Library/Meeting Prep & Discovery/Discovery Question Design/Generate Discovery Questions Tailored to a Specific Title
TestedMeeting Prep & DiscoveryQuick Win (under 10 min)
About this prompt
This prompt helps AEs, sales engineers, and inside sales reps build a targeted set of discovery questions for a meeting with a specific [SPECIFIC TITLE], such as a CISO, VP of Finance, or Head of Operations. It produces 5–7 conversational questions focused on that role's KPIs, top challenges in the current period, what success looks like in their position, and how decisions get made under them. Use it before a first meeting with a new title or buying role you haven't sold to before.A VP of Finance and a VP of Operations will have completely different definitions of success, different KPIs, and different objection patterns — using the same discovery questions for both is a reliable way to have a surface-level conversation. This prompt generates 5–7 role-specific discovery questions for [SPECIFIC TITLE] that are calibrated to their unique KPIs, their top 2–3 challenges in [CURRENT QUARTER/YEAR], their personal definition of success in the role, and how decisions flow through their organization. Populate [SPECIFIC TITLE] and [CURRENT QUARTER/YEAR] to get questions anchored to the actual role and timing; including the industry in the prompt context will sharpen the KPI and challenge framing further. Use this prompt when preparing to sell to a new persona or a title you haven't encountered before; for calls where you've already mapped the specific pain, the business-impact quantification questions (0078) are more appropriate. For best results, run the prompt once for each stakeholder title in a multi-threaded deal to prepare distinct question sets for each conversation rather than using one generic set across the buying group.The prompt
Generate discovery questions tailored to a [SPECIFIC TITLE: e.g., CISO, VP of Finance, Head of Operations]. Focus on:
- Their unique KPIs and how they are measured
- Their top 2-3 challenges in [CURRE
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Variables to replace
SPECIFIC TITLE: E.G., CISO, VP OF FINANCE, HEAD OF OPERATIONS|CURRENT QUARTER/YEAR
How to run it
- Copy the prompt and paste it into Claude, ChatGPT, Gemini, or Copilot — it's tuned to run in any of them.
- Replace the variables — swap each bracketed token for your deal's specifics. The variables list above explains every field.
- Make it yours — run it, keep what's strong, and tighten your inputs on the next pass. The prompt improves with your context.
What good output looks like
Make it yours
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