How does "Prepare questions you genuinely don’t know the answer to" work?

Generic questions ("What do you like about your job?") signal low preparation and produce generic answers. Questions about specific, non-public realities of the work — the actual daily texture, the common failure modes, the skills that surprised them as important — engage the person’s real expertise and produce information you genuinely couldn’t find elsewhere, which is the whole point.

How does "Listen for what isn’t in the job description" work?

Job descriptions describe the formal structure of a role; conversations with incumbents reveal the actual experience — the hidden costs, the informal power dynamics, the skills that matter most, the culture that doesn’t fit in a values statement. This tacit knowledge is the most decision-relevant information available and is only accessible through direct conversation.

How does "Close every informational interview with one forward step" work?

One of the most reliable outcomes of a well-run informational interview is a referral to the next conversation. The person you just spoke to has validated your approach, been impressed by your questions, and now feels mild reciprocal motivation to help further. Asking explicitly for a referral at this moment — while they’re engaged — converts their goodwill into a concrete next step before it dissipates.

How does "Build and work a target list of roles and organisations" work?

Passive job searching — waiting for the right posting to appear — puts you in competition with every other applicant and limits you to officially open roles. Active research into target organisations means you understand roles before they’re posted, build relationships with insiders, and are often referred before the job is public — none of which is possible by applying cold.

How does "Practise your story before you need it" work?

When asked "so what are you looking for?" most people give unfocused, rambling answers — not because they lack substance but because they’ve never organised and practised their own narrative. A clear, practised story signals that you know yourself, makes it easy for others to advocate for you accurately, and gives the conversation a foundation to build on rather than a vague starting point.

How does "Send a meaningful thank-you note" work?

A generic thank-you is expected and forgettable; a specific one that demonstrates you listened and acted on what you heard signals genuine engagement and competence. Reporting back — "I reached out to the person you suggested and had a fascinating conversation" — closes the loop and gives the person a sense that their investment produced something, which makes them willing to invest again.

Richard Bolles

How do informational interviews actually help your career?

Using curious conversations to research careers, build relationships, and find hidden opportunities

Short answer

An informational interview is a low-stakes conversation with someone in a role or field you’re curious about — you ask questions, they share experience, and no job is on the table. Richard Bolles’s What Color Is Your Parachute? popularised this as a career research tool; the evidence is largely observational and practitioner, but it consistently shows that direct conversation with insiders produces better career decisions and unexpected referrals.

Most career decisions are made with almost no first-hand information — job postings and LinkedIn profiles substitute for actual understanding of what a role or field is like. The informational interview flips this: you request a short, no-pressure conversation with someone doing the work, with zero transactional expectation. The paradox is that these no-ask conversations frequently produce referrals and opportunities that cold applications never do.

The practices (7)

Why it works

People decline generic networking requests because the cost-benefit is unclear — what do you want, how long will it take, what’s in it for them? Specificity removes these unknowns: a clearly scoped 20-minute conversation about a specific topic, with an explicit "no job ask," lowers the perceived cost dramatically. Flattery about their specific work (not generic praise) activates the desire to be seen as a valued expert.

How to do it

1Find someone 2–3 levels above you doing work you genuinely want to understand.
2Write a 3–4 sentence message: who you are, exactly what you’re trying to understand, a specific thing about their work that makes them the right person to ask, and a request for 20 minutes.
3Include the explicit line: "I’m not looking for a job — I’m doing research and would love your perspective."
4Offer to accommodate their schedule entirely.

Evidence

Mechanistic

Direct outreach with a clear, low-cost ask has higher response rates than vague networking requests; this is consistent with cognitive load and reciprocity research. Bolles’s recommendation is practitioner consensus refined over decades of career counselling.

Honest caveat: Response rates vary enormously by industry, seniority, and medium; no controlled study has benchmarked informational interview request formats.

Common mistake: Being vague about what you want or letting the "no job ask" promise erode during the meeting — both make the conversation feel like a disguised job application.

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