Informational interviews: how to get them, run them, and not waste them

Job postings tell you what a company wants; only people tell you what the work is like. An informational interview is the tool for that gap — 25 borrowed minutes with someone living the path you’re considering, no job ask attached. Done in sequence, these conversations beat any amount of online research.

What it is, and why it works when it’s honest

Richard Nelson Bolles, whose What Color Is Your Parachute? has steered job seekers since 1970, popularized the informational interview as a research method: before you commit years to a field, interview the people already in it. Not a stealth job application — an actual interview, where you bring the questions and they bring the lived experience.

The honesty isn’t etiquette; it’s the load-bearing wall. The entire format runs on a favor — a stranger giving you twenty-five minutes — and people grant that favor happily when the frame is curiosity. Most people enjoy talking about their path to someone genuinely interested; it’s flattering and zero-risk. The moment the frame is suspected of hiding a pitch, the same conversation becomes an ambush, and the generosity evaporates retroactively.

So hold the two purposes apart. The interview’s job is information: what does this work cost, what does it give, what separates the people who thrive from the ones who leave. Opportunities are a real but strictly downstream effect — a good conversation gets your name passed along, sometimes months later. Chase the downstream effect directly and you lose both.

What it’s for, concretely: switching fields, choosing between two paths, scouting a company culture before applying, mapping a market you’re new to, or — the underrated case — filling seats on a personal board of advisors, since these conversations reveal exactly who gives generous, concrete counsel.

The ask: specific, bounded, agenda-free

Requests fail in two predictable ways: too vague (“I’d love to pick your brain”) and too big (“could we get coffee sometime?” — an unbounded commitment to a stranger). The ask that works is the mirror image. Three sentences:

Hi Priya — I’m a data analyst figuring out whether product management is my next move, and your switch from analytics to PM at a health company is exactly the path I’m trying to understand. Could I ask you about it for 25 minutes, whenever suits — call or coffee? To be clear, I’m not job hunting with you; I’m trying to map the field before I commit.

The why them sentence does the heavy lifting — it proves this isn’t a mail-merge and tells them what conversation they’re agreeing to. The 25 minutes makes the cost concrete and small. The non-ask removes the suspicion that would otherwise make a busy person hesitate. Send it where they’re reachable: a warm introduction through a shared contact converts best, a short LinkedIn note or email works cold. Expect roughly half of cold asks to land nothing — that’s the format working, not failing; the people who say yes are self-selected for generosity.

No reply? One nudge a week later, then let it go — an informational ask doesn’t earn a third touch. And run the asks as a small pipeline, three or four out at any time: response rates are lumpy, and a pipeline keeps any single silence from feeling like a verdict on the whole project.

Running the 25 minutes

You asked for the meeting, so you run it. Structure is what respects their time; winging it is what wastes it.

Preparation is asymmetric here: ten minutes with their LinkedIn profile and their last talk or two upgrades every minute of the call, because each question can start where public information ends. If they ask for questions in advance, send three — it signals seriousness and lets them think — and keep the follow-ups live in the room.

1. Minutes 0–3: context, compressed

   Thirty seconds of who you are and the question you’re researching — rehearsed enough to be tight. Then hand over the floor: “Mostly I want to hear how this actually works from inside.” Resist narrating your CV; they need just enough context to calibrate their answers to you.

2. Minutes 3–18: their experience, your prepared questions

   The core. Five or six questions prepared, asked in whatever order the conversation suggests, with follow-ups on anything surprising — the craft of probing without interrogating is its own skill, covered in how to ask better questions. Take notes visibly; it signals their answers are worth writing down.

3. Minutes 18–22: the advice turn

   Pivot from their story to your decision: “Knowing what you know, what would you do in my position, starting today?” This question outperforms because it forces synthesis — they compress everything into a recommendation, and the reasoning they attach is usually the best material of the call.

4. Minutes 22–25: the two closing moves

   First: “Based on what I’ve told you, who else should I be talking to?” — the question that turns one conversation into a chain; a name plus an offered intro is the best possible exit. Second: “Could I write you once I’ve acted on some of this?” — securing the open door you’ll walk through in week three. Then end on time, out loud, offering the choice to continue.

Questions that earn their minutes share one property: only this person, from inside, can answer them. What does a bad week look like? What surprised you after the switch? What do outsiders get wrong about this field? If you left, what would pull you out? Questions answerable from their LinkedIn profile spend scarce time proving you didn’t prepare.

The follow-up that turns a call into a relationship

Most people send a thank-you note and consider the transaction closed. That’s the mistake — not because the note is wrong, but because the note is the first half of a two-part move, and the second half is where all the relationship value sits.

Same day: short thanks, naming the one specific insight that most changed your thinking. Specificity is the whole content — “your point that PM interviews test storytelling more than analysis reordered my prep” proves the 25 minutes landed somewhere. Three sentences. The follow-up email templates include this exact pattern.

Three to six weeks later: the report-back. “You suggested I talk to the platform team before deciding — I did, and it changed my view. I’ve started the certification you mentioned. Thank you again for pointing me.” This is the message almost nobody sends, which is precisely why it works: advice-givers wonder, quietly, whether anything they said mattered. Closing that loop converts you from one of many polite coffee-askers into the rare person who acts on counsel — the category of person worth introducing, recommending, and remembering.

From there, maintenance is ordinary relationship craft: a genuinely relevant article some months later, a congratulations when their news crosses your feed, value flowing back as your own position improves. The mechanics — and the line between staying warm and pestering — are the same as for any professional contact after a first meeting, covered in how to follow up after a networking event.

The operational layer matters more than it sounds, because a serious exploration means five to eight interviews, each generating advice, names, and a report-back due weeks later — exactly the kind of state human memory drops. Log the three essentials per conversation (advice given, names mentioned, follow-up date), in a spreadsheet or a personal CRM like Endearist where the report-back date becomes a reminder instead of a hope. The person who sends the week-three message isn’t more grateful than you. They just wrote the date down.