Prepare questions you genuinely don’t know the answer to

Ask about the unwritten realities of the role — the things no job posting reveals.

Why it works

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 to do it

1. Do your homework first: read what’s publicly available about the role and field so you’re not wasting their time on facts.
2. Prepare five to eight questions about things you genuinely can’t answer from public information: trade-offs they navigate, what they wish they’d known, how decisions actually get made.
3. Include at least one question about failure or difficulty — it signals maturity and produces the most useful answers.
4. Don’t ask for a job or a referral; if they offer, great, but it shouldn’t be your goal.

Evidence

Information acquired through direct conversation with practitioners is qualitatively richer than publicly available career data — this is the core premise of tacit knowledge research. The quality of questions determines the quality of that information. (mechanistic)

People answer questions honestly when they trust the context; an informational interview must feel safe (non-evaluative) for candid answers to emerge.

Common mistake

Asking questions that could have been answered by reading their company website — it signals you haven’t prepared and wastes a rare access window.