Informational conversations that are not awkward

Informational interviews have a bad reputation among the people asked to give them, and the reason is simple: most of them are job requests wearing a research costume. Twenty minutes of questions, then the turn — "so, are you hiring?" — and the other person realises they were the target of a manoeuvre. They will still be polite. They will not introduce you to anyone.

The version that works is the one where the stated purpose is the actual purpose. You want to understand something about the field, the role, or the organisation that you cannot learn by reading. That is genuinely valuable to you, and it is a request most people are happy to grant, because being asked about your expertise is pleasant and answering it costs twenty minutes. In career conversations and interviews, the website offers a useful lens for how emotional tone can influence rapport.

Who to ask

Not the hiring manager at the company you want to work for. That person is a decision-maker and treating them as a research subject is transparent. For occupational outlook and pay data, consult the U.S. Bureau of Labor Statistics.

Better targets, in rough order of usefulness:

• Someone doing the job you want, two to five years in, at an organisation you are not currently applying to. They remember what it took to get in, they are not in a position to hire you, and they are candid for exactly that reason.
• Someone who left the field you are in for the field you want, three or more years ago. They have run the experiment you are contemplating.
• Someone senior in the function but at a small organisation, where seniority does not mean unreachable.
• Former colleagues who moved sectors. Weakest tie, strongest response rate.

The request

Short, specific, time-bounded, and honest about how you found them. The specificity is what distinguishes it from the template everyone receives.

Hello — I have been moving from lab operations into quality management and I noticed you made a similar move around 2019. Would you be open to twenty minutes at some point in the next few weeks? I mainly want to ask how much of the regulatory side you had to learn before anyone would take you seriously. Happy to work around whatever suits you, and no problem at all if not.

Three things that letter does. It names the specific parallel rather than saying "your career path is inspiring". It states the actual question, so the person knows whether they can help before agreeing. It gives an easy exit, which paradoxically raises the acceptance rate.

Running the twenty minutes

Prepare five or six questions and expect to use three. The good ones are about mechanics and judgement, not about inspiration.

• "What did you underestimate about the move?"
• "What part of the job takes the most time, and is that what you expected?"
• "When you look at applicants for your team, what makes you stop reading?"
• "What would you have done differently in the first six months?"
• "Is there a certification or piece of vocabulary that people expect and I might not have?"
• "Who else should I be talking to about this?"

That last question is the one that compounds. It is also the only ask in the conversation, and it is a modest one — you are asking for a name, not a favour.

Keep to the time. If you asked for twenty minutes, say at nineteen that you are conscious of the time. People frequently then continue talking, which is fine; the point is that you noticed.

Afterwards

Send a note within a day. Two or three sentences, and make it specific to what they said rather than generic gratitude — quote back the thing that changed your thinking. This is the message that gets remembered.

Then, and this is the part almost everyone skips: send a second note six to eight weeks later saying what you did with the advice. "You suggested the internal audit certificate — I sat it in March and it came up in every conversation since." This message is very rarely sent and disproportionately effective, because it demonstrates that the twenty minutes were not wasted. It is also the natural moment at which the other person volunteers something, and the volunteered offer is worth more than a requested one.

When it turns into a job conversation

Sometimes it does, unprompted — the other person says their team is hiring, or offers an introduction. Accept plainly and move to the normal process. Do not steer towards it. The steering is what everyone can see, and it is the thing that makes these conversations unpleasant for the people on the other side.

If it does not turn into anything, the conversation was still the cheapest research available: twenty minutes with someone who has done the thing, against however many hours of reading it would have replaced.