Strategy · 7 min read

Informational interviews: how to ask, and what to actually ask for

A large share of roles are filled through someone who already knows the candidate, which means the most efficient job-search activity is often not applying at all. It is talking to people. Most candidates know this and do not do it, because the mechanics feel awkward and the standard advice — network more — offers no instruction on how.

The specific tool worth learning is the informational interview: a short conversation with someone doing work you are interested in, where you are asking about their work rather than for a job. Done properly it is comfortable for both sides. Done badly it is a job request in a thin disguise, and everyone can tell.

Why people say yes

The reason this works is that most people enjoy talking about their own work to someone genuinely interested, and it costs them fifteen minutes. Requests get declined when they are vague, long, or clearly the opening move in an ask for something bigger.

The counterintuitive part is that senior people often say yes more readily than mid-level ones. They have more control over their calendar, they are asked less often than you would think, and many of them remember being helped early. Do not filter yourself out of asking someone because they seem too senior.

The request that works

Short, specific, easy to refuse. Say who you are in one line, why you are contacting this person specifically rather than anyone, exactly what you are asking for, and give them an easy exit.

Something like: I am a data analyst moving into product analytics, and I saw your talk on how your team measures activation. Would you be open to fifteen minutes to talk about how you moved from analysis into product? Entirely fine if not — I know it is a busy time.

Notice the components. A specific reason it is them, which proves it is not a mass mailing. A defined and small ask. And a stated exit, which makes yes feel voluntary rather than obligatory. The most common failure is the message that could have been sent to four hundred people, because it obviously was.

Where to find people

Start with weak ties rather than strangers: former colleagues, people from your course, people who left your company for somewhere interesting. The research on job-finding has consistently pointed at these loose connections rather than close friends, because your close circle knows the same things and the same openings you do.

Beyond that, look for people who have publicly signalled willingness to talk — those who write, speak, post about their work, or mentor. Alumni networks work far better than their reputation suggests, because the shared institution supplies the reason it is them.

The mistake that wastes the meeting

Asking for a job. It converts a low-stakes conversation into a transaction the other person probably cannot fulfil, and it retroactively makes your request feel dishonest.

This does not mean hiding that you are looking; that would be its own kind of awkward. It means the purpose of the meeting is genuinely to understand their work. If they can help further, they will offer — and they offer far more often when they have not been asked, because helping is then their idea rather than an obligation.

The second-worst mistake is asking questions you could have answered yourself. What does your company do wastes the meeting and signals you did not prepare. Every minute spent on something available publicly is a minute not spent on what only this person knows.

What to actually ask

Ask about the reality of the work rather than the description of it. What does a normal week actually look like. What surprised you most when you moved into this. What do people underestimate about it.

Ask about the path. How did you get here, what would you do differently, what did you think mattered that turned out not to.

Ask about the market as they see it. What are teams like yours struggling to hire for. What does someone need to be able to demonstrate to be taken seriously for this.

And ask one question that only they can answer, drawn from something specific they have done. That is the question that turns a generic conversation into a memorable one.

The ask at the end, and how to phrase it

In the last couple of minutes, one question is appropriate and it is not for a job. Is there anyone else you think I should talk to?

This is the mechanism that makes the whole approach compound. One conversation becomes two, and an introduction from someone inside the field is worth more than any number of cold messages. If they offer a name, ask whether they would be comfortable introducing you, and make it easy by offering to write the message they can forward.

If they do not offer anyone, do not push. Thank them and leave it.

The follow-up almost nobody sends

Send a thank-you the same day, and then — this is the part that matters — send a second note weeks later saying what you did with their advice. I took your suggestion about learning the experimentation stack and have built X.

Almost nobody does this, which is exactly why it works. It converts a one-off favour into someone who is now invested in how you get on, and those are the people who forward you a role before it is posted. That is the entire mechanism behind the roles that never reach a job board.

Keeping track without it becoming a chore

Keep a simple record: who you spoke to, when, what you learned, what you promised. Job searches run for months and the details blur, and following up on something you said you would do is the single easiest way to be remembered well.

Aim for a small, sustainable rate — one or two conversations a week — rather than a burst. This works cumulatively and the value compounds slowly. Ten conversations over two months will teach you more about a field than a hundred applications, and will usually produce more interviews.

The short version

Ask specific people a specific, small question, with an easy way to say no. Prepare so you never ask what you could have looked up. Ask about the reality of the work, not the job description. Close by asking who else you should talk to. Send the second follow-up weeks later saying what you did — that one is the whole point.

Doing this while employed

Most people having these conversations already have a job, which raises the obvious question of discretion. In practice informational conversations are far less exposing than applications: you are asking someone about their work, which is ordinary professional behaviour and not evidence of anything.

Keep it off work systems anyway — personal email, personal device, and outside working hours where you can. And be thoughtful about who you approach inside your own industry if your search is confidential; a conversation with someone two desks removed from your manager's friend travels faster than you would like.

Where the person works at a company you might apply to, it is fine to say you are exploring options. It is not fine to imply you are not looking and then appear in their applicant tracking system a fortnight later, because that is the version people remember badly.

The version of this that fails

Worth naming the failure modes plainly, because they are common and avoidable. Asking for an hour rather than fifteen minutes. Sending a long message about yourself with the request buried at the end. Not turning up, or rearranging twice. Arriving with no questions and expecting the other person to run the conversation.

And the most damaging: asking them to refer you for a role in the first conversation. A referral puts the other person's reputation on the line for someone they have spoken to once, and asking for it that early tells them you understood the meeting as a transaction. If a referral is going to happen, it happens because they offered — which is much more likely after a second contact where you demonstrated you did something with the first.

How this differs by seniority

Early in a career the conversations are mostly about what the work actually involves and how people got in, and almost anyone will take them. Later, they shift towards specific problems — how your team handles this, what you learned from that migration — and the exchange becomes more mutual, because you have something to offer in return.

That mutuality is worth leaning into once you have any experience at all. The best of these conversations stop being one-directional quite quickly, and the ones that turn into a genuine professional relationship are the ones where you were useful too.

Making the fifteen minutes count

Have four or five questions ready and expect to use three. The conversation will go somewhere you did not plan, which is usually the valuable part, and a rigid list stops you following it.

Say at the start what you are hoping to get out of it — I am trying to work out whether product analytics is actually what I think it is — because that lets the other person aim their answers rather than guessing what would help. Most people want to be useful and are simply unsure what would be.

And end on time. Offering to wrap up at the fifteen-minute mark, even when the conversation is going well, is the single strongest signal that you respect the arrangement you asked for. People frequently wave it off and keep talking, and they remember that you offered.

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