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How to improve your discovery in one prompt

This follow-up prompt transforms surface level discovery into pain-revealing conversations.

July 09, 2025

Difficulty: Easy | Impact: Deeper Discovery | Read Time: 1 min

Before:
You've got your shiny new pain points from Monday's prompt, but you're still asking the same boring questions as everyone else.

"So... what keeps you up at night?" Crickets.

You're asking surface-level questions that don't get to the heart of a genuine issue.

I feel a ghosting coming.

After:
You've got an arsenal of precision-targeted discovery questions that make prospects think "How did they know EXACTLY what to ask?"

Your calls become diagnostic sessions where people reveal the real business problems they need solving.

You uncover pain so specific that prescribing your solution becomes inevitable.

The Workflow

  1. After completing Monday’s prompt to build a list of pain points, fire this follow-up prompt into ChatGPT:

Now imagine you are a seasoned sales trainer helping account executives master discovery calls.

Take these customer pain points and for each one: 

* Reverse-engineer 3–5 open-ended, curiosity-based discovery questions
* Ensure the questions help the AE explore whether the problem exists, how severe it is, the business impact, and who else is affected
* Make the tone natural and inquisitive, not leading or assumptive
* Avoid "loaded" questions or ones that imply the problem must exist
* Format as:

PAIN POINT: [description]
DISCOVERY QUESTIONS:
* [question 1]
* [question 2]
* …

  1. Pre-meeting, use these questions to build your discovery framework

  2. Watch prospects open up like never before

Important: Don't machine-gun all the questions at your prospect! Pick the 3-5 that feel most natural for the conversation flow.

Why it works:
Great discovery isn't about what YOU want to know. It's about what THEY need to reveal.

When you ask the right questions, prospects convince themselves they have a problem worth solving. And feel the urgency to solve.

Tools Used: 

ChatGPT (Free)

What sales challenge should we tackle next? Comment below and let us know.

Darryl and the Leveraged Team