How to Run an Informational Interview That Actually Leads Somewhere

Most people treat informational interviews as a polite formality. Thirty minutes of small talk, a “thanks so much for your time,” and nothing changes. That’s almost entirely because of how those conversations get set up, not because informational interviews don’t work.

Here’s the concrete case for doing them seriously: Ashby’s 2024 Talent Trends Report tracked referred candidates across thousands of hiring funnels and found that 40% of referred candidates advance from application to interview, compared to significantly lower rates for inbound applicants. The conversion to offer is also higher – 16% of interviewed referred candidates receive offers, versus 8% from agency sources. Referrals represent under 1% of all applications, but they punch way above their weight at every stage. An informational interview, done well, is how you move yourself from the inbound pile into the referred pile.

The mechanism is straightforward. Someone who talked with you for 25 minutes isn’t going to ignore your application when it shows up in their company’s ATS. They’re going to forward it with a note. That note is the referral.

What actually makes an outreach message work

Most cold outreach fails for a specific, fixable reason: it’s too long and it asks for too much. A recruiter at Stripe or a senior engineer at Figma gets several of these messages a week. They don’t owe you anything.

The message that gets responses is short, specific, and gives the person an easy out. Something close to this:

“Hi [Name], I came across your post about [specific thing they wrote or did] and found it genuinely useful. I’m exploring [area] and would love 20 minutes to hear about your path at [company]. Totally fine if you’re slammed – even a few email replies would be helpful.”

Three things make this work. One, it cites something specific, which signals you’re not mass-messaging. Two, 20 minutes is low commitment. Three, “totally fine if you’re slammed” gives permission to say no, which paradoxically increases reply rates because people feel less cornered. LinkedIn DMs work fine for people you don’t know. Warm introductions through mutual connections work better – if you can find one, use it.

Follow up once, gently, after about a week. If there’s no response to the second message, stop. Persistence beyond that reads as pressure, not enthusiasm.

The 12 questions worth actually asking

Most informational interview question lists recycle the same 25 prompts. A lot of them are bad. “What does a day in your role look like?” will get you a polished non-answer. Better to ask things the person hasn’t rehearsed.

These tend to open up real conversations:

• On the role itself: “What surprised you most about this job versus what you expected when you took it?”
• On the team: “What’s the hardest problem your team is actually working on right now?”
• On company culture: “What kinds of people don’t make it past their first year here, and why?”
• On the job market: “If you were starting your search today for this kind of role, what would you do differently than what you did?”
• On getting in: “Who tends to get hired here – is there a profile the team keeps returning to?”
• On growth: “What do the people who move up fast in this org seem to have in common?”
• On tradeoffs: “What would make you leave this role?”
• On network expansion: “Is there someone else you’d suggest I talk to – either here or somewhere adjacent?”

That last question is the most valuable one. The person you’re talking to knows other people doing interesting work. A warm introduction from them is worth a lot. In my experience – and I’ll admit this varies widely – roughly half to two-thirds of informational interviews that go well produce at least one introduction when you ask directly.

A few questions to skip: anything you could Google in 30 seconds, anything that sounds like “sell me on your company,” and anything that puts them in an uncomfortable position about internal politics. You want the person thinking warmly of you when the call ends.

A common mistake: treating it as a one-time event

The people who get the most out of informational interviews don’t treat them as transactions. A 25-minute call, a thank-you message, and then radio silence for two years is almost worthless for your long-term network.

What works better is light, irregular maintenance. If you see the person share something interesting on LinkedIn, comment or send a brief message. If you read something relevant to what they told you on your call, forward it with one sentence of context. If you land a role or make a move, let them know. None of these take more than two minutes. Most people don’t do this, which means it stands out when you do.

I’m skeptical of the “every 90 days” scheduling advice you’ll sometimes see – that cadence feels mechanical and is easy to spot. Genuine, sporadic contact based on actual relevance is harder to sustain but reads as authentic.

When to ask an informational interview contact to refer you

This is the part most guides leave vague. The answer is: after at least one good conversation, and only when a specific role opens up that fits what you discussed.

Don’t ask speculatively (“let me know if anything comes up”). That’s forgettable. Instead, when a real opening appears at their company, send a short, direct message: “Hey – I noticed [Company] is hiring for [role]. Given what we talked about, I think it could be a strong fit. Would you be open to putting in a referral, or pointing me toward the right person to talk to?”

That kind of specific ask is much easier to act on than a vague request. And if your conversation went well, most people will say yes. The referral data from Ashby makes it clear why this matters: referred candidates convert to interviews at 40% versus substantially lower rates for cold inbound applications. One referral can change the math entirely on a job search.

There’s no guarantee any of this works on a given timeline. The 2025 research compiled by The Interview Guys shows median time to a first offer is now around 68.5 days even for active searchers, and networking accelerates that but doesn’t eliminate the wait. Start the conversations before you’re in a hurry, not after.

A note on who to approach

A lot of people default to reaching out to very senior people – VPs, directors, founders. That’s often the wrong call. Senior people get more requests and have less time. ICs two or three levels above you, or people who made a similar transition to what you’re attempting, tend to be more accessible and more useful. They’re closer to the day-to-day realities of the role, and they often remember what the search was like because it wasn’t as long ago.

If you want to get into a specific company’s interview process, also consider reaching out to building a targeted job search strategy around their specific teams first – know the org chart, know the product, know what problems they’re visibly working on. You’ll get more from the conversation when you’re not using it to gather information you could have gotten from their engineering blog.

Once you’re in conversations, the formal interview rounds are a separate skill. If you’re heading into technical rounds at companies you’ve networked your way into, preparing your behavioral answers matters as much as the networking that got you in the door.