Write guest interview questions

You are an interview producer. Guests who do many interviews have stock answers to stock questions ("How did you get started?", "What's your advice for beginners?"), and those answers make forgettable episodes. Memorable interviews come from questions that show the host did the homework: they reference a specific decision, a contradiction between two things the guest said or did, or a moment the bio skips over, and they ask for stories and specifics rather than opinions in general. Good questions are open, ask one thing at a time, and are short; the follow-up is often where the real answer comes out.

Write 15 main interview questions.

1. Summarise the angle in one sentence and list research gaps: what you would need to know about the guest to ask sharper questions that the bio does not tell you.
2. Write the questions as a path in five stages, with roughly this share of the total:

• Warm-up (10%): easy, specific, and still interesting; not "tell us about yourself".
• Context (20%): the background the listener needs for the angle, asked through a specific moment or decision from the bio.
• Depth (35%): the core of the angle: how they actually do the thing, the decisions, trade-offs and failures, with requests for stories and examples.
• Tension (15%): respectful challenges, such as counter-arguments, contradictions in their record, or what critics say, framed so the guest can answer well.
• Practical and close (20%): what a listener can do, and a closing question that is not "Where can people find you?" (save that for the outro).

1. For each question give: the question (under 25 words, one question only), why you are asking it (what it should draw out, and the bio detail it references), and one or two follow-ups that dig deeper ("What did that cost you?", "What would you do differently?"). Mark the three to five questions you must not skip.
2. List topics to handle with care or avoid, based only on what the bio and angle suggest (for example a recent setback, a legal matter, private life), with how to approach each if at all.
3. List facts about the guest to verify before recording.

• Use only facts from the bio and angle. Do not invent books, companies, quotes, dates or events in the guest's life; if a question would need a fact you do not have, put it under research gaps instead.
• No double-barrelled questions, no yes/no questions in the depth stage, no leading questions that answer themselves.
• Avoid the stock questions above unless reframed around something specific.

Angle and research gaps

Question path

Grouped by stage. Each item: the question in bold, then "Why:" and "Follow-ups:" lines. Mark must-ask questions with (must-ask).

Handle with care

Verify before recording