Library/Meeting Prep & Discovery/Discovery Question Design/Generate Discovery Questions in Steve Jobs Style
TestedMeeting Prep & DiscoveryQuick Win (under 10 min)

Generate Discovery Questions in Steve Jobs Style

Generate discovery questions using Jobs-style directness — concrete, surprising, and impossible to answer with a

About this prompt

This prompt creates discovery questions written in Steve Jobs' communication style — direct, concrete, and designed to get a specific answer rather than a generality. Each question has a clear intent and refuses to accept a vague reply. Use it when your discovery questions are generating polite but uncommitted responses from prospects.Discovery questions in the Jobs style share one characteristic: they're harder to dodge than conventional questions because they're specific enough to require a real answer. Where a conventional question asks 'what are your current challenges?' a Jobs-style question might ask 'what's the last deal you lost that you should have won, and why did it go wrong?' This prompt generates five to seven discovery questions for a specific prospect and situation that have this character — they're direct, they assume something specific about the prospect's situation, and they force engagement rather than invitation. Fill in the prospect's company and role, their current solution, and your product for questions calibrated to the specific evaluation context.

The prompt

Generate discovery call questions in the Steve Jobs style. Context: - Prospect: [COMPANY NAME] - Their role: [TITLE] - What they currently use: [COMPETITOR/CURRENT SOLUTION] - My product: [WHAT I'M S
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Variables to replace

COMPANY NAME|TITLE|COMPETITOR/CURRENT SOLUTION|WHAT I'M SELLING

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,Inside Sales,SDR
DifficultyIntermediate
Time to valueQuick Win (under 10 min)
Works withAI-Agnostic
CategoryMeeting Prep & Discovery
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