talking about why I'd be perfect for their open role. She was polite, but the conversation went nowhere. I'd broken the implicit contract.

The paradox is that informational interviews lead to job opportunities precisely because you're not asking for one. People like helping. They like sharing what they know. And when a relevant position opens up, you're the person they think of — not because you pitched them, but because you had a genuine conversation that stuck.

How to Ask (With a Script That Gets 80% Responses)

Most people overthink the outreach. They write long, formal messages that read like cover letters. The messages that work are short, specific, and easy to say yes to. Here's the template I've refined over dozens of attempts:

"Hi [Name], I came across your work on [specific thing] and found it really interesting. I'm exploring [career area/transition] and would love to hear about your experience at [company]. Would you have 20 minutes for a quick call sometime in the next couple weeks? Totally understand if not — I know you're busy."

Why this works: it's specific (you've done your homework), it's low commitment (20 minutes, not lunch), it's flexible (next couple of weeks), and it gives them an easy out (no guilt if they say no). That last part actually increases response rates because people feel less pressured.

Where to send it depends on the person. LinkedIn messages work for people you don't know. Email is better if you can find it — it feels more personal and stands out from the LinkedIn noise. For people in your extended network, ask for a warm intro. A mutual connection saying "you should talk to my friend" is worth more than any cold message.

One thing I stopped doing: following up more than once. If someone doesn't respond to my initial message and one gentle follow-up a week later, I move on. Persistence has a line, and crossing it damages your reputation in small industries.

Questions That Lead to Real Conversations

The questions you ask determine whether this is a forgettable 20 minutes or a conversation the person remembers. Skip the generic stuff ("What does a typical day look like?") and ask things that show genuine curiosity:

"What surprised you most about this role compared to what you expected?" This one always generates great answers because it asks people to reflect honestly. You'll learn things that never show up in job descriptions.

"What's the hardest problem your team is working on right now?" This gives you insight into the actual challenges — way more useful than the polished version on the careers page. It also lets you gauge whether those problems excite you.

"If you were starting your career over knowing what you know now, what would you do differently?" People love this question because it lets them play advisor. The answers are almost always surprisingly honest and useful.

"Who else would you recommend I talk to?" This is the most important question, and you should always ask it at the end. It turns one conversation into a chain of conversations. About 70% of the time, people will give you a name and even offer to make an intro.

After the Conversation: What Separates Good Networkers

Most people send a "thanks for chatting!" message and then disappear forever. That's a wasted opportunity. The follow-up is where relationships are actually built.

Within 24 hours, I send a thank-you that references something specific from our conversation. Not a generic template — something that shows I was actually listening. "Your point about how the data team restructured around product squads really changed how I'm thinking about my next role" is infinitely better than "Thanks for your time!"

Then — and this is the part nobody does — I stay in touch. Not in a creepy way. I'll send an article relevant to something we discussed, congratulate them on a work anniversary, or share an update on how their advice influenced a decision I made. Maybe once every two or three months. This keeps the connection warm without being annoying.

I keep a simple spreadsheet tracking everyone I've had informational interviews with: their name, company, date we talked, key takeaways, and when I last followed up. Sounds very Type A, but it means I never lose a connection and I can reference specific details from past conversations when we reconnect.

The biggest mistake I see people make with informational interviews is treating them as a one-time transaction. They're not. They're the beginning of a professional relationship that might pay off in ways you can't predict — six months from now, two years from now, maybe never directly. But the compound effect of having genuine relationships across your industry is the most powerful career asset you can build. No resume, no interview prep tool, and no certification can replace it.