Library/Meeting Prep & Discovery/Discovery Question Design/Write Five Open-Ended Discovery Questions by Role
TestedMeeting Prep & DiscoveryQuick Win (under 10 min)

Write Five Open-Ended Discovery Questions by Role

Generate five thoughtful open-ended discovery questions tailored to a specific title, industry, and problem area.

About this prompt

This prompt generates five open-ended discovery questions calibrated to a specific job title, industry, and problem area — designed to uncover the prospect's actual pain and priorities rather than confirming what you already believe. Use it before a discovery call to ensure your questions are specific to the buyer's context.Generic discovery questions produce generic answers — 'what are your biggest challenges' gets a rehearsed response that doesn't advance the conversation. This prompt generates five questions that are specific to the buyer's role and industry context, open-ended enough to produce a substantive answer, and sequenced to build naturally from situation to problem to implication. Fill in the title, industry, and problem area for questions that reference the specific language and context of the buyer's world. Use two or three of the five in a given call rather than all five — discovery is a conversation, not an interrogation, and the best questions generate follow-up questions that couldn't have been planned in advance.

The prompt

Write five thoughtful, open-ended discovery questions I can ask a [title, e.g., VP of Operations] in the [industry] industry to uncover pain points and priorities related to [problem area].
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Variables to replace

TITLE, E.G., VP OF OPERATIONS|INDUSTRY|PROBLEM AREA

How to run it

  1. Copy the prompt and paste it into Claude, ChatGPT, Gemini, or Copilot — it's tuned to run in any of them.
  2. Replace the variables — swap each bracketed token for your deal's specifics. The variables list above explains every field.
  3. 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

StageDiscovery
SeatAE, SDR
DifficultyBasic
Time to valueQuick Win (under 10 min)
Works withAI-Agnostic
CategoryMeeting Prep & Discovery
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